Search Your Destination Now!

Cumberland Area Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Update Results Reset Dates
Filter

Results: 1,000 Rentals

  • Sebago Waterfront with Dock.
    From $509 per night (USD)

    VRBO

    Sebago Waterfront with Dock.

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    OCCUPANCY LIMIT 6- Located in the Northwest Shores Association. This 3 bedroom 1 bath has a dock, mooring, and easy ac ...

    From $509 per night (USD)

    VRBO

    Details
  • Located in desirable Knights Hill Association on Moose Pond in Bridgton
    From $526 per night (USD)

    VRBO

    Located in desirable Knights Hill Association on Moose Pond in Bridgton

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    19

    OCCUPANCY LIMIT 19 MOOSE POND - KNIGHT'S HILL COMMUNITY. **This Place Has It All** Located in desirable Knights Hill ...

    From $526 per night (USD)

    VRBO

    Details
  • Shorefront on Sebago Lake.  Private Sandy Beach
    From $698 per night (USD)

    VRBO

    Shorefront on Sebago Lake. Private Sandy Beach

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    OCCUPANCY LIMIT 8 - NO PETS - LIMIT OF 2 OCCASIONAL DAY GUESTS. This 3 bedroom 1.5 bath has everything you need for your ...

    From $698 per night (USD)

    VRBO

    Details
  • Shorefront on Highland Lake
    From $540 per night (USD)

    VRBO

    Shorefront on Highland Lake

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    10

    OCCUPANCY LIMIT 7-10 - OCCASIONAL DAY GUESTS - - HIGHLAND LAKE BEACHFRONT. This is a very comfortable and well equipped ...

    From $540 per night (USD)

    VRBO

    Details
  • SANDY BEACH!!  Northeast shore of Frye Island
    From $724 per night (USD)

    VRBO

    SANDY BEACH!! Northeast shore of Frye Island

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    10

    OCCUPANCY LIMIT 10 is located on the northeast shore of Frye Island with views of Frye's Leap. It is also conveniently ...

    From $724 per night (USD)

    VRBO

    Details
  • Nicely appointed four bedroom shorefront home
    From $877 per night (USD)

    VRBO

    Nicely appointed four bedroom shorefront home

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    OCCUPANCY LIMIT 12 - NO PETS - LIMIT OF 4 CARS!! LIMIT OF 4 OCCASIONAL DAY GUESTS!! Nicely appointed four bedroom shor ...

    From $877 per night (USD)

    VRBO

    Details
  • Rustic shorefront cottage with a small sandy beach
    From $277 per night (USD)

    VRBO

    Rustic shorefront cottage with a small sandy beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    OCCUPANCY LIMIT 4 - SEBAGO LAKE SHOREFRONT. DOG CONSIDERED WITH $125 PET FEE. Rustic shorefront cottage with a small san ...

    From $277 per night (USD)

    VRBO

    Details
  • Cottage nestled in the woods overlooking Sebago Lake.
    From $385 per night (USD)

    VRBO

    Cottage nestled in the woods overlooking Sebago Lake.

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    OCCUPANCY LIMIT 8 - SEBAGO LAKE SHOREFRONT. Welcome charm of yesteryear abounds throughout this roomy classic Maine cot ...

    From $385 per night (USD)

    VRBO

    Details
  • Great Place for a Family Retreat! Sleeps 10
    From $437 per night (USD)

    VRBO

    Great Place for a Family Retreat! Sleeps 10

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    OCCUPANCY LIMIT 10. This 3-bedroom 2 bath home is close to Sebago State Park Beach. Canoe/paddles with four unisex life ...

    From $437 per night (USD)

    VRBO

    Details
  • Short walk to Association Beach and your own private dock
    From $293 per night (USD)

    VRBO

    Short walk to Association Beach and your own private dock

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    OCCUPANCY LIMIT 6 guests - This single level cottage has 3 bedrooms and 1 bath. Located a short walk away from Kettle C ...

    From $293 per night (USD)

    VRBO

    Details
  • Panoramic Oceanfront Views Of Garrison Cove, Wills Gut And Casco Bay
    From $942 per night (USD)

    VRBO

    Panoramic Oceanfront Views Of Garrison Cove, Wills Gut And Casco Bay

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Experience charming, picturesque Bailey Island, a Maine Casco Bay Coastal Island destination for vacationers from all ov ...

    From $942 per night (USD)

    VRBO

    Details
  • Entire House - three suites - conferences, reunions, retreats
    From $1158 per night (USD)

    VRBO

    Entire House - three suites - conferences, reunions, retreats

    Bedrooms:
    3
    Bathrooms:
    7
    Sleeps:
    22

    Guests have the entire house: a Great room. dining room, patio, and 3 separate suites. The Yellow sleeps 5 with bathroom ...

