Cumberland Area Rentals
From $3550 per night (USD)VRBO
40-acre Luxury Beach Front Estate-Ideal for Reunions & Retreats
- Bedrooms:
- 9
- Bathrooms:
- 16
- Sleeps:
- 34
This spectacular, 40-acre estate is located on clear, warm Highland Lake in Bridgton, Maine, halfway between the Atlanti ...
From $3550 per night (USD)VRBO
From $205 per night (USD)VRBO
! Enjoy beautiful Orr's Island. .
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Rose House is a quaint New England Cape located on the southerly end of Orr's Island in the Town of Harpswell, Maine ...
From $205 per night (USD)VRBO
From $541 per night (USD)VRBO
Charming Great Diamond Island Cottage w/Waterviews - Bus. Lic.# STHR-003849-2021
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This quintessential Maine cottage on Great Diamond Island is as charming as it gets. You get the best of all worlds here ...
From $541 per night (USD)VRBO
From $397 per night (USD)VRBO
3 Bedroom Cozy Vacation Home on Beautiful Panther Pond in Raymond, Maine
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Nestled in the heart of Raymond, this charming 3-bedroom vacation home offers the perfect escape for your next getaway. ...
From $397 per night (USD)VRBO
From $519 per night (USD)VRBO
Spacious Waterfront Estate & Cabins W/ Porch, Fireplace, Kayaks & Free WiFi
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 15
Saganook Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $519 per night (USD)VRBO
Click For PricingExpedia
Paradise Point - where memories are made!
- Bedrooms:
- 0
- Bathrooms:
- 2
- Sleeps:
- 8
If you are looking for a clean, picturesque, cozy, fun but relaxing, vacation, look no further! You will enjoy making me ...
Click For PricingExpedia
From $249 per night (USD)VRBO
Quaint Maine Farmhouse near Portland
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
One hundred year old restored Maine farmhouse located in Gorham, Maine (15-20 minutes from Portland). Beautiful propert ...
From $249 per night (USD)VRBO
From $474 per night (USD)VRBO
Enjoy fabulous four season fun on Hancock Pond
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our spacious and welcoming home on Hancock Pond is a delightful spot for four season getaways. Enjoy summertime boating ...
From $474 per night (USD)VRBO
From $353 per night (USD)VRBO
Luxury, Spacious, 4 BR Chalet, 1 Minute walk to beach, lakefront, pools, skiing
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Luxury spaceous, modern and open design house in beautiful, private, wooded area within exclusive Knight's Hill communi ...
From $353 per night (USD)VRBO
From $189 per night (USD)VRBO
Sea Smoke Cottage Adorable Beachy Cottage Perfect Getaway For Two
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
WELCOME TO Sea Smoke Cottage located at Tween Water Cottages this adorable cottage is perfect for a getaway to the beach ...
From $189 per night (USD)VRBO
From $403 per night (USD)VRBO
City Amenities, Casco Bay Sunrises and Natural Beauty
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Martin's Point high end home. This is a unique space that includes a beautiful view of Casco Bay with a waterfront park ...
From $403 per night (USD)VRBO
From $646 per night (USD)Expedia
The Monument Garden SWEET!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
We call this first floor of our modified 1890`s Victorian the `Garden SWEET` because it`s a huge suite that is so attrac ...
From $646 per night (USD)Expedia
From $357 per night (USD)VRBO
Classic turn of the century Maine cottage
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Come experience Maine island living in this beautifully preserved turn of the century home. Libby Cottage is located in ...
From $357 per night (USD)VRBO
From $863 per night (USD)Expedia
Beautiful, spacious lake home w/mooring & swim raft. Walk to shops & restaurants
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Hi there, ACCEPTING RESERVATIONS NOW for Summer 2025--take a good look at our lake house because we have something for ...
From $863 per night (USD)Expedia
From $166 per night (USD)VRBO
Highland Cottage: Nestled Between the Atlantic Coast and the White Mountains
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Highland Cottage Nestled Between the Atlantic Ocean and White Mountains. Still, WiFi Internet Service is available at Hi ...
From $166 per night (USD)VRBO
From $533 per night (USD)VRBO
Perfect Year-Round Getaway Location For Those Who Enjoy The Outdoors.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
With unspoiled forests and waterways, the Greater Bridgton Lakes Region is a year-round outdoor playground and sportsman ...
