Cumberland Area Rentals
From $597 per night (USD)VRBO
Traditional pet-friendly Maine home featuring an incredible sandy beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the Beauty of Brandy Pond at this traditional Maine summer home, complete with a cozy guest cottage – perfect ...
From $597 per night (USD)VRBO
From $424 per night (USD)Expedia
PRIVATE SANDY BEACH ON SEBAGO LAKE!!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
OCCUPANCY LIMIT 8 - NO PETS - SEBAGO LAKE BEACHFRONT. Classic four bedroom lakeside cottage overlooking Sebago Lake. G ...
From $424 per night (USD)Expedia
From $383 per night (USD)VRBO
West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome! Our 2-bedroom apartment is located tucked away in the West End of Portland with easy walking to great restauran ...
From $383 per night (USD)VRBO
From $201 per night (USD)Expedia
Cottage in the Woods on Picturesque Island
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Nestled in the woods on picturesque Peaks Island, this delightful cabin 'Sequester' offers guests a tranquil escape. Wit ...
From $201 per night (USD)Expedia
Click For PricingVRBO
The Coastal Nest – Charming Maine Retreat Near Pine Point Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to The Coastal Nest, a freshly updated 2-bedroom, 1-bath home just a short distance from Pine Point Beach. This p ...
Click For PricingVRBO
From $1905 per night (USD)VRBO
Pine Point Beach's Crown Jewel-New 4 BR, 3 BA, 3 deck Beach House with hot tub
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Brand new extraordinary 4 BR, three deck, beach house. The home is steps from a 7 mile white sand beach, every room ha ...
From $1905 per night (USD)VRBO
From $621 per night (USD)VRBO
Hummingbird Hollow: 4BR, Lakefront, Private Beach
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to Hummingbird Hollow, a charming 4BR, 1.5-bath lakefront retreat in Windham, Maine. Enjoy a private beach for y ...
From $621 per night (USD)VRBO
From $874 per night (USD)VRBO
Luxury Lake House w/ Home Theater, Hot Tub & Gym
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This modern 4-bedroom home offers a private lake escape with resort-style amenities, just steps from the water. You'll e ...
From $874 per night (USD)VRBO
From $535 per night (USD)VRBO
Lovely waterfront home on Panther Pond with private tennis/pickleball court!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the best of Panther Pond at this charming year-round home situated at the end of a lane, offering a private a ...
From $535 per night (USD)VRBO
From $210 per night (USD)Expedia
Spring into Summer at Turtle Lane Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
As you step foot into Turtle Lane Cottage, you will never want to leave. Large water frontage located on a quiet canal l ...
From $210 per night (USD)Expedia
From $670 per night (USD)VRBO
Lakefront, brand new, craftsman style 4-bedroom 2 bath house home on Long Lake.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Your Bridgton getaway awaits at this beautiful 4-bedroom house. With 3 queen beds, 1 bunk bed, and 1 sofa bed, there's p ...
From $670 per night (USD)VRBO
From $532 per night (USD)Expedia
Latitude Adjustment – Walk to Beach & Dining!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Have you been seeking a peaceful, coastal Maine beach vacation away from the hustle and bustle of the crowds bu ...
From $532 per night (USD)Expedia
From $2138 per night (USD)VRBO
Private Lakefront Estate with 180 Degree Views
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 20
Sebago Lake is waiting for you at this secluded 6-bedroom estate where you will be surrounded by the beauty of nature. B ...
From $2138 per night (USD)VRBO
From $334 per night (USD)Expedia
The Coastal Nest – Stay for 5!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Escape to The Coastal Nest, a freshly updated 2-bedroom, 1-bath home just a short distance from Pine Point Beac ...
From $334 per night (USD)Expedia
From $542 per night (USD)VRBO
Spurwink Meadows Homestead Property perched amongst tranquil pastoral farmland
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Sun Drenched Southern Exposure Circa 1978 Rancher featuring fresh paint throughout, new Ashley furniture from The Furnit ...
From $542 per night (USD)VRBO
From $326 per night (USD)Expedia
Spacious home just 1.5 mi from Pleasant Mtn. Spectacular views of Mt Washington
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This unique home sits on a ridge that overlooks The White Mountains, specifically The Presidential Range. It's just a mi ...