    From $1158 per night (USD)

    VRBO

    Details
  • Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free
    From $231 per night (USD)

    VRBO

    Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    COME VISIT US AND MAKE SOME AMAZING MAINE MEMORIES! BOOKINGS FOR SUMMER, FALL, AND WINTER ARE BEING ACCEPTED! PETS ARE F ...

    From $231 per night (USD)

    VRBO

    Details
  • Magnificent Log Home on Lake
    From $716 per night (USD)

    VRBO

    Magnificent Log Home on Lake

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Magnificent Log Home on Crescent Lake, situated in the middle of 15 privately owned acres, 750 feet of water-frontage. S ...

    From $716 per night (USD)

    VRBO

    Details
  • Crescent Lake Lakefront gorgeous sunsets, outdoor firepit , big dock, swim float
    From $604 per night (USD)

    VRBO

    Crescent Lake Lakefront gorgeous sunsets, outdoor firepit , big dock, swim float

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    11

    Looking for that perfect Maine lake experience, look no further. This is a large 4 bedroom home just steps from the crys ...

    From $604 per night (USD)

    VRBO

    Details
  • Beautiful Pine Point Cottage!
    From $272 per night (USD)

    VRBO

    Beautiful Pine Point Cottage!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Cozy and quiet describes this adorable cottage! One block from the beach and one block from the marsh makes this spot id ...

    From $272 per night (USD)

    VRBO

    Details
  • OCEAN VIEWS, Rooftop Deck, HOT TUB, new back deck!  3-min walk to Willard Beach
    From $1270 per night (USD)

    VRBO

    OCEAN VIEWS, Rooftop Deck, HOT TUB, new back deck! 3-min walk to Willard Beach

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    WILLARD BEACH VACATION HOME. 150 yards to Willard Beach, 8 mins to downtown Portland, Walk to fantastic restaurants/foo ...

    From $1270 per night (USD)

    VRBO

    Details
  • Oceanview, Handicap Friendly, Dogs & Babies Welcome. Watch the Seashore parade!
    From $528 per night (USD)

    VRBO

    Oceanview, Handicap Friendly, Dogs & Babies Welcome. Watch the Seashore parade!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Cagasa Cottage is a friendly place originally designed for an inter-generational family with mobility issues and a dog. ...

    From $528 per night (USD)

    VRBO

    Details
  • HEATED SALTWATER POOL, Pickleball. Higgins Beach Estate~sleeps 32.  12 min to DT
    From $3272 per night (USD)

    VRBO

    HEATED SALTWATER POOL, Pickleball. Higgins Beach Estate~sleeps 32. 12 min to DT

    Bedrooms:
    4
    Bathrooms:
    9
    Sleeps:
    27

    5600 square foot Higgins Beach Estate: POOL opens In June. ***NEW HEATED SALTWATER POOL ***New PICKLE BALL and BOCCE ...

    From $3272 per night (USD)

    VRBO

    Details
  • Fully Furnished Executive/Garden Apartment In Falmouth, Maine
    From $142 per night (USD)

    VRBO

    Fully Furnished Executive/Garden Apartment In Falmouth, Maine

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Bright and sunny one bedroom, one bathroom apartment with ample parking located in a beautiful garden setting. The Apar ...

    From $142 per night (USD)

    VRBO

    Details
  • Prouts Neck, Steps to the Beach
    From $600 per night (USD)

    VRBO

    Prouts Neck, Steps to the Beach

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Our wonderful home can now be used 365 days a year after a 2021 winterization which added air conditioning and heat to t ...

    From $600 per night (USD)

    VRBO

    Details
  • Oceanside Cottage On A Beautiful Private Beach - Enjoy Your Maine Vacation!
    From $353 per night (USD)

    VRBO

    Oceanside Cottage On A Beautiful Private Beach - Enjoy Your Maine Vacation!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Quaint, Quiet, Peaceful and Picturesque - The Getaway - An Adorable Cottage steps from a Private Maine Beach. Sitting o ...

    From $353 per night (USD)

    VRBO

    Details
  • Authentic ME 4 BR log cabin on flat land, sandy beach, Little Sebago waterfront
    From $447 per night (USD)

    VRBO

    Authentic ME 4 BR log cabin on flat land, sandy beach, Little Sebago waterfront

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    12

    Want to truly relax? Spend time at a fully furnished home away from home surrounded by Little Sebago Lake. Located on ...

