Cumberland Area Rentals
From $203 per night (USD)VRBO
Lakefront cabin with shared firepit & access to Sebago Lake
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Wellhouse Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $203 per night (USD)VRBO
From $391 per night (USD)Expedia
Charming Lakefront Cottage with Screened Porch, Firepit, Canoe & WiFi - 1 Dog OK
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Pines Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $391 per night (USD)Expedia
From $362 per night (USD)VRBO
Lakefront Cottage with Screened Deck, Great Lake View, WiFi & Shared Firepit
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Boathouse Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $362 per night (USD)VRBO
From $462 per night (USD)Expedia
Amazing Ocean View Summer Cottage Rental w/ Boat Mooring on Great Diamond Island
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Vacation summer house on Great Diamond Island, with a boat mooring. Our 4 bedroom house sports a grand view of Casco Ba ...
From $462 per night (USD)Expedia
From $646 per night (USD)VRBO
Panoramic Ocean Views, Private Beach, next to Portland.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Enjoy UNOBSTRUCTED OCEAN VIEWS and a PRIVATE BEACH at Shipwreck Cottage (2100 square feet) in Cape Elizabeth, Maine. Bui ...
From $646 per night (USD)VRBO
From $3079 per night (USD)Expedia
5STAR Professionally cleaned rustic lakefront luxury-We’ll take good care of you
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 22
NOW BOOKING 2024-25 SEASONS! PERFECT FOR MICRO WEDDINGS AND INTIMATE CELEBRATIONS! SHILOH VILLA OFFERS PROFESSIONALLY ...
From $3079 per night (USD)Expedia
From $420 per night (USD)VRBO
The Hidden Cove by Bayley Vacation Rentals
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
**This rental is brought to you by Bayley Vacation Rentals!** The Hidden Cove is a stylish, coastal retreat for up to f ...
From $420 per night (USD)VRBO
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The Cove by Bayley Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
**This rental is brought to you by Bayley Vacation Rentals!** The Cove is your ideal vacation home for a relaxing getaw ...
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From $258 per night (USD)VRBO
Bright & Spacious Apartment with Amazing Shower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Spend your vacation, work-trip, or weekend getaway in our lovely, downtown apartment. Apartment 3 is located on the thir ...
From $258 per night (USD)VRBO
From $301 per night (USD)VRBO
Highland Lake - Eastern shore - Mt. Views and Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Highland Lake House boasts a beautiful view down Highland Lake with the White Mountains in the distance. Perched on the ...
From $301 per night (USD)VRBO
From $384 per night (USD)VRBO
Panoramic Water, Island & City Views w/Private Roof Deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We call our beautiful 3rd floor apartment ‘The Crow’s Nest’ not only because of the circular staircase that leads up to ...
From $384 per night (USD)VRBO
From $463 per night (USD)VRBO
Tide Mill Cottage - Luxury Home on Nonesuch River
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This cozy cottage blends vintage aesthetic, luxury décor, and modern convenience. On a private drive next to a tidal ri ...
From $463 per night (USD)VRBO
From $290 per night (USD)VRBO
Private setting Sparkling Lake Sebago. Newly Renovated spring 2025.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Swim in Sebago Lake, one of the cleanest lakes in the US. This property has been owned and used as a private vacation h ...
From $290 per night (USD)VRBO
From $416 per night (USD)VRBO
Enchanted Summer/Fall lakefront Cottage, 20 mins from downtown Portland!
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 5
This is our cherished summer spot. Lake front, beautiful sunsets, 4 bedroom, sleeps 4 adults comfortably, 1 bath, kitche ...
From $416 per night (USD)VRBO
From $194 per night (USD)VRBO
Sand Pond Escape located in Picturesque East Baldwin, ME.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
This seasonal property is located on a very quiet 70 acre pond in the rural Town of East Baldwin. The camp is located ri ...
From $194 per night (USD)VRBO
From $462 per night (USD)VRBO
Charming Pine Point Cottage - 2 Blocks to Ocean!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Treat yourself to a tranquil northeast retreat by staying at this 3-bed, 1.5-bath vacation rental cottage! Backing up to ...
From $462 per night (USD)VRBO
From $277 per night (USD)VRBO
Lakeside Story - Log Cabin, Fire Pit, Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Built in 1963, this classic Maine Log Cabin is a real charmer! You'll love the warmth of the natural wood interior and ...
