
House holiday rentals in Winthrop
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Top-rated house rentals in Winthrop
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Popular amenities for Winthrop house rentals
House rentals with a pool

Pleasant River 3 bed | 2 bath, Pool, Hot Tub
Josh's place was great. close to our activities, not far from restaurants. josh was very quick to respond and remedy the only issue we had, which was with the hot tub. the only thing we didn't have that I personally wish there was, was a broom. the place was clean but I hate feeling dirt on my feet inside, so I bought a broom, but that was my decision. great place, thanks Josh

Luxe Liberty: Getaway with Heated Indoor Pool!
this was the 3rd time our family has stayed,again we had a fantastic time! We chose to return due to the great space, a fabulous indoor pool, great kitchen and an amazing view. Great attention to details, comfortable for large families or groups and peaceful for just 2.

Lovely home with hot tub and pool
Beautiful Airbnb! Everything in the Airbnb was very well thought out. The host was super nice and always quick to respond. My only regret was not spending more time here!

House in the woods
Booked this place for our anniversary to get away from the city for a weekend.. we found exactly what we were looking for! The hot tub was wonderful, the house was clean and cute, and we had everything we could have needed! Estelle was very responsive and gave clear instructions for everything. Would recommend this place for a quiet getaway or a small group trip in the summer!

SummerFun! NEW Pool, JungleGym, Dome, HotTub&Sauna
We had the most incredible stay at Spruce Mountain Manor! The views were absolutely breathtaking—those expansive windows made it feel like we were on top of the world. Every detail of the home was thoughtfully designed, from the stunning décor to the warm, welcoming ambiance that made us feel right at home. Tanya was a phenomenal host—kind, responsive, and attentive to every question or need we had. Her hospitality truly made our three-day stay seamless and special. Spruce Mountain Manor is absolutely worth every penny, and we’re already looking forward to returning once the pool, jungle gym, and putting green are completed. It was an unforgettable experience and made my birthday celebration one of the most memorable yet. My entire family was in awe—thank you, Tanya, for helping create such lasting memories!

Pine Haven Hideaway
We had a wonderful stay! The place was absolutely amazing—offering a pure connection with nature. It was very spacious, spotless clean, and perfectly maintained. The game area was super fun and added a great touch to our experience. Although we didn’t use the pool, it looked really nice and inviting. Everything was well-organized, making our stay comfortable and enjoyable. Highly recommended!

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
Angela’s place was wonderful! Very cozy, clean and comfortable, well stocked, close to downtown Portland. Snacks was a nice touch! Angela was very responsive. Hope to come back soon!

There's No Place Like Home
Kathi’s place was great! Super close to the Downtown Portland/Old Port area. Kathi was a great host, extremely responsive and genuinely nice, plus she even made my family and I some delicious blueberry muffins for our stay! Her instructions were clear and she made us feel right at home! Would definitely stay again whenever we’re in the area!
Weekly house rentals

2 Acre Waterfront w/Canoes & Kayaks, Game Room
If you want a private, well furnished home in the woods with fishing access on the stream and 2 fire pits this is your place!! Staying at this house made a work trip for my crew and I, feel like we were on vacation for 2 nights while staying there. Worth the money and great hosts!

Newly built in 2024, Long Pond lake access
We had a short two nights at Amy’s place. We stayed to attend our son’s graduation from Colby college. The school was about 32 minutes away from campus and the house worked out great. I’d love to return and stay longer in the future. Home and host were exceptional.

Sunset Waterfront Retreat • Cozy 3BR + Kids’ Nook
A five star setting in a true Maine oasis. If you're looking for a great , clean and comfortable house with a pondfront setting in a small Maine town, look no further. Every amenity you would hope for is there. Furniture is nice and lots of homey personal touches. Great bed which isn't always the case in even better AirBnBs. Hosts were good communicators and responses to questions came quickly. No complaint on anything. Dog friendly is a bonus!

WillowsAwake Winery Stay
This was the perfect getaway. Brenda took my reservation last minute and was extremely accommodating. The pictures do not do this house justice. Absolutely amazing decor and a relaxing place to refresh. Thank you so much.

2 BR Waterfront house with stunning view.
This was a really nice house on a beautiful lake. The beds were comfortable and there were enough to accommodate us. It was very clean and easy to enjoy your stay. We really enjoyed our stay.

Breathtaking Bay Views!
I can’t say enough about what a nicely appointed home in a beautiful setting this is. I came for peace and tranquility and it did not disappoint. I haven’t had such good sleep in over 2 years. Highly recommend and plan to return next year! Thank you all so much for sharing your lovely home.

