House vacation rentals in Winthrop

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Top-rated house rentals in Winthrop

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

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Guest favorite

The welcoming living area includes a wooden dining table adorned with a vibrant flower arrangement. A cozy seating area features a patterned armchair and a large window allowing natural light. Exposed wooden beams enhance the warm character of the space.

Home in Falmouth

4.89 out of 5 average rating, 247 reviews

Amazing Bay View Home with Hot Tub

This enchanting 2-bedroom home is a coastal dream come true! Luxurious and well-appointed, Casco Bay House sleeps up to six, provides a five-star stay, offers all of the comforts of home AND a relaxing hot tub spa. With stunning views of the water, the house also has easy access to dining, shopping, and sightseeing in Portland's lively Old Port district (just 5 minutes away). Whether you seek quiet tranquility or want to hit the town, this waterside house is the perfect home away from home!

Top guest favorite

A light-filled entryway features a staircase leading down to an open space. A wooden dining table is set beside large windows offering views of the exterior greenery. A wall clock hangs near the doorway, adding a touch of practicality to the modern design.

Home in Windham

4.94 out of 5 average rating, 126 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.

Superhost

A fire pit is positioned near the water's edge, surrounded by two adirondack chairs. The setting sun reflects off the river, casting warm hues across the sky and water. Green trees frame the tranquil scene, creating a peaceful atmosphere.

Home in West Bath

4.85 out of 5 average rating, 102 reviews

Oak Leaf

Take it easy at this unique and tranquil getaway. This sweet cottage offers scenic water views and much more. Overlooking the New Meadows river, it is nestled in a quiet area and surrounded by 100 yr old oak trees. It is loaded with charm yet offers modern amenities. You feel tucked away, yet the place is only 10 to 20 minutes from beautiful beaches, hiking, fine dining, and shopping opportunities. Enjoy beautiful sunsets from the back porch and cozy up to fire pit while you make memories.

Superhost

A screened-in porch features comfortable seating, including rocking chairs, and a coffee table. Views of the peaceful lake and lush greenery are visible through large windows. Natural light enhances the relaxing atmosphere, inviting moments of leisure while enjoying the scenic surroundings.

Home in Litchfield

4.92 out of 5 average rating, 134 reviews

Beautiful lake house on Tacoma Lakes near Coast

Beautiful 4BR on Tacoma Lakes 50' from water, amazing views Screened in Porch w/peaceful views 3 spring fed lakes joined by 2 bridges Private dock Bring your boat or local company can rent/deliver motor boat Canoe/2 Kayaks Wifi/3 SmartTV/Alarm System FirePit, Gas Grille, Lawn Chairs Shuffleboard table Washer/Dryer Provided: linens/towels/soap/shampoo/detergent NO SMOKING-NO PETS-NO SHOES INSIDE (please) *Must sign separate water front liability waiver after booking No cameras inside or out

Guest favorite

Four colorful Adirondack chairs are arranged in a row on a grassy area overlooking the lake. The vibrant orange and turquoise chairs provide a comfortable seating option, while the calm lake and distant trees are visible against a clear blue sky.

Home in Buxton

4.88 out of 5 average rating, 126 reviews

Charming 4 bedroom lake front, with private beach

Will not consider less than weekly rentals for July and August and the last week in June.The house sits 80 ft off the lake. It has over 150 ft of lake shore and own private beach. We supply several kayaks paddle boards canoes and tubes . You will be required to sign a waiver to use them and you Must wear lifejackets .The home is located down a private gravel road .We are only 20 miles from the city of Portland, Old Orchard beach, Lake Sebago. Come explore and relax. 2 hours from Boston

Top guest favorite

A serene outdoor patio features a functional hot tub surrounded by snow. Soft blue lighting emanates from the hot tub, while a small fire pit is framed by two cozy chairs. The fenced area includes a door leading to the house and festive string lights adding warmth.

Home in Portland

4.97 out of 5 average rating, 218 reviews

Stunning & Spacious 6BR Waterfront House + Hot Tub

A charming craftsman-style home with beautiful water views, comfort, and character! This house features six bedrooms, three bathrooms, ample common spaces, and a fully outfitted kitchen. Hardwood floors and original trim add warmth and charm to the space, and modern updates ensure a comfortable stay. Just minutes from Portland's Old Port, the house commands sweeping water views of Casco Bay and the Presumpscot River. Guests will enjoy the hot tub, private patio, yard and plenty of parking.