From $277 per night (USD)VRBO
From $443 per night (USD)Expedia
Centerview cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This is a newly renovated home, with a nice size kitchen with everything you made need for preparing your meals. Childr ...
From $443 per night (USD)Expedia
From $832 per night (USD)VRBO
The Perfect Maine Vacation House
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Beautiful house Located on Sebago Cove. Minutes to Naples Center. Great water view Large private dock Extra Large sun ...
From $832 per night (USD)VRBO
From $246 per night (USD)VRBO
Waterfront 3BR Home on Little Sebago Lake
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
3 bedroom waterfront home located on Little Sebago Lake. This property includes a private dock and waterfront access. ...
From $246 per night (USD)VRBO
From $351 per night (USD)VRBO
Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Located in a quiet neighborhood, this home on Highland Lake is perfect - boasting 3 BD-2 BA, with gorgeous lake views an ...
From $351 per night (USD)VRBO
From $1028 per night (USD)Expedia
Industrial Farmhouse Chic in Portland's Most Desirable Neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Registration #2018-4090. Walk everywhere from the SWEET! This huge, beautifully furnished space w/4 full bedrooms, plu ...
From $1028 per night (USD)Expedia
From $446 per night (USD)VRBO
Spectacular Views & Comforts of Home in Portland s Most Desirable Neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Windows with massive water & city views from the kitchen, dining and living areas, and 360 degrees from your private roo ...
From $446 per night (USD)VRBO
From $595 per night (USD)Expedia
Swim, Kayak, lawn games. Walk to ice cream. Live Theatre , firepit smores!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
64 Main sits on a large corner lot in the Friendly Village of Harrison, Maine. The current owner grew up in Harr ...
From $595 per night (USD)Expedia
From $185 per night (USD)VRBO
Ski chalet located in a quiet neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Perfectly maintained chalet 5 minutes from Shawnee peak and moose pond. Located in a quiet neighborhood just off of 302. ...
From $185 per night (USD)VRBO
From $245 per night (USD)Expedia
2King Bed BR Private Apt Downtown Brunswick
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Completely Newly Renovated 2 Bedroom (KING SIZE BEDS!) Private Apartment Located 1 Minute Walk From Maine Street In Brun ...
From $245 per night (USD)Expedia
From $360 per night (USD)VRBO
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lowell’s Cove Getaway is a beautiful 2 story home which overlooks the sparkling waters of Lowell’s Cove on beautiful Orr ...
From $360 per night (USD)VRBO
From $291 per night (USD)Expedia
Rustic Charm close to Portland
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
My place is a quiet cabin in the woods hidden away just outside of the biggest city in Maine. Peaceful and private. My h ...
From $291 per night (USD)Expedia
From $258 per night (USD)VRBO
Beautiful 1st Floor Apartment & Amazing Shower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Portland, ME, the secret vacation destination that is no longer a secret. Come stay with us and enjoy the ent ...
From $258 per night (USD)VRBO
From $304 per night (USD)VRBO
Cozy Point Sebago Cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Vacationland Maine! Our clean and comfortable 3 BR cottage in Point Sebago is the perfect destination for a f ...
From $304 per night (USD)VRBO
From $428 per night (USD)VRBO
Sebago Lake Retreat with Private Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Looking for an escape from the hustle and bustle? We've got the retreat for you! Come enjoy this spacious and comfortabl ...
From $428 per night (USD)VRBO
From $794 per night (USD)Expedia
A marvelous house on the coast of Maine, just a short trip to Portland.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
For a few weeks each summer, we offer our beautifully designed home to people who are looking for a peaceful retreat sur ...
From $794 per night (USD)Expedia
From $344 per night (USD)VRBO
Vintage Maine & Modern Convenience in Portlands Exclusive East End
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our beautiful 2nd floor apartment is nicknamed ‘The Haven’ because it’s a perfect retreat. After a day of exploring, re ...
From $344 per night (USD)VRBO
From $208 per night (USD)Expedia
Dog-Friendly Lakefront Cottage w/Lake Access, Deck, Gas Grill, A/C
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Loons Nest Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $208 per night (USD)Expedia
From $903 per night (USD)VRBO
Chic 3 BR Retreat- Prime Old Port Spot with parking- Park and walk the town
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Our Greek Revival home, built in 1875, combines beautiful historic details with modern updates to create a cozy and ecle ...
