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Results: 332 Rentals

  • 3+BR/ 2 bath in Grove Beach Improvement Association Community... Central AC
    From $412 per night (USD)

    VRBO

    3+BR/ 2 bath in Grove Beach Improvement Association Community... Central AC

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Looking for a quintessential family vacation on the Connecticut shore? Our family vacation home has Central Air, 3 bedr ...

    From $412 per night (USD)

    VRBO

    Details
  • Waterfront Retreat overlooking Long Island Sound w/gorgeous sunrises & sunsets!
    From $458 per night (USD)

    VRBO

    Waterfront Retreat overlooking Long Island Sound w/gorgeous sunrises & sunsets!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    *******************************************NOTE************************************************** I DO NOT LIST THIS PRO ...

    From $458 per night (USD)

    VRBO

    Details
  • Spectacular Lakefront home with expansive decks
    From $374 per night (USD)

    VRBO

    Spectacular Lakefront home with expansive decks

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Escape to charming Lake front home with water views from virtually every room. Indoor/outdoor living at it's best with ...

    From $374 per night (USD)

    VRBO

    Details
  • Luxurious Beach Home!
    From $775 per night (USD)

    VRBO

    Luxurious Beach Home!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Enjoy you vacation time at this Newly Remodeled Luxurious Beach Home,With two first floor full Baths and bedrooms With ...

    From $775 per night (USD)

    VRBO

    Details
  • Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
    From $240 per night (USD)

    VRBO

    Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    Our Great Hammock Beach cottage is a seasonal rental with 4 bedrooms and 1 bath. Recently installed central air conditio ...

    From $240 per night (USD)

    VRBO

    Details
  • Charming Lakefront Home with Sunset Views
    From $476 per night (USD)

    Expedia

    Charming Lakefront Home with Sunset Views

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    Newly renovated home on beautiful Lake Pocotopaug. This private 650-acre lake is closed to the public! Located in a sm ...

    From $476 per night (USD)

    Expedia

    Details
  • Upscale Beach Home!! PRIME WEEKS STILL AVAILABLE !! Discounted Rate of 200 off
    From $734 per night (USD)

    VRBO

    Upscale Beach Home!! PRIME WEEKS STILL AVAILABLE !! Discounted Rate of 200 off

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Thinking of having your wedding at Waters Edge? Stay at this beautiful beach home . . Relax at this Newly Remodeled Spac ...

    From $734 per night (USD)

    VRBO

    Details
  • Charming Beach House With Totally Private Backyard - 500 Ft. From Private Beach
    From $262 per night (USD)

    VRBO

    Charming Beach House With Totally Private Backyard - 500 Ft. From Private Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    (Disregard the GPS map - The beach house is 500 feet from Island View Beach) This cozy and very clean beach house offer ...

    From $262 per night (USD)

    VRBO

    Details
  • Beach front property steps from Long Island Sound!
    From $1030 per night (USD)

    VRBO

    Beach front property steps from Long Island Sound!

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    The Salty Seahorse Cottage is a charming vacation destination located directly on the beach in Westbrook, CT. It is ava ...

    From $1030 per night (USD)

    VRBO

    Details
  • Beautiful Cottage Cove!
    From $586 per night (USD)

    VRBO

    Beautiful Cottage Cove!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    Come stay at this tastefully updated 4 bedroom-2.5 bath home. Large kitchen and spacious rooms. Each room has its own TV ...

    From $586 per night (USD)

    VRBO

    Details
  • Cozy, Beach Cottage on West Beach
    From $322 per night (USD)

    VRBO

    Cozy, Beach Cottage on West Beach

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    4

    Cozy cottage, with water views, steps from West Beach and Coral Sands Beach. A wonderful family community with many recr ...

    From $322 per night (USD)

    VRBO

    Details
  • Newly Constructed 3 Bedroom, 2 Bath Home on 12.5 Acres, Water Access and Views
    Click For Pricing

    Expedia

    Newly Constructed 3 Bedroom, 2 Bath Home on 12.5 Acres, Water Access and Views

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Water views from every room of this private, newly constructed haven. Spend some time lounging on the private dock whil ...

