
House vacation rentals in Winthrop
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Quick stats about house rentals in Winthrop

Total vacation rentals
Explore 30 vacation rentals in Winthrop

Nightly prices starting at
Winthrop vacation rentals start at G$25,099 GYD per night before taxes and fees

Verified guest reviews
Over 810 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Winthrop vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winthrop rentals

4.9 Average rating
Winthrop stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated house rentals in Winthrop
Guests agree: these houses are highly rated for location, cleanliness, and more.

Privacy, River, Pond, A frame Hot Tub EPIC Views,
14 Acres Secluded A-frame nestled along Clean Crooked River, Hot tub with breathtaking VIEWS and world-class fishing. Swim in the river, private pond or explore hiking trails right from your door. Central AC - Gas Fireplace - Modern Kitchen. Just minutes from pristine lakes, primo golf courses, and thrilling ski slopes, this charming private oasis offers an ideal mix of tranquil relaxation and outdoor adventure. Invite a private chef, florist or yoga teacher to fully unwind. Heated bath floors.

Quiet Lakefront Home, Private Dock!
Spacious four-season lakefront camp on peaceful Dexter Pond in central ME. Enjoy great fishing, canoeing, stand-up paddle boarding, kayaking, or relax and watch the sunsets and loons from the large porch overlooking the pond. The home is in a great location close to Winthrop Center and Wayne (10 mins to local grocery store/ farmers market) 30 mins to Augusta/airport. Many hiking trails nearby and lots of other areas to explore. It's beautiful in all seasons. Private dock, firepit, and laundry!

Moss House: A Modern Waterfront Cabin in the Woods
Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Spacious Lakeside Comfort - Fall/Winter Wonderland
This spacious home is just steps from the shore of Anabessacook Lake. Here you will enjoy the comfort and luxury of a well-equipped house, surrounded by the best of what Maine has to offer. The Red Top House features an incredible stone fireplace, large screened porch, and stone patio with outdoor fire pit. Bedrooms are comfortable with water views. The kitchen is very well equipped for the whole family. Rental includes use of non-motorized boats and firewood. Ice fishing is steps away!

Riverside
Overlooking Kennebec River, Riverside is a perfect setting. Open 365 days per year; 2BR, 1 BA, kitchen, DR/common area. Situates 4 comfortably, 6 with the use of couches, 8 with added use of floor mattresses. Renovated, open concept, our home is wheelchair accessible. We accept Service dogs and will consider family dogs and other pets on a case-by-case; please ask. Owners reside on property in separate building. Outdoor trail cameras and AOSU cams in use to monitor exterior of residence only.

Carriage House
Renovated circa 1920 carriage house in a quaint New England college town. Eight-minute walk to busy downtown with restaurants, bars, shops, and grocery store. Elegant contemporary style. Open concept downstairs with sofa, daybed (napping in the sun!), and chef-designed kitchen. Second level with two queen beds and small balcony. Adjoins miles of walking trails and forest, full of wildlife. Less than 5-minute drive to a 1.5 mile running trail along the Sandy River, with refreshing swimming.

Brook Ridge Retreat
Work, play, & relax at Brook Ridge Retreat! Come visit your Colby or Thomas College student and have the comforts of home. Do some grilling or cook up a favorite meal in the full kitchen. Remotely connect to work or school at our custom-made desk and dedicated office area with wireless printer and available computer monitor. Splash in the brook or in the basin, and sit under the waterfalls. WiFi, firepit, Keurig or french press, electric fireplace, large decks, & big yard.

Hallowell Hilltop Home
Discover this newly renovated 2-bedroom, 1-bathroom home in a quiet family-friendly neighborhood in Hallowell. This home's rustic-modern design, natural light, and all-new amenities make it a perfect getaway. Relax in the hot tub, grill on the deck, enjoy the backyard or visit downtown Hallowell and explore its restaurants, cafes, live music and antique shops. This home is also minutes away from several hiking and walking trails that can all be found in our guidebook.