From $903 per night (USD)VRBO
From $496 per night (USD)Expedia
2-room downtown home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A great experience starts with a wonderful location. This 2 Bedroom Apartment Style Residence features a full kitchen, d ...
From $496 per night (USD)Expedia
From $1113 per night (USD)VRBO
Downtown Penthouse Suite - Stunning Harbor Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2023 City of Portland Registration #20182242-ST Private 1850's Old Port Penthouse w/Breathtaking Views and Complimentar ...
From $1113 per night (USD)VRBO
From $243 per night (USD)Expedia
Falmouth Waterfront Carriage House Apt
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Light and airy detached apartment in historic waterfront Town Landing community. 1 bedroom, pull-out sofa, full kitchen ...
From $243 per night (USD)Expedia
From $243 per night (USD)VRBO
Adorable cottage set among tall pines with sandy beach -only .5 mile from town.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Original 1950's 2 BR, 1 bath seasonal cottage (offering heat and A/C), with gleaming wood floors, knotty pine walls, a l ...
From $243 per night (USD)VRBO
From $1569 per night (USD)Expedia
Penthouse Two Master Waterfront Suite with Rooftop
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2023 City of Portland Registration #20185280-ST Stunning penthouse suite with exposed beams, brick accents, and whitewa ...
From $1569 per night (USD)Expedia
From $1306 per night (USD)VRBO
Sea Breeze by Bayley Vacation Rentals
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
**This rental is brought to you by Bayley Vacation Rentals! ** This spacious vacation home offers plenty of space for t ...
From $1306 per night (USD)VRBO
From $1239 per night (USD)Expedia
Waterfront Two Master Suite Penthouse with Rooftop
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2023 City of Portland Registration #20185280-ST Penthouse suite w/modern amenities, exposed beams and brick, poplar wal ...
From $1239 per night (USD)Expedia
From $1511 per night (USD)VRBO
Old Port Penthouse Suite - Amazing Harbor Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2023 City of Portland Registration #20182242-ST Private Old Port Penthouse w/Breathtaking Views + Your Own Cupola. Quie ...
From $1511 per night (USD)VRBO
From $267 per night (USD)VRBO
Welcome To Salty Breezes 2/BD Cottage Located At Tween Waters
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This 2 bedroom cottage is nestled in Pine Pont and just steps to the gorgeous white sandy beach of the Point ! Come and ...
From $267 per night (USD)VRBO
From $613 per night (USD)VRBO
Modern, Luxury Lakefront Home on Crescent Lake, Maine
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Gorgeous lakefront home with modern amenities and authentic Maine charm. The wrap-around deck overlooks the peaceful tra ...
From $613 per night (USD)VRBO
From $356 per night (USD)VRBO
2 Bedroom ranch located in the heart of Pine Point steps to white sandy beach.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
WELCOME TO CHANGING TIDES LOCATED AT TWEEN WATER COTTAGES 2/BD ranch beautiful back yard with deck. Relax on the your de ...
From $356 per night (USD)VRBO
From $124 per night (USD)VRBO
Sebago Lake Cottage on Raymond Cape
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Bunk House (450 ftsq). Built for our children and grand children visits. We added a 8 x 12 Screen Room on the front. ...
From $124 per night (USD)VRBO
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Water front lake house with private beach area.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2 bedroom lakefront property - with 131' of lakefront property. Main floor has 2 bedrooms, bathroom and open ...
Click For PricingExpedia
From $240 per night (USD)VRBO
Newly Renovated Cottage in the Village area of Orr`s Island near the Scenic Cribstone Bridge
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Compass Rose! This newly renovated cottage is situated in the heart of the village area of Orr s Island. Walk ...
From $240 per night (USD)VRBO
From $864 per night (USD)VRBO
Spectacular Sunsets and Sandy Beach on Long Lake!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Gorgeous lakefront home with beautiful private sandy beach area, dock, views of the White Mountains and epic sunsets! En ...