From $533 per night (USD)VRBO
From $884 per night (USD)VRBO
Lovely, Sprawling Log Home On Pretty, Pristine Trickey Pond.
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
Originally a modest log cabin, this home has been expanded to a generous 6 bedroom home with lake views from all living ...
From $884 per night (USD)VRBO
From $319 per night (USD)VRBO
Sebago Point - 26 Purple Road
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Resort cottage with sun room and two large decks. Our cottage contains a master bedroom with a queen sized bed. A second ...
From $319 per night (USD)VRBO
From $981 per night (USD)VRBO
Sebago Lake Home with Sandy Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
New Sebago Lake home with a great lawn to a wonderful sandy beach. First floor master suite with master bathroom. Open c ...
From $981 per night (USD)VRBO
From $206 per night (USD)VRBO
Waterfront home on scenic cove.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
General Description (Please note: Our rental period for 2024 is May 31 to August 4. However, we have tentatively bloc ...
From $206 per night (USD)VRBO
From $1737 per night (USD)VRBO
Stunning Entire Three Units Apts (USM AREA)
- Bedrooms:
- 6
- Bathrooms:
- 9
- Sleeps:
- 22
This 4200 sq.ft newly renovated entire three units apartments are located in a quiet Oakdale neighborhood, short walk to ...
From $1737 per night (USD)VRBO
From $663 per night (USD)Expedia
Spacious Sebago Lake waterfront house with game room, hot tub, and covered deck.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Shimmering Cove makes a perfect year round getaway! Summer fun in the lake, amazing fall colors and lots of opportuniti ...
From $663 per night (USD)Expedia
From $453 per night (USD)VRBO
Completely remodeled 2 bedroom apartment in Portland's West End
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come stay in this brand new 2 bedroom 1.5 bath apartment in the heart of Portland's West End. Located just steps away f ...
From $453 per night (USD)VRBO
From $269 per night (USD)VRBO
4 bedroom home in Bridgton, Maine. 3 min to Pleasant Mtn. 2 min to Moose Pond.
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
4 bedroom, 1 1/2 baths with large open concept living room and dining area in Bridgton, Maine. Great for family getaways ...
From $269 per night (USD)VRBO
From $672 per night (USD)VRBO
Sebago Lake Luxurious House on Raymond Cape-Great for Families
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3 Plus Bed, 2 Baths, Sleeps 8. Waterfront, Dock, Multiple Decks, Waterfront Deck, Swim Float, Gradual Entry Sandy Beach. ...
From $672 per night (USD)VRBO
From $277 per night (USD)VRBO
The Nugget- Perfect 1 bedroom cottage. Across from Mackerel Cove, Johnson Field.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Nugget is a fully renovated 1 bedroom cottage with bathroom, kitchen and washer/dryer. Perfect for 2 people. Views o ...
From $277 per night (USD)VRBO
From $624 per night (USD)VRBO
Sebago Lake Waterfront Rental on Frye Island
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 13
Outstanding Waterfront Property on the shores of Frye Island, Maine in pristine Sebago Lake. Main cottage sleeps 9 with ...
From $624 per night (USD)VRBO
From $341 per night (USD)Expedia
Cozy, Elegant and Bright 2 bed in the East End
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy and elegant 2 bed apartment in Portland’s East End. Whether you want to walk into town for dinner or sample the loc ...
From $341 per night (USD)Expedia
From $178 per night (USD)VRBO
Old Farm Cottage - Harpswell, Maine
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
"Old Farm Cottage" located in North Harpswell just 10 minutes from Bowdoin College and downtown Brunswick. The cottage ...
From $178 per night (USD)VRBO
From $717 per night (USD)VRBO
Private Lake Front Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Great veiws of Mount Washington and Shawnee Peak! Quiet lake front home with 3 floors, 3 bedrooms, 2 bathrooms, den, la ...
From $717 per night (USD)VRBO
From $494 per night (USD)VRBO
Architectural Lighthouse
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 10
Pineplace Lights is a uniquely designed elegant architectural lighthouse designed by architect Mark Ruhle. It was his v ...