    From $447 per night (USD)

    VRBO

    Details
  • Little Sebago Lake - Private Sandbar With A White Sand Beach - Full Sun
    From $716 per night (USD)

    VRBO

    Little Sebago Lake - Private Sandbar With A White Sand Beach - Full Sun

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    Grandview Point offers you an opportunity to enjoy a traditional Maine Lake experience in an updated summer cottage e ...

    From $716 per night (USD)

    VRBO

    Details
  • Simonson Lakeside 4 Bedrooms
    From $394 per night (USD)

    VRBO

    Simonson Lakeside 4 Bedrooms

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Sorry, this is a NO SMOKING, NO PETS property. This is a newly renovated home ready for your visit. It consists of a 4 ...

    From $394 per night (USD)

    VRBO

    Details
  • PLEASE READ REVIEWS of SEBAGO LAKE COTTAGE - 2026 BOOKINGS BEGINNING Oct 1st
    From $250 per night (USD)

    VRBO

    PLEASE READ REVIEWS of SEBAGO LAKE COTTAGE - 2026 BOOKINGS BEGINNING Oct 1st

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Sebago Lake reaches a depth of 316 feet . It's clarity is magnificent. It's great for boating , fishing, diving, swimmin ...

    From $250 per night (USD)

    VRBO

    Details
  • West End Apartment next to Longfellow Boutique Hotel
    From $275 per night (USD)

    VRBO

    West End Apartment next to Longfellow Boutique Hotel

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    3rd-Floor Apartment at 762 Congress Street, Portland, Maine Overview This third-floor apartment is located at 762 Congr ...

    From $275 per night (USD)

    VRBO

    Details
  • Cozy Sebago Lake Retreat
    From $481 per night (USD)

    VRBO

    Cozy Sebago Lake Retreat

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    A cozy Sebago Lake retreat with ample room for you and your guests. This home has 3 bedrooms, 1 bathroom, and 100’ of ...

    From $481 per night (USD)

    VRBO

    Details
  • Sea Rose Cottage - Cozy, Comfortable, Ocean Views on Orr's Island, Harpswell, ME
    From $315 per night (USD)

    VRBO

    Sea Rose Cottage - Cozy, Comfortable, Ocean Views on Orr's Island, Harpswell, ME

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    4

    Experience coastal living in our sunny and cozy cottage on Orr's Island in Harpswell, Maine! Relax on the covered porch ...

    From $315 per night (USD)

    VRBO

    Details
  • Fall In Love With Portland!
    From $349 per night (USD)

    Expedia

    Fall In Love With Portland!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    City of Portland Registration #4803 Live in a Comfortable Home, in Portland’s popular Munjoy Hill & Eastern Promenade a ...

    From $349 per night (USD)

    Expedia

    Details
  • Walk the Beautiful Beaches of Chebeague Island
    From $448 per night (USD)

    VRBO

    Walk the Beautiful Beaches of Chebeague Island

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Chebeague Island is relatively easy to get to and located close to Portland, Maine’s biggest city. We host by the week o ...

    From $448 per night (USD)

    VRBO

    Details
  • Panther Pond Cabin w/ 200 Ft Sand Beach & Dock!
    From $220 per night (USD)

    Expedia

    Panther Pond Cabin w/ 200 Ft Sand Beach & Dock!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Sitting on Panther pond with a sandy beach and dock, this 2-bedroom, 1-bath Raymond vacation rental makes for a peaceful ...

    From $220 per night (USD)

    Expedia

    Details
  • ON THE MARSH WITH WATER VIEWS AND SUNSET CENTRAL AIR
    From $665 per night (USD)

    VRBO

    ON THE MARSH WITH WATER VIEWS AND SUNSET CENTRAL AIR

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    16

    This totally renovated beach house is graciously appointed with top drawer furnishing, linens, and all refinished hardwo ...

    From $665 per night (USD)

    VRBO

    Details
  • Point Sebago Recently Renovated Cottage
    From $265 per night (USD)

    Expedia

    Point Sebago Recently Renovated Cottage

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    10

    We have a cottage that sleeps 6 very comfortably in Point Sebago Resort at 1472 Paleo Woods Way, a few minutes walk to ...

    From $265 per night (USD)

    Expedia

    Details
  • Charming Cottage By The Shore Of Beautiful Long Lake, Harrison, Maine
    From $475 per night (USD)

    VRBO

    Charming Cottage By The Shore Of Beautiful Long Lake, Harrison, Maine

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Charming 3 bedroom cottage located along the shore of beautiful Long Lake features a family room at the lower level with ...

