Cumberland Area Rentals
From $228 per night (USD)VRBO
Sebago Lake studio-style condo with enclosed sunroom and sunset views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Furnished Lakefront Condo Easy Access to St. Josephs College, Maine Medical, Mercy, and More Recharge between shifts in ...
From $228 per night (USD)VRBO
From $123 per night (USD)VRBO
2 QUEEN BEDS. HDTV 2 QUEEN BEDS. HDTV
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $123 per night (USD)VRBO
From $504 per night (USD)VRBO
Ski & Lake Retreat With Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
The Pleasant Mountain Retreat – We don't just host - we make your stay the best part of your getaway Escape to this ser ...
From $504 per night (USD)VRBO
From $567 per night (USD)Expedia
'Valhalla': Family Home on Frye Island w/ Golf!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Group BBQs | Steps to Community Pool Welcome to ‘Valhalla,’ a newly built 3-bedroom, 2-bath vacation rental perfect for ...
From $567 per night (USD)Expedia
From $450 per night (USD)VRBO
Round House/GolfCart/BeachAccess/FamilyFriendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Escape to Maine’s beautiful Lakes Region at Round House — a peaceful lake retreat tucked away at the end of a quiet road ...
From $450 per night (USD)VRBO
From $3389 per night (USD)Expedia
Cabin Retreat for Nature and City Exploration near Sebago Lake State Park, ME
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 18
A remarkable retreat to the Sebago Lake region awaits when you book this one-of-a-kind house in Casco! Situated less tha ...
From $3389 per night (USD)Expedia
From $142 per night (USD)VRBO
Pet-Friendly Glamping Stay with Beach Views in Naples, Maine
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Wake up to breathtaking views of the beach and the sparkling waters of Trickey Pond from this cozy deluxe cabin. Blendin ...
From $142 per night (USD)VRBO
From $142 per night (USD)Expedia
Pet-Friendly Glamping Vacations at this Waterfront Safari Tent in Naples, Maine
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Beautiful 10'x12' waterfront glamping tent with views of the sunset. Full-size bed, and full-size pull-out couch availab ...
From $142 per night (USD)Expedia
From $592 per night (USD)VRBO
Atlantic View - on the eastern cliffs of Bailey Island!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Entire Oceanfront Bailey Island Home: Views of Cliffs, Cove & Casco Bay Have the Entire Place to Yourself Escape to the ...
From $592 per night (USD)VRBO
From $430 per night (USD)Expedia
Cozy home - 5 minutes to private beach access on Moose Pond, 5 minutes to ski
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the perfect getaway in Bridgton, Maine! This cozy Alpine Village home sits just a short walk to the Alpine V ...
From $430 per night (USD)Expedia
From $223 per night (USD)VRBO
Cozy Guest Suite with Fireplace
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked just outside the heart of Freeport, this charming coastal loft suite is the perfect blend of cozy retreat and Mai ...
From $223 per night (USD)VRBO
From $219 per night (USD)Expedia
Beautiful Restored Historic Property
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to 87 on Pine, a one-of-a-kind townhouse in Portland’s historic West End. Built in 1865 this home still shows of ...
From $219 per night (USD)Expedia
From $390 per night (USD)VRBO
SEBAGO LAKE SHOREFRONT. MONDAY - FRIDAY RENTAL. SECLUDED BUT CLOSE TO DOWNTOWN.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
OCCUPANCY LIMIT 6 - NO PETS - SEBAGO LAKE SHOREFRONT. MONDAY - FRIDAY RENTAL. 11AM check in. 1PM check out. This Gues ...
From $390 per night (USD)VRBO
From $342 per night (USD)Expedia
•Peaceful Private Freeport 2 BR Home on the Ocean•
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the perfect Maine coastal escape — where quiet beach days meet the charm of downtown Freeport. Just steps fro ...
From $342 per night (USD)Expedia
From $2171 per night (USD)VRBO
Long Lake Luxury - Lakefront, Hot Tub, Home Theater, Private Dock, Sleeps 15
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to Long Lake Luxury! Set in a quiet cove on Long Lake in Harrison, ME, this 4,400 sqft stunner is one of a kind. ...
