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

Epic Views, 9Mi SR, GameRm+Theater, HTub, Sauna
**⭐⭐⭐⭐⭐ Exceptional Experience - Exceeded Every Expectation!** This property absolutely blew us away! Without hesitation, I can say this is hands down the best place we've ever stayed. The photos, while beautiful, simply don't do it justice - the reality was even more stunning. Our host was absolutely incredible. Their attention to detail was flawless, and their communication throughout our stay was prompt, helpful, and genuinely caring. You can tell they take immense pride in providing an outstanding guest experience. Everything about this stay was perfection, and we're already planning our next booking with Vacation Alchemy. If you're looking for a truly memorable getaway, this is it. Highly recommended! *Would definitely stay again and recommend to friends and family.*

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.

Heated POOL|Views|HotTub|Sauna|2mi to SR Golf Club
Eshi was very responsive when needing help with the sauna instructions and other things! Beautiful views and a great place to host a sweet 16 🩷

"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!

OOB Oasis - 5BR private Retreat w/ Pool
Great house! Very spacious, plenty of bathrooms, and fantastic location. Very easy to communicate with the owners and check in/out was simple. My minor only critique is that we wish the grill were a bit bigger and nicer. We wanted to grill one day, but we were a little disappointed and unable to do so due to the grill quality. Would definitely stay again!
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.

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!

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!

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

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.

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.

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

Waterfront |Near White Mountains |Firepit
The property was beautiful! The furniture was comfy. We absolutely loved the beds. (so much we are considering buying a new mattress) The lake was great. My daughter loved getting on the lake. (just bring your bug spray!) The air conditioning unit was amazing! We would love to stay here again!

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!

Luxury Lakefront Paradise w/ Private Beach
My family and I had a serene experience staying here. Although the weather was mostly rainy or cloudy, we loved the lake location and maximized the indoor, outdoor, and nearby activity options. The hosts were so responsive, regardless of the question, and made this a truly delightful visit. This was my parents’ first Airbnb experience and it set the bar higher than I could have imagined! My family and I are already talking about coming back!!

#1 View in Maine, Theater, HTub, Xbox, Golf, Lake
We had an absolutely amazing time here. We spent a lot of time cooking and sharing meals on the back porch that had a breathtaking view of the mountains and water. The movie theatre was such a fun addition to an already stunning home. I chose this place because of its beautiful scenery and interior so that I could propose to my girlfriend of 7 years. She said yes! I can’t thank Darryl enough for sharing such a beautiful home and fun experience. We would absolutely rent again!

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!

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!
Quick stats about house rentals in Winthrop
Total rentals
20 properties
Nightly prices starting at
$51 SGD 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