Cumberland Area Rentals
From $207 per night (USD)VRBO
Crescent Lake 1-Min Walk to Public Beach, Boat Launch, Kayaks, Paddleboards
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Crescent Oak Cottage 🛏️ 3 sleeping areas – Queen bedroom, twin bunk room, and loft with 2 twin floor mattresses (ages ...
From $207 per night (USD)VRBO
From $615 per night (USD)VRBO
Falmouth Foreside Home Near the Ocean
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This home is very sun-filled and tastefully furnished with a true East Coast, Maine style! Open-concept, 4 bedroom, 3.5 ...
From $615 per night (USD)VRBO
From $612 per night (USD)VRBO
Long Island Retreat at Sunset Landing close to Portland, Maine
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to a peaceful Casco Bay Island in Maine and still be only a short Ferry Ride away from Portland, an exceptional ...
From $612 per night (USD)VRBO
From $151 per night (USD)VRBO
Welcoming Room in Portland w/ Casco Bay Views – Steps to Old Port District
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a chic waterfront stay in Portland’s lively Old Port, minutes from top sights. Stroll Casco Bay, shop boutiques, d ...
From $151 per night (USD)VRBO
From $151 per night (USD)VRBO
Serene Portland Room - Perfect for Unwinding Near Casco Bay Ferry
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a chic waterfront stay in Portland’s lively Old Port, minutes from top sights. Stroll Casco Bay, shop boutiques, d ...
From $151 per night (USD)VRBO
From $151 per night (USD)VRBO
Unwind in Stylish Room Near Trails & Outdoor Activities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a chic waterfront stay in Portland’s lively Old Port, minutes from top sights. Stroll Casco Bay, shop boutiques, d ...
From $151 per night (USD)VRBO
From $151 per night (USD)VRBO
Designer Chic Room Perfect for Outdoor Enthusiasts & Couples
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a chic waterfront stay in Portland’s lively Old Port, minutes from top sights. Stroll Casco Bay, shop boutiques, d ...
From $151 per night (USD)VRBO
From $184 per night (USD)Expedia
The Wild Yard Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a cozy, peaceful and centrally-located place. Rustic hand finished walnut headboards, live plants, and sun drenc ...
From $184 per night (USD)Expedia
From $671 per night (USD)VRBO
The Copper Fox Treehouse
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen ...
From $671 per night (USD)VRBO
From $407 per night (USD)Expedia
Quiet Spot in lovely Freeport desert pines neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
NEW LISTING!! This is a cozy one-bedroom apartment in the Desert Pines neighborhood of Maine, in walking distance to ...
From $407 per night (USD)Expedia
From $283 per night (USD)VRBO
Gorgeous Newly Renovated Historic Home
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your Portland home base in the heart of the West End. This newly renovated 3-bedroom, 2-bath unit is outfitte ...
From $283 per night (USD)VRBO
From $170 per night (USD)Expedia
Rustic Lakefront Cabin, Unplug & Unwind, w/AC - Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Experience quintessential Maine camp life on Long Lake in Bridgton! Unplug in this authentic, rustic retreat featuring e ...
From $170 per night (USD)Expedia
From $400 per night (USD)VRBO
Cliffside 2 BD/1 BA home. Quiet sunsets, beach access, and relaxation await you.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax, enjoy and create memories at Sunset Haven, a newly-constructed, single floor cottage overlooking Middle Bay in Ha ...
From $400 per night (USD)VRBO
From $327 per night (USD)VRBO
Bridgton Maine Cottage on Highland Lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Original 4th generation owned cozy cottage nestled in pine grove with beautiful waterfront and mountain views. On Highla ...
From $327 per night (USD)VRBO
From $423 per night (USD)VRBO
NEW!!! Charming 2-Bedroom in Beautiful Freeport!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Mimi’s Place, a charming 2-bedroom, 2-bathroom home nestled in the woods just 5 minutes from Freeport Village. ...
From $423 per night (USD)VRBO
From $250 per night (USD)VRBO
With an easy, scenic walk to the beach, you'll enjoy daily tides and sunsets.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Loon Landing! This romantic one-bedroom coastal cottage is surrounded by three separate Rights of Way offeri ...
From $250 per night (USD)VRBO
From $426 per night (USD)VRBO
Experience the History of Portland - The Hope Island Room
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to your home base in coastal Maine—an elegantly restored 1800 historic property just steps from Portla ...
