
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

Coastal Retreat with Pool and Cheerful Vibes
We had a wonderful stay at John’s place, house was clean, comfortable, and stocked with everything we needed for a month stay. Private and beautiful surroundings, responsive and friendly host, and a great location to explore Maine and the upper east coast. Memories to last a lifetime! Would recommend anyone wanting to enjoy to coast of Maine to stay here and have a great time, so much to see and do. Thanks for sharing your home with us!

Luxe Liberty: Getaway with Heated Indoor Pool!
This was one of the most memorable places I have ever lived at! The property is huge, well maintained and just a perfect getaway spot with the right amount of amenities. Will definitely recommend this place 10/10 to anyone visiting Acadia National Park.

Lovely home with hot tub and pool
I had a wonderful stay., they were fantastic in accommodations for me and my service dog who loved the yard. The home is beautiful and the host was very accommodating. communication was great. I look forward to staying there when I’m in that area again.

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!

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
We loved staying here! Everything was clean and well stocked, and Angela was extremely responsive and helpful!

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!

NEW Marty's Magic Haus Ski, Bike & Hike Retreat
Marty’s Magic Haus was exactly as advertised. We had a wonderful family vacation with multiple family members spanning teens to 70s enjoying all the home had to offer. The home was well stocked with everything we needed to make meals and enjoy our time together. We loved the pool, the hot tub, the sauna and all of the games. We had great relaxing times on the deck and around the fire pit. It was very clean and we were very happy with the stocked items that we did not have to bring along such as towels, beach towels and soaps. It was so beautiful! Thanks for such a well maintained place to vacation!
Weekly house rentals

Bluebird Cottage on Woodbury Pond
Justin’s house was spacious and clean and had everything we could need. The kitchen is fully equipped and when we were there it all seemed brand new. Beds are comfortable and the upstairs loft bedroom is a great space. Every amenity was provided! We were not able to take advantage of the lake due to the weather. We didn’t realize when we booked that the house is right off the road and is part of a cottage community development that is still being built. Nevertheless, it was peaceful and quiet and lovely to be steps from the lake and to be near so many places in central Maine. We highly recommend a stay here.

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.

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!

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

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.

Beautiful Maine Lakeside Cottage
This cozy cottage was definitely the right choice for our family. The location of it was perfect for the things we already had planned to do in the area, with a beautiful scenic view. The cottage was accommodating and had everything we could’ve needed asides from tooth brushed and toothpaste. The host was quite responsive as well. I would most definitely recommend this cottage as a place to stay for anyone!

Lakefront 3 bedroom pet friendly on Messalonski
Diane was amazing - very fast response with all questions, beautiful property, location, amazing front lawn that leads down to the fire pit and waterfront. We had a blast and wouldn't hesitate to stay there again when back in the area.

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!

Family Escape w/ Kayaks, Fire Pit, & Water Access
What a whimsical town! In the middle of nowhere So peaceful Yet, Wallace's General Store, right up the road Maybe a mile Amazing food and Sandwiches and just about everything under sun to Need So, just down the road is this Amazing Place! Three Sisters Farm Heaven Awaits Must check out

The River House
We stayed here for our first wedding anniversary and it was absolutely perfect. The place was peaceful, spotless, and had everything we needed for a relaxing getaway. We loved how close it was to all kinds of fun activities, but honestly, we could have spent the whole time just enjoying the property. The sound of the river right outside was so calming—we fell asleep to it each night. There’s a cozy outdoor firepit we made good use of, and the hosts even left us a thoughtful local Maine gift at check-in, which was such a sweet surprise. Can’t recommend this spot enough!

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.

Unique Octagonal House with Private Beach!
Simply magical! Cozy and fun space. We enjoyed watching eagles and ospreys fish, seals pop their heads up, and even an adorable family of foxes from the comfort of the living room! Kitchen had all necessities for cooking most meals at home. A nice trail for walking down the road and an awesome beach where the kids threw stones and searched for seaglass each afternoon. We were all sad to leave!

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.

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!
Quick stats about house rentals in Winthrop
Total rentals
20 properties
Nightly prices starting at
$62 AUD 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
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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