    Click For Pricing

    Expedia

    Details
  • Romantic Cottage by the Sea, steps to private beach, sleeps 2!
    From $289 per night (USD)

    VRBO

    Romantic Cottage by the Sea, steps to private beach, sleeps 2!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This adorable little studio cottage is located in a private association with beach just 200 steps away! The property ha ...

    From $289 per night (USD)

    VRBO

    Details
  • Relax with a beautiful lake view
    From $282 per night (USD)

    Expedia

    Relax with a beautiful lake view

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Serene setting on beautiful and quiet Lake Hayward. Quick walk to the beach. Spacious deck for dining and relaxing. G ...

    From $282 per night (USD)

    Expedia

    Details
  • Saybrook Almost Beach-Front, Private Beach,  Boat Launch, Shallow Dock, Secluded
    From $419 per night (USD)

    VRBO

    Saybrook Almost Beach-Front, Private Beach, Boat Launch, Shallow Dock, Secluded

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    This water view, beach access home is located just one house away from the beach. The house features four bedrooms, one ...

    From $419 per night (USD)

    VRBO

    Details
  • 'Grandma's Cottage' w/ Sunroom: Walk to Beach
    From $299 per night (USD)

    VRBO

    'Grandma's Cottage' w/ Sunroom: Walk to Beach

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Take a step back in time and embrace a peaceful retreat from the comfort of this 3-bedroom, 1-bathroom vintage vacation ...

    From $299 per night (USD)

    VRBO

    Details
  • Stunning cottage
    From $380 per night (USD)

    VRBO

    Stunning cottage

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    6

    Great Hammock beach is an exceptional summer community with fishing, swimming and kayaking. enjoy walking the beautiful ...

    From $380 per night (USD)

    VRBO

    Details
  • Relaxing summer rental, walking distance to the beach, short ride to the outlets
    From $411 per night (USD)

    Expedia

    Relaxing summer rental, walking distance to the beach, short ride to the outlets

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy your summer vacation on the Connecticut coast in this beautiful 3 bedroom beach house. Enjoy the clean, renovated, ...

    From $411 per night (USD)

    Expedia

    Details
  • Charming Beach House - Steps to private beach! Sleeps 4
    From $320 per night (USD)

    VRBO

    Charming Beach House - Steps to private beach! Sleeps 4

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This adorable house is located in a great private beach community, 6 houses away from beach (200 steps!) with a water vi ...

    From $320 per night (USD)

    VRBO

    Details
  • Adorable Cottage close to Beaches and Town
    From $359 per night (USD)

    VRBO

    Adorable Cottage close to Beaches and Town

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Our sweet cottage has 2 bedrooms and one bath. The home has been newly updated and ready for your summer vacation. Our h ...

    From $359 per night (USD)

    VRBO

    Details
  • Family friendly beachfront escape
    From $1055 per night (USD)

    VRBO

    Family friendly beachfront escape

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Relax and spend time with family on this beautiful beachfront home! Originally built in 1890, this newly renovated bunga ...

    From $1055 per night (USD)

    VRBO

    Details
  • Casa Yamagoya
    Click For Pricing

    Expedia

    Casa Yamagoya

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    This Mid- Century home was designed and built by a Yale Architect who Studied under Louis Kahn and Frank Lloyd Wright. ...

    Click For Pricing

    Expedia

    Details
  • Paradise in Clinton! AIR-CONDITIONED
    From $1782 per night (USD)

    VRBO

    Paradise in Clinton! AIR-CONDITIONED

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Rates from 5/14-9/30 are for short term stays. Rentals during this period have a 1 week minimum requirement and begin o ...

    From $1782 per night (USD)

    VRBO

    Details
  • Cozy Getaway w/lots of Natural Light :) 5 mins to adventures
    From $171 per night (USD)

    Expedia

    Cozy Getaway w/lots of Natural Light :) 5 mins to adventures

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This modern apartment is perfect for a night away from home , or a long term stay . This hidden gem is tucked away in mi ...