From $326 per night (USD)Expedia
From $137 per night (USD)VRBO
NEW! Stylish Loft in the Heart of Downtown Portland
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Immaculate urban oasis in the heart of downtown Portland. Ideal for remote work. An easy walk to dozens of downtown’s mo ...
From $137 per night (USD)VRBO
From $2184 per night (USD)Expedia
Spacious 7-bedroom house in marvelous Portland with AC, WiFi
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Discover this charming 7-bedroom gem in Portland. This lovely house boasts heating, AC, and WiFi for your comfort. With ...
From $2184 per night (USD)Expedia
From $446 per night (USD)VRBO
Water Front 4 Bedrooms w/ shared dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 18
Location, Location, Location! That is why you want to rent this popular property. It is located just 5.5 miles from Co ...
From $446 per night (USD)VRBO
From $644 per night (USD)VRBO
Sea Forever! Waterfront, Dog-Friendly Retreat, Seasonal Dock, 12min to Brunswick
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This exquisite 3-bedroom, 2.5-bathroom waterfront home is waiting for you. Long standing rental with steady history of 5 ...
From $644 per night (USD)VRBO
From $787 per night (USD)VRBO
5 bed 4 bath in the Basin of Sebago Lake with 200 ft. of shared beach frontage
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to New Marblehead Lodge, a compound located in the Basin of Maine's most desirable Sebago Lake. This property fe ...
From $787 per night (USD)VRBO
From $483 per night (USD)VRBO
Bright, updated century old cottage two blocks from the ocean
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
*Transitioning from other STR site to VRBO so reviews and ratings are on that platform. Newly renovated 2 bedroom cotta ...
From $483 per night (USD)VRBO
From $208 per night (USD)VRBO
Studio Unit Walkable Everywhere
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Recently updated clean & no frills 1st floor unit in a 3 floor brick building walkable to all in-town Portland hot spots ...
From $208 per night (USD)VRBO
From $225 per night (USD)Expedia
Private Entrance Residential Portland
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A great, simple1 bedroom apartment in a 3 unit building located in quiet suburban neighborhood of outer Portland. A 10-1 ...
From $225 per night (USD)Expedia
From $433 per night (USD)VRBO
A beautiful 3 bedroom home overlooking Basin Cove.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Wild Air! Located on the heart of Basin Cove rests this bright and beautiful 3 bedroom, 2.5 bath home with g ...
From $433 per night (USD)VRBO
From $630 per night (USD)VRBO
Steps to the Sand, Modern Home on Willard Beach, Fenced in Yard, Deck & Grill
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Wake up to the sound of waves, enjoy coffee with ocean views, and step out onto the soft sands of Willard Beach—just a 3 ...
From $630 per night (USD)VRBO
From $290 per night (USD)VRBO
Willard Beach: Cozy Apartment with a King Size Bed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This luxurious first floor apartment is filled with sunshine all day long and on chilly nights the gas fireplace provide ...
From $290 per night (USD)VRBO
From $385 per night (USD)Expedia
Willard Beach–Private Apt Near Portland & Parks
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Many guests have remarked that this stylish, first floor apartment is much larger than it appears in the photos. Just a ...
From $385 per night (USD)Expedia
From $926 per night (USD)VRBO
Lakefront Retreat Near Portland – Modern Comfort with Classic Charm.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 11
Lakefront Retreat Near Portland – Modern Comfort with Classic Charm. Note: Bookings from June 14th to September 27th sh ...
From $926 per night (USD)VRBO
From $238 per night (USD)Expedia
Modern 1-bedroom apartment in beautiful Brunswick, Maine
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Fully furnished modern 1 bedroom apartment on second floor. Private setting, yet within walking distance to restaurants, ...
From $238 per night (USD)Expedia
From $269 per night (USD)VRBO
Portland Island View 2BR Apt.\nViews of Casco Bay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy all Portland has to offer! Sunny first floor apartment in a friendly neighborhood on Casco Bay. Water views from ...
From $269 per night (USD)VRBO
From $241 per night (USD)VRBO
Quaint secluded cottage nestled in the woods minutes from lake Sebago!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Windham is waiting for you at this 1-bedroom cottage. This nice and tranquil retreat offers all the comforts you need fo ...
