
House holiday rentals in Winslow
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Top-rated house rentals in Winslow
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Holiday rentals for every style
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Popular amenities for house rentals in Winslow
House rentals with a pool

Cozy, fun, 3 bedroom home with a pool and Hot Tub.
Nice place! I had a great time here with my dog. The host gave us instructions when we arrived, and he response very quickly and friendly. Highly recommend

Nature, Pool, Hot tub&Lakes! Mins to Sebago &More
We would 100% recommend Dina’s place to ANYONE (and we hope to be back)! The place is beautiful and would accommodate a small to large family. The pool and hot tub are incredibly nice and peaceful surrounded by trees. The furniture is incredibly comfortable and the kitchen great to use. Dina is also incredibly thoughtful and quick with her replies. We got a little turned around arriving at night (the GPS lead us up the road a bit), but we found it!

New Boho Cape with Pool! Fenced yard, pet friendly
Thank you Christina! Great weekend stay for UMaine graduation. Great location from campus and stores for the things we forgot (haha).

Coastal Retreat with Pool and Cheerful Vibes
We felt like at home. The house is located in a private property with swimming pool and tennis courts. It’s very clean and very peaceful. Just a clarification about the description : there’s no bathroom in the basement. Then if you come with elderly people or very young kids, it could be annoying. If you like cooking, the kitchen is very well equipped. We´ll keep a very good memory of our stay in Ducktrap Retreat during the colorful foliage season.

Luxe Liberty: Getaway with Heated Indoor Pool!
What a wonderful experience! Rebecca was an absolutely outstanding host, always quick to respond and went above and beyond to ensure we had everything we needed. My family and I had such a peaceful stay. The home and location were incredibly tranquil, perfect for a relaxing getaway. The house and property were absolutely beautiful, and we loved sipping our morning coffee on the amazing balconies with the breathtaking views. There is so much space, and every room in the house is well thought out, functional, and cozy. The pool is even better than we hoped, so big and clean and in immaculate condition. We spent most of our time swimming and relaxing by the pool. We also enjoyed playing pool and having so many rooms to gather in with the comfort of plenty of new comfy furniture. Highly recommend for anyone looking to unwind for a vacation away from all the noise and chaos of daily life. Every single area was as described in the listing and better. Thank you for an unforgettable stay!

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!

The Boathouse at Spruce Harbor
My return visit to the Boathouse was even lovelier than I hoped it would be. The location can't be matched by anything else I've seen. I enjoyed a September visit with my dog and was lucky to have pristine weather. I lived a very simple and healthy outdoors life and came home the better for it. The Boathouse is true to its description: it is simple and rustic and uncomplicated but well-equipped, and is perfect for one-and-dog, or for two people. A little coming-and-going from the neighboring houses meant that I didn't feel isolated. Margaret is truly an exceptional and friendly host who communicates promptly and clearly. I almost hesitate to share "my" Boathouse location with too many of my back-home friends because it feels so intimate and special. I already want to be back there. I offer my deep thanks to Margaret and to the place that I could - briefly - call home.

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!
Weekly house rentals

Lake-House on water, East Lake, Near Waterville
The location is gorgeous and peaceful, so close to the water so that we could enjoy it right out the window, or down at the dock. The weather was too rainy for paddling but we heard the loons. The space is comfortable and Mark had so many nice touches that made us feel welcome. We hope to be back!

Cute house in town Skowhegan.
We really enjoyed our stay at Donald's house in Skowhegan. Only positive things to say: Exactly as described, clean, great location, easy access. Friendly and courteous host goes out of his way to be helpful. Would definitely stay here again, Mike from Nova Scotia

Classy AF Home, walk across the street to Colby!
The photos don’t do this place justice! It is extremely pretty and bigger than I thought! Its location is perfect and made for an easy reunion weekend at Colby!

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.

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

Zeus's Landing| Lakefront | Close to Colby
Great location and price for our group. Beds were comfortable and house was very clean. We will be staying here next year!