    From $171 per night (USD)

    Expedia

    Details
  • Spacious 5-bedroom, 6 bath vacation home just 30 min drive to beaches and casino
    From $1083 per night (USD)

    VRBO

    Spacious 5-bedroom, 6 bath vacation home just 30 min drive to beaches and casino

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    14

    What you will LOVE - PRIVATE RESORT STYLE PATIO - stunning pool, hot tub, cabana bar and grill, 65" TV and more! Tons o ...

    From $1083 per night (USD)

    VRBO

    Details
  • ⚓️Perfect Summer Oasis with nautical touches….. 59 steps to private beach ⛱
    Click For Pricing

    Expedia

    ⚓️Perfect Summer Oasis with nautical touches….. 59 steps to private beach ⛱

    Bedrooms:
    1
    Bathrooms:
    5
    Sleeps:
    5

    Spacious 4 bedroom, 2-story cottage with large yard, steps to private beach and basketball court in sought after Saybroo ...

    Click For Pricing

    Expedia

    Details
  • Center of CT shoreline.
    From $414 per night (USD)

    VRBO

    Center of CT shoreline.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The Beach Barn is a guest house behind our Clinton, shoreline home.  Updated, the converted barn has an open floor plan ...

    From $414 per night (USD)

    VRBO

    Details
  • Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12  Linens Included
    From $861 per night (USD)

    Expedia

    Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Escape to this ultimate beachfront retreat at our beautifully updated home, where cooling sea breezes and the warmth of ...

    From $861 per night (USD)

    Expedia

    Details
  • Rent A Room In This Spacious Victorian
    From $41 per night (USD)

    VRBO

    Rent A Room In This Spacious Victorian

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    1

    Rent a room in this spacious vintage Victorian style colonial. This home is located in an ideal central location, a blo ...

    From $41 per night (USD)

    VRBO

    Details
  • Luxury Waterfront Home-Labor Day Weekend is available
    From $818 per night (USD)

    VRBO

    Luxury Waterfront Home-Labor Day Weekend is available

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Perched along a luxurious peninsula jutting into the Long Island Sound, the Obstreperous Octopus sinks its tentacles int ...

    From $818 per night (USD)

    VRBO

    Details
  • Now has TV + linens - Relaxing 4-bedroom cottage in Westbrook, CT at West Beach
    From $326 per night (USD)

    VRBO

    Now has TV + linens - Relaxing 4-bedroom cottage in Westbrook, CT at West Beach

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    Nestled in the charming town of Westbrook, this 4-bedroom cottage offers the perfect escape for your next vacation. As y ...

    From $326 per night (USD)

    VRBO

    Details
  • Spacious And Luxurious Beach Home Steps From The Water
    From $512 per night (USD)

    Expedia

    Spacious And Luxurious Beach Home Steps From The Water

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    This house is perfect for families or groups that want to enjoy beautiful Old Saybrook in a spacious, newly remodeled, t ...

    From $512 per night (USD)

    Expedia

    Details
  • LAKE HOUSE! Walking distance to Lake Pocotopaug!
    From $291 per night (USD)

    VRBO

    LAKE HOUSE! Walking distance to Lake Pocotopaug!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to The Mohawk Cottage! Perfectly located walking distance to Lake Pocotopaug in East Hampton, Connecticut. Our ...

    From $291 per night (USD)

    VRBO

    Details
  • Magnificent Riverfront home, completely private.  BOOK  7 NIGHTS GET 10% OFF
    From $700 per night (USD)

    Expedia

    Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    9

    Quoted from a renter " This property has a million dollar view!" Featured in the 2022 movie Damons Revenge https://yout ...