From $241 per night (USD)VRBO
From $678 per night (USD)VRBO
Amazing West End apartment walkable to downtown and the waterfront.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in Portland’s charming West End, this spacious and bright 2 BR offers upscale amenities and a refined sense of c ...
From $678 per night (USD)VRBO
From $521 per night (USD)Expedia
Spacious retreat with peaceful seclusion, Wifi, Patio & BBQ Grill
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beech Hill Lodge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $521 per night (USD)Expedia
From $335 per night (USD)VRBO
Sebago Lake Retreat - Sunset Views, Fire Pit, Family Fun
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy 3BR, 1BA cottage with peaceful lake views of Sebago. Enjoy sunsets from the deck, unwind by the fire pit, or relax ...
From $335 per night (USD)VRBO
From $677 per night (USD)VRBO
Surfside Pine Point, Scarborough Maine with AC, WiFi, walk to beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Get ready to relax in this marvelous 2024 construction 3-bedroom apartment steps from Pine Point Beach. Apartment inclu ...
From $677 per night (USD)VRBO
From $294 per night (USD)VRBO
Lake view home with water access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Although this home was remodeled recently it still maintains that Maine country, cottage feel. With pine cathedral ceili ...
From $294 per night (USD)VRBO
From $872 per night (USD)VRBO
New - Cozy Cape on Peaks Island overlooking Casco Bay and Portland skyline
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
The whole group will enjoy easy access to everything from this centrally located, charming cape overlooking Casco Bay an ...
From $872 per night (USD)VRBO
From $230 per night (USD)VRBO
THE LILLIPAD.Off-grid A frame. Sebago lake region!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
About this space Take it easy in the woods at this cozy, off-grid A frame located in the Sebago Lakes Region. Kick back ...
From $230 per night (USD)VRBO
From $273 per night (USD)Expedia
2-bedroom apartment in Portland, ME with WiFi, AC. Enjoy your stay!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Get ready to relax in this 2-bedroom apartment in Portland. The space features 2 cozy queen beds, WiFi, heating, and AC. ...
From $273 per night (USD)Expedia
From $187 per night (USD)VRBO
“The MBB”-Excellent location, game room w P Pong, Darts, Cards, Karaoke and more
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The McTomney’s Bridgton Bungalow is your private escape tucked away in the woods of Bridgton, Maine. This 3-bedroom, 1.5 ...
From $187 per night (USD)VRBO
From $1570 per night (USD)Expedia
Downtown Portland Retreat | 3 Units | Near Breweries & Scenic Harbor!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $1570 per night (USD)Expedia
From $1046 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 $1046 per night (USD)VRBO
From $1046 per night (USD)Expedia
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 $1046 per night (USD)Expedia
From $295 per night (USD)VRBO
Coastal Charm Awaits at This Orr’s Island Retreat !
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Welcome to Island Breeze Retreat, a charming 4-bedroom, 1.5-bath getaway nestled on peaceful Orr’s Island. The getaway ...
From $295 per night (USD)VRBO
From $524 per night (USD)Expedia
Stylish Stay | Savor Seafood & Explore Portland’s History!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $524 per night (USD)Expedia
From $512 per night (USD)VRBO
Spacious Downtown Waterfront Unit | Pets Are Welcome | Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $512 per night (USD)VRBO
From $2093 per night (USD)Expedia
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 $2093 per night (USD)Expedia
From $395 per night (USD)VRBO
Relaxing Couple Pet-Friendly Stay | Seafood & Portland Attractions
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $395 per night (USD)VRBO
From $258 per night (USD)Expedia
Cozy 4 Season Mtn Retreat in Bridgton with Beach Access!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your perfect four-season retreat nestled in the serene Knights Hill community! This warm and inviting 3-bedro ...
From $258 per night (USD)Expedia
From $198 per night (USD)VRBO
Marvelous 2-bedroom apartment in Portland
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Portland is waiting for you at this delightful 2-bedroom apartment. With a queen bed, a full bed, and a cozy living room ...