From $864 per night (USD)VRBO
From $222 per night (USD)VRBO
COZY,Newly renovated,West Shores ,short walk to Nasons Beach 🏖🏠
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
After extensive renovation we just posted new photos on line. Cozy cottage sleeping 4,with full kitchen and gorgeous de ...
From $222 per night (USD)VRBO
From $323 per night (USD)Expedia
Beachy Vibes Only !! Updated Oceanfront Gem for 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Oceanfront, One bedroom, newly renovated cottage conveniently located ~ Our newly renovated, one bedroom cottage is situ ...
From $323 per night (USD)Expedia
From $305 per night (USD)VRBO
Frye Island 3br +Loft Home w/Semi-Private Beach, Dock, & Mooring Across Street
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 9
3Br (plus loft), 1 Bath Home With A Large Living Room and Eat In Kitchen The home has a master bedroom with a king size ...
From $305 per night (USD)VRBO
From $567 per night (USD)Expedia
Modern West End 2 Bedroom Apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 10
You will not be disappointed in this Modern 2 bedroom apartment walk-in 1st floor unit able to comfortably accommodate ...
From $567 per night (USD)Expedia
From $713 per night (USD)VRBO
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Guest Reviews: " Loved this place so much we stayed here again and will be back. Can’t say enough great things." Nove ...
From $713 per night (USD)VRBO
From $390 per night (USD)Expedia
Waterfront home on Forest Lake in Gray, Maine. Perfect for 1 or 2 couples.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Hear the call of the loons on this private lake in southern Maine! This recently renovated, open concept, year round hom ...
From $390 per night (USD)Expedia
From $464 per night (USD)VRBO
Ocean front cottage with private beach.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful Maine cottage with extra large porch with rocking chairs and 200 degree views of Casco Bay. Charming 2 bedroom ...
From $464 per night (USD)VRBO
From $463 per night (USD)Expedia
Historical 1st Floor 3BR APT Brunswick @ Bowdoin
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Kick back and relax in this calm, stylish space, we have this beautiful 3 bedroom apartment in downtown Brunswick ready ...
From $463 per night (USD)Expedia
From $680 per night (USD)VRBO
Lake Front Home on Long Lake with Beautiful Views of Mountains!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Come Relax and Recharge at Stone Oak Cottage! A Three Bedroom, Two Bathroom Lakefront Home with Expansive Views Overlook ...
From $680 per night (USD)VRBO
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Modern West End Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Modern top floor studio apartment in a walk up 3 floor building which has been recently fully renovated located in the h ...
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From $681 per night (USD)VRBO
The Globe House on Munjoy Hill - Walk to Breweries
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A fun, modern, cozy apartment sitting on top of Munjoy Hill on North Street. Enjoy some of the best views in the city fa ...
From $681 per night (USD)VRBO
From $697 per night (USD)Expedia
Private cabin on 3Acres with private hot tub! Lake access, Skiing, Snowmobiling!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Stunning newly renovated custom Ward Log home set back on 3 acres. Brand new furnishings, private hot tub, new kitchen ...
From $697 per night (USD)Expedia
From $5594 per night (USD)VRBO
MAINE WATERFRONT + MOUNTAIN COMPOUND • SLEEPS 50!
- Bedrooms:
- 8
- Bathrooms:
- 18
- Sleeps:
- 50
If you are looking for a large waterfront compound to rent- then look no further. This property comfortably sleeps up to ...
From $5594 per night (USD)VRBO
From $361 per night (USD)Expedia
Charming Lakeside Retreat
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Good Cheer Cottage is located in North Bridgton, Maine, sited directly on Long Lake with 200' of lake frontage. This cha ...
From $361 per night (USD)Expedia
From $419 per night (USD)VRBO
Spacious Family Home W/in 3 Min Of The Largest Night Skiing Facility In N E
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Spacious family home offering that "little piece of heaven" to a small or large family. Skiing, beautiful sandy beach ac ...
From $419 per night (USD)VRBO
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Historic Bakery House on Great Diamond Island with Lots of Charm
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The historic Bakery is a freestanding one level 3 bedroom, 2 bath home with lots of charm. Large open floor plan in livi ...
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From $293 per night (USD)VRBO
Clean & cozy updated family resort cottage! Located on quiet dead end street.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Two bedroom, 1 bath resort cottage located on the 7th hole of the well kept Point Sebago Resort golf course. With full ...
