Cottage vacation rentals in Cumberland County

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Top-rated cottage rentals in Cumberland County

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Cottage in Windham

4.91 out of 5 average rating, 85 reviews

Tranquil waterfront cottage

A private clean tranquil cottage, dock, parking, deck, grill, hammock, kitchen & all amenities, bathroom, 2 bedrooms, sleeps 5, futon, WIFI, cable, bidet, washer & dryer, granite outdoor table, kayaks, paddle boards, floats, fire pit and fireplace. Minutes from great restaurants, bars, hiking trails, and shopping. The most amazing sunsets. 30 minutes from Portland. Winter rentals as well. 40 min. from Shawnee Peek, 1 mile from Seacoast tubing. This place is privately yours. Smoke free please!

Guest favorite

A wooden dock extends into calm waters, flanked by greenery. Two Adirondack chairs are positioned at the end of the dock, providing a serene spot for relaxation and waterfront views. Sunlight reflects off the water under a clear blue sky.

Cottage in Topsham

4.93 out of 5 average rating, 249 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.

Superhost

A cozy fire pit area is surrounded by several white Adirondack chairs and black wire stools. Warm light strings hang overhead, creating a relaxed atmosphere. In the background, a pond is visible with a kayak on the shore and trees providing natural privacy.

Cottage in Lyman

4.82 out of 5 average rating, 101 reviews

RK North : All season Waterfront cottage with dock

Waterfront get away !You will love the cottage in any season - right on the pond! Enjoy a private dock, swimming and floating right at your door. Relax at the fireplace under twinkle lights , enjoy birdwatching, hiking and swimming during your stay. Lots of ATV and snowmobile trails near by. A close drive to Kennebunkport where your find beach’s , shops and restaurants galore. The cottage has 2 kayaks and a canoe for use during your stay. There are 2 Smart TVs for streaming. Shows and DVD

Guest favorite

A wooden dock extends over calm water, surrounded by lush greenery. A ladder provides access to the water, while a shaded umbrella rests above a seating area. Colorful floats and potted plants enhance the serene lakeside setting.

Cottage in Windham

4.9 out of 5 average rating, 77 reviews

Covered Bridge Cottage - Maine woods and river

Covered Bridge Cottage is on the Presumpscot River. Historic Babb's bridge adjoins the property. This peaceful, secluded woods cottage sleeps 5. Eat-in kitchen, dishwasher, full bath with washer and dryer. Wifi, Sony TV, a/c , heat, weber grill, porch. Use of dock, 2 kayaks, floats, campfire, picnic table, hammock. A wonderful spot to relax and explore the river. Swim in shimmering water. Portland 12 mi., beaches, or Sebago. owner has dog and chickens and lives next door .

Guest favorite

The exterior of the coastal cottage is framed by lush greenery, with a screened porch and a gas grill positioned on a stone path. A manicured lawn enhances the inviting atmosphere, while the cottage features a classic white facade accentuated by a decorative light fixture.

Cottage in Scarborough

4.95 out of 5 average rating, 79 reviews

Pine Point Beach OOB Coastal Cottage Tiny Home

Ask about shorter stays! Privately located at the back of the quiet Rest Point Cottages, this adorable coastal cottage has a screened porch overlooking the Scarborough Marsh that is the perfect place to enjoy morning coffee or a glass of wine after your day in the sun. Spend your days reading, sunbathing & walking along 7 miles of sandy beach, relax in the beautiful shared backyard, and evenings enjoying some of the best restaurants on the east coast, at the Pier or nearby in Portland.

Top guest favorite

A charming cottage is surrounded by lush greenery, with a spacious lawn and soft sunlight filtering through the trees. In the foreground, two blue chairs are positioned invitingly, and a gas grill is set up nearby, enhancing the outdoor living space.

Cottage in Scarborough

4.97 out of 5 average rating, 212 reviews

Bright, clean, private cottage near Higgins Beach!