From $198 per night (USD)VRBO
From $661 per night (USD)Expedia
SANDY BEACH ON THOMAS POND
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
OCCUPANCY- LIMIT 8 - This 3-bedroom 1.5 bath with family room in the daylight basement, is just steps away from Thomas P ...
From $661 per night (USD)Expedia
From $300 per night (USD)VRBO
KENDALLS COTTAGE AT SEBAGO LAKE
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
OCCUPANCY LIMIT 6 One minute walk to beautiful Sebago Lake's crystal clear waters as well as Long Beach Marina where you ...
From $300 per night (USD)VRBO
From $385 per night (USD)Expedia
Enjoy Stunning Ocean Views & Coastal Access at Sea Mist Overlook!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to Sea Mist Overlook – a peaceful Harpswell cottage with stunning ocean views and classic coastal charm! Locate ...
From $385 per night (USD)Expedia
From $251 per night (USD)VRBO
Six minutes to skiing/GAME ROOM/Adventure awaits!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
WELCOME YA'LL Come kick your boots off and stay a while. Drink your coffee on the porch, cozy up in front of the firep ...
From $251 per night (USD)VRBO
From $381 per night (USD)Expedia
Near Portland Trails: Walkable Apartment w/ Deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Open Layout | In-Unit Laundry | Half-Mi to Restaurant & Market Discover Portland, ME, like a local at this 1-bedroom, 1 ...
From $381 per night (USD)Expedia
From $202 per night (USD)VRBO
Cozy, Secluded Work/Stay Space
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cozy and secluded, but a stone's throw to downtown Portland and the Old Port. Bright, with lots of windows and light, ov ...
From $202 per night (USD)VRBO
From $747 per night (USD)Expedia
Elegant Oceanfront House with Breathtaking Views, Private Dock, and Fireplace
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Tide's Edge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $747 per night (USD)Expedia
From $428 per night (USD)VRBO
Beautiful Unit in Serene Countryside Setting Near Wineries – Onsite Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Explore Maine's coastal charm with nearby wineries and breweries, or stroll through Old Port for the perfect blend of se ...
From $428 per night (USD)VRBO
From $429 per night (USD)Expedia
The Maine Frame: Fall Getaway, 7 Min to LL Bean
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
- Framed by nature. Designed for the way life should be - Welcome to The Maine Frame! Perfect for small families or ...
From $429 per night (USD)Expedia
From $405 per night (USD)VRBO
Charming Sebago Lake 3-bedroom cabin with lake access, WiFi and AC in Windham
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Relax with the whole family at this peaceful place to stay. Located 250 feet from beach entry lake. Relax on the dock ...
From $405 per night (USD)VRBO
From $611 per night (USD)Expedia
Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your perfect Maine getaway! Our spacious, dog-friendly apartment is ideal for exploring Portland and beyond. ...
From $611 per night (USD)Expedia
From $2144 per night (USD)VRBO
Large Historic Home with Pool & Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Very Unique, large historial home in beautiful Falmouth, Maine. Originally built in 1725, this nearly Three-Hundred-Year ...
From $2144 per night (USD)VRBO
From $399 per night (USD)VRBO
Charming 3-bedroom cabin in Bridgton, ME with WiFi, AC, lake, pool area, skiing
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Get ready to relax in this phenomenal 3-bedroom cabin in Bridgton. This welcoming retreat offers a tremendous array of a ...
From $399 per night (USD)VRBO
From $372 per night (USD)VRBO
Sauna & fire table near Portland's Back Cove
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sunny open space, near Payson Park & Back Cove. Enjoy the newly added sauna in the backyard, surrounded by nature and st ...
From $372 per night (USD)VRBO
From $448 per night (USD)Expedia
Oceanfront Escape: Deck & Granite Steps to Shore
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spectacular Oceanfront Getaway on the Shores of Harpswell Water's Edge Shore Cottage – Wake up to breathtaking ocean v ...
From $448 per night (USD)Expedia
From $471 per night (USD)VRBO
Charming 3-bedroom cabin with private sandy beach and dock
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the perfect blend of vintage charm and modern luxury in this fully renovated 1960s lakefront cabin. Completed ...
From $471 per night (USD)VRBO
From $716 per night (USD)Expedia
Spacious 4-bedroom house in nice South Portland with WiFi, AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
30 day minimum. This 4-bedroom house in South Portland is perfect for your escape. With 1 king bed, 1 queen bed, and 2 t ...