    From $700 per night (USD)

    Expedia

    Details
  • 5 Bedroom Cottage Steps From The Beach @ Great Hammock Beach - JULY RENTAL ONLY
    From $402 per night (USD)

    VRBO

    5 Bedroom Cottage Steps From The Beach @ Great Hammock Beach - JULY RENTAL ONLY

    Bedrooms:
    1
    Bathrooms:
    5
    Sleeps:
    12

    We are booked for the 2022 season! Check back with us next year! We will not reply to any inquiries for 2022. Thank yo ...

    From $402 per night (USD)

    VRBO

    Details
  • Vintage Cottage- 2 Bedrooms, Sleeps 6 Comfortably, Chalker Beach
    From $270 per night (USD)

    VRBO

    Vintage Cottage- 2 Bedrooms, Sleeps 6 Comfortably, Chalker Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Chalker Beach has been part of our family since 1966; come and enjoy our cozy renovated vintage cottage. Two bedrooms co ...

    From $270 per night (USD)

    VRBO

    Details
  • OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW
    From $697 per night (USD)

    VRBO

    OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Ocean front, sunset facing, property is the only one in the area that has a huge yard and beach. 4-bedrooms, beautiful ...

    From $697 per night (USD)

    VRBO

    Details
  • Historic Essex Home w/ Large Yard Near Downtown!
    From $245 per night (USD)

    VRBO

    Historic Essex Home w/ Large Yard Near Downtown!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Brimming with small-town charm, Essex should be the next stop on your bucket list! This inviting 2-bedroom, 1.5-bathroom ...

    From $245 per night (USD)

    VRBO

    Details
  • Cape Overlooking South Cove of Old Saybrook
    From $467 per night (USD)

    VRBO

    Cape Overlooking South Cove of Old Saybrook

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Wonderful home just a quick walk from the historic town of Old Saybrook and 2 miles from the Town Beach. Spectacular vi ...

    From $467 per night (USD)

    VRBO

    Details
  • Secluded Family escape w/ pool & jacuzzi
    From $657 per night (USD)

    VRBO

    Secluded Family escape w/ pool & jacuzzi

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    11

    This beautiful property is a secluded escape as it sits on 3.5 acres of land with an in-ground Pool and Jacuzzi. Plan t ...

    From $657 per night (USD)

    VRBO

    Details
  • Charming Cottage with L.I. Sound and Marsh Views
    From $330 per night (USD)

    VRBO

    Charming Cottage with L.I. Sound and Marsh Views

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Completely renovated with new septic, solar, appliances,.. 1000 SF home sleeps 7 directly across the street from one hou ...

    From $330 per night (USD)

    VRBO

    Details
  • You and your Family deserve a break. Relax and enjoy lake front living
    Click For Pricing

    Expedia

    You and your Family deserve a break. Relax and enjoy lake front living

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    2 story lake front cottage. Sleeps 8 in 2-Bedrooms 10 steps off the rear deck lies the Modus Reservoir, a 450 acre fresh ...

    Click For Pricing

    Expedia

    Details
  • Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
    From $545 per night (USD)

    VRBO

    Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beautiful resort condo. Resort hotel is on the water - Sleeps 6. Indoor and outdoor pool and beach access. Water's Ed ...

    From $545 per night (USD)

    VRBO

    Details
  • DIRECT WATERFRONT PRIVATE BEACH
    From $319 per night (USD)

    Expedia

    DIRECT WATERFRONT PRIVATE BEACH

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    NOW RENTING FOR SUMMER On the water, beautiful views of Long Island Sound. The rental is located directly on a private ...

    From $319 per night (USD)

    Expedia

    Details
  • The Perfect Family Beachfront Cottage  The Viola Cottage
    From $500 per night (USD)

    VRBO

    The Perfect Family Beachfront Cottage The Viola Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    Guests at this beach cottage will appreciate convenient onsite amenities such as a playground and barbecue grills. The c ...

    From $500 per night (USD)

    VRBO

    Details
  • Gorgeous Designer Contemporary Beach House with Views
    From $394 per night (USD)

    Expedia

    Gorgeous Designer Contemporary Beach House with Views

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Enjoy the most relaxing vacation in this exquisite beach contemporary built in 2003. Over 700 sq. ft. of decking on 3 l ...

