Dogtown woods, Massachusetts Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Dogtown woods, Massachusetts on RentalSaver.com!

Dogtown woods Rentals

From $677 per night (USD)
VRBO
Stroll to SeaView/Beach; Great Yard
Bedrooms:
1
Bathrooms:
4
Sleeps:
7
The Ledge House is an idyllic retreat nestled in the heart of Gloucester's charming Bay View village. The historic farmh ...
From $677 per night (USD)
VRBO
From $439 per night (USD)
Expedia
Life of Reilly - Private & Serene Rockport Escape
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
New for Summer 2025! Life of Reilly is a stylish 2-bedroom, 1.5-bathroom vacation home tucked away on a serene 4.5-acre ...
From $439 per night (USD)
Expedia
From $651 per night (USD)
VRBO
Maids Quarters; private beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This simple and quiet home is behind a Victorian mansion and was used as the Maid's quarters to house staff. It's now a ...
From $651 per night (USD)
VRBO
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Expedia
The Quarry
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Take it easy at this unique and tranquil magical getaway. What this place offers Lake view Public or shared beach access ...
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Expedia
From $551 per night (USD)
VRBO
Location Location Location walk to all the favorite Rockport attractions
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This 2 bedroom 1 full bath is super convenient. The property is walking distance to all the favorite Rockport attractio ...
From $551 per night (USD)
VRBO
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Expedia
The Solar Powered Dogtown Cabin at Applecart Farm
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Beautiful hand built very private cabin with master bedroom and large loft located deep in the woods of Cape Ann. Walkin ...
Click For Pricing
Expedia
From $443 per night (USD)
VRBO
Clean Waterfront Classic Cottage with Private Beach
Bedrooms:
1
Bathrooms:
4
Sleeps:
7
Location x3! This classic, cozy, waterfront cottage that sits on a private beach overlooking the Annisquam River in Glou ...
From $443 per night (USD)
VRBO
From $251 per night (USD)
Expedia
Annisquam Village Bunny Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 ...
From $251 per night (USD)
Expedia
From $403 per night (USD)
VRBO
Amazing Waterfront/Access 4BDRM in Riggs Point
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Come and relax at our amazing home fully equipped with everything to make you feel right at home. With spacious rooms to ...
From $403 per night (USD)
VRBO
From $398 per night (USD)
VRBO
Walk to Beach, Shops & Train – 3BR, AC, Parking, Pets OK
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Just an hour from Boston, this classic New England cottage puts you in the heart of Rockport. Stroll to Front and Back ...
From $398 per night (USD)
VRBO
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VRBO
Beautiful Rockport, steps to Front Beach, restaurants, shopping
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Beautiful fully furnished condo, just steps to Front Beach with ocean views. Accommodations for up to 4 guests, with se ...
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VRBO
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Expedia
A walk up to heaven!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Very cozy Victorian home Fully renovated with brand new furniture and fresh paint Very convenient and plus location 5 ...
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Expedia
From $166 per night (USD)
VRBO
Cozy Cottage Old Fashioned Charm
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Please Read carefully and check out photos with captions on room details. Walk to beaches from this adorable old fashio ...
From $166 per night (USD)
VRBO
From $658 per night (USD)
Expedia
Tuna Wharf Townhouse has been sold and is no longer available to rent.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Feel free to contact me and I can refer you to other STR's Thanks! Jonathan Steps from the junction of Bearskin Ne ...
From $658 per night (USD)
Expedia
From $369 per night (USD)
VRBO
Seaside Elegance with a Private Balcony – Wake Up to Harbor Views!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Experience coastal charm in The Captain's Quarters, a beautifully designed retreat at The Sail Loft. This inviting space ...
From $369 per night (USD)
VRBO
From $285 per night (USD)
Expedia
Cozy oceanfront home with unique architecture
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Rustic Rockport Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $285 per night (USD)
Expedia
From $604 per night (USD)
VRBO
Cape Ann, Annisquam panoramic ocean views from every room.
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
This charming shingled house, built in 1917 and respectfully renovated in recent years, sits atop a rocky hill overlooki ...
From $604 per night (USD)
VRBO
From $758 per night (USD)
Expedia
Luxury Home in the Heart of Rockport
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Gorgeous house in Rockport, steps to beach, town, train, Shalin Liu performance center! This home is located on a quiet ...