From $426 per night (USD)VRBO
From $681 per night (USD)Expedia
The Loft - private suite in historic home
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: The Thomas Delano House offers an intimate, boutique inn–style experience in the heart of Portland. Enjoy t ...
From $681 per night (USD)Expedia
From $361 per night (USD)VRBO
The Diamond Island Suite - Suite in Historic Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The Thomas Delano House offers an intimate, boutique inn–style experience in the heart of Portland. You wil ...
From $361 per night (USD)VRBO
From $525 per night (USD)Expedia
Experience the History of Portland - Two Room Suite w/Private Bath
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to your home base in coastal Maine—an elegantly restored 1800 historic property just steps from Portla ...
From $525 per night (USD)Expedia
From $295 per night (USD)VRBO
Experience the History of Portland - The Hope Island Room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Welcome to your home base in coastal Maine—an elegantly restored 1800 historic property just steps from Portla ...
From $295 per night (USD)VRBO
From $502 per night (USD)Expedia
Hilltop Family Escape | River Rock Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
This spacious 3BR, 3,000 sq. ft. contemporary home sits on 2 private acres of Maine forest, offering the perfect year-ro ...
From $502 per night (USD)Expedia
From $276 per night (USD)VRBO
All Season Thompson Lake House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Experience the perfect lake getaway—where the water is just a short stroll away and the comforts of home are everywhere. ...
From $276 per night (USD)VRBO
From $653 per night (USD)Expedia
TWO CABINS ON ONE PROPERTY!! ACCESS TO KAYAKS AND A BEACH AREA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
OCCUPANCY LIMIT 6 - Welcome to Wildflower Cabins In the heart of Sebago Lakes Region with private boat access, swimming, ...
From $653 per night (USD)Expedia
From $738 per night (USD)VRBO
FOUR BEDROOM / TWO BATH HOME NEAR HIGHLAND LAKE
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
OCCUPANCY LIMIT 8 - Welcome to Stargazer Shores, your ideal family getaway in Bridgton, Maine, where relaxed lake days a ...
From $738 per night (USD)VRBO
From $488 per night (USD)VRBO
Wake to spectacular easterly ocean views and unforgettable Atlantic sunrises.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your perfect coastal escape at Puffin's Perch on beautiful Bailey Island where classic Maine charm meets swee ...
From $488 per night (USD)VRBO
From $295 per night (USD)VRBO
Cozy Winter Suite & Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Take it easy at this unique and tranquil getaway. Enjoy the seasons of Maine in this newly renovated 4 unit farm house o ...
From $295 per night (USD)VRBO
From $808 per night (USD)VRBO
Beautiful Sebago Lake Getaway!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 11
Your Perfect Sebago Lake Getaway Escape to the lake and enjoy the best of Maine from this beautifully renovated Sebago ...
From $808 per night (USD)VRBO
From $353 per night (USD)VRBO
Golden Summer Suite & Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 7
Enjoy the seasons of Maine in a newly renovated four-unit farmhouse set on a 5-acre fielded lot. Welcome to your comple ...
From $353 per night (USD)VRBO
From $190 per night (USD)Expedia
Sunny 1-bedroom apartment in the quiet part of Portland, close to UNE medical
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This 1-bedroom apartment is perfect for your visit to Portland. Inside, guests find a charming space featuring a queen b ...
From $190 per night (USD)Expedia
From $1518 per night (USD)VRBO
Steps from Old Port. New, Beautifully Appointed Home. Sleeps up to 11.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 11
Brand New Listing! Experience the best of Portland, Maine in this stunning, newly built home just ...
From $1518 per night (USD)VRBO
From $227 per night (USD)Expedia
Portland Stately 3-BR, 2.5 BA | Walk to Back Cove
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Settle into Portland like a local in a character-filled 1884 home near Back Cove, with a sun-filled porch, and the Old P ...
From $227 per night (USD)Expedia
From $1494 per night (USD)VRBO
Year-Round Lakefront Cabin on Trickey Pond
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 15
Enjoy a peaceful stay at this 4-bedroom house in Naples. This charming cabin is your home away from home on Trickey Pond ...
From $1494 per night (USD)VRBO
From $216 per night (USD)Expedia
Quiet & cozy apartment on a Christmas Tree Farm.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover this 1-bedroom apartment in Windham. Step into a beautiful space where comfort meets convenience. The cozy bedr ...