Cozy New Home with Hot Tub: Cornerton
A wonderful little cottage. Peaceful, private and comfortable. I stayed for a night because I needed a break from moving and I didn’t want to be surrounded by all the boxes… between the hot tub and wicked comfy bed, I left the next day feeling far more capable of continuing to move furniture and unpack boxes. I will absolutely stay again when I need a break from my world for a night.

House on Lake St. George
Corie was so responsive with answers to questions about wifi and check-in to fun day trips we should try while we are there. The view of the lake is the best and the swimming was wonderful. Plus loved the paddle boat. Very relaxing!!
Private house rentals

Sunset Retreat on Brewer Lake
My husband and I really enjoyed our stay in Holden, ME! This Airbnb was so nice and clean and pretty close to Acadia National Park. I needed to stay close to work in the park and this spot was the perfect distance away. It was quiet, peaceful, and away from tourist traffic. Also close to gas stations and a grocery store. The hosts were so friendly and nice and we would highly recommend anyone stay here! Thank you Dana + family!

Pond House
We stayed for two months while I was on a temporary work assignment in the area. Check-in was simple, any questions were quickly answered. We had no problems with anything during our stay; everything was exactly as anticipated from the description. We immediately loved the view of the lake from the front windows! The kitchen was perfect, and we felt right at home. I was working long shifts, and a quiet, peaceful location was important for me to get enough sleep--this place provided it exactly. We were able to watch the lake go from ice covered when we arrived to open water when we left. We saw robins and loons arrive, and heard them calling as they settled into their summer homes. I would highly recommend this location to anyone who enjoys a quiet lake setting.

The Maine Lake House with an Amazing Sand Beach!
The main house perfectly met our needs. The view to the lake was beautiful and the house was very clean. Beds were comfy (we did not use top bunks)

Beautiful Maine Lakeside Cottage
Very clean and Host was very responsive, the setting matched the description 100%. Peceful sleeping with the water hitting the beach and the call of the Loon heard throughout the night. Can’t wait to return another day!!

River Front Maine Stay
Went for a fishing weekend with my brother. We were both very happy with the place. Boat launch for great pond was a 3 minutes drive and the boat launch for long pond was 7 minutes away which was nice so we could fish multiple lakes easily. Had dock access from great pond for the boat and was the end of channel that was well marked. We were able to dock the boat overnight there were no issues. A few places to eat nearby with access via boat (just a bit further up the channel with public dock behind the post office) and are also walkable. Clean space and great view. Beds were very comfortable for an Airbnb. Would recommend, great value, will stay here again if we come back to Belgrade.

Modern Lake Front Home with Hot Tub
Enjoyed our stay. The screened in porch was our saving grace due to rainy weather. Very relaxing trip!

Modern Cornville Ranch
We stayed for 10 days while working in our cabin! We felt right at home, enjoyed all of the amenities, and would stay again!

Wildwood Acadia Salt House: 55 minutes from Acadia
I had a lovely visit with a good friend. The air bnb stood out to us because of how beautiful the photos were and they didn’t do the place justice. It was so nice to stay in a place that felt like it was cut from a magazine. The home is in a private space but not far from restaurants and other towns with cute shops. We were close to lots of hiking trails and coastlines. I am quite sure I’ll be back!
Quick stats about house rentals in Winslow
Total rentals
40 properties
Nightly prices starting at
₹861 before taxes and fees
Total number of reviews
680 reviews
Wifi availability
30 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Local attractions
Walmart Supercenter, Big G's Deli and Governor's Restaurant & Bakery
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- Pemaquid Beach
- Brunswick Golf Club
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Samoset Resort
- Belgrade Lakes Golf Club
- Pemaquid Point Lighthouse
- Sugarloaf Golf Club
- Maine Maritime Museum
- Dragonfly Farm & Winery
- Hermon Mountain Ski Area
- Rockland Breakwater Light
- Eaton Mountain Ski Resort
- Pinnacle Park
- Spragues Beach
- Lost Valley Ski Area
- Pebble Beach
- Narrow Place Beach
- Bear Island Beach
- Three Island Beach
- Lighthouse Beach
- Black Mountain of Maine
- Farnsworth Art Museum
- The Camden Snow Bowl