From $2171 per night (USD)VRBO
From $758 per night (USD)Expedia
New Listing! Peaceful Oceanfront Home with Dock, Decks, and Shore Access in Cundy’s Harbor
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
New Listing for 2026 ! Welcome to Bird’s Harbor Landing, a true coastal escape tucked at the end of a quiet road in the ...
From $758 per night (USD)Expedia
From $184 per night (USD)VRBO
Mast Landing Mini Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Come enjoy the 32nd Annual Freeport Sparkle Celebration! Starting December 5th with the Sparkle Parade down Main Street, ...
From $184 per night (USD)VRBO
From $2803 per night (USD)VRBO
Pleasant Moose Hygge | Luxury Lakefront Retreat
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Luxury lakefront retreat on Moose Pond with 200ft of private waterfront on 1.87 acres. Features include a new dock, sand ...
From $2803 per night (USD)VRBO
From $606 per night (USD)VRBO
Rare West End Home • Walk to Old Port, Harbor View
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This rare 1875 single-family home in Portland’s West End offers the perfect blend of historic charm and modern comfort. ...
From $606 per night (USD)VRBO
From $335 per night (USD)Expedia
Pine Point Beach private, quaint, charming studio.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This delightful studio is a quaint private space with all the amenities of home. Private entrance and parking available ...
From $335 per night (USD)Expedia
From $1036 per night (USD)VRBO
Waterfront home has 3-bedroom 3 bath
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
OCCUPANCY LIMIT 9 - Waterfront home has 3-bedroom 3 bath. This stunning waterfront property offers the perfect blend of ...
From $1036 per night (USD)VRBO
From $685 per night (USD)Expedia
Waterfront 4 Bedroom 2 Bath on Barker Pond in Sebago
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
OCCUPANCY LIMIT 8 - Waterfront 4 Bedroom 2 Bath on Barker Pond in Sebago. This property offers great outside area with a ...
From $685 per night (USD)Expedia
From $489 per night (USD)VRBO
Gorgeous ocean views with private beach access.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Blue House! Tucked away on one of Bailey Island's premier locations overlooking Casco Bay, this gorgeous ...
From $489 per night (USD)VRBO
From $545 per night (USD)VRBO
Peaks & Pines | 5 Min to Ski Resort, HotTub, Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Peaks & Pines is a brand-new, fully secluded mountain cabin just 5 minutes from Pleasant Mountain. Enjoy incredible fore ...
From $545 per night (USD)VRBO
From $329 per night (USD)VRBO
The Coastal Connection
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to The Coastal Connection, a bright and comfortable two-bedroom apartment in the heart of South Portland. This u ...
From $329 per night (USD)VRBO
From $401 per night (USD)VRBO
Sebago Lake Escape - sandy beach/swim/ski/hike
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your Four-season Sebago Lake escape! Discover our recently updated 4-bedroom, 2-bath lake house, elegantly fu ...
From $401 per night (USD)VRBO
From $253 per night (USD)VRBO
Pet-Friendly Stay | 2 Units | Close to Victoria Mansion & Lighthouse!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $253 per night (USD)VRBO
From $253 per night (USD)VRBO
Pet-Friendly Stay | 2 Units | Close to Victoria Mansion & Lighthouse!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $253 per night (USD)VRBO
From $253 per night (USD)VRBO
2 Family Ready Rooms | Pet-Friendly Stay, Walking Distance to Museum of Art
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $253 per night (USD)VRBO
From $505 per night (USD)VRBO
4 Cozy Units | Downtown Stay, Waterfront & Near Vibrant Old Port District
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $505 per night (USD)VRBO
From $208 per night (USD)VRBO
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to HomeAwhile, where our thoughtfully designed suites are tailored to adapt to your lifestyle, offering plush ki ...
From $208 per night (USD)VRBO
From $564 per night (USD)VRBO
The Cove Retreat is the perfect spot to walk the family or dog down to Stover's Point Beach.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to The Cove Retreat! If you're dreaming of an easy, relaxing coastal Maine getaway within walking distance to S ...
From $564 per night (USD)VRBO
From $1169 per night (USD)VRBO
Waterfront 4 bedroom and 3 bath home on the Raymond Cape
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 16
OCCUPANCY LIMIT 16 - Waterfront 4 bedroom and 3 bath home on the Raymond Cape. The home also has 2 basement bunk areas ...