From $216 per night (USD)Expedia
From $289 per night (USD)VRBO
Welcome to Harbor Heights- your cozy coastal getaway in Cundy's Harbor
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Harbor Heights- your cozy coastal getaway in the heart of Cundy's Harbor! This inviting vacation rental offer ...
From $289 per night (USD)VRBO
From $407 per night (USD)Expedia
Casco Bay Vista
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Big, bold view of Casco Bay from 2nd story deck, living room and bedroom. Short drive to Old Port/Downtown, Falmouth Fo ...
From $407 per night (USD)Expedia
From $429 per night (USD)VRBO
Charming Coastal Falmouth 2BR Retreat – Minutes to Portland
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Perfectly located in Falmouth, this charming cottage offers a quiet seaside setting just minutes from Portland’s vibrant ...
From $429 per night (USD)VRBO
From $177 per night (USD)VRBO
Nice 1-bedroom, groundfloor apt in Brunswick near Bowdoin
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This 1-bedroom apartment is perfect for your escape to Brunswick. Inside, guests find a fabulous queen bed and a cozy li ...
From $177 per night (USD)VRBO
From $561 per night (USD)VRBO
Delightful 2-bedroom cottage on Hen Cove in Cundy's Harbor
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to Hen Cove Cottage – a rustic waterfront retreat This 3+-acre, 4-season property is nestled into idyllic Hen C ...
From $561 per night (USD)VRBO
From $404 per night (USD)VRBO
In the heart of beautiful Bailey Island, this coastal retreat offers a blend of comfort and charm.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to beautiful Briar Rose! Perched in the heart of beautiful Bailey Island, this inviting coastal retreat offers t ...
From $404 per night (USD)VRBO
From $1035 per night (USD)VRBO
The Nest | Lake Access, Pool, HotTub, 5BDRM, Sauna
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
The Nest is a beautiful 5-bedroom, 3-bath mountain cabin located just 3 min from Pleasant Mountain and 10 minutes from d ...
From $1035 per night (USD)VRBO
From $581 per night (USD)VRBO
Charming Bailey Island Coastal Getaway with Stunning Casco Bay Views.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Your Brand-New Coastal Maine Getaway! Be among the first to stay in this beautifully rebuilt coastal cottage ...
From $581 per night (USD)VRBO
From $1184 per night (USD)VRBO
Oceanfront Escape on Lish’s Cove – Private Dock & Sunrise Views
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Brand New Listing for 2026!!! – The Rogue Island Retreat- Set on two private acres at the tip of Cundy’s Harbor, The Ro ...
From $1184 per night (USD)VRBO
From $368 per night (USD)Expedia
Pine Point Beach Lookout Entire 1 bedroom rental unit .5 miles from the beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Kick back and relax in this calm, stylish beach-inspired retreat featuring a private deck overlooking the marsh — the pe ...
From $368 per night (USD)Expedia
From $342 per night (USD)VRBO
Cozy Oceanfront Cottage w/ Wharf, Kayaks & Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Escape to this charming oceanfront cottage on Basin Cove, featuring sweeping water views, direct access to the shore, an ...
From $342 per night (USD)VRBO
From $579 per night (USD)Expedia
Harmony House/Walk to Downtown/Parking/Balcony
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Harmony House- your Portland retreat-where comfort, convenience, and city charm come together. This thoughtfu ...
From $579 per night (USD)Expedia
From $582 per night (USD)VRBO
Urban Ease/By Downtown/Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Urban Ease, your elevated Portland stay-where modern finishes, spacious interiors, and thoughtful amenities c ...
From $582 per night (USD)VRBO
From $1136 per night (USD)Expedia
Maine Social House/By Downtown/Balcony
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to The Maine Social House, your ultimate Portland group stay where space, comfort, and location come together se ...
From $1136 per night (USD)Expedia
From $731 per night (USD)VRBO
Cozy Lakefront Cabin Portland - Windham area
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Relax & enjoy the "Rustic Luxury" custom 9 room lakefront cabin. Escape & experience the best vacation ME has to offer. ...
From $731 per night (USD)VRBO
From $597 per night (USD)Expedia
The Tides: oceanfront, private beach + kayaks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy the Maine coast from a beautifulthree-story home perched on a bluff over majestic ocean views with private steps ...
From $597 per night (USD)Expedia
From $711 per night (USD)VRBO
Little Sebago Getaway: 4 BR, 2 BA House in Raymond, Sleeps 9
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
New for 2026! Enjoy this spacious 4-bedroom, 2-bathroom home just 75 feet from the shore of Little Sebago Lake. Fully eq ...