Guest favorite

A modern, two-story home is set against a backdrop of trees, featuring large windows that invite natural light. A spacious deck extends out, with multiple wooden chairs arranged in the foreground to create a welcoming outdoor seating area.

Home in Oakland

5 out of 5 average rating, 24 reviews

Peaceful 5 bedroom 4.5 bath waterfront house

This newly built (2021) Colonial has over 75 ft of shore frontage adjacent to the hosts 6 bedroom Cape Cod style house. Centrally located minutes from Intersate 95 and Colby College , Thomas college, and other Belgrade lakes destinations. Bar Harbor and Acadia National Park are only a couple hour drive through scenic countryside. In the winter you can ice fish, cross country ski, snowmobile, or enjoy the quite of the lake. Sugarloaf and Sunday River ski resorts are a 60 minute drive.

Top guest favorite

A wooden deck leads down to a sandy beach, surrounded by lush greenery. Several blue Adirondack chairs are positioned for relaxation, with steps providing access to the beach area. The lake house is visible in the background, framed by tall trees and a clear sky.

Home in Harrison

5 out of 5 average rating, 6 reviews

2BR Lake House on Private Beach w/hot tub & sauna

Romantic getaway or peaceful family vacation, this lake house is right on a private beach, and perfect all year round!The beach is literally your back yard! Experience beautiful views while enjoying a cozy outdoor fire. Relax and take amazing sunset pics in the covered hot tub, or unwind indoor w/the sauna and fire place. Cook up a delicious meal in the fully stacked kitchen. Centrally located near hiking trails, and 45min from North Conway outlets. Book now and make memories! ✨

Guest favorite

Home in Harpswell

4.96 out of 5 average rating, 25 reviews

Charming, Victorian-Era house, Ocean Views

Located on Harpswell Neck, on the picturesque Coast of Maine, this 5 bedroom, 2 bath custom, newly renovated home sleeps 8 comfortably, with one king bed, and 3 queen beds~ Come enjoy our delightful, Victorian Era Estate, perched on a hill, with stunning ocean views, located in the highly sought-after Pott's Point neighborhood ! The elegance of this property will certainly delight you and your guests. The westerly water views over Pott's Harbor will be sure to please !

Guest favorite

A dining area is illuminated by natural light, featuring a dark wooden table with a decorative centerpiece of fruit. Large windows offer a view of the water and nearby boats, while comfortable seating is arranged alongside the table.

Home in Cushing

4.95 out of 5 average rating, 131 reviews

Dockside Retreat - 2025 booking quickly

This beautiful, newly renovated home is three bedrooms and two bathrooms, with an open living and dining room waiting to give your family or group of friends the ideal Maine vacation experience! On site parking, a lovely yard, a new sauna on a beautiful deck overlooking the water, nearby fields and steps away from the famous Olson House on one side, you can sit on the deck and overlook the working lobster wharf with fishermen coming and going daily on the other side!

Guest favorite

A historic house with a charming exterior is set amidst lush green lawns and colorful trees. A stone pathway leads to the entrance, flanked by well-maintained shrubs. A spacious front porch is adorned with a stylish railing and seasonal decorations.

Home in Bethel

5 out of 5 average rating, 62 reviews

Dream Vacation Home - Full Amenities & Hot Tub

The Bingham House in Bethel / Sunday River is the ultimate vacation home to meet all your needs. Sleeps up to 18 people in 6 bedrooms, 6 bathrooms. Full service amenities include: wifi, 10 HD TVs with premium cable (including HBO), 8-person hot tub, fire pit, billiards room, bar w/ wine fridge, game room, elevator, full kitchen & walk-in pantry, gas grill, fireplaces, parking, free shuttle to Sunday River, crib + high chair + booster seat

Superhost

Home in Greenwood

4.97 out of 5 average rating, 109 reviews

Lakeside getaway for 6 by Sunday River!

Located along Main Street, this beautifully restored lake front home had a private dock and yard facing the lake. Come enjoy summer on the lake with our canoes, kayaks and corn hole. In the winter come to ice skate in the front yard and ski at Sunday River (20mins) or Mt Abrams (5mins). House offers high speed internet, a smart TV and modern amenities. Custom dining nook, custom kitchen and modern, yet cozy finishes throughout.

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What guests are saying

Newly renovated 3BR house w/ stunning ocean views

4.98 out of 5 average rating, 83 reviews1 month ago

Jennifer was responsive and helpful. The house is great. It is the most well furnished home (I want that kitchen) we have rented, and my girlfriend group and I get away twice a year. Beautiful ocean view from two bedrooms, but easy walk to the beach. Cool to see two lighthouses in the distance and the gorgeous moon shining on the water. Very interesting shoreline, and also a nice walk to Fort Popham. Lots of room in this very comfortable air b and b, and that rain shower water spout in the downstairs bathroom is amazing. This nearby area is quintessential Maine.