From $716 per night (USD)Expedia
From $1883 per night (USD)VRBO
**BRAND NEW** Incredible Luxury Log Home Elevated Above Sebago Lake
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Be one of the first to experience this stunning, brand-new log home nestled in the woods with elevated views overlooking ...
From $1883 per night (USD)VRBO
From $1353 per night (USD)Expedia
6BR Sleeps 16 w/ Balcony 10 mins to Downtown
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
Bringing everyone together? This 6BR, 4.5BA setup combines two private apartments in the same building—perfect for group ...
From $1353 per night (USD)Expedia
From $613 per night (USD)VRBO
State of Charm | Historic West End Haven
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience Portland’s charm in this beautifully restored 2 bed, 1.5 bath Victorian apartment in the heart of the downtow ...
From $613 per night (USD)VRBO
From $676 per night (USD)Expedia
Lofty Ambition | Stunning West End Rooftop Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Step into this dazzling retreat perched atop Portland’s historic West End! Bathed in sunlight and bursting with characte ...
From $676 per night (USD)Expedia
Click For PricingVRBO
Historic Charm at 236 - Elegant West End Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Stay in the heart of Portland’s historic West End at an iconic landmark property, blending Victorian charm with modern c ...
Click For PricingVRBO
From $426 per night (USD)Expedia
Luxury on Back Cove - Three Gables
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Live like a local in this grand, two‑level flat on a quiet, tree‑lined street 5 minutes from Portland’s buzzing Old Port ...
From $426 per night (USD)Expedia
From $553 per night (USD)VRBO
The Cityside Maple House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to The Cityside Maple House, a spacious four-bedroom, three-bathroom home nestled in one of Falmouth's most desi ...
From $553 per night (USD)VRBO
From $212 per night (USD)Expedia
Charming 2-bedroom house with AC, WiFi in lovely Falmouth
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Make yourself at home in this superb 2-bedroom Falmouth retreat. This serene house features 2 full beds, a cozy loft wit ...
From $212 per night (USD)Expedia
From $232 per night (USD)VRBO
Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
LOON CALL COTTAGE AT LITTLE SEBAGO LAKE: Sleeps 4 very comfortably. Lake is directly across the quiet neighborhood road ...
From $232 per night (USD)VRBO
From $508 per night (USD)VRBO
Cozy Bridgton Townhome – Perfect for Family Fun On Pleasant Mountain
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Make yourself at home in this peaceful 3-bedroom townhome retreat in beautiful Bridgton, Maine. Spread across three spac ...
From $508 per night (USD)VRBO
From $665 per night (USD)VRBO
Long Lake Happiness--Private Dock/Kayaks/Waterfront
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to Long Lake Happiness, your peaceful home away from home in the heart of Harrison, Maine. From the moment you w ...
From $665 per night (USD)VRBO
From $238 per night (USD)Expedia
Manor Suite,cozy newly renovated,downtown & beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This cozy, newly renovated one bedroom suite has everything you need for a relaxing getaway. Just a 5 min walk to Highla ...
From $238 per night (USD)Expedia
From $467 per night (USD)VRBO
Beautifully maintained, 1905 original lakefront summer home – super pet friendly
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 13
TCV is a lakeside family summer home which welcomes everybody: one of the first few cabins ever built on Watchic Lake in ...
From $467 per night (USD)VRBO
From $611 per night (USD)Expedia
Large, luxurious geodesic dome - 09
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Enjoy a luxury outdoor camping experience like no other! Sleep out in nature in our 22' diameter geodesic with ...
From $611 per night (USD)Expedia
From $348 per night (USD)VRBO
Charming 1-bedroom cottage in fabulous Bridgton with WiFi, AC, private dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Consider this quaint waterfront cottage with fantastic lake views your home away from home while you visit Bridgton. Thi ...
From $348 per night (USD)VRBO
From $410 per night (USD)Expedia
Spacious Lakehouse +Private Dock+Firepit+Kayaks
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your perfect lakefront escape on beautiful Panther Pond in Raymond, Maine! Nestled on 3 serene acres shared w ...