From $494 per night (USD)VRBO
From $615 per night (USD)VRBO
NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Panoramic Oceanfront and island view direct sunrise. Nature preserves and hiking trail next door and nearby. Away from ...
From $615 per night (USD)VRBO
From $522 per night (USD)VRBO
Charming, Spacious Remodeled Pine Point Beach House Steps to the Sandy Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Bright, spacious, and tastefully decorated, featuring stunning hardwood and tile floors throughout. With 3 large bedroom ...
From $522 per night (USD)VRBO
From $190 per night (USD)VRBO
Long Beach Sebago Lake Cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Quaint cottage a 90 second walk away from sandy long beach on the quiet side of Lake Sebago. Four bed rooms, living room ...
From $190 per night (USD)VRBO
From $1343 per night (USD)VRBO
Private Oceanfront Island Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 20
Beautiful private oceanfront property on Long Island, ME! This property has 3 buildings: the main house, the stand alo ...
From $1343 per night (USD)VRBO
From $418 per night (USD)Expedia
Get away at Crystal Lake
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Escape the lake region crowds on the calm water of Crystal Lake. Watch the sunset from the private waterfront/dock, kay ...
From $418 per night (USD)Expedia
From $434 per night (USD)VRBO
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Brand New two bedroom apartment located right on downtown Brunswick at Noble street, 1 minute walk away from Maine stree ...
From $434 per night (USD)VRBO
From $394 per night (USD)VRBO
Amazing Vacation Island House - Great Location!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy seclusion from the rest of the planet. Enjoy life the way it use to be. This immaculate, updated, non-smoking, Cap ...
From $394 per night (USD)VRBO
From $713 per night (USD)VRBO
Knotty Nauti by Bayley Vacation Rentals
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
**This rental is brought to you by Bayley Vacation Rentals!** At Knotty Nauti, the cozy beach cottage, natural wood and ...
From $713 per night (USD)VRBO
From $555 per night (USD)Expedia
The Otis House by Bayley Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
**This rental is brought to you by Bayley Vacation Rentals! ** Step into the Otis House and be charmed by the elegant f ...
From $555 per night (USD)Expedia
From $270 per night (USD)VRBO
Romantic getaway for 2\n\nPEAK fall foliage!!!\n\n\n\n\n\n\n\n
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Small camp on Trickeypond only 1.3 miles to the center of Naples ...
From $270 per night (USD)VRBO
From $214 per night (USD)Expedia
Midcentury Modern 2 Bedroom Village Oasis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
1st Floor. Updated and fully furnished 2 bedroom, living room, kitchen one bath apartment in the heart of Yarmouth Villa ...
From $214 per night (USD)Expedia
From $439 per night (USD)VRBO
Classic Maine Cottage on Water's Edge
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
We purchased our dream property in May 2019 and have been hard at work making it perfect for our rentersj. We just start ...
From $439 per night (USD)VRBO
From $548 per night (USD)VRBO
Newly Renovated 4-BR House in Quiet Neighborhood Near Beaches & Portland
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 7
Welcome to Whispering Pines Hideaway, a serene sanctuary nestled in a charming residential area. Our inviting, newly ren ...
From $548 per night (USD)VRBO
From $477 per night (USD)VRBO
Dream Lakefront Modern Cabin
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Everything for your perfect Maine getaway on Moose Pond during any season! Our immaculate lakefront cabin is the perfect ...
From $477 per night (USD)VRBO
From $437 per night (USD)Expedia
Back yard paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Wake up to the sounds of chickadees (Maine’s state bird), you sip your coffee in this furnished family home. With except ...
From $437 per night (USD)Expedia
From $1030 per night (USD)VRBO
Nicest Waterfront in Maine w/ Private Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Beautiful, classic, recently built luxury home located at the center of Mackerel Cove, known as the most photographed wa ...
From $1030 per night (USD)VRBO
From $291 per night (USD)Expedia
Five miles from the beach, newly remodeled home with lots of privacy.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This handicap accessible private home is 5 miles from the beach, 12 miles from downtown Portland, and 9 miles from Portl ...
From $291 per night (USD)Expedia
From $616 per night (USD)VRBO
Long Lake Maine - Create Your Family Vacation Memories Here at Flatrock!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful home directly on Long Lake east shore (incredible sunsets) with a private beach area, private dock and over 30 ...