From $293 per night (USD)VRBO
From $671 per night (USD)Expedia
Tranquil, serene Sebago Lakefront House on 2 wooded acres - 300ft waterfront!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Your Luxury Lakeside Retreat on Sebago Lake ----------------------------------------------------------------- ...
From $671 per night (USD)Expedia
From $480 per night (USD)VRBO
Lakefront, sunsets, serenity in charming home on Panther Pond
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Friday to Friday rentals only please. Let the sights and sounds of Panther Pond create a vacation rhythm for your stay ...
From $480 per night (USD)VRBO
From $180 per night (USD)Expedia
Sea-clusion by the sea! Cozy cottage within step of the beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Adorable, and recently renovated 1 bed/ 1 bath with new eat-in kitchen, comfortable living room and spacious bedroom. Si ...
From $180 per night (USD)Expedia
From $421 per night (USD)VRBO
Brand New 2 Bedroom Apartment in Heart of West End
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Come and enjoy this fully remodeled 2 bedroom apartment located on the first floor of a historic brownstone row house in ...
From $421 per night (USD)VRBO
From $1334 per night (USD)Expedia
Waterfront, Luxury, Spacious home in Freeport!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Newly furnished and renovated! Set on 3.5 acres tucked away in the woods on Harraseeket Cove & South Freeport Harbor, gr ...
From $1334 per night (USD)Expedia
From $327 per night (USD)VRBO
Private setting for a couple-just two people in the whole house!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Glorious Long Island Maine! Quiet, peaceful, friendly neighbors. Looking for a place to relax and rekindle your romanc ...
From $327 per night (USD)VRBO
From $448 per night (USD)Expedia
Spacious 3 Bedroom, 2 bath, new home, ocean views, close to Maine seafood!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
What sets “Epilogue” apart from other new rentals ?? This elite two- level home is newly constructed, and is situated on ...
From $448 per night (USD)Expedia
From $307 per night (USD)VRBO
Cheerful cottage with All inclusive family fun!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Point Sebago is a family focused destination with endless opportunities for summer fun. Resort Features: - Gorgeous L ...
From $307 per night (USD)VRBO
From $383 per night (USD)Expedia
Sebago Lake Getaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This home has direct access to Big Sebago and the Songo River with a boat launch. Across the street from Sebago State Pa ...
From $383 per night (USD)Expedia
Click For PricingVRBO
Point Sebago 3 BR, 1.5 bath Maine lake cottage near beach on Purple Rd
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The perfect Maine vacation for your family! Our cottage is at the beginning of Purple Road, one of the most desirable lo ...
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From $333 per night (USD)Expedia
Back Cove Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy Downtown Getaway w/ Free WiFi, a Full Kitchen, & Back Cove Bay Views Find yourself right in the heart of Portland a ...
From $333 per night (USD)Expedia
From $577 per night (USD)VRBO
EPIC VIEWS - Pond - Crooked River 14 ACRES - SECLUDED
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 2
Pets Welcome. Hot tub with a EPIC view. Escape to complete privacy on 14 acres of stunning riverfront property on the Cr ...
From $577 per night (USD)VRBO
From $459 per night (USD)VRBO
Dog friendly getaway w/ hot tub, sauna and skiing!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Year round fun at this majestic home located in Knights Hill Association. We are just 1 mile away from Pleasant Mt./Shaw ...
From $459 per night (USD)VRBO
From $374 per night (USD)VRBO
Family Friendly Cottage in Point Sebago Resort on Sebago Lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Family friendly Maine cottage located in the gated Point Sebago Resort Community offers guests complete and convenient a ...
From $374 per night (USD)VRBO
From $300 per night (USD)Expedia
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
“Footnote” is an ideal quintessential 1920’s Maine cottage located on Orr’s Island. presenting stunning ocean views and ...
From $300 per night (USD)Expedia
From $1166 per night (USD)VRBO
Spacious Waterfront Luxury Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Two Ocean-View Master Suites And Two Additional Bedrooms Spectacular oceanfront home with 4 bedrooms, 4 bathrooms, hot ...
From $1166 per night (USD)VRBO
From $594 per night (USD)Expedia
Updated 2 Bedroom with Roof deck and backyard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
You will not be disappointed in this Modern 2 bedroom apartment walk-in 1st floor unit able to comfortably accommodate ...