From $711 per night (USD)VRBO
From $636 per night (USD)Expedia
Falmouth Foreside Cottage Escape - Luxe Kitchen + Walk to the Water!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your coastal Maine cottage retreat. Located in the heart of Falmouth Foreside, this beautifully renovated ho ...
From $636 per night (USD)Expedia
From $560 per night (USD)VRBO
Sebago Lake Beach House, 3 Bedrooms, Sleeps 6, Sandy Beach, Dock & Mooring
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy a beautiful private 60’ sandy beach with dock, mooring (up to 25’ boat) and water toys (kayaks, paddle boards and ...
From $560 per night (USD)VRBO
From $425 per night (USD)VRBO
Exchange Street Skylight Loft
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your Portland home away from home. This unique top-floor condo combines historic New England charm with mode ...
From $425 per night (USD)VRBO
From $342 per night (USD)VRBO
Downtown Brunswick 1st FL Sun Drenched With Porch
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a stylish experience at this centrally-located 1st floor apartment. Open the oversized windows and let the sunshin ...
From $342 per night (USD)VRBO
From $475 per night (USD)Expedia
Gorgeous 4-bedroom house in Harrison. Walking distance to 2 public beaches,
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Located in Harrison, this gorgeous house offers a soothing retreat for guests. With four spacious bedrooms, including th ...
From $475 per night (USD)Expedia
From $318 per night (USD)VRBO
Cozy private waterfront cabin w/AC and Hot Tub; swim, fish, kayak, dog friendly
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This Bridgton cabin boasts 3 bedrooms, including a full bed, a queen bed, and two twin beds. Guests enjoy a welcoming sp ...
From $318 per night (USD)VRBO
From $805 per night (USD)Expedia
Spacious 5-bedroom lake house in Standish, ME
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 13
Get ready to relax in this 5-bedroom house in Standish. The space features a mix of cozy beds, including 2 queen beds, a ...
From $805 per night (USD)Expedia
From $976 per night (USD)VRBO
Luxe 5 Bed/ 3 Bath with Game Room & AC
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This house is a luxury, home between Portland and Freeport. Fully renovated 5BR/3BA Cape Cod sleeps 10 — organic mattres ...
From $976 per night (USD)VRBO
From $725 per night (USD)VRBO
Cozy Coastal Retreat: Steps to Beach, Expansive Yard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Your Cozy Beach Retreat in South Portland! Nestled in a peaceful, quiet neighborhood, this charming home off ...
From $725 per night (USD)VRBO
From $533 per night (USD)VRBO
Spacious Naples Retreat Near Sebago
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 13
The Space Experience the ultimate group getaway in this sprawling Naples log home! Set on 3.5 private acres, enjoy a mas ...
From $533 per night (USD)VRBO
From $1233 per night (USD)Expedia
Spacious 4-bedroom house with AC in peaceful Naples
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Consider this house your home away from home while you visit Naples. With four spacious bedrooms, including three king b ...
From $1233 per night (USD)Expedia
From $272 per night (USD)VRBO
Ski Getaway! Mtn views. Close to Pleasant Mtn, Mt. Abram’s and Sunday River
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
( More pics to come) Your Harrison adventure begins at this terrific 1-2 bedroom house. Guests will find a cozy bedroom ...
From $272 per night (USD)VRBO
From $311 per night (USD)Expedia
Renovated Exchange St. Loft w/Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This renovated loft-style condo is right in the heart of the Old Port. Located on Portland`s bustling Exchange Street, t ...
From $311 per night (USD)Expedia
From $347 per night (USD)VRBO
Cozy Two Bedroom on Munjoy Hill
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This cozy first floor 2 bedroom apartment is close to everything the Portland Peninsula has to offer, making it easy to ...
From $347 per night (USD)VRBO
From $487 per night (USD)Expedia
Post and Beam House on Three Wooded Acres on Chebeague Island
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This post and beam house style barn structure offers a quirky blend of island vibe: furnished with log furniture, antiqu ...
From $487 per night (USD)Expedia
From $478 per night (USD)VRBO
Relax & Recharge at the Tranquil Bubbling Brook Ranch
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Bubbling Brook Ranch, a cozy home near Long Lake and Bridgton’s charming downtown. Set beside a peaceful ...