From $616 per night (USD)VRBO
From $236 per night (USD)Expedia
Charming Retro 3BR+Office Home in Town
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful three bedroom plus a small bonus private office room single family house in town Brunswick. Within 5 minutes d ...
From $236 per night (USD)Expedia
From $125 per night (USD)VRBO
Back Cove Charmer Close to Everything
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunny Fresh Newly Renovated 1 Bedroom Apt w/Queen (and separate "full" size pullout couch in living room). Well appointe ...
From $125 per night (USD)VRBO
From $227 per night (USD)Expedia
New South Portland Cottage, 10 Minutes to Downtown, Great for Entertaining
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
South Portland Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $227 per night (USD)Expedia
From $491 per night (USD)VRBO
Newly Renovated 2nd Floor Apt near USM
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This gorgeous apartment features 3 bedrooms plus a bonus room off master bedroom, one with king size bed, two queen size ...
From $491 per night (USD)VRBO
From $620 per night (USD)Expedia
Classic New England Waterfront Cottage
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 12
Our beach house is a classic, turn of the century beach front cottage nestled on Pine Point Beach. It’s been in our fami ...
From $620 per night (USD)Expedia
From $580 per night (USD)VRBO
+Sunny+ Design Inspired, Modern, Lakeside, Historic Beauty!!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Excellent, Sunny, Fresh, Lakeside Beauty! Located on Misty cove with direct access to Long Lake via the cove. Once a his ...
From $580 per night (USD)VRBO
From $314 per night (USD)Expedia
Chic One Bedroom Apartment In Portland's Arts District
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This beautifully furnished one bedroom apartment for 2 is on the first floor of a historic 1890 building. Completely re ...
From $314 per night (USD)Expedia
From $405 per night (USD)VRBO
Waterfront Camp on Sebago Lake!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Waterfront cabin on Sebago Lake! Interior remodel was completed April 2023. The camp features a fully stocked kitchen, ...
From $405 per night (USD)VRBO
From $699 per night (USD)Expedia
TWO Waterfront Camps on Sebago Lake
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Newly remodeled waterfront cabins on Sebago Lake available for weekly rentals! Updates include new kitchen in the green ...
From $699 per night (USD)Expedia
From $203 per night (USD)VRBO
Water View Beach Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Street View and Google are not updated, this home and neighboring homes have been recently renovated, fully furnished ho ...
From $203 per night (USD)VRBO
From $245 per night (USD)Expedia
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy spacious accommodations and two floor living with 1200 square feet of living space. Walk to the local markets and ...
From $245 per night (USD)Expedia
From $531 per night (USD)VRBO
Private Beach Sunset Views Getaway on Sebago Lake
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Newly renovated lake front cabin / house with private beach and private dock, two person kayak, single person kayak and ...
From $531 per night (USD)VRBO
From $567 per night (USD)Expedia
Njoy Luxury - MUST experience this exclusive and stunning lakeview home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 15
Welcome to Luxury! Nested in Western Maine Lakes Region area, this magnificent 4500 sqft home is as comfortable as it is ...
From $567 per night (USD)Expedia
From $209 per night (USD)VRBO
The Nest ~ Quiet location close to shops, dining and Downtown Freeport.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Nest is a newly renovated apartment with attention to detail showing exposed beams, vaulted ceiling, and hardwood th ...
From $209 per night (USD)VRBO
From $311 per night (USD)VRBO
2025 rentals filled ⁷Tranquil Sandy beach, launch, dock, lawn games and firepit.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Cabin has been 7/8 completely rebuilt from inground up. Large Whole House water filter with lowest Micron and filter i ...
From $311 per night (USD)VRBO
From $407 per night (USD)VRBO
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cumberland Charm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $407 per night (USD)VRBO
From $258 per night (USD)Expedia
Cozy Year-round House right outside Portland Maine on Highland Lake.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Just finished renovations!!!!! The perfect year round get-a-way. Sit, relax and enjoy the beautiful view of the lake an ...
From $258 per night (USD)Expedia
From $458 per night (USD)VRBO
2 Bedroom Apartment on Top Floor in Portland's West End
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Come stay in the heart of Portland's West End. Located just steps away from some of the best restaurants, cafes and bars ...