Home in Phippsburg

What guests are saying

Mountain Views | Hot Tub | 3 mins to Sunday River

4.93 out of 5 average rating, 43 reviews3 weeks ago

Beautiful place and location! We had a smaller group so the house was very spacious, comfortable, we all felt at home. Everyone had their own room. It was the perfect weekend for our last ski trip of the season. We got snow and plowing was taken care of. It was definitely a weight off our shoulder that we didn’t have to worry about that. The restaurants in the area were great! Food and live music! Smooth check in and out process. Recommend this place highly! Would love to come back and see how it is in the summer, but most definitely would love to come back in the winter! :D

Home in Newry

What guests are saying

Log Cabin 15 acreshunting* snowmobile*skiing

4.75 out of 5 average rating, 20 reviews3 months ago

great place for a group of friends to get away from the city ! hot tub was spacious, pool table was a great addition to the house, and the large property was awesome for exploring the woods. overall, 10/10 would definitely come back !! only downside, there were only 11 forks for 12 guests !

Home in Otisfield

What guests are saying

Ocean Paradise Sunrise/Sunset Peaks Portland

5 out of 5 average rating, 47 reviews1 month ago

A beautiful location, quiet, peaceful. House was loaded with everything you need to cook on an otherwise low traffic and amenities island. The beds and mattresses were outstanding, bed sheets and towels 'fist class!' Ther TV had several options for watching viewer programs and movies. And Lisa/Scott had cabinets for full of other items for usage although we came well stocked and did not need to use any of them. Scott was very helpful upon arrival and responded to requests in a very quick manner. All in all, a senstional spot if you're looking to get away for rest and relaxation. The ocean waves lull you to sleep each night and all day long. A must visit if your travels take you to Maine. quick ferry ride, easy to access.

Home in Peaks Island

What guests are saying

NEW! Serenity Escape: Countryside Retreat/HOT TUB

5 out of 5 average rating, 13 reviews1 month ago

This place for was perfect for our ski trip. The home had plenty of beds for all of us and enough room for us to all hang out. The hot tub was an excellent addition to relax after a long day of skiing. The house is very private and gives that secluded feeling. Overall, we loved the house and would totally stay again.

Home in Harrison

What guests are saying

Modern Lake Front Home with Hot Tub

4.9 out of 5 average rating, 70 reviews1 month ago

Spenser's place was pretty perfect for our needs. Loved the hot tub, lots of towels, lots of kitchen supplies and room for the 7 of us. Would suggest have a few more chairs for the dining room since the home can fit 8 people. We just took a chair from the deck, which was fine. There were a lot of flies just hanging out with us, a few lady bugs too. The many flies were slow, so easy to catch. But still 5 stars! Thanks so much!

Home in Liberty

What guests are saying

2023 Build - Under 10 Minutes To Sunday River

4.87 out of 5 average rating, 30 reviews1 month ago

Alex’s house was great for a large group - big kitchen, dining and living room. It was a central place for us to all hang out on a weekend where we weren’t able to do a lot of skiing. Alex was very responsive to any questions we had regarding finding the house, trash, etc. the bedrooms were large and comfy. Hot tub was an added bonus for the winter weather!

Home in Bethel

What guests are saying

#1 View in Maine, Theater, HTub, Xbox, Golf, Lake

5 out of 5 average rating, 87 reviews3 days ago

A true gem! Its impossible not to be impressed by the mountain views that this place offers, for me it's one of a kind! You can see they care a lot about the house, the movie theater is a lot of fun and adds a lot to the house, the rooms are spacious and comfortable, the arcade and the hot tub are the cherry on top. The host was nice and responsive the whole trip! I would love to come back and spend more time in this amazing home! Don't think twice, just book it

Home in Woodstock

What guests are saying

Ahhh, Sweet Maine! Your Perfect Vacation Awaits!

4.9 out of 5 average rating, 21 reviews7 months ago

Pete and Jen’s place was exactly what we needed! Friends were getting married at the 1774 House and this home was only a 10 minute drive from the venue! We loved the fact that all 9 of us could stay in the same place. One of our favorite places at the property was the covered outdoor porch, where we drank coffee in the mornings and played card games! Would definitely recommend Pete and Jen’s home to people visiting the area!

Home in Phippsburg