From $410 per night (USD)Expedia
From $330 per night (USD)VRBO
Brand new 2BR, 1.5BA-close to amenities yet feels secluded. 2 story, AC, wifi!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Peaceful, Cozy Family & Pet-Friendly Getaway Near Pleasant Mountain, plenty of accessibility to nearby amenities, includ ...
From $330 per night (USD)VRBO
From $184 per night (USD)Expedia
Cozy Lakefront Cabin with Beach & AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your cozy lakefront getaway at the heart of Maine’s Lake Region, with small sandy beach 10 feet away from you ...
From $184 per night (USD)Expedia
From $448 per night (USD)VRBO
Private 2-bedroom cottage on Purple Road in Point Sebago Resort
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Unwind in Point Sebago at this lovely cottage. Very close to the beach and activities this charming retreat features 2 c ...
From $448 per night (USD)VRBO
From $340 per night (USD)Expedia
Sun-lit, 2 Bedroom Guest cottage on 27 Acres in Freeport
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to our serene, sunlit cottage on 27 private wooded acres—just 8 minutes from downtown Freeport and 10 from Brunsw ...
From $340 per night (USD)Expedia
From $506 per night (USD)VRBO
Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Get ready to relax in this 4-bedroom cottage in Raymond. This adorable property features 2 queen beds, 1 full bed, and 2 ...
From $506 per night (USD)VRBO
From $520 per night (USD)Expedia
Swim, Kayak & Relax in Coastal Comfort from this Charming, Pet-Friendly Home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Discover your perfect coastal retreat at this charming seaside home nestled on Clark Cove. Wake up to breathtaking sunri ...
From $520 per night (USD)Expedia
From $506 per night (USD)VRBO
4-bedroom house in Scarborough with fully equipped kitchen, WiFi, near beaches..
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Charming 4-Bedroom Vacation Home in Scarborough, Maine Welcome to our delightful 4-bedroom, 2-bathroom home, perfectly n ...
From $506 per night (USD)VRBO
From $347 per night (USD)Expedia
The Lori House in Westbrook
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked into a quiet Westbrook neighborhood, this bright and freshly updated home offers the perfect Maine base—peaceful, ...
From $347 per night (USD)Expedia
From $687 per night (USD)VRBO
The Anchorage Cottage, Pine Point Maine, offers a wonderful vacation experience
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 9
Welcome to Fisherman's Cove in Pine Point Maine. We offer two beautiful waterfront cottages in Pine Point for summer wee ...
From $687 per night (USD)VRBO
From $322 per night (USD)Expedia
Oceanfront Studio w/ Private Dock in Harpswell!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Sleek Interior | BBQ Ready | Wildlife Sightings Retreat with your loved one to the Northeast and book this 1-bath vacat ...
From $322 per night (USD)Expedia
From $550 per night (USD)VRBO
Large, luxurious geodesic dome - 06
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Enjoy a luxury outdoor camping experience like no other! Sleep out in nature in our 22' diameter geodesic with ...
From $550 per night (USD)VRBO
From $497 per night (USD)Expedia
Large, luxurious geodesic dome - 08
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Enjoy a luxury outdoor camping experience like no other! Sleep out in nature in our 22' diameter geodesic with ...
From $497 per night (USD)Expedia
From $372 per night (USD)VRBO
Whale of a Time Summa
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Whale of a Time is a perennial favorite. Located in a quiet neighborhood within walking distance to the ferry b ...
From $372 per night (USD)VRBO
From $634 per night (USD)Expedia
New for 2025! Frye Island Gem with Dock, Firepit, & Sandy Beach!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
New for 2025! Enjoy classic Frye Island charm at this 4-bedroom, 2-bathroom lakefront retreat - pet-friendly and packed ...
From $634 per night (USD)Expedia
From $463 per night (USD)VRBO
Private 4 bedroom Cumberland Lake House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This property offers privacy on a 2.3 acre peninsula on Forest Lake with westward views. With around 800 feet of waterfr ...
From $463 per night (USD)VRBO
From $646 per night (USD)VRBO
Hideaway on the Lake
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this elegant home on this serene lake where comfort meets nature. This spacious 4-bedroom, 2-bathroom home of ...
From $646 per night (USD)VRBO