From $458 per night (USD)VRBO
From $463 per night (USD)VRBO
Well Appointed House on a Secluded Sandy Beach Cove - West Shore - Sebago Lake
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This very spacious, centrally heated three bedroom house is 60 feet from the lake with lawn opening onto a secluded sand ...
From $463 per night (USD)VRBO
From $222 per night (USD)VRBO
Charming cottage on the water, beautiful lawn, dog friendly, ideal for summer!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Wigwam is a charming camp that will take you back in time. With 2 bedrooms, it is perfect for families or friends. T ...
From $222 per night (USD)VRBO
From $420 per night (USD)Expedia
Lakefront Paradise on Northern Tip of Long Lake
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Quiet, Private house with great lakefront, modern style and one of the premier locations on the lake Newly renovated mai ...
From $420 per night (USD)Expedia
From $454 per night (USD)VRBO
Charming Cabin on Beautiful Big Sebago Lake
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Come enjoy your vacation at Sebago Lake in this charming cabin set back in the woods. Nestled in the entrance of Kettle ...
From $454 per night (USD)VRBO
From $506 per night (USD)Expedia
Spectacular 3rd Floor Apt Near Downtown Portland
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This 1,400 sq.ft newly renovated third floor apartment is located in a quiet Oakdale neighborhood, short walk to Back Co ...
From $506 per night (USD)Expedia
From $334 per night (USD)VRBO
Sunny, cheerful, 3 bedroom family cottage on Sebago Cove. Sleeps 8!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This family-oriented, sunny, 3 bedroom cottage is situated on a quiet road along Sebago Cove. A fun, outdoor family spac ...
From $334 per night (USD)VRBO
From $556 per night (USD)VRBO
Brand New Lake Home with Great Sandy beach on Sebago’s Basin
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 11
Brand new (completely rebuilt in 2023, completion April 2024) 3 bedroom (including kids bunk room) and 3 bath w/ large k ...
From $556 per night (USD)VRBO
From $434 per night (USD)VRBO
Morningside. Waterfront home with seasonal dock and float, Pet friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located on Gun Point Road in picturesque Harpswell, set back from the bustle of summer traffic, "Morningside" awaits yo ...
From $434 per night (USD)VRBO
From $400 per night (USD)VRBO
Recharge at the Red Fox Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to the Red Fox Retreat! Our home is in the beloved Knights Hill Association neighborhood of idyllic Bridgton, Ma ...
From $400 per night (USD)VRBO
From $765 per night (USD)VRBO
Highland Dream: All Season Beauty! 5BR/2BA, Lakefront, Stay and Play. 4 Season
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
If you’re looking for the perfect private getaway you found it here. Highland Dream is a 5 bedroom waterfront home featu ...
From $765 per night (USD)VRBO
From $233 per night (USD)VRBO
Juniper Cottage on Bailey Island – A Peaceful, Relaxing, CLEAN Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Juniper Cottage on Bailey Island is ready to be your oasis in the coming summer months. This charming shake shingle summ ...
From $233 per night (USD)VRBO
From $394 per night (USD)VRBO
Simonson Lakeside on Highland Lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is the first level of our home on Highland Lake. The house has been in my family since 1954. In 1983, the first ...
From $394 per night (USD)VRBO
From $182 per night (USD)VRBO
Family & Pet Friendly Log House On Casco Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful waterfront property on Orr's Island. Walking distance to famous Cribstone Bridge, Cook's Lobster House, The Sa ...
From $182 per night (USD)VRBO
From $379 per night (USD)VRBO
Point Sebago Resort, 30 Purple Road, Walking distance to beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy an amazing family vacation at a lakeside cottage. Point Sebago Resort is a great family vacation spot with endles ...
From $379 per night (USD)VRBO
From $271 per night (USD)VRBO
Perfect spot for a couples get-away, ocean views from the balcony and sitting area
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Goldsmith Apartment! This studio garage apartment is located right on Harpswell Sound. It offers beautiful s ...
From $271 per night (USD)VRBO
Click For PricingVRBO
Woodhaven Hideaway on Woods Pond..
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Woodhaven Hideaway, located directly across from the beautiful Woods Pond Beach. The beach is known for its a ...