    From $394 per night (USD)

    Expedia

    Details
  • Now with TV - Relax in our 3-bedroom Westbrook cottage at West Beach
    From $292 per night (USD)

    VRBO

    Now with TV - Relax in our 3-bedroom Westbrook cottage at West Beach

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Nestled in the charming town of Westbrook, this 3-bedroom cottage offers a delightful escape for your next vacation. As ...

    From $292 per night (USD)

    VRBO

    Details
  • adorable ranch in beach community
    From $478 per night (USD)

    Expedia

    adorable ranch in beach community

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    4

    beautiful beautiful private beach-knollwood beach old saybrook, so much to do in the area three bedroom, one bathroom ad ...

    From $478 per night (USD)

    Expedia

    Details
  • Family Friendly, Beach Themed Cottage - Chalker Beach
    From $294 per night (USD)

    VRBO

    Family Friendly, Beach Themed Cottage - Chalker Beach

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    This is a beautiful, Cape Cod style cottage that is only an 8 minute walk from the beach. Located in the private Chalker ...

    From $294 per night (USD)

    VRBO

    Details
  • Lake Front Cottage #7!
    From $185 per night (USD)

    VRBO

    Lake Front Cottage #7!

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    0

    This lake front cottage is a step back in time. Crooked floors and ceilings only add to the charm. A simple clean w ...

    From $185 per night (USD)

    VRBO

    Details
  • Chalker Beach House Steps to the Water!
    From $986 per night (USD)

    VRBO

    Chalker Beach House Steps to the Water!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Newly renovated beach home available for the first time! Beautifully updated home in the Chalker Beach community of Old ...

    From $986 per night (USD)

    VRBO

    Details
  • Lovely Cottage by Lake Hayward
    From $278 per night (USD)

    VRBO

    Lovely Cottage by Lake Hayward

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Stay in this lovely, recently renovated cottage that is just a quick walk (or drive) to 3 lakeside beaches and just 30 m ...

    From $278 per night (USD)

    VRBO

    Details
  • Cozy Beach House: Shared Private Beach, Incredible Sand Bar, Stunning Views
    From $819 per night (USD)

    VRBO

    Cozy Beach House: Shared Private Beach, Incredible Sand Bar, Stunning Views

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    We have only a couple of prime weeks remaining for summer 2026. This lovely family vacation home has 5 bedrooms, 2.5 ba ...

    From $819 per night (USD)

    VRBO

    Details
  • Seasonal cottage rental,waterview
    From $393 per night (USD)

    VRBO

    Seasonal cottage rental,waterview

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Guests are sure to enjoy a memorable vacation in this fully furnished, 3 bedroom/1 bath cottage. The space is comforta ...

    From $393 per night (USD)

    VRBO

    Details
  • Lake Front Home on the water
    From $542 per night (USD)

    VRBO

    Lake Front Home on the water

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

    5 bedrooms, 3 & 1/2 bathrooms, sleeps up to 10 Beautiful renovated home on Lake Pocotopaug. This private 553 acre lake i ...

    From $542 per night (USD)

    VRBO

    Details
  • Essex Village home within walking distance to downtown.
    From $527 per night (USD)

    VRBO

    Essex Village home within walking distance to downtown.

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Take a break and relax at this private home located in historic Essex Village. One of the most desirable locations in Es ...

    From $527 per night (USD)

    VRBO

    Details
  • Lovely, cozy Cottage on a non working farm in a rural town.  Quiet and private.
    From $322 per night (USD)

    VRBO

    Lovely, cozy Cottage on a non working farm in a rural town. Quiet and private.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Selden Cottage is a charming, cozy, comfortable place with views of fields, stone walls and barns. It has a private dri ...

    From $322 per night (USD)

    VRBO

    Details
  • Waterfront Long Island Sound Luxury Home, Cornfield Pt Old Saybrook, CT
    From $1290 per night (USD)

    VRBO

    Waterfront Long Island Sound Luxury Home, Cornfield Pt Old Saybrook, CT

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Waterfront, 3 bed, 2.5 marble baths, 2400 sq ft Exquisitely appointed, completely renovated, luxury waterfront year roun ...