From $758 per night (USD)
Expedia
From $250 per night (USD)
VRBO
WATERFRONT 1BDRM SPACIOUS STUDIO APARTMENT
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Come to the Cape named after a Queen NOT an Ugly Fish!! 🤣FABULOUS, quiet, dead end location! Incredible views of the An ...
From $250 per night (USD)
VRBO
From $297 per night (USD)
VRBO
A tranquil ocean retreat steps from the water's edge
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
On the Cove is a spacious three-room apartment is located directly on Lanes Cove in Lanesville (Gloucester) with spectac ...
From $297 per night (USD)
VRBO
From $447 per night (USD)
VRBO
Rockport Home with Beautiful Ocean Views
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Enjoy stunningly beautiful ocean views from all 3 decks at this quirky 1820 colonial house with easy access to local ame ...
From $447 per night (USD)
VRBO
From $242 per night (USD)
Expedia
Dog-friendly apartment in a prime location - walk to town beaches
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Olde New House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $242 per night (USD)
Expedia
From $497 per night (USD)
VRBO
'We can't wait to return to Four Winds'
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
PARKING SPOT 10 SECOND WALK AWAY, Four Winds is a two bedroom condo located directly on Tuna Wharf. If you love the sou ...
From $497 per night (USD)
VRBO
From $356 per night (USD)
Expedia
Quaint getaway with full kitchen and lush yard - close to the beach and downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Vintage Rockport Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $356 per night (USD)
Expedia
From $440 per night (USD)
VRBO
Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Escape to our idyllic retreat, the ultimate vacation spot for you, your family, and friends. Nestled between the picture ...
From $440 per night (USD)
VRBO
From $537 per night (USD)
Expedia
Downtown Home near the Beach & Downtown w/Gas Grill, Washer/Dryer & Deck
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
High Street Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $537 per night (USD)
Expedia
From $742 per night (USD)
VRBO
Gorgeous New Home w/ Ocean Views- 2 Private Beaches Steps Away
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
THE HOME: This house was built in 2018 with every modern amenity and comfort for vacation life. Vaulted ceilings in the ...
From $742 per night (USD)
VRBO
From $289 per night (USD)
Expedia
Harborside Oasis ★ Harbor View ★ Heart of Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
KEY FEATURES: 🌊 Sleeps 2 adults; 1 bedroom 🌊 Newly Renovated Modern Bathroom with standing shower 🌊 Modern and well-e ...
From $289 per night (USD)
Expedia
From $389 per night (USD)
VRBO
NEW 2BR Home Minutes to Downtown Rockport+Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This charming cottage is newly renovated with plenty of original character and fun details. Tucked away on a quiet lane ...
From $389 per night (USD)
VRBO
From $401 per night (USD)
VRBO
Charming Coastal Cottage, Steps to Ocean & Rockport Village!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step into the charming 1BR 1Bath cottage in a tranquil area just a few steps away from Shalin Liu Performance Center, ar ...
From $401 per night (USD)
VRBO
From $324 per night (USD)
VRBO
NEW Rockport Studio · Walk to Bearskin Neck · Reserved Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
→ Perfect Rockport getaway only 5 minute walk to Old Garden Beach → Walk 5-10 minutes to Downtown Rockport where you'll ...
From $324 per night (USD)
VRBO
From $266 per night (USD)
VRBO
Chic Downtown Loft ☆ Private Parking ☆ Ocean View
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy the coastal and seaside views from the renovated and bright "jewel" located in the charming seaside New England to ...
From $266 per night (USD)
VRBO
From $506 per night (USD)
VRBO
NEW Home w/firepit l Walk to Bearskin Neck+Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Set amidst a quiet oasis off the beaten path this exquisite shingled cape residence epitomizes refined elegance while ef ...
From $506 per night (USD)
VRBO
From $297 per night (USD)
Expedia
The Crow’s Nest – Loft with Stunning Ocean Views!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Perched above the heart of Bearskin Neck, The Crow’s Nest is a bright and airy studio apartment offering a cozy yet styl ...
From $297 per night (USD)
Expedia
From $421 per night (USD)
VRBO
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This charming seaside cottage is newly renovated with lots of modern conveniences and plenty of original character. You' ...