From $1169 per night (USD)VRBO
From $253 per night (USD)VRBO
2 Family Ready Rooms | Pet-Friendly Stay, Walking Distance to Museum of Art
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $253 per night (USD)VRBO
From $748 per night (USD)VRBO
Windham Lakefront: Fire Pit and Modern Comforts
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Escape to this tranquil 3-bedroom, 2-bathroom retreat in the heart of Windham, ME. Built in 2019, this bright ...
From $748 per night (USD)VRBO
From $369 per night (USD)Expedia
2 BEDROOM 1 BATH. SHORT WALK TO A LARGE SANDY BEACH.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
OCCUPANCY LIMIT 5 - 2-bedroom 1 bath cottage just a short walk away from an association beach. Two bedrooms, 1 with a q ...
From $369 per night (USD)Expedia
From $2857 per night (USD)VRBO
Rare 4-Home Compound on Sebago Lake Peninsula With 360° Views
- Bedrooms:
- 7
- Bathrooms:
- 9
- Sleeps:
- 22
Experience a truly one-of-a-kind Sebago Lake retreat designed for large families and multi-generational gatherings of up ...
From $2857 per night (USD)VRBO
From $706 per night (USD)Expedia
A rambling farmhouse, now a modern and comfortable sanctuary for you to enjoy!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 11
Make yourself at home in this 5-bedroom Harpswell farmhouse retreat. With 2 queen beds, 1 king bed, and 5 twin beds, gue ...
From $706 per night (USD)Expedia
From $535 per night (USD)VRBO
Watch sunrises and enjoy views of Lowell's Cove.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Whale Watch! This relaxed and inviting coastal retreat on Orr's Island is perfectly situated just steps from ...
From $535 per night (USD)VRBO
From $426 per night (USD)VRBO
Guesthouse Retreat just minutes from the Beaches!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This unique Barn Guesthouse is located at the end of a private lane in a peaceful rural setting. With three popular beac ...
From $426 per night (USD)VRBO
From $524 per night (USD)VRBO
Charming Home minutes to Old Port & Thompson Point
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to your quiet Maine getaway, perfectly located just minutes from Thompson Point, Downtown Portland, and the city ...
From $524 per night (USD)VRBO
From $1110 per night (USD)Expedia
Salty Dolphin by Bayley Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
**This rental is brought to you by Bayley Vacation Rentals!** Beautiful 4-bed, 3-bath home in Pine Point with a charmin ...
From $1110 per night (USD)Expedia
From $604 per night (USD)VRBO
West End Stylish & Creative Home w/ Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to The Walker House! A spacious, multi-level private apartment located in Portland’s beautiful and hi ...
From $604 per night (USD)VRBO
From $488 per night (USD)Expedia
West End Charm: Walk to All | Private Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Welcome to The Walker House! A spacious, multi-level private apartment located in Portland’s beautiful and his ...
From $488 per night (USD)Expedia
From $969 per night (USD)VRBO
Two Beautiful Apartments- Ideal for Groups!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Enjoy the perfect balance of togetherness and privacy in this unique property featuring two separate apartment ...
From $969 per night (USD)VRBO
From $559 per night (USD)Expedia
FIRST-YEAR SPECIAL: Long Lake Retreat with Beach Access Near Naples Causeway
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Be among the first to experience this stunning brand new build in the heart of Naples, Maine. Thoughtfully customized wi ...
From $559 per night (USD)Expedia
From $631 per night (USD)VRBO
Lakefront Escape in Casco - 4BR Waterfront Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This peaceful 4 bedroom waterfront home is the perfect Maine getaway. Spend your days hiking, biking, swimming, kayaking ...
From $631 per night (USD)VRBO
From $224 per night (USD)Expedia
Munjoy Hill apartment w/ AC, walk to town & promenade
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your perfect getaway in the heart of Portland, Maine! This charming apartment is nestled in the desirable Mun ...
From $224 per night (USD)Expedia
From $1746 per night (USD)VRBO
Hobson's Landing Condo in the heart of Portland's Historic Old Port Exchange
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience premiere city living at Portland's newest condominium community, located in Portland's downtown waterfront. H ...
From $1746 per night (USD)VRBO
From $180 per night (USD)Expedia
Lakefront cabin with shared firepit & access to Sebago Lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Spend a classic summer in Maine at this darling, studio-style cottage on the shores of Sebago Lake and Sebago Lake Basin ...