    From $475 per night (USD)

    VRBO

    Details
  • Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
    From $348 per night (USD)

    Expedia

    Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    City of Portland Registration #4803 A well cared for and comfortable home, in Portland’s popular Munjoy Hill & Eastern ...

    From $348 per night (USD)

    Expedia

    Details
  • Spacious Ocean View Getaway, 3 min walk to beach with large fenced in yard
    From $872 per night (USD)

    VRBO

    Spacious Ocean View Getaway, 3 min walk to beach with large fenced in yard

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

    2024 updates: mini splits AC in all rooms and living areas except the primary bedroom and the 2nd floor bonus room (thes ...

    From $872 per night (USD)

    VRBO

    Details
  • Summers in Maine...\nPine-cone Lodge on Sabbathday Lake
    From $272 per night (USD)

    Expedia

    Summers in Maine...\nPine-cone Lodge on Sabbathday Lake

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    The Pinecone Lodge is nestled among the trees in a sandy cove on Sabbathday Lake in New Gloucester, Maine, home of the n ...

    From $272 per night (USD)

    Expedia

    Details
  • Comfortable cottage style home.  Family friendly.  Sleeps six.
    From $416 per night (USD)

    VRBO

    Comfortable cottage style home. Family friendly. Sleeps six.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Comfortable family friendly home that will sleep 6 with Infant pak and play & crib. All three bedrooms with baths, a qua ...

    From $416 per night (USD)

    VRBO

    Details
  • PRIVATE OCEANFRONT RETREAT - enjoy the peace and quiet of an historic Maine home
    From $616 per night (USD)

    Expedia

    PRIVATE OCEANFRONT RETREAT - enjoy the peace and quiet of an historic Maine home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    HISTORIC ISLAND COTTAGE Built in 1918, The Gills is an original summer cottage perched above the sea at the very end of ...

    From $616 per night (USD)

    Expedia

    Details
  • Family Cabin w/ Beach Access on Panther Pond
    From $291 per night (USD)

    VRBO

    Family Cabin w/ Beach Access on Panther Pond

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Get out on the water with a stay at this 2-bedroom, 1-bathroom Raymond vacation rental cabin. Sitting on Panther Pond, t ...

    From $291 per night (USD)

    VRBO

    Details
  • Ideal 2-family, Huge Main Room, Great Beach, Screened Porch/Patio with Fireplace
    From $987 per night (USD)

    VRBO

    Ideal 2-family, Huge Main Room, Great Beach, Screened Porch/Patio with Fireplace

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    14

    Enjoy a 5-star vacation home and all of your favorite freshwater activities - swimming, kayaking, playing on a sandy bea ...

    From $987 per night (USD)

    VRBO

    Details
  • Glamorous cottage-glamping at Sebago Lake
    From $288 per night (USD)

    VRBO

    Glamorous cottage-glamping at Sebago Lake

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Wonderful 2 bedroom cottage with huge porch sleeping 6 people. Outdoor bbq and fire pit.Pet friendly andJust short walk ...

    From $288 per night (USD)

    VRBO

    Details
  • Classic Summer Cottage With Full Amenities For Your Maine Island Vacation!
    From $372 per night (USD)

    VRBO

    Classic Summer Cottage With Full Amenities For Your Maine Island Vacation!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Beautifully up-kept and modernized classic cottage built circa 1897. Fantastic views, and great proximity to many island ...

    From $372 per night (USD)

    VRBO

    Details
  • Waterfront comfort & quiet, 200' private beach, overlooks miles of lake
    From $867 per night (USD)

    VRBO

    Waterfront comfort & quiet, 200' private beach, overlooks miles of lake

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Sited on a bluff above 200’ of private beach, in a peaceful setting among tall pines. Spectacular views can be seen from ...

    From $867 per night (USD)

    VRBO

    Details
  • 'Camp Card Cove' the Way Life Should Be
    From $529 per night (USD)

    Expedia

    'Camp Card Cove' the Way Life Should Be

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    This is 'the way life should be'... Camp Card Cove is a comfortable shingle-style Maine camp/cottage on large private 2 ...

    From $529 per night (USD)

    Expedia

    Details
  • THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room
    From $692 per night (USD)

    VRBO

    THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    THE RED HOUSE The 100 year old Red House at the head of Mackerel Cove was built when most of Bailey Island was wild and ...

    From $692 per night (USD)

    VRBO

    Details
  • TOWNHOUSE RETREAT AT PLEASANT MOUNTAIN/SHAWNEE PEAK - SKI IN/SKI OUT
    From $380 per night (USD)

    Expedia

    TOWNHOUSE RETREAT AT PLEASANT MOUNTAIN/SHAWNEE PEAK - SKI IN/SKI OUT

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    SUPER SUMMER SAVINGS SPECTACULAR! SAVE ON YOUR SUMMER VACATION! BOOK NOW AND SAVE! And what better place than right her ...