From $421 per night (USD)
VRBO
From $398 per night (USD)
Expedia
Beachmont: 3 bedroom house near beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Just 1/3 of a mile from Good Harbor Beach in East Gloucester! Enjoy a relaxing beach getaway in Historic Gloucester, MA. ...
From $398 per night (USD)
Expedia
From $267 per night (USD)
VRBO
Private Deck and Apartment in the treetops. The Admiral's Loft!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Close to downtown but set back on a quiet dead end street, The Admiral's Loft sits high in the treetops with keyhole vie ...
From $267 per night (USD)
VRBO
From $815 per night (USD)
Expedia
Tidebend: River views and gracious comfort
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
Welcome to Tidebend, your next Gloucester escape! This stunning 6-bedroom, 2.5-bath home overlooks the picturesque Annis ...
From $815 per night (USD)
Expedia
From $365 per night (USD)
VRBO
The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Your cozy getaway awaits in Rockport at this brilliant house. With 2 bedrooms, a bathroom, and essential amenities like ...
From $365 per night (USD)
VRBO
From $1251 per night (USD)
Expedia
One of a kind ocean front property - private section of Wingaersheek Beach.
Bedrooms:
3
Bathrooms:
1
Sleeps:
4
This property offers stunning views from every vantage point of Coffin's Beach, Crane Beach, the New Hampshire and Main ...
From $1251 per night (USD)
Expedia
From $899 per night (USD)
VRBO
Elegant Bayview Victorian Home; walk to beach
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
Discover the historic charm of Bayview, a stunning private estate once home to Civil War General Benjamin F. Butler. Spa ...
From $899 per night (USD)
VRBO
From $822 per night (USD)
Expedia
Walk to Front Beach: Dtwn Rockport Retreat!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Walk to Eats, Coffee Shops & Candy Stores | Furnished Balcony | Bikes + Beach Gear Located in the lively heart of Rockp ...
From $822 per night (USD)
Expedia
From $495 per night (USD)
VRBO
Oceanfront penthouse 2 bed 2 bath situated on beach and downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Renovated top floor apartment in the heart of the downtown Rockport historic district on the water. Private balcony with ...
From $495 per night (USD)
VRBO
From $447 per night (USD)
VRBO
New 2-bedroom apartment in charming Rockport with AC, WiFi and Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This Rockport apartment boasts 2 inviting bedrooms with 2 queen beds. The space includes AC, a washing machine, WiFi, an ...
From $447 per night (USD)
VRBO
From $436 per night (USD)
VRBO
Downtown Dahlias fully remodeled in the heart of Gloucester
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Relaxing spot close to everything in Gloucester. Our three bedroom home is a two level home filled with everything to ma ...
From $436 per night (USD)
VRBO
$NEW \Tranquil Seas\ Rockport SUMMER Rental - Convenience, Comfort and Charm$
From $386 per night (USD)
VRBO
NEW \"Tranquil Seas\" Rockport SUMMER Rental - Convenience, Comfort and Charm
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This meticulous, cozy, air conditioned home requires nothing but your suitcase and the desire to relax and have fun. Par ...
From $386 per night (USD)
VRBO
From $359 per night (USD)
VRBO
The Waterline – A Private Harborfront Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nestled in the historic Sail Loft building on Bearskin Neck, The Waterline offers a charming ground-floor retreat with s ...
From $359 per night (USD)
VRBO
From $637 per night (USD)
Expedia
Sunset Cove: Waterfront home in Goose Cove section of Gloucester.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Waterfront on the Annisquam River in Gloucester, this exceptional vacation rental boasts wonderful views of the river an ...
From $637 per night (USD)
Expedia
From $596 per night (USD)
VRBO
Ocean views just steps to Back Beach, Front Beach, and downtown Rockport
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come enjoy the ocean in Rockport. Fully furnished 3 bedroom 2 bath charming antique home with updated kitchen and baths. ...
From $596 per night (USD)
VRBO
From $533 per night (USD)
Expedia
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Get away from it all and unwind at this comfortable riverfront vacation retreat. Located in a quiet neighborhood, Thurst ...
From $533 per night (USD)
Expedia
From $535 per night (USD)
VRBO
Helena House: European flair, close to Plum Cove Beach.
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Situated on a knoll in Gloucester's Bay View neighborhood, Helena House offers peekaboo views of Ipswich Bay from the se ...