From $180 per night (USD)Expedia
From $244 per night (USD)VRBO
Dog-Friendly Lakefront Cottage w/Lake Access, Deck, Gas Grill, A/C
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Loons Nest Cottage at the Sebago Lake Lodge and Cottages is one of the prettiest and most peaceful settings in Maine ...
From $244 per night (USD)VRBO
From $388 per night (USD)Expedia
Cozy wooded cabin with lake access, firepit & kitchenette
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled in a superb region known for its tranquility and peacefulness, this lovely tiny home is the perfect launchpad fo ...
From $388 per night (USD)Expedia
From $1693 per night (USD)VRBO
Lakefront house with private beach, firepit, dock, 4 kayaks, grill & hot tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Find a true escape in the luxe comfort of this beautifully rebuilt (2024) lakefront home! This splendid escapade offers ...
From $1693 per night (USD)VRBO
From $466 per night (USD)Expedia
Charming lakeside home near skiing w/ shared pool, tennis courts, & washer/dryer
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 14
Cozy Lakeside Retreat Near Pleasant Mountain Ski Area w/ Shared Pool, Tennis Courts & Washer/Dryer Embrace the magic of ...
From $466 per night (USD)Expedia
From $312 per night (USD)VRBO
Lake Cabin | Fire Pit | Direct Lake Access | Pool | Near Ski Area
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this charming 3-bedroom, 1.5-bath home in the heart of Bridgton, Maine, the perfect year-round getaway for fam ...
From $312 per night (USD)VRBO
From $335 per night (USD)Expedia
Charming Retreat House with Game room and Outdoor Firepit
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this charming house in Naples, ME, where comfort and convenience await you amidst the beauty of Maine's Lakes ...
From $335 per night (USD)Expedia
From $399 per night (USD)VRBO
Inviting Bridgton House with Cozy Interiors and Modern Amenities
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Located in the charming town of Bridgton, ME, this spacious house offers a prime location with a public boat ramp and pa ...
From $399 per night (USD)VRBO
From $659 per night (USD)Expedia
Naples Lakefront Retreat | Private Beach, Dock & Kayaks | Family + Dog friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to your perfect Maine lakefront getaway on Brandy Pond, ideally located just minutes from the Naples Causeway. Se ...
From $659 per night (USD)Expedia
From $356 per night (USD)VRBO
Cozy 3BR home for outdoor enthusiasts, deck, pool, tennis, w/d, trails & BBQ
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled in the charming town of Bridgton, ME, 'The Good Knight' is a uniquely designed home located in the Knights Hill ...
From $356 per night (USD)VRBO
From $990 per night (USD)Expedia
Private waterfront cabin with large deck, private dock, kayaks & gas grill
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in the quiet woods of Maine, you'll be able to enjoy a much-needed relaxing vacation at this home away from home ...
From $990 per night (USD)Expedia
From $304 per night (USD)VRBO
Lakefront cabin with private dock, 2 kayaks & panoramic views
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the family lakehouse that will remind you of your childhood summers and give your kids an experience just as ...
From $304 per night (USD)VRBO
From $468 per night (USD)Expedia
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This beautiful and modern condo offers a spacious escape in downtown Portland. After long days exploring the city, come ...
From $468 per night (USD)Expedia
From $320 per night (USD)VRBO
Historic Condo w/ Casco Bay Views, WiFi & 2 Bikes - Walk Everywhere
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Beautifully situated in a historic 1898 building overlooking scenic Casco Bay, this charming Portland condo offers an id ...
From $320 per night (USD)VRBO
From $506 per night (USD)Expedia
Elegant condo - walk to Portland's best restaurants & Old Port
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Polished, elegant, and perfectly located within walking distance of the Old Port, this beautiful condo offers a wonderfu ...
From $506 per night (USD)Expedia
From $627 per night (USD)VRBO
Beautiful Combo Home Located in Downtown Portland - Close to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This downtown Portland property hosts two separate, fully equipped living spaces that are perfect for a family or group ...
From $627 per night (USD)VRBO
From $242 per night (USD)Expedia
Munjoy Hill hideaway with AC - walk to dining & Eastern Promenade
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Within easy walking distance of bakeries and restaurants, this comfortable abode boasts a superb location, quality furni ...