    From $380 per night (USD)

    Expedia

    Details
  • Island Escape - Spacious 4 BR House with Car included!
    From $327 per night (USD)

    VRBO

    Island Escape - Spacious 4 BR House with Car included!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Long Island is a tranquil 400 year old fishing community known for its beautiful white sandy beaches and rocky coast. - ...

    From $327 per night (USD)

    VRBO

    Details
  • Beautiful Pt Sebago Home - Availability for 2025
    From $387 per night (USD)

    VRBO

    Beautiful Pt Sebago Home - Availability for 2025

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome and thanks for considering our home for your vacation. Please scroll down to the "Ask owner a question" button ...

    From $387 per night (USD)

    VRBO

    Details
  • Lakefront, private dock & deck, dog friendly, fast wifi on crystal clear Panther
    From $349 per night (USD)

    VRBO

    Lakefront, private dock & deck, dog friendly, fast wifi on crystal clear Panther

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    6

    This lakefront cabin with a charming deck, is set just 25 feet from the water. Panther Pond, a mile wide and two miles ...

    From $349 per night (USD)

    VRBO

    Details
  • Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!
    From $149 per night (USD)

    Expedia

    Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!

    Bedrooms:
    1
    Bathrooms:
    5
    Sleeps:
    10

    COME VISIT US AND MAKE SOME AMAZING MAINE MEMORIES! PEAK SUMMER WEEKS BEING ACCEPTED! PETS ARE FREE, AND NO CLEANING FE ...

    From $149 per night (USD)

    Expedia

    Details
  • 4 BR/3 Bath Lakefront Sleeps 12
    From $659 per night (USD)

    VRBO

    4 BR/3 Bath Lakefront Sleeps 12

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    This beautiful, tastefully decorated, lakefront home sits just yards from the shore of Little Sebago and features lots o ...

    From $659 per night (USD)

    VRBO

    Details
  • Charming Maine Seaside Cottage near private beach
    From $409 per night (USD)

    VRBO

    Charming Maine Seaside Cottage near private beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    The Quintessential Cozy Maine Cottage – steps from the beach in the most beautiful location in a charming seaside neighb ...

    From $409 per night (USD)

    VRBO

    Details
  • Renovated Ranch 5 Bed 2 Bth, Open concept. Close to beaches, airport & Portland
    From $727 per night (USD)

    VRBO

    Renovated Ranch 5 Bed 2 Bth, Open concept. Close to beaches, airport & Portland

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    12

    This 5 bedroom home has everything you would need for your stay. Luxury linens and towels are provided for each guests. ...

    From $727 per night (USD)

    VRBO

    Details
  • Vienna's Place
    From $296 per night (USD)

    Expedia

    Vienna's Place

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Cozy two-bedroom apartment in private, wooded neighborhood. Completely remodeled in 2022. Main bedroom has a sitting roo ...

    From $296 per night (USD)

    Expedia

    Details
  • Yurt on private island with beaches & epic views
    Click For Pricing

    VRBO

    Yurt on private island with beaches & epic views

    Bedrooms:
    0
    Bathrooms:
    1
    Sleeps:
    4

    This yurt is part of Fortland, a small luxury campground & event venue. Set within historic Fort Scammell on House Islan ...

    Click For Pricing

    VRBO

    Details
  • First Floor Little Cozy Studio with King Size Bed Downtown
    From $217 per night (USD)

    Expedia

    First Floor Little Cozy Studio with King Size Bed Downtown

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    This cozy little apartment is located Page St and Union St, one of the most desirable neighborhood in Downtown Brunswick ...

    From $217 per night (USD)

    Expedia

    Details
  • Skyline 138: Charming West End Mansard Penthouse
    From $569 per night (USD)

    VRBO

    Skyline 138: Charming West End Mansard Penthouse

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Skyline 138! Experience the fusion of old world charm and modern comfort in this top floor apartment, nestled ...

    From $569 per night (USD)

    VRBO

    Details
  • Gorgeously renovated, 2-condo property in the West End - walk everywhere
    From $778 per night (USD)

    Expedia

    Gorgeously renovated, 2-condo property in the West End - walk everywhere

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Four Ensuite The Heart of the West End #3 & #4 Our calendar is updated in real-time & our nightly rates are accurately ...

