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Waterfront vacation rentals in Cumberland County

Find and book unique waterfront accommodations on Airbnb

Top-rated waterfront accommodations in Cumberland County

Guests agree: these waterfront accommodations are highly rated for location, cleanliness, and more.

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Treehouse in Sanford

4.9 out of 5 average rating, 486 reviews

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Guest favourite

Cottage in Topsham

4.94 out of 5 average rating, 245 reviews

Cozy waterfront home on Merrymeeting Bay.

Our cozy cottage is the perfect romantic getaway or quiet retreat in any season. Located on a private rd with scenic waterfront view. Guests can enjoy sitting on the dock (May- October) or the jetty, watch the eagles and Osprey, use our kayaks, do some fishing, walking or biking. Sit by the propane fueled fireplace on a chilly night. Brunswick, home of Bowdoin College and a # of great restaurants and unique shops is just 5 mi. Travel by bus or train to/from Boston. Portland is @ 30 min away.

Guest favourite

Tiny homes in Windham

4.98 out of 5 average rating, 139 reviews

Private riverside retreat

Private tiny house situated on the Pleasant river in Windham Maine surrounded by woods and nature! River is stocked with brook trout and lots of bass. Canoes are available for guest use to explore the river. The camp is located behind the main property ~500ft down a dirt road. 4X4 is recommended or you can park at the main house and it's a 3 minute walk. House is very comfortable with modern amenities. Running hot water, electricity, smart TV, wifi , firepit, outdoor shower, king sized bed.

Guest favourite

Home in Windham

4.93 out of 5 average rating, 116 reviews

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Guest favourite

Guest suite in Freeport

4.97 out of 5 average rating, 207 reviews

Waterfront Private Apartment just 5 min to LL Bean

Guest apartment with private entrances, king bed, pull out sofa, kitchenette, walk-in shower, and porch facing the water providing the perfect relaxing coastal Maine experience! Custom built home on 7.5 acres tucked away in the woods with waterfront access to Harraseeket Cove & South Freeport Harbor, great for kayaking! Located 5 minutes from LL Bean and Freeport's many shops, restaurants, bars, etc. Wolfes Neck State Park and its stunning coastal trails and forests are less than a mile away.

Guest favourite

Cottage in Brunswick

5 out of 5 average rating, 153 reviews

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering property right on historic Route 24, a busy thoroughfare between Brunswick & the islands of Harpswell. All rooms have ocean views. There is a beach & the dock (May-Dec) is ideal for seasonal fishing, lounging & swimming. Check out our Insta @gurnetvillage for photos & calendar release dates

Guest favourite

Home in Oxford

5 out of 5 average rating, 197 reviews

The Modern Lakehouse

This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.

Guest favourite

Apartment in Gray

4.94 out of 5 average rating, 123 reviews

Two bedroom duplex across st from crystal lake

Relax, have fun, spend quality time with friends and family right here at our quiet little place. Two bedrooms, three beds, one pull out couch, we can accommodate up to six guests. We have walking trails, firepit, and a barbecue area. The house sits across the street from crystal lake, with a boat launch 3/4 mile down the road with a parking area. An easy 20-minute drive to Portland. Supermarket, gas station, and restaurant less than five minutes away and ten minutes from Gray exit to 95.

Guest favourite

Tiny homes in Bowdoinham

4.91 out of 5 average rating, 107 reviews

Sweet Fern Cabin on Merrymeeting Bay

Nestled in the woods on 2.5 waterfront acres where the Muddy River meets Merrymeeting Bay. The cabin is 350 square feet of simple living with a panoramic view. There is a three season hot water outdoor shower and wood burning stove with plenty of wood included. Kitchen is fully stocked with cooking supplies and has off grid cold water sink. Outbuilding with composting toilet is right out the back door. Kayaks and stand up paddle board are available to rent for an additional fee.

Guest favourite

Cabin in Freeport

4.97 out of 5 average rating, 502 reviews

Cozy Cottage-Near Harbor & Park

Bailiwick Cottage is a cozy, private cottage that looks south down Freeport (Harraseeket) Harbor in Freeport, ME. It is a 4 season accommodation that is close to Freeport shopping, Portland eating, and the Adventure Schools of LL Bean. The cottage sits approximately 50 yards from our main house, has its own parking space and patio, and offers the ability to come and go as you wish. We have had 12 honeymoons in the cottage. Freeport Registration # STRR-2022-59

Guest favourite

Cottage in Gray

4.9 out of 5 average rating, 200 reviews

Sunset Haven - Little Sebago Lake

Sunset Haven is a beautiful 3BR, 1.5 bath year round lakeside cottage on Little Sebago Lake in Gray, Maine. It boasts a private beach and water frontage in the heart of Maine's Sebago Lakes Region. Located only about half an hour max from Portland, Maine and the Atlantic coastline, approximately an hour or less from Shawnee Peak and the Sunday River Ski areas, 40 minutes from Oxford Casino, this area is truly a great destination for four season recreation.