The Barnhouse with hot tub
Get away with your whole family at this peaceful home in the country. Hear the frogs chirping in the pond, birds tweeting in the treetops and watch chickens roam around. Enjoy the clear, starry nights while relaxing in the hot tub or cozying up by the fire. Centrally located between coast and mountains. Head a hour north to take the family hiking or on the slopes to enjoy the mountains. Head 40 minutes south to take in the coast and see the iconic Maine lighthouse.

Luxury Timber Frame Home | On the Water
Escape to Serenity at Timber House Maine, surrounded by tranquil conservation land on the shores of Little Cobbosseecontee Lake. Our stunning 4,500 sq. ft. timber home features 3 stories of windows flooding the space with natural light. With 4 bedrooms, 3 bathrooms, cozy modern bohemian decor, and direct waterfront access for boating and kayaking, it is the perfect lakeside getaway! Enjoy our playroom with ping-pong, air hockey, basketball, and board games.

Sunny Artist’s Home Filled with Plants
A classic 1920s Maine bungalow lovingly renovated. Our plant-filled home is an Auburn favorite. Guests love the original artwork and cozy touches that make this a home. Unwind in our sunlit yoga studio - ideal for meditation, painting, or movement. Whisper-quiet heat-pump HVAC plus a hybrid water heater for eco-friendly year-round comfort. 5 min to Bates, 40 min to Portland, Brunswick, Bath, and Freeport - the ideal central Maine retreat.

Beautiful Maine Lakeside Cottage
This beautiful cabin on the Lake is perfect for fun and relaxation, including swimming, kayaking, fishing, and more. Enjoy your morning coffee on the enclosed porch overseeing all of the beauty that Maine has to offer, with beautiful lakeside sunsets in the evening. Two complimentary kayaks and life vests are provided. The Vista winery is just 2 miles away and offers amazing views and drink selections.
Popular amenities for Winthrop house rentals
House rentals with a pool

Faith Lane with community pool

Pleasant River 3 bed | 2 bath, Hot Tub

Coastal Retreat with Pool and Cheerful Vibes

Cozy Riverside Cottage

House in the woods

Farmhouse: Hot Tub, Mini Golf, Pickleball, POOL

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

The Getaway - A River Paradise
Weekly house rentals

Large Private Lakefront Home with outdoor Hot Tub

2 Acre Waterfront w/Canoes & Kayaks, Game Room

Lakefront Peninsula Home | 4BR with Private Dock

July 7-14 Available: Large Porches & Living Space!

2 BR Waterfront house with stunning view.

Perfect Maine retreat!

Your Trail's End in Maine

Sandy Beach on Cobbosseecontee Lake!
Private house rentals

The Little Castle

Mountain Escape | Views • Firepit • Near Sugarloaf

Maine Coastal Retreat

Maine Carriage House

Cozy Modern Mountain Cabin~

The Loon's Nest - Guest Lodge

Five Islands Waterfront Retreat

Cobbossee Lake House - Waterfront
Destinations to explore
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- Rentals with lake access Winthrop
- Rentals with a kayak Winthrop
- Family-friendly rentals Winthrop
- Rentals with a fire pit Winthrop
- Waterfront rentals Winthrop
- Rentals with a washer and dryer Winthrop
- Pet-friendly rentals Winthrop
- Rentals with outdoor seating Winthrop
- Rentals with a patio Winthrop
- House rentals Maine
- House rentals United States
- Sebago Lake
- Sunday River Resort
- Popham Beach, Phippsburg
- Willard Beach
- Pemaquid Beach
- East End Beach
- Pemaquid Point Lighthouse
- Popham Beach State Park
- Coastal Maine Botanical Gardens
- Wolfe's Neck Woods State Park
- Pleasant Mountain Ski Area
- The Camden Snow Bowl
- Rockland Breakwater Light
- Maine Maritime Museum
- Portland Museum of Art
- Bradbury Mountain State Park
- Farnsworth Art Museum
- Bug Light Park
- Mt. Abram
- Grafton Notch State Park
- Camden Hills State Park
- Cellardoor Winery
- Maine Lighthouse Museum
- Maine Mineral & Gem Museum