    From $1290 per night (USD)

    VRBO

    Details
  • SeaStar Beach House\nCLOSE WALK TO OCEAN Private Beach Access
    From $332 per night (USD)

    VRBO

    SeaStar Beach House\nCLOSE WALK TO OCEAN Private Beach Access

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    4

    *****SEASTAR****** Enjoy the beauty and Seascape of Knollwood Beach located in beautiful and scenic Old Saybrook Conne ...

    From $332 per night (USD)

    VRBO

    Details
  • Fun Lake Front Cottage!
    From $250 per night (USD)

    VRBO

    Fun Lake Front Cottage!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This cottage was lovingly remodeled with lake décor and fun in mind. Come enjoy this two bedroom with open living room ...

    From $250 per night (USD)

    VRBO

    Details
  • Cornfield Point Cottage
    From $1198 per night (USD)

    VRBO

    Cornfield Point Cottage

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    Our NEWLY RENOVATED cozy cottage is right on the beach. 🏖 You can’t get any closer than a home on the beach. Great fish ...

    From $1198 per night (USD)

    VRBO

    Details
  • 🌅A Lakefront Sunrise retreat for Couples or Families🌅
    From $671 per night (USD)

    Expedia

    🌅A Lakefront Sunrise retreat for Couples or Families🌅

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    Welcome to Lake Pocotopaug! Enjoy four seasons of fun, relaxation and adventure! This lakefront destination offers it a ...

    From $671 per night (USD)

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  • Beautiful Beach Front Home
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    Beautiful Beach Front Home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Beautiful waterfront home on private beach. Walk right out the back door on to your very own sandy beach. This newly ren ...

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  • Beach community with private beaches
    From $411 per night (USD)

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    Beach community with private beaches

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Spacious Beach house within a 5 minute walk to private association beaches. Plenty of space on the sand even in peak sea ...

    From $411 per night (USD)

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  • Cozy newly remodeled home close to major amenities  in Connecticut a
    From $226 per night (USD)

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    Cozy newly remodeled home close to major amenities in Connecticut a

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Clean, spacious, beautiful kitchen and bath newly remodeled closed to major stores and restaurants 46 Braeburn Ln is a ...

    From $226 per night (USD)

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  • Romantic Lakefront Cottage #5
    From $265 per night (USD)

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    Romantic Lakefront Cottage #5

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This lovely renovated 1950's Lakefront Cottage is a perfect romantic get away. It boasts an open floor plan with kitche ...

    From $265 per night (USD)

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  • The Beach House
    From $439 per night (USD)

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    The Beach House

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    12

    Welcome to our beautiful Beach House, on Long Island sound in Westbrook ct. the house is located directly on the beautif ...

    From $439 per night (USD)

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  • Cozy cottage near downtown Clinton, Marina & Hammonasset Park
    From $210 per night (USD)

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    Cozy cottage near downtown Clinton, Marina & Hammonasset Park

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Imagine a clean New England cottage with a beautiful outside deck to see spring emerge! It's cozy, nicely decorated and ...

    From $210 per night (USD)

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  • Contemporary Loft Apartment
    From $167 per night (USD)

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    Contemporary Loft Apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Spacious loft style apartment located on second floor with views of Long Island Sound. Single bedroom with Queen size ...

    From $167 per night (USD)

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  • Newly Renovated Private Quiet Cape 1/2 mile from the beach
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    Newly Renovated Private Quiet Cape 1/2 mile from the beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Located on a private drive surrounded by pastures overlooking the Oyster River. Peaceful and Quiet. Close to beaches, pa ...

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  • Tiny Lakefront Cottage!
    From $196 per night (USD)

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    Tiny Lakefront Cottage!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This lake front cottage is approx. 325sq. of adorable efficiency living space. It has an open floor plan with full siz ...