From $478 per night (USD)VRBO
From $191 per night (USD)Expedia
Sunny House, By The Beach, Minutes From Portland
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 3 bedroom home, with ample space in South Portland, Maine. 10-minutes from the hospital, downtown Portland, Hi ...
From $191 per night (USD)Expedia
From $265 per night (USD)VRBO
South Portland Beach area rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Clean, comfortable, and perfectly located—this 1 bed, 1 bath coastal retreat sits just steps from Willard Beach. Enjoy t ...
From $265 per night (USD)VRBO
From $461 per night (USD)VRBO
A home away from home!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Nestled in Naples, this tremendous house offers a perfect retreat for guests seeking comfort and space. With two cozy be ...
From $461 per night (USD)VRBO
From $359 per night (USD)VRBO
Newly renovated home with water views in the heart of Bailey Island
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Newly renovated 3 bedroom home on a hill with water views from both sides. Coffee with the sunrise, dinner with the suns ...
From $359 per night (USD)VRBO
From $988 per night (USD)Expedia
Shimmering Cove Retreat
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Discover Shimmering Cove, a year-round waterfront lake home on Sebago Lake in Naples, Maine. This updated property offer ...
From $988 per night (USD)Expedia
From $306 per night (USD)VRBO
The Ultimate Two-Lake Access Bungalow: Peaceful Riverfront Living
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled along the scenic Songo River, this classic Maine retreat offers the ultimate gateway to the Lakes Region, positi ...
From $306 per night (USD)VRBO
From $748 per night (USD)Expedia
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Try something unique? Stay at this little stylish 3 bedroom 2 full bath single family home in downtown Brunswick, walkin ...
From $748 per night (USD)Expedia
From $725 per night (USD)VRBO
Trailside Chalet at Pleasant Mt.
- Bedrooms:
- 4
- Bathrooms:
- 1
- Sleeps:
- 12
Enjoy summer at this modern trailside retreat at Pleasant Mountain Ski Area. Surrounded by nature, this light-filled cha ...
From $725 per night (USD)VRBO
From $885 per night (USD)Expedia
NEW FOR 2026! Spacious Long Lake Home – Peaceful Retreat for Families of 8
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
NEW FOR 2026! This spacious five-bedroom home in Bridgton, Maine, sits above Long Lake and offers beautiful elevated vie ...
From $885 per night (USD)Expedia
From $837 per night (USD)VRBO
Historic Home • Room to Gather • Off-Street Parking • 10Min to Old Port
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Set within a beautifully restored Victorian duplex, we purposefully designed The Cornerstone to bridge the gap between t ...
From $837 per night (USD)VRBO
From $235 per night (USD)VRBO
Sebago Lake cozy cabin!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This 1-bedroom cabin is perfect for your escape to Sebago. Inside, guests find open concept living and included a charmi ...
From $235 per night (USD)VRBO
From $299 per night (USD)VRBO
The Yellow Cottage is a 2-bedroom little getaway located right on its own private beach.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the Yellow Cottage ! Your Private-Beach Escape on Casco Bay Perched in one of Bailey Island's most desirable ...
From $299 per night (USD)VRBO
From $493 per night (USD)VRBO
Peaceful Frye Island Stay – Cozy Family Comfort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Escape to Sebago Serenity, a cozy and family-friendly retreat on scenic Frye Island! This charming lake home offers two ...
From $493 per night (USD)VRBO
From $730 per night (USD)VRBO
WATERFRONT ON SEBAGO LAKE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
OCCUPANCY LIMIT 8 - 3 bedrooms and 2 baths with sleeping space in the basement. 3 bedrooms and one bath on the main flo ...
From $730 per night (USD)VRBO
From $565 per night (USD)Expedia
Gorgeous 3-bedroom house in charming Portland
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this charming house in Portland that has its own backyard, bqq, and large deck. With three cozy bedrooms feat ...
From $565 per night (USD)Expedia
From $134 per night (USD)VRBO
West End 2 Bedroom
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in Portlands historic West End, this furnished 2-bedroom, 1-bath apartment sits on the second floor of a small, ...
From $134 per night (USD)VRBO
From $1432 per night (USD)VRBO
Island View on Sebago Lake
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Lakefront living is awaiting! Island View is a newly updated home that sits on 100 feet of sandy shore frontage on Sebag ...