From $535 per night (USD)
VRBO
From $388 per night (USD)
Expedia
Granite Cottage: Charming cottage in Rockport with private deck and views.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
From it's private deck, enjoy the views of Sandy Bay dotted with sailboats. Or, walk down the quiet lane to Granite Pier ...
From $388 per night (USD)
Expedia
From $341 per night (USD)
VRBO
You will love our location and will return for our hospitality!
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
After the success of A Breezy Cottage, we set our sails on The Life of Reilly! The property was purchased in September, ...
From $341 per night (USD)
VRBO
From $356 per night (USD)
Expedia
Jewel Box: A gem of a rental home close to Good Harbor Beach.
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Situated at the end of a quiet street and down the road from Good Harbor Beach, Jewel Box is a gem of a rental home. Thi ...
From $356 per night (USD)
Expedia
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VRBO
Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
You'll find river life at its best when you stay at this newly-built vacation rental home that sits along the banks of s ...
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VRBO
From $807 per night (USD)
Expedia
Granite Pier: Blends craftsmanship with modern amenities. Water views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Granite Pier, with its unparalleled ocean views, is a traditional Cape Ann home with an unusual history. Built in the mi ...
From $807 per night (USD)
Expedia
From $210 per night (USD)
VRBO
Cozy, Waterview Old Quarryman boarding house
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Adorable 1 bedroom (with memory foam folding cot for xtra guests) Sleep Sofa. Has foma topper, High ceilings, laundry, ...
From $210 per night (USD)
VRBO
$\Absolutely lovely. The cottage, the beach, the town, the owners.\$
From $322 per night (USD)
VRBO
\"Absolutely lovely. The cottage, the beach, the town, the owners.\"
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
A Breezy Cottage is a very short walk to the charming beaches of Rockport, MA. It comfortably sleeps up to 7 people inc ...
From $322 per night (USD)
VRBO
From $956 per night (USD)
VRBO
Family home – 40 Atlantic Ave., Rockport, MA. Minutes walk to town and beach
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Leave your car in the driveway and walk to beach and town: 4-minutes to secluded Old Garden Beach, the Atlantic Pat ...
From $956 per night (USD)
VRBO
From $246 per night (USD)
VRBO
VIEWS! Annisquam Bridge House at Lobster Cove. June dates discounted.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Annisquam Bridge House-a renovated second floor unit high above Lobster Cove, Perfect getaway for a couple. It can acco ...
From $246 per night (USD)
VRBO
Click For Pricing
VRBO
Sandy Bay: An oceanfront gem vacation rental with ocean views in Rockport.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape to an oceanfront gem with exquisite views of Rockport's Sandy Bay and the Atlantic Ocean. Located just a short di ...
Click For Pricing
VRBO
From $826 per night (USD)
Expedia
Landmark Lookout: Lovely views of Sandy Bay and the Atlantic Ocean.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Enjoy beautiful views of Sandy Bay and the Atlantic from this classic New England vacation rental home on Rockport's Pig ...
From $826 per night (USD)
Expedia
From $603 per night (USD)
VRBO
Squam Light: Nestled in the heart of Annisquam
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Located in the heart of the quaint and charming village of Annisquam, this newly renovated Gloucester cottage offers the ...
From $603 per night (USD)
VRBO
From $222 per night (USD)
Expedia
Come home to Rockport!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Spend a weekend or a week enjoying the beauty and culture of Rockport. Enjoy panoramic views of Sandy Bay.and Straights ...
From $222 per night (USD)
Expedia
From $978 per night (USD)
VRBO
Sunrise on the Cove: Unobstructed 180 degree views of Pigeon Cove.
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
From its waterfront perch, this vacation rental home overlooks Rockport's picturesque Pigeon Cove harbor and has spectac ...
From $978 per night (USD)
VRBO
From $385 per night (USD)
Expedia
Joseph's Way: A charming cottage in a quiet setting, near Good Harbor Beach.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Just 4/10 of a mile from Gloucester's sandy Good Harbor Beach, Joseph's Way is delightful two bedroom property is nestle ...
From $385 per night (USD)
Expedia
From $1109 per night (USD)
VRBO
Beach & King - Stunning Ocean Views!
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Located across from Rockport's Front Beach, Beach & King is a beautiful Cape Ann Beach House rental on the North Shore i ...