    From $196 per night (USD)

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  • Cozy Beach House - 5 min walk!  to  Knollwood Beach
    From $390 per night (USD)

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    Cozy Beach House - 5 min walk! to Knollwood Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Walk to beach! Comfy older house in CT most special shoreline. Private beach & tennis and basketball courts with short d ...

    From $390 per night (USD)

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  • Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage
    From $476 per night (USD)

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    Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    If you are looking for a beach front property then look no further! This beautiful freshly remodeled 2 bedroom cottage s ...

    From $476 per night (USD)

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  • Adults Only Toes In The Sand Beachfront Charmer
    From $954 per night (USD)

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    Adults Only Toes In The Sand Beachfront Charmer

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    Welcome to the Salt Island Inn! (It’s not really an inn, that's just our family name for the house). PLEASE NOTE: This ...

    From $954 per night (USD)

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  • 4BR Beach Cottage sits on private beach.  Sleeps 12 with comfort, Outdoor grill
    From $867 per night (USD)

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    4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    12

    OCEAN FRONT HOME WITH SPECTACULAR views of Duck Island and the Long Island Sound. The front of the house faces the Menu ...

    From $867 per night (USD)

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  • Cabin Deck House - Formidable Cabin in Laurel Island
    From $497 per night (USD)

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    Cabin Deck House - Formidable Cabin in Laurel Island

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    10

    Rental basis: Entire house or apartment Number of bedrooms: 4; Number of other rooms with beds: 0 Number of bathrooms: 1 ...

    From $497 per night (USD)

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  • Walk to Beach, pool, tennis court and kids playscape.
    From $193 per night (USD)

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    Walk to Beach, pool, tennis court and kids playscape.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beautiful summer escape in Westbrook CT. Quiet beach community. Relax in the pool, play tennis, or walk to the beach. In ...

    From $193 per night (USD)

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  • Little House on River - architectural gem
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    Little House on River - architectural gem

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Cozy Little House designed by renowned architect offers wonderful opportunity to vacation, work from home, or simply enj ...

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  • Driftwood Cottage @  Saybrook Point Marina, 2 King Beds
    From $386 per night (USD)

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    Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Nestled between the Long Island Sound and the Connecticut River, Cove Street Cottage is your luxury getaway. You won’t h ...

    From $386 per night (USD)

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  • PRIVATE LAND ....OPEN SPACE 30 ACRES with POND, Very Basic
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    PRIVATE LAND ....OPEN SPACE 30 ACRES with POND, Very Basic

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    During this difficult time...I want to share a little gem! Pitch your tent, RV or Camper, you're welcome.... I call t ...

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  • Lovely 3 BR Beach house with beach just a 1 block walk away
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    Lovely 3 BR Beach house with beach just a 1 block walk away

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Lovely 3 bedroom beach house 1 block from 3 private association beaches. Cottage includes 3 bedrooms on the second floor ...

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  • Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
    From $545 per night (USD)

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    Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beautiful resort condo on the water - Sleeps 6. Indoor and outdoor pool and beach access. Water's Edge Resort and Spa ...

    From $545 per night (USD)

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  • Cheerful, private cottage in Essex village.
    From $323 per night (USD)

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    Cheerful, private cottage in Essex village.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Take a break and relax at this peaceful cottage tucked away in historic Essex Village. One of the most desirable locatio ...

    From $323 per night (USD)

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  • Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston
    From $763 per night (USD)

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    Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    9

    Escape to this stunning, recently restored, 5 bedroom retreat in a historic village only two hours away from NYC and Bos ...

    From $763 per night (USD)

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  • Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
    From $545 per night (USD)

    VRBO

    Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Beautiful resort condo on the water - Sleeps 6. Indoor and outdoor pool and beach access. Water's Edge Resort and Spa ...

    From $545 per night (USD)

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    Details
  • Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
    From $545 per night (USD)

    Expedia

    Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beautiful resort condo on the water - Sleeps 6. Indoor and outdoor pool and beach access. Water's Edge Resort and Spa ...