From $1432 per night (USD)VRBO
From $293 per night (USD)VRBO
Wooded Retreat w/ Pet-Friendly Yard in Standish
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Recently Built | On 3 Acres w/ Surrounding Wildlife | 7 Mi to Sebago Lake Modern convenience and country serenity aboun ...
From $293 per night (USD)VRBO
From $669 per night (USD)VRBO
Charming 3-bedroom cottage on the water with private dock in Freeport
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This 3-bedroom cottage is perfect for your escape to the coast of Maine! Cottage is appointed with 3 bedrooms and sleep ...
From $669 per night (USD)VRBO
From $301 per night (USD)VRBO
Serene cottage with a spectacular view on charming Bailey Island.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cross over the iconic Cribstone Bridge and escape to the beauty of Bailey Island in this charming one-bedroom cottage, p ...
From $301 per night (USD)VRBO
From $891 per night (USD)Expedia
New and Spacious Family Home Close to Sebago Lake
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
Summary: Full of light and thoughtful touches, this giant five bedroom home is perfect for your Sebago Lake getaway. Sp ...
From $891 per night (USD)Expedia
From $474 per night (USD)VRBO
Cozy Family Home w/ Beach Access
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Complete remodel with access to a private beach, boat ramp, and dock. This charming open floor plan ranch feat ...
From $474 per night (USD)VRBO
From $536 per night (USD)Expedia
Fully Updated Lake View Home on Thomas Pond
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Full of light and thoughtful touches, this lake view home on Thomas Pond is perfect for your Sebago Lake getaw ...
From $536 per night (USD)Expedia
From $268 per night (USD)VRBO
Ocean Views / 2BR King Beds / Pet-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
About this space Discover this stunning 3rd-floor penthouse offering breathtaking panoramic views of Casco Bay. Perfectl ...
From $268 per night (USD)VRBO
From $368 per night (USD)VRBO
Walk to East End Beach / 2BR King Beds / Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
About This Space Luxury Retreat! Discover this stunning 2nd floor condo with modern living amenities. Perfectly located ...
From $368 per night (USD)VRBO
From $395 per night (USD)VRBO
Munjoy Hill 2BR / King Beds / Pet-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Luxury Retreat! Discover this stunning 1st floor condo with modern living amenities. Perfectly located in Portland’s vi ...
From $395 per night (USD)VRBO
From $2759 per night (USD)VRBO
Stunning 6BR Luxury Retreat King Beds Ocean Views
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to 46 Turner Street, a rare East End gem. Rent all three modern 2-BR condos together—6 bedrooms, 6 king beds, 1 ...
From $2759 per night (USD)VRBO
From $442 per night (USD)VRBO
Experience Portland’s charm in this beautifully restored 2-bed, 1.5-bath Victorian apartment! Located downtown, enjoy modern comforts, historic elegance, a private backyard, AC, and 1 free parking spot. Perfect for your Maine getaway! 🦞
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your historic Portland oasis! Nestled on State Street in the heart of downtown, this stunning first-floor Vic ...
From $442 per night (USD)VRBO
From $530 per night (USD)Expedia
Stillhouse: Serene sanctuary in coastal Maine
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Stillhouse is a sanctuary located in coastal Maine. Seated in a beautiful little cove, this property is nestled amongst ...
From $530 per night (USD)Expedia
From $344 per night (USD)VRBO
Newly renovated 3 BR beachfront w/ panoramic view of Sebago Lake, Raymond, ME
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Newly renovated beachfront property w/ panoramic view of Sebago Lake, Raymond, ME. Two bathrooms, 3 BRs, w/ 3 queen beds ...
From $344 per night (USD)VRBO
From $381 per night (USD)Expedia
4-Bedroom Condo Steps Away from Moose Pond & Pleasant Mountain Ski Resort!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This beautiful, well-appointed 4-bedroom condo on Moose Pond in Bridgton offers the perfect year-round getaway. Enjoy th ...
From $381 per night (USD)Expedia
From $1369 per night (USD)VRBO
Oceanfront Cottage on Casco Bay in Yarmouth
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Introducing The Cottage on Casco Bay, North & Nautical’s newest luxury vacation rental in Yarmouth. Explore this fully r ...
From $1369 per night (USD)VRBO
From $461 per night (USD)VRBO
Lakefront, newly renovated cottage perfect for a Maine summer getaway
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our Cottage in Casco. Newly renovated, it offers a charming yet modern atmosphere throughout. Whether you’re ...
From $461 per night (USD)VRBO