From $1109 per night (USD)
VRBO
From $496 per night (USD)
VRBO
Private Pet Friendly hideaway near the beach and town center.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Cottage on the Pond is tucked away from the summer crowds at the end of a picturesque lane with ocean views from the fro ...
From $496 per night (USD)
VRBO
From $678 per night (USD)
VRBO
Sea Glass on South: Modern rustic chic, just steps from downtown Rockport
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Nestled on the edge of the village of Rockport, Sea Glass on South is a brand new and modern retreat, inspired by the Ne ...
From $678 per night (USD)
VRBO
From $390 per night (USD)
Expedia
Historic charm meets contemporary comfort at Pigeon Hill.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Steeped in history, this traditional early victorian home has been newly remodeled and renovated blending original detai ...
From $390 per night (USD)
Expedia
From $129 per night (USD)
VRBO
Gloucester Studio - Om Suite Om~ near Good Harbor Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Om Suite Om is a comfortable, cozy and convenient studio efficiency space, with a separate key and entry, in the lower l ...
From $129 per night (USD)
VRBO
From $491 per night (USD)
VRBO
Charming year round cottage - Pet Friendly with Wi-Fi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Please contact us for more details. We would love to discuss your vacation plans at our Home Away from Home. We are Pe ...
From $491 per night (USD)
VRBO
From $395 per night (USD)
VRBO
Seaside Village of Lanesville - North Gloucester, MA
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This quaint, cozy, quiet two bedroom fully furnished apartment in the Village of Lanesville has views of the Ipswich Bay ...
From $395 per night (USD)
VRBO
From $208 per night (USD)
VRBO
Quaint Waterfront Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Relax and breathe the salt air in this charming waterfront cottage. It is on well-known Bearskin Neck with a large deck ...
From $208 per night (USD)
VRBO
From $402 per night (USD)
VRBO
Harborfront House Directly on Rockport’s Quiet and Beautiful Old Harbor
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Idyllic for a couple or solo travelers who appreciate quality .Our historical, 19th-century comfortable waterfront house ...
From $402 per night (USD)
VRBO
From $310 per night (USD)
VRBO
Picturesque Rockport Queen Anne Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Great location in beautiful Rockport. The house is a ten minute walk into town - Bearskin Neck shopping, art galleries, ...
From $310 per night (USD)
VRBO
From $694 per night (USD)
VRBO
Beautiful vacation home. Reduced mos rates Oct-May. Plz contact for details.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to our charming 3-bedroom vacation home in the heart of Rockport, just a short walk from the Shalin Liu Performan ...
From $694 per night (USD)
VRBO
From $639 per night (USD)
Expedia
Gloucester: 5 Bedroom Summer Cottage with Sunset Views and Private Beach Access
Bedrooms:
2
Bathrooms:
5
Sleeps:
11
This finely maintained summer cottage built in the 1820s overlooks Hodgkins Cove in Gloucester Massachusetts. Unique an ...
From $639 per night (USD)
Expedia
From $653 per night (USD)
VRBO
Rockport direct Waterfront 3 bedroom, 3 bathroom home
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Breakwater House is a spacious contemporary home offering direct waterfront location in quiet, residential Pigeon Cove n ...
From $653 per night (USD)
VRBO
From $172 per night (USD)
VRBO
Seaside vacation studio steps from beaches and harbor area in historic Rockport
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
RESERVATIONS NOW BEING ACCEPTED FOR SUMMER 2023 starting May through October! Ground floor efficiency studio private r ...
From $172 per night (USD)
VRBO
From $352 per night (USD)
VRBO
Peaceful retreat, newly-renovated, short walk to Good Harbor Beach + WIFI
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Enjoy your vacation sojourn in this newly-renovated home, a short walk to one of New England's most beautiful beaches. ...
From $352 per night (USD)
VRBO
From $419 per night (USD)
VRBO
Bayview Guest Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
This property is a 650 sq. foot cozy cottage on Ipswich Bay with unbeatable views facing west, making for beautiful suns ...
From $419 per night (USD)
VRBO
From $1049 per night (USD)
VRBO
Beautiful Oceanfront Home in Estate Setting, Gloucester
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
A spacious, beautiful contemporary home on a private oceanfront estate near Gloucester's coveted Annisquam district, wit ...