    From $545 per night (USD)

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  • Historic Mansion 1841 - The listed price is per Bedroom
    From $167 per night (USD)

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    Historic Mansion 1841 - The listed price is per Bedroom

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    The Mansion is a 3,200 square foot structure. You are renting 1 bedroom with a full en-suite bathroom on the first floor ...

    From $167 per night (USD)

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  • Direct Lakefront, 2 docks, private, easy access from I 91.
    From $416 per night (USD)

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    Direct Lakefront, 2 docks, private, easy access from I 91.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Rental of this property is subject to The State of Connecticut Travel Restrictions.This property is cleaned and disinfec ...

    From $416 per night (USD)

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  • Charming Old Saybrook Cottage < 1 Mi to Beach
    From $332 per night (USD)

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    Charming Old Saybrook Cottage < 1 Mi to Beach

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    5

    Slip on your sandals and embrace the seaside when you book this Old Saybrook vacation rental! Ideally situated less than ...

    From $332 per night (USD)

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  • Marina Guest House
    From $216 per night (USD)

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    Marina Guest House

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This beautifully decorated, clean and comfortable space is 600 square feet, has one bedroom with a queen size bed, a ful ...

    From $216 per night (USD)

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  • Cozy Cottage at The Cabins
    From $168 per night (USD)

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    Cozy Cottage at The Cabins

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    A one bedroom cottage in historic Westbrook, a quaint shoreline community on the banks of Long Island Sound, halfway bet ...

    From $168 per night (USD)

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  • Sister Sands - Waterfront Boho Beach House
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    Sister Sands - Waterfront Boho Beach House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Summary: Summary: Nestled in sunny Westbrook, CT this 3BD / 2BA waterfront beach house (sleeps 8-10) is close to casinos ...

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  • Down the street from the beach.
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    Down the street from the beach.

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    A cozy three bedroom cottage has an open floor concept which makes for spacious and roomy living. The cottage is right ...

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  • Cottage at the Marina
    From $209 per night (USD)

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    Cottage at the Marina

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This beautifully decorated, clean and comfortable space is 600 square feet, has one bedroom with a queen size bed, a ful ...

    From $209 per night (USD)

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  • Summer at the Haddam House
    From $246 per night (USD)

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    Summer at the Haddam House

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    You cannot miss this beautifully renovated waterfront cottage in Haddam with stunning views of the East Haddam Swing Bri ...

    From $246 per night (USD)

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  • Lakefront Home East Haddam CT-Peaceful - Crystal Clear Lake-also Academic rental
    From $281 per night (USD)

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    Lakefront Home East Haddam CT-Peaceful - Crystal Clear Lake-also Academic rental

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Lakefront home, situated 30 feet from lake. Available for Summer Rentals beginning second week of June. ALSO AVAILABLE ...

    From $281 per night (USD)

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  • Wonderful location, walk to beach, private yard, credit cards
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    Wonderful location, walk to beach, private yard, credit cards

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    The Cottage was chosen as one of the top ten unique places to stay in Ct. 'Awesome Cottage! Great Owner! Absolutely love ...

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  • Classic Lake House w/ private waterfront, 4 steps to water, FirePit/Kayaks/canoe
    From $461 per night (USD)

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    Classic Lake House w/ private waterfront, 4 steps to water, FirePit/Kayaks/canoe

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    *Please note this property does not allow for Saturday check in or check out dates* Make memories with family and friend ...

    From $461 per night (USD)

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  • Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
    From $425 per night (USD)

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    Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    8

    SPECIAL RATES FOR OCT AND NOV. Built in 1795 by Captain Nathaniel Clarke (a descendant of Capt. Thomas Clarke. The Nat ...

    From $425 per night (USD)

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  • Historic Sanctuary on the Pond
    From $575 per night (USD)

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    Historic Sanctuary on the Pond

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    The Parker Bull House circa 1754. Stunning renovation of a fantastic antique gem sitting on a pond with waterfall. This ...

    From $575 per night (USD)

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