Guest favourite

Barn in Portland

5 out of 5 average rating, 430 reviews

Garrison Cove Studio

Rare, Portland waterfront studio located in the heart of the historic Stroudwater neighborhood, awaits one or two guests looking for an urban hideaway. The newly created studio occupies a 150 year old post and beam barn situated on the banks of the Stroudwater and Fore Rivers. Enjoy morning coffee on the river swing, meditate to the soothing sound of the nearby waterfall or linger over your favorite glass of wine under the splendid backyard grape arbor.

Vacation rentals for every style

Get the amount of space that is right for you.

Houses

A space that's all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Cumberland County waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Guest favourite

Apartment in Cape Elizabeth

4.98 out of 5 average rating, 107 reviews

Beautiful Kettle Cove Apt Steps to Beaches

Guest favourite

Apartment in Old Orchard Beach

4.91 out of 5 average rating, 183 reviews

Beachside Penthouse Paradise on Old Orchard Beach

Guest favourite

Apartment in Orr's Island

4.92 out of 5 average rating, 120 reviews

Shore House, Posey Unit - Ocean Front Property

Guest favourite

Apartment in Portland

4.91 out of 5 average rating, 139 reviews

Downtown Walker Paradise! Free Parking!

Guest favourite

Apartment in Portland

4.95 out of 5 average rating, 103 reviews

"Henry" Penthouse Waterfront Suite

Guest favourite

Apartment in Freeport

4.98 out of 5 average rating, 265 reviews

Beekeeper's Cottage- Peaceful,Quiet - Ocean Front

Apartment in Portland

4.78 out of 5 average rating, 263 reviews

Parkside Retreat on Portland's Eastern Promenade

Guest favourite

Apartment in Portland

4.99 out of 5 average rating, 695 reviews

Old Port / Parking / Patio

Waterfront house rentals

Guest favourite

Home in Freeport

5 out of 5 average rating, 27 reviews

Waterfront Cottage in Freeport

Guest favourite

Home in Limerick

4.93 out of 5 average rating, 115 reviews

Lakefront Getaway

Guest favourite

Home in Gray

4.97 out of 5 average rating, 33 reviews

Little Sebago Lakefront Getaway

Guest favourite

Home in Bridgton

4.98 out of 5 average rating, 106 reviews

Fish Tales Cabin

Guest favourite

Home in Raymond

5 out of 5 average rating, 13 reviews

Cozy Cottage on Big Sebago Lake

Home in Freeport

4.85 out of 5 average rating, 261 reviews

Home On Pond in Woods - Guest Suite

Guest favourite

Home in Windham

4.93 out of 5 average rating, 27 reviews

Lakehouse on Highland Lake

Guest favourite

Home in South Portland

4.91 out of 5 average rating, 116 reviews

Cottage style home 2 blocks from the beach!

Waterfront condo rentals

Guest favourite

Condo in Old Orchard Beach

4.9 out of 5 average rating, 394 reviews

Luxury Beach Front Condo! Prime Location!

Guest favourite

Condo in Old Orchard Beach

4.88 out of 5 average rating, 93 reviews

Oceanfront Condo with Awesome Views

Guest favourite

Condo in Portland

4.93 out of 5 average rating, 14 reviews

Eastern Prom 2 Bed w/ Stunning Views of Casco Bay

Condo in Old Orchard Beach

4.64 out of 5 average rating, 102 reviews

Oceanfront condo with Breathtaking view remodeled

Guest favourite

Condo in Portland

4.89 out of 5 average rating, 180 reviews

Rustic Downtown Duplex with Private Deck

Guest favourite

Condo in Old Orchard Beach

4.83 out of 5 average rating, 84 reviews

The Brunswick

Guest favourite

Condo in Old Orchard Beach

4.72 out of 5 average rating, 116 reviews

Attractive 1 bedroom cabin only 50 ft from beach#1

Guest favourite

Condo in South Portland

4.95 out of 5 average rating, 161 reviews

Rustic Willard Beach condo ten mins from Old Port!

Destinations to explore