    From $778 per night (USD)

    Expedia

    Details
  • Expansive Retreat - All-Season Contemporary Farmhouse  [Lakes & Mountains]
    From $363 per night (USD)

    VRBO

    Expansive Retreat - All-Season Contemporary Farmhouse [Lakes & Mountains]

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    14

    Relax & enjoy over 2,000 sq. ft. of tastefully detailed and fully furnished space set back from the road on a private lo ...

    From $363 per night (USD)

    VRBO

    Details
  • Charming 4 bedroom Chalet
    From $160 per night (USD)

    Expedia

    Charming 4 bedroom Chalet

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    4 bedroom, 2 bath home open concept kitchen/living area. Family room in walk out basement with wood burning stove. New ...

    From $160 per night (USD)

    Expedia

    Details
  • Cozy oceanfront cottage on Orr's Island
    From $311 per night (USD)

    VRBO

    Cozy oceanfront cottage on Orr's Island

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This one bedroom guest cottage is great for a couple looking for an island escape. The property is located on a quiet c ...

    From $311 per night (USD)

    VRBO

    Details
  • Rose Cottage Oceanfront with Private Dock
    From $486 per night (USD)

    Expedia

    Rose Cottage Oceanfront with Private Dock

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    4

    Oceanfront cottage sleeps 4 people. Close to other Maine attractions. Enjoy your morning coffee on the covered porch loo ...

    From $486 per night (USD)

    Expedia

    Details
  • Waterfront Cottage
    From $309 per night (USD)

    VRBO

    Waterfront Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Waterfront cottage on waters edge recently remodeled and new to the rental market. Cottage is nicely decorated and has e ...

    From $309 per night (USD)

    VRBO

    Details
  • Updated Long Island Maine Cottage
    From $304 per night (USD)

    Expedia

    Updated Long Island Maine Cottage

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Relax on Long Island Maine, With three bedrooms - a queen bed, a full bed, and two twin beds and a daybed on the first ...

    From $304 per night (USD)

    Expedia

    Details
  • Large waterfront family lake house - everything for the lake!
    From $1790 per night (USD)

    VRBO

    Large waterfront family lake house - everything for the lake!

    Bedrooms:
    5
    Bathrooms:
    8
    Sleeps:
    18

    Large lakefront home on Sebago Lake. Ideal for family reunions or large groups! Built for entertaining with a large dini ...

    From $1790 per night (USD)

    VRBO

    Details
  • Lawless Log Cabin - cozy, newly renovated cabin
    From $313 per night (USD)

    VRBO

    Lawless Log Cabin - cozy, newly renovated cabin

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Come stay at our peaceful, newly renovated cabin, located on the outskirts of Brunswick, close to Harpswell ! This log c ...

    From $313 per night (USD)

    VRBO

    Details
  • Spacious Country Home Freeport, Only 5 min to LL Bean!
    From $642 per night (USD)

    VRBO

    Spacious Country Home Freeport, Only 5 min to LL Bean!

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    Fully furnished and recently renovated! Fast WiFi, Smart TVs, spacious backyard with fire pit, back deck with grill & ou ...

    From $642 per night (USD)

    VRBO

    Details
  • Long Lake - Gorgeous Sandy Beach
    From $1145 per night (USD)

    Expedia

    Long Lake - Gorgeous Sandy Beach

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    12

    Welcome to Naples Maine, located 35 miles west of Portland. The home is located on long lake with 100+ of gorgeous sandy ...

    From $1145 per night (USD)

    Expedia

    Details
  • Peaceful House in the Woods near Desert of Maine
    From $1095 per night (USD)

    VRBO

    Peaceful House in the Woods near Desert of Maine

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Relax with family and friends at this peaceful home in the woods. This 4-bedroom, 3000 sq.ft. house has lots of space f ...

    From $1095 per night (USD)

    VRBO

    Details
  • Quiet lakeside Maine Camp with Dock, Boat Mooring and Swim Float.
    From $545 per night (USD)

    VRBO

    Quiet lakeside Maine Camp with Dock, Boat Mooring and Swim Float.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Quiet lakeside Maine camp for fun all year round. Has all the amenities and views for a relaxing getaway. Huge deck ...

    From $545 per night (USD)

    VRBO

    Details
  • Waterledge Cottage - Orrs Island, Maine
    Click For Pricing

    VRBO

    Waterledge Cottage - Orrs Island, Maine

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Waterledge has four bedrooms, two full bathrooms - a fully equipped kitchen, dining area and living room with fireplace. ...

    Click For Pricing

    VRBO

    Details
  • Betty's Place - Cozy ocean front getaway , Relax, Reconnect and Recharge on the Maine Coast
    From $285 per night (USD)

    Expedia

    Betty's Place - Cozy ocean front getaway , Relax, Reconnect and Recharge on the Maine Coast

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    A wonderful place to getaway and relax. Fish, swim, enjoy the views from the deck or the rocky coast. Enjoy walks along ...