From $1049 per night (USD)
VRBO
From $476 per night (USD)
Expedia
WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VACATION or WORK or do a bit of both if it means you'll have longer to play here on Cape Ann! The preferred spot for all ...
From $476 per night (USD)
Expedia
From $611 per night (USD)
VRBO
Summer Cottage on Ipswich Bay
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
This quiet summer cottage was built in the 1890's, it's original charm has been retained, while updates have made it a c ...
From $611 per night (USD)
VRBO
From $361 per night (USD)
VRBO
Sunset Views, Waterfront Property, Dock - Sleeps 12
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Stunning sunsets, a parade of boats going by, a charming marina, and a beach brimming with natural beauty — these are th ...
From $361 per night (USD)
VRBO
From $243 per night (USD)
VRBO
Holbrook House: Charming Rockport Village House, Walk To Everything!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A cozy, lovingly restored 1950's house. Walking distance to all that Rockport village and Bear Skin Neck has to offer. ...
From $243 per night (USD)
VRBO
From $614 per night (USD)
VRBO
Brilliant Ocean Views. Two Cottages - One price.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
'Back Beach Cottages' is a unique property with a two cottage set up. Both houses have wonderful views of the ocean and ...
From $614 per night (USD)
VRBO
From $654 per night (USD)
VRBO
Experience seaside charm near Good Harbor Beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Come and enjoy this new home with roof top deck overlooking Good Harbor Beach. We are a 5 minute walk to the beach! We ...
From $654 per night (USD)
VRBO
From $799 per night (USD)
Expedia
Evensong: Oceanview Retreat with Dock
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Unobstructed Water Views of The Annisquam in this newly-renovated "walls of glass" home boasting panoramic views of The ...
From $799 per night (USD)
Expedia
From $378 per night (USD)
VRBO
Good Harbor Beach Retreat ~ Walk to beach, shops, restaurants ~Dog Friendly
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Our adorable, 3 bedroom home is in a prime location for your vacation, with plenty of windows for ocean breezes. If yo ...
From $378 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Experience Rockport charm, walk to the beach ,restaurants & Shalin Liu Center
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Welcome to our charming 3-bedroom vacation home in the heart of Rockport! Nestled just a short walk from the Shalin Liu ...
From $408 per night (USD)
Expedia
From $220 per night (USD)
VRBO
Charming 3 bdrm Apartment in Heart of Rockport-Bearskin Neck-Walk to Beach -WiFi
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Immerse yourself in the heart of America's most famous seaside artists' colony. Located on Bearskin Neck and nestled in ...
From $220 per night (USD)
VRBO
From $659 per night (USD)
VRBO
Waterfront Home with Spectacular Viewsof the Annisquam River
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
Watch the beautiful sunsets over the Annisquam River from the deck or just enjoy the scenic views all day long of Mercha ...
From $659 per night (USD)
VRBO
From $353 per night (USD)
VRBO
Quaint Simplicity on Quiet Lane, Spacious and Relaxing, Walk to Shops, Beaches
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
This peaceful location on a quiet lane just outside of Rockport's downtown offers an easy place from which to enjoy the ...
From $353 per night (USD)
VRBO
From $419 per night (USD)
Expedia
Perfect Rockport Downtown Vacation Destination
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our fully renovated 3 bedroom cottage style unit offers all of the amenities needed for a perfect Rockport vacation. Ent ...
From $419 per night (USD)
Expedia
From $354 per night (USD)
VRBO
Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to a historical harborside treasure at our breathtaking 3rd-floor walk-up. As you step into the unit, prepare to ...
From $354 per night (USD)
VRBO
From $628 per night (USD)
Expedia
The Spinnaker: A hidden gem in Rockport village with roof deck and a garden.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located in Rockport village, The Spinnaker is the perfect rental home to feel worlds away from it all with a delightful ...
From $628 per night (USD)
Expedia
From $319 per night (USD)
VRBO
Single Level Home - Steps to Downtown Gloucester & A/C throughout
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This darling property is private and steps to everything in Gloucester. We own both upstairs and downstairs units. The ...
From $319 per night (USD)
VRBO
From $391 per night (USD)
VRBO
Majestic summer rental
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Single family home with ocean view close to Old Garden Beach and Bearskin Neck. Sleeps eight on large spacious property. ...
From $391 per night (USD)
VRBO

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