Auburn Roots Getaways Bunkhouse
I found the house very comfortable, a home away from home, with everything I needed. it was very clean and neat. While there are 2 other houses under construction on the road and one that seems to be a part time residence, the area is very quiet. I walked my dog along Rt 219 East and found a post office, church and an eclectic general store with snacks. coffee and used items for sale. All the activities I wanted to do were within 30 minutes to an hour away with my favorite in Bethel of the Wheeler Mica Mine tour and the Maine Gem and Mineral Museum. The Highland Grille at the golf course has fantastic food!

Lakeside retreat on quiet cove on Cobbessee Lake!
This lake camp is spacious and comfortable. The kitchen is well stocked. It was so nice to get up every morning and be greeted with beautiful close up lake views when you walk down the hallway towards the lake! Great location, close to Augusta, Readfield, Winthrop and plenty of restaurants, shopping, etc. William was responsive whenever I had a question. Great place, great location! Such a peaceful spot!
Private house rentals

Stunning, private Maine lakefront home w/ hot tub.
We went to Jon’s place for our yearly Ice fishing trip. We had 8 guys there and were comfortable. House was clean with towels and linens for us in the rooms and extras in the closets. Place is right on the water and we had a blast using the fire pit outside while Ice Fishing.. Only thing I would say is the appliances are quite old and the house could use a little fixing up. With that said it was still a comfortable nice stay. I would definitely stay again.

Lakehouse with 100ft of private waterfront
My wife and I spent our first year anniversary in this wonderful home. We had a great time enjoying the fall colors and over looking the beautiful pond, especially in the morning as the fog broke. Within 15 minutes there were several grocery shopping options, restaurants, and breweries. Perfect balance of being in a quiet setting but having amenities nearby. Would recommend and hope to go back next autumn!

River Valley Sunset Home Near Bethel and Newry.
What can I say, this place is truly amazing as well as Joao is an amazing host. This is my second time booking this place and I have no complaints. By the far the best air bnb I have stayed in. It checks all the boxes, every detail and every carefully thought out extra down to having smores and camp fire supplies to the grill supplies to the carefully placed throws in the living room. This place feels like your home while you’re there, tranquil and so safe. This place is better than pictured and is HUGE in person. Everyone I brought with me just kept repeating how much they loved the space and how it was perfect. Joao also personally went out of his way to refund half of my stay due to the fact of me having to leave early the first time I stayed for emergency reasons, I didn’t ask or request for a refund but he did it off his own choice, which he did not have to do. 10/10 experience all around the board. Anytime I’m in the area, I’ll be staying here ! Don’t double think it, just BOOK.

Original "Moonlight Bay"
We recently moved from Alaska to Maine and needed a place to stay while looking for a house. We stayed at David’s for 2 months and it felt like being in our own home. The view on the lake was beautiful and everything was provided upon arrival. David periodically checked with us to make sure everything Wes going well and was very responsive if we had a question. We would definitely stay at David’s place again!!! I highly recommend David’s place if visiting central Maine.

Family's Paradise: 3BR/2BA,Game Room & Lake Access
Great rental property in a great place.

Lakefront 3 bedroom pet friendly on Messalonski
The house was awesome! Able to use the kayaks and paddle boards to go fishing and it’s right in a peaceful relaxing area!

Red Cedar Haven | Lakefront • Dock • Kayaks
If you're looking for the perfect lakeside retreat, look no further! This property offers everything one would want. Private location, gorgeous view, water toys of every kind, outdoor living spaces for all interests and a updated living space with all the comforts of your own home! Feras was such an amazing host from the moment we booked to the final moments of our stay! Thank you for allowing our family and friends the perfect weekend @ Red Cedar Lane!

Adorable single family house.
Debi's house was perfect, comfortable bed and she was super friendly. Definitely recommend her house
Quick stats about house rentals in Winthrop
Total rentals
20 properties
Nightly prices starting at
$66 NZD before taxes and fees
Total number of reviews
770 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Destinations to explore
- China Holiday rentals
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- Rentals with lake access Winthrop
- Waterfront rentals Winthrop
- Rentals with a kayak Winthrop
- Kid-friendly rentals Winthrop
- Family-friendly rentals Winthrop
- Pet-friendly rentals Winthrop
- Rentals with a patio Winthrop
- Rentals with a fire pit Winthrop
- Rentals with outdoor seating Winthrop
- Rentals with a washing machine and dryer Winthrop
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- Sebago Lake
- Sunday River Resort
- Popham Beach State Park
- Samoset Resort
- Pemaquid Beach
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Cliff House Beach
- East End Beach
- Brunswick Golf Club
- Belgrade Lakes Golf Club
- Pemaquid Point Lighthouse
- Wolfe's Neck Woods State Park
- Sunday River Golf Club
- Portland Museum of Art
- Maine Maritime Museum
- Bradbury Mountain State Park
- Rockland Breakwater Light
- Pinnacle Park
- Eaton Mountain Ski Resort
- Head Beach
- Pebbly Beach
- Lost Valley Ski Area
- The Camden Snow Bowl