    From $285 per night (USD)

    Expedia

    Details
  • Cozy Waterfront Cottage in Harpswell, Maine
    From $299 per night (USD)

    VRBO

    Cozy Waterfront Cottage in Harpswell, Maine

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Located on an ocean cove in Harpswell, Maine this cozy waterfront cottage is the perfect base camp for coastal adventure ...

    From $299 per night (USD)

    VRBO

    Details
  • Green Goddess - Single family - Munjoy Hill
    From $285 per night (USD)

    Expedia

    Green Goddess - Single family - Munjoy Hill

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Our newly restored, single-family home mixes Victorian architecture with vintage furnishings, local artworks, and modern ...

    From $285 per night (USD)

    Expedia

    Details
  • Beautiful and quiet Cottage with 230' Frontage on Gun Point Cove
    From $431 per night (USD)

    VRBO

    Beautiful and quiet Cottage with 230' Frontage on Gun Point Cove

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    The cottage is located on the west side of Gun Point Cove 20 feet above and 50 feet from the water’s edge on a very priv ...

    From $431 per night (USD)

    VRBO

    Details
  • Converted 1830 Church - Newly Renovated For your Stay
    From $578 per night (USD)

    Expedia

    Converted 1830 Church - Newly Renovated For your Stay

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    It's rare to find a place that's both historic, one-of-a-kind and located .5 mi from Both Long & Crystal Lakes in Maine. ...

    From $578 per night (USD)

    Expedia

    Details
  • Adorable, Bright and By the Bay!
    From $705 per night (USD)

    VRBO

    Adorable, Bright and By the Bay!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Adorable, clean, and updated home with 4 spacious bedrooms! Walking distance to Mackworth Island, and a stone’s throw to ...

    From $705 per night (USD)

    VRBO

    Details
  • Lakeside Cabin With Private Sandy Beach
    From $552 per night (USD)

    Expedia

    Lakeside Cabin With Private Sandy Beach

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    5

    Directly on Little Sebago – Unusual Combination of Privacy and Convenience Recently renovated 1920s craftsman-style Ma ...

    From $552 per night (USD)

    Expedia

    Details
  • Waterfront property on long lake Maine
    From $529 per night (USD)

    VRBO

    Waterfront property on long lake Maine

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    This home is located directly on Long Lake in Harrison Maine. View of Shawnee Peak across the lake can be seen from home ...

    From $529 per night (USD)

    VRBO

    Details
  • Cozy Scarborough home 2 miles from beaches
    From $436 per night (USD)

    VRBO

    Cozy Scarborough home 2 miles from beaches

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    This is a 4BR/2 Ba home with a huge backyard and fire pit. It is 2 miles from Scarborough Beach, Ferry Beach and Higgins ...

    From $436 per night (USD)

    VRBO

    Details
  • Charming Waterfront House and Guest House - Long Lake
    From $550 per night (USD)

    VRBO

    Charming Waterfront House and Guest House - Long Lake

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Escape to this stunning waterfront retreat, featuring a beautifully crafted log home and a cozy guest house, both nestle ...

    From $550 per night (USD)

    VRBO

    Details
  • Point Sebago Resort - Spacious 3 Bed House - Saturday to Saturday reservations
    From $447 per night (USD)

    VRBO

    Point Sebago Resort - Spacious 3 Bed House - Saturday to Saturday reservations

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    - Saturday to Saturday rentals ONLY - Only 6 people allowed per day. - Guests must bring their own linens and towels. - ...

    From $447 per night (USD)

    VRBO

    Details
  • A stunning \Green Home\ on the coast of Maine.
    From $1415 per night (USD)

    VRBO

    A stunning \"Green Home\" on the coast of Maine.

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to Longview Farm! This beautiful, elegant home is perfectly positioned to capture all of the natural elements o ...

    From $1415 per night (USD)

    VRBO

    Details
  • Cute 1st Floor 1BR Downtown Brunswick @ Bowdoin
    From $311 per night (USD)

    Expedia

    Cute 1st Floor 1BR Downtown Brunswick @ Bowdoin

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Enjoy this cute little 1st floor 1 BR apartment right in downtwon Brunswick, 1 block from Maine street, less than 5 minu ...

    From $311 per night (USD)

    Expedia

    Details
  • Cozy waterfront private camp; kayaking, fishing, swimming - summer/fall wks open
    From $306 per night (USD)

    VRBO

    Cozy waterfront private camp; kayaking, fishing, swimming - summer/fall wks open

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    NEW Outdoor shower and family room Additional information and photos here: https://www.krainin.com/vacation-rentals/ren ...