From $242 per night (USD)Expedia
From $297 per night (USD)VRBO
Historical & dog-friendly West End condo with parking - walk to all of Portland
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Portland ME STR License: 20180761-ST Experience a quintessential Portland setting in the city's most desirable neighbor ...
From $297 per night (USD)VRBO
From $305 per night (USD)Expedia
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A tranquil and scenic getaway awaits when you book this fantastic vacation rental in a quaint and delightful historical ...
From $305 per night (USD)Expedia
From $307 per night (USD)VRBO
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A tranquil and scenic getaway awaits when you book this fantastic vacation rental in a quaint and delightful historical ...
From $307 per night (USD)VRBO
From $851 per night (USD)Expedia
Gorgeously renovated, 2-condo property in the West End - walk everywhere
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Portland ME STR License: 20180761-ST Find the perfect Portland setting for a group of friends or several couples at thi ...
From $851 per night (USD)Expedia
From $378 per night (USD)VRBO
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
If you're looking for a peaceful, lakefront getaway where you can choose to either relax at home with your feet up or he ...
From $378 per night (USD)VRBO
From $708 per night (USD)Expedia
Waterfront home with furnished deck, ocean views, & full kitchen
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
This charming, oceanfront home boasts spectacular views of Maquoit Bay from the moment you open the door! Nestled among ...
From $708 per night (USD)Expedia
From $447 per night (USD)VRBO
Spacious retreat with peaceful seclusion, Wifi, Patio & BBQ Grill
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to this delightful retreat in Freeport, ME, offering peace and seclusion within easy reach of local attractions. ...
From $447 per night (USD)VRBO
From $375 per night (USD)Expedia
Charming cottage w/ access to Sebago Lake, private boat mooring, & cozy sunroom
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Charming Sebago Lake Cottage – Your Perfect Vacation Retreat! Escape to this cozy cottage in Sebago, ME, just steps fro ...
From $375 per night (USD)Expedia
From $270 per night (USD)VRBO
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Escape to the beautiful Maine wilderness and find yourself reconnecting with nature! Set up like an old-fashioned camp, ...
From $270 per night (USD)VRBO
From $656 per night (USD)Expedia
Waterfront home with a fireplace, grill, deck, washer/dryer, & AC - dog-friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to the Maine countryside and unwind at Panther Run River Retreat. Located directly across the street from the His ...
From $656 per night (USD)Expedia
From $355 per night (USD)VRBO
Charming Log Cabin w/ Free WiFi plus a Community Pool, Tennis, & Clubhouse
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Immerse yourself in rural Maine charm at this Knights Hill log cabin with knotty pine walls, ceilings, and other feature ...
From $355 per night (USD)VRBO
From $1941 per night (USD)Expedia
Lakefront properties with private beach, hot tub, dock, kayaks, grill & firepit
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 14
Welcome to Super Birch, a unique lakefront getaway on Little Sebago Lake featuring two separate homes on the same proper ...
From $1941 per night (USD)Expedia
From $352 per night (USD)VRBO
Adorable waterfront gem with 2 kayaks, high-speed WiFi, full kitchen & dock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Say hello to Little Birch, an adorable cottage right on the Upper Bay here in Gray. With calm water right outside your b ...
From $352 per night (USD)VRBO
From $377 per night (USD)Expedia
Lakefront condo with on-site pool, dock, swimming, firepit, & tennis
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Moose Pond is just steps from the front door and Pleasant Mountain Ski Area is only a half-mile away from this perfect y ...
From $377 per night (USD)Expedia
From $436 per night (USD)VRBO
Summer Fun, Lake View, Firepit, Outdoor grilling, walk to the lake
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
The owner's love for this home shines through in the beautiful views of Sebago Lake, the sandy beach, and the convenient ...
From $436 per night (USD)VRBO
From $433 per night (USD)Expedia
Tranquil Mountain Escape with Modern Comforts, Deck, Fire Pit, and Shared Pools
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your ideal getaway in Bridgton, ME! This exceptional vacation home offers breathtaking views of Moose Pond ju ...
From $433 per night (USD)Expedia
From $1021 per night (USD)VRBO
Serene Coastal Home with Private Beach Access, Hot Tub, and Spacious Decks
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Serene Coastal Retreat with Beach Access & – Cumberland Foreside, ME Escape to your tranquil Maine getaway in this stu ...