Nestled amongst the trees and located just 2 miles from beautiful Higgins Beach and just 5 miles to Portland, this recently renovated, sparkling clean, bright, private, stunning cottage is waiting just for you! Your private entrance is just steps away from your parked car. The cottage is 16 x 20 so it's super cozy! We live on the property (so we're here if you need us) but you are 100 feet from us, way out in the backyard. (It's private!) Our location is perfect for your Maine vacation!

Guest favorite

A wooden dock extends over the calm lake water, surrounded by lush greenery and rocks. The distant shoreline is outlined by trees under a cloudy sky, while a buoy can be seen floating in the water, adding a touch of color to the serene landscape.

Cottage in Raymond

4.91 out of 5 average rating, 110 reviews

Relax by a Quiet Lake

Charming lakeside cottage only 29' from the waterline, w/65' of private waterfront. The cottage is a 3-season, classic L.C. Andrews, log-sided Maine summer lake home. Cozy atmosphere and a wonderful enclosed porch with amazing waterfront views. Enjoy fishing off the dock, hiking, canoeing, camp fire, and exploring surrounding areas. Air conditioning units will ensure your comfort on warm summer nights and high-speed internet will keep your devices connected. Furnishings are family mix.

Superhost

A glimpse into the cottage reveals an open living space featuring a cozy seating area and a television. Natural light fills the room through windows, and polished wooden floors enhance the inviting atmosphere. A decorative plant adds a touch of greenery to the scene.

Cottage in Old Orchard Beach

4.94 out of 5 average rating, 298 reviews

#1 Cozy cottage minutes from the beach!

3 night Min. 6/1 to Labor Day. This charming one bedroom cottage is beautifully decorated with a blend of vintage pieces and modern decor, creating a cozy and stylish atmosphere. It features a fully stocked kitchen, complete with pots and pans, perfect for cooking when you choose to stay in. The cottage also includes a private patio with a gas grill and outdoor seating for your enjoyment. Just a short 7-minute walk to the beach and pier. And yes, pets are welcome at no extra charge.

Top guest favorite

Cottage in Brunswick

5 out of 5 average rating, 160 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, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Superhost

A wooden deck overlooking the water is seen, with a table set for breakfast. A coffee mug sits on the railing as the sun rises in the background, casting warm light across the tranquil scene. Trees frame the edge of the deck.

Cottage in Harpswell

4.89 out of 5 average rating, 153 reviews

Classic Maine Cottage - dock, sauna & kayaks

The Perfect Maine Cottage! On the edge of the ocean, carefully preserved with traditional details. Charming, open floor plan, with a wall of windows to the ocean. Sunny large wrap-around deck and screen porch creates beautiful outside spaces to enjoy. Perfect for listening to waves and watch lobstermen pull up their traps. Cathedral ceilings and Scandinavian design gives the cottage an exclusive feeling. Gentle stairs lead to the private deep water dock for all kinds of boating.

Top guest favorite

Cottage in Bridgton

4.9 out of 5 average rating, 235 reviews

Rustic Pebble Cottage in beautiful Bridgton, Maine

Pebble Cottage is a one hundred year old quirky camp that was enlarged some years back. It is located in Bridgton near plenty of lakes and skiing. The public beach is a short skip down the hill. The cottage is a rustic little haven that was saved from demolition, and updated with a brand new bathroom, a cute little kitchen with a dishwasher, with two heat pumps to keep the space cozy and three homey comfortable bedrooms, a large yard with a picnic table, very quiet retreat.

Guest favorite

A charming cottage is nestled among tall trees, framed by a peaceful natural setting. A spacious wrap-around porch is visible, providing shaded outdoor seating to enjoy the surrounding landscape.

Cottage in Bridgton

4.91 out of 5 average rating, 180 reviews

True Maine Artist Cottage with Outdoor Shower

Featured on Huckberry!! Beautifully decorated seasonal artist cottage with brand new soaking tub and outdoor shower. Solo stove fire pit and Adirondack chairs. Huge wrap-around porch with outdoor seating and glorious sunset views across blueberry fields. Also amazing stargazing!! Close to Naples, Bridgton, Sebago Lake. Tons of lakes nearby, hiking, swimming, boating, restaurants, music and local beer! Great place to stay to explore the area or also just relax and hang out.