Click For PricingVRBO
From $1074 per night (USD)Expedia
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to your home away from home in Portland, Maine! This charming six-bedroom, three-bath Craftsman-style house offe ...
From $1074 per night (USD)Expedia
From $354 per night (USD)VRBO
Lakefront Cottage - private dock, large decks, large fire pit
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Your family and friends will love this lakefront retreat on the shores of Watchic Lake! Enjoy lazy afternoons on the wat ...
From $354 per night (USD)VRBO
From $725 per night (USD)Expedia
Sunrise Catcher with a Panoramic View!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy all that Maine has to offer in this 3900+sq ft contemporary home located on 180 ft of ocean front property. This ...
From $725 per night (USD)Expedia
From $234 per night (USD)VRBO
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy spacious accommodations and two floor living with 1200 square feet of living space. Amenities Include a well equip ...
From $234 per night (USD)VRBO
From $387 per night (USD)Expedia
Njoy Charm - Gorgeous Family and Pet Friendly Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
You will fall in love with this charming log sided chalet style home! Warm pine interior, large open concept living, won ...
From $387 per night (USD)Expedia
From $335 per night (USD)VRBO
Victorian architecture dipped in refined modernity. May-June-July special!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Aged and sturdy, yet eminently modernized, this two bedroom boutique loft is perfectly situated in the heart of Portland ...
From $335 per night (USD)VRBO
From $404 per night (USD)Expedia
The perfect refinement of vintage seduction. May-June-July special!!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This recently remodeled open-plan living area is spacious in size and flooded with natural daylight that bounces off the ...
From $404 per night (USD)Expedia
From $164 per night (USD)VRBO
Ultra cool new modern flat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
“This is the best basement apartment I have seen, wow!" This historic unique one of a kind 1600sqft boutique basement a ...
From $164 per night (USD)VRBO
From $1000 per night (USD)Expedia
Stylish & Spacious Townhouse w/Garden, Family-friendly, walk to downtown!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Our light-filled three story home is perched on a lovely, quiet corner of the historic West End residential neighborhood ...
From $1000 per night (USD)Expedia
From $565 per night (USD)VRBO
Peaks Island Maine Seaside Cottage: hot tub/roof decks/4 season
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Summer 7 day minimm (otherwise 2 night min except 3-5 nights for holidays) Gather with loved ones at Selkies' Rest: Coz ...
From $565 per night (USD)VRBO
From $349 per night (USD)VRBO
July 4 week open!! Walk to beach! BOOK NOW1
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
NOTE: Point Sebago has instituted a new rental registration fee of $10 per guest per night. This charge will be paid vi ...
From $349 per night (USD)VRBO
From $370 per night (USD)VRBO
Brand New 1 Bedroom Apartment in Portland
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Come and enjoy this fully remodeled 1 bedroom apartment located on the 2nd floor of a historic brownstone row house in P ...
From $370 per night (USD)VRBO
From $423 per night (USD)VRBO
\"THE CALLING LOON\". A sunny 5 bedroom, 2 bath house on Crystal Lake! Sleeps 9.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
THE CALLING LOON on Crystal Lake in Harrison, Maine. Grill must be kept away from the house, and cannot be moved up ont ...
From $423 per night (USD)VRBO
From $193 per night (USD)VRBO
4 bdrm, 2 bath, cozy Chalet with Long Lake access in Harrison, Maine
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
4 bedroom winterized Cabin with deck that sleeps 9 comfortably with a shared 400 foot shoreline on Long Lake in Harrison ...
From $193 per night (USD)VRBO
From $157 per night (USD)VRBO
Adorable cottage with million dollar view and short walk to stunning beach.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
If you grew up experiencing summers on the Maine coast, our cottage will bring you back in time. Our cottage offers a m ...
From $157 per night (USD)VRBO
From $383 per night (USD)VRBO
Nature with in-town living that feels a world away. May-June-July special!!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Immerse in the tranquility of nature while allowing your comfort be seduced by this architect's successful attempt at a ...
From $383 per night (USD)VRBO
From $741 per night (USD)VRBO
Classic oceanfront cottage and cabin on stunning 8 acres with sunset water views
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Beautiful family cottage with additional separate cabin adjacent to a fishing harbor on Casco Bay. Stunning views and na ...
From $741 per night (USD)VRBO