From $1021 per night (USD)VRBO
From $297 per night (USD)Expedia
Renovated condo with prime West End location, 2 en suite bathrooms, & HGTV style
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Portland ME STR License: 20180761-ST Surround yourself with historic homes, tree-lined streets, and some of the best re ...
From $297 per night (USD)Expedia
From $253 per night (USD)VRBO
Lakefront camp with cozy cottage-style interior and board games - kayaks welcome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Treat yourself and a couple of friends to a weekend getaway in Maine's colorful and dense forest at this lakefront camp. ...
From $253 per night (USD)VRBO
From $457 per night (USD)Expedia
Private 2BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to this charming house located on a serene 10-acre pond in Scarborough, ME, offering a private sandy beach and st ...
From $457 per night (USD)Expedia
From $377 per night (USD)VRBO
Cozy 2-bedroom Cottage on the Naples Causeway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Causeway Cottage - Suite is located on the Hamilton House property on the famous Naples Causeway across the street f ...
From $377 per night (USD)VRBO
From $365 per night (USD)Expedia
Close to Ocean! Family-Friendly Orrs Island Escape
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 5
Welcome to your charming retreat on Orrs Island, ME, where relaxation meets adventure! This delightful house is perfect ...
From $365 per night (USD)Expedia
From $916 per night (USD)VRBO
Private lakeside hideaway, 4 bedroom one-story home with stunning water views.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Tucked away at the end of a private dirt road, The Hogan is a true escape. Built in 1960 this mid-century design summer ...
From $916 per night (USD)VRBO
From $278 per night (USD)Expedia
1 Mi to Maine Street! MCM-Style Home in Brunswick
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Minimalist Aesthetic | 1 Mi to Amtrak Station Settle into this 2-bedroom, 1.5-bath Brunswick vacation rental, wrapped i ...
From $278 per night (USD)Expedia
From $185 per night (USD)VRBO
Charming Coastal Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Perfect for couples, small families, or friends exploring the Maine coast, this cozy and thoughtfully designed suite of ...
From $185 per night (USD)VRBO
From $140 per night (USD)VRBO
Unit 3- The Inn on Shore (duplicate)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This is a 2/br 1bth 3rd floor rental. It`s been beautifully remodeled with a full kitchen, hardwood floors, air conditio ...
From $140 per night (USD)VRBO
From $3289 per night (USD)VRBO
Spacious West End Retreat. Walk Everywhere, Prime Portland Location. 5 BR/3BTH. 6 BEDS.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
This property boasts one of the most desirable locations in Portland, w/easy walking access to excellent restaurants, th ...
From $3289 per night (USD)VRBO
From $549 per night (USD)Expedia
Prime Location, Private Rooftop Deck.Walk to Old Port,waterfront, Museums& Music
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your private top-floor retreat in Portland’s sought-after West End. Located in a charming historic building, ...
From $549 per night (USD)Expedia
From $129 per night (USD)VRBO
LL Bean King Room with Pool & Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Relax in a comfortable 1 King Bed Room in the heart of downtown Freeport—ideal for business or leisure stays within walk ...
From $129 per night (USD)VRBO
From $382 per night (USD)Expedia
Cozy West End apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This spacious open concept one-bedroom apartment is located in a restored house built in 1845. A colorful, cozy space th ...
From $382 per night (USD)Expedia
From $308 per night (USD)VRBO
Serene 2-bedroom apartment with AC in charming Yarmouth
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This fully furnished apartment has its own private entrance with a walkway/side yard access. First floor entryway with m ...
From $308 per night (USD)VRBO
From $685 per night (USD)Expedia
Lakeside Casita with Hot Tub: little Sebago Lake
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to La Casita on Little Sebago Lake. Escape to this newly built, modern-style retreat where the lake takes center ...
From $685 per night (USD)Expedia
From $242 per night (USD)VRBO
Cozy, Private 1-bedroom house with stream frontage in tranquil Bridgton with AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Get ready to relax in this 1-bedroom house in Bridgton. Come experience the solitude and serenity of the Maine woods whi ...
From $242 per night (USD)VRBO
From $382 per night (USD)VRBO
Cedar Brook Cabin - a modern tiny house in Maine
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Luxury two-bedroom tiny cabin offering contemporary style near the best of Maine's "Vacationland" - Portland, ...
From $382 per night (USD)VRBO