    From $306 per night (USD)

    VRBO

    Details
  • Sunny Tree Top 2BR Next to Bowdoin Downtown Brunswick
    From $269 per night (USD)

    Expedia

    Sunny Tree Top 2BR Next to Bowdoin Downtown Brunswick

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    We are located in downtown Brunswick on Page St and Union St, you can walk to Bowdoin campus within 5 minutes and also w ...

    From $269 per night (USD)

    Expedia

    Details
  • Spacious Portland Home: Walk Downtown!
    From $1021 per night (USD)

    VRBO

    Spacious Portland Home: Walk Downtown!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Experience coastal city living like a local with a stay at this 3-bedroom, 2.5-bath vacation rental in Portland, Maine. ...

    From $1021 per night (USD)

    VRBO

    Details
  • Newly Renovated, Classy, and Elegant!
    From $662 per night (USD)

    Expedia

    Newly Renovated, Classy, and Elegant!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Bright and airy, spacious apartment just minutes from downtown! Bright colors, perfect for couples, small families, retr ...

    From $662 per night (USD)

    Expedia

    Details
  • Wards cove Sebago Lake <br>
    From $529 per night (USD)

    VRBO

    Wards cove Sebago Lake <br>

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Clean, Cute, and Cozy, Furnished lake property located in the popular Wards Cove community on Sebago Lake. This property ...

    From $529 per night (USD)

    VRBO

    Details
  • Contemporary Home with Historic Charm
    From $1226 per night (USD)

    Expedia

    Contemporary Home with Historic Charm

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    8

    A recently renovated historic 5-bedroom home, formerly a Post Headquarters building. Enjoy the beautiful front porch, l ...

    From $1226 per night (USD)

    Expedia

    Details
  • New & Modern, Lakeside Home
    From $818 per night (USD)

    VRBO

    New & Modern, Lakeside Home

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Wake up to the sounds of loons and enjoy peaceful meals on the shores of Highland lake. Our home is newly built with all ...

    From $818 per night (USD)

    VRBO

    Details
  • 37(B)Shore Road Raymond Maine - Dragonfly Landing
    From $577 per night (USD)

    Expedia

    37(B)Shore Road Raymond Maine - Dragonfly Landing

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Newly constructed 3 BR home with incredible water views. Lower level provides a full bath and separate laundry room. Bun ...

    From $577 per night (USD)

    Expedia

    Details
  • Falmouth Vacation Rental On Highland Lake!
    From $255 per night (USD)

    VRBO

    Falmouth Vacation Rental On Highland Lake!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Travel to this charming Falmouth vacation rental and spend your days relaxing in and by Highland Lake! This 2-bedroom, 1 ...

    From $255 per night (USD)

    VRBO

    Details
  • Charming 2-Story Cottage with Hot Tub, Near Downtown and Back Cove.
    From $396 per night (USD)

    VRBO

    Charming 2-Story Cottage with Hot Tub, Near Downtown and Back Cove.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Charming private guest cottage at the back of a beautiful property in the fantastic Oakdale neighborhood of Portland. Op ...

    From $396 per night (USD)

    VRBO

    Details
  • Lakefront House
    From $612 per night (USD)

    VRBO

    Lakefront House

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Newly Renovated, lakefront home right on Highland Lake. Over 50 feet of private frontage, along with a private dock/boat ...

    From $612 per night (USD)

    VRBO

    Details
  • A Cozy Cabin on Frye Island
    From $259 per night (USD)

    Expedia

    A Cozy Cabin on Frye Island

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    10

    Our island home is nestled in a wooded area on Frye Island. It is just steps from the golf course! This is a great place ...

    From $259 per night (USD)

    Expedia

    Details
  • Charming pet-friendly waterfront home with beautiful views of Highland Lake!
    From $563 per night (USD)

    VRBO

    Charming pet-friendly waterfront home with beautiful views of Highland Lake!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to your own slice of paradise on Highland Lake in Bridgton! This charming lakefront home features 2 cozy bedroom ...

    From $563 per night (USD)

    VRBO

    Details
  • **SPRING SPECIAL** Charming pet-friendly camp on peaceful Panther Pond!
    From $466 per night (USD)

    Expedia

    **SPRING SPECIAL** Charming pet-friendly camp on peaceful Panther Pond!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    ** NOW OFFERING A SPRING SPECIAL ** Experience the serenity of Panther Pond at this charming 2-bedroom camp, complete wi ...

    From $466 per night (USD)

    Expedia

    Details