From $594 per night (USD)Expedia
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Fabulous studio apartment with roof deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Modern top floor studio apartment in a walk up 3 floor building which has been recently fully renovated with direct acce ...
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From $286 per night (USD)VRBO
Family Friendly Four Season Cottage at Point Sebago Beach & Golf Resort
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
2 Bedroom 1 & 1/2 half bathroom Four Season Resort Cottage in Family Friendly gated Point Sebago community. This clean a ...
From $286 per night (USD)VRBO
From $611 per night (USD)VRBO
Executive Falmouth Waterfront Home on the Presumpscot River
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This tastefully renovated single family Waterfront Home is ready for your immediate weekly or monthly stay. Designed to ...
From $611 per night (USD)VRBO
From $289 per night (USD)Expedia
Adorable Portland getaway on the Eastern Promenade
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Lovely third-floor apartment on the East End, just steps from the glorious Eastern Promenade! Cozy and cute, this adora ...
From $289 per night (USD)Expedia
From $676 per night (USD)VRBO
Beautiful house on the Harpswell Peninsula over looking Casco Bay
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 15
Spacious house overlooking casco bay with a wrap around porch with three sets of Patio furniture and a fire pit on the f ...
From $676 per night (USD)VRBO
From $1390 per night (USD)VRBO
SEBAGO LAKE HOME WITH 2 WALK OUT SANDY ASSOC BEACH
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Beautiful lakeside home on winding, quiet, dead-end, paved road in a family friendly neighborhood. Our home has a custom ...
From $1390 per night (USD)VRBO
From $366 per night (USD)VRBO
Beautiful Munjoy Hill Private Oasis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This cozy, freshly remodeled apartment is fully furnished with new appliances, spectacular views of Casco Bay and the is ...
From $366 per night (USD)VRBO
From $280 per night (USD)VRBO
Peaceful Waterfront Apt w/ Deck, 22 Mi to Portland
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Retreat to Maine and explore the Casco Bay Area from this 1-bedroom, 1-bathroom unit just outside of Freeport. Boasting ...
From $280 per night (USD)VRBO
From $1908 per night (USD)VRBO
Designer decorated in an amazing central location w/rooftop deck!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Amazing location in Portland's West End within walking distance of everything due to central location. This building ha ...
From $1908 per night (USD)VRBO
From $313 per night (USD)VRBO
Modern, Spacious Guest Suite Near the Ocean
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our neighborhood is picturesque, woodsy, and charming. Our home is modern, clean, and comfortable. Your private guest su ...
From $313 per night (USD)VRBO
From $1152 per night (USD)VRBO
Historic Officer's Quarters House on Great Diamond Island Near Beaches
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Gorgeous 5 BR, 3.5 BA Historic Officer’s Quarters at Diamond Cove. This island home is situated in a prime location righ ...
From $1152 per night (USD)VRBO
From $218 per night (USD)VRBO
~Maine Glamping at its Finest~
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Robins Nest! Bathed in sunlight, this freshly renovated 784 square foot, 2 bedroom apartment is conveniently ...
From $218 per night (USD)VRBO
From $1213 per night (USD)VRBO
Sunny Waterfront Family Friendly Little Sebago Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Summer 2026 is almost fully reserved! Enjoy our 7th year on VRBO with the last two weeks in August! Camp Cal-a-Mac-ki i ...
From $1213 per night (USD)VRBO
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Waterfront home in Tide Mill Cove
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
A delightful vintage Maine cottage on quiet Tide Mill Cove. Deck overlooks the bay with room for sunbathing, birdwatchi ...
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From $318 per night (USD)VRBO
Views! Cozy, Private 3BR Condo with lake access!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy this Beautiful, Modern 4-season Condo with 3 Bedrooms, 2.5 Baths. Gorgeous Views of Crystal Lake and mountains fro ...
From $318 per night (USD)VRBO
From $363 per night (USD)VRBO
Great Vacation Home, Heart of Lakes/Ski Region in Bridgton Me
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Perfect home to spend your vacation... Whether its spring, summer, fall, or winter, Bridgton has it all; boating, water ...
From $363 per night (USD)VRBO