
Vacation rentals in Winslow
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Top-rated vacation rentals in Winslow
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Popular amenities for Winslow vacation rentals
Other great vacation rentals in Winslow

The Epic Sugarloaf Family Getaway!
This place was very convenient to the mountain with a lift nearby and it was very clean and incredibly spacious. David is very accommodating and helpful. We sorely missed having coffee available in the morning but really that was our fault for not bringing it as it was not advertised that there would be any I just assumed for the price there would be a little coffee. Overall though great stay and very nice place - thank you!

Lakefront Home, Sandy Beach, Belgrade Lakes Maine
This property was awesome we were all very happy with the location, amenities, price and host. Hillary was polite and very helpful. This trip almost didn’t happen as our previous reservation was canceled 12 hours before check in from a different host. Luckily Hillary saved the week with her quick response time and answering questions about sleeping situations etc. would stay here again in a heart beat highly recommend!

cozy 3 bedroom ranch with deck and screen porch
The house is lovely and, if it’s not new, it sure feels that way. In a very quiet area with tons of outdoor space yet just a mile or two from more main roads. Had a lovely white Christmas/Hanukkah with fresh snow on the 24th. Diana was a great host, always answering questions promptly and rolling with some last minute travel issues. Would love to stay here in warmer months to take advantage of the outdoors and the lovely sun porch.

Log Cabin *15 acres*hunting* snowmobile*skiing
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 !

The Great Moose in Stunning Maine Swim, Fish & Ka
My kids and I had an amazing time during our Labor Day weekend stay. The neighbors were so friendly and nice. The house was beautiful and had everything we needed. A market nearby for quick things. Beautiful area, access to water was great. We even got to enjoy the Harmony Free Fair and fireworks! Great weekend thank you!

Cabins/Sporting camps-great location
This is a gem of a place. Very close to where we wanted to bird hunt. Access to ATV trails (be respectful and drive slow on access/shared roads). All that you need is in this place. We stayed in Cabin #1. As she mentioned just bring a towel and toiletries. We ate out all the time. Breakfast and lunch at Bingham General Store. Dinner at Patrick’s Pub one night, next night at Kennebec River Brewing. We’ll be back for sure.

Waterfront Farmhouse with Modern Flair!
The home was very welcoming and accommodating for our family of 5. The views were spectacular at sunrise, sunset and during the snowstorm. Bald Eagles and hawks would land in the trees right in front of the house. Also, there was a skating pond down the street my family love to visit almost each evening. There was an alarm going off as soon as we arrived, Debbi was incredibly fast responding and sending someone to check it out clear it up. On the plus someone came and plowed the driveway after the snowstorm it was great. She left a basket of local food and my family ate it up. We are so thankful for our relaxing week and would love to return.

Great Pond Getaway|Lakefront|Dock|Sunset Views
Wonderful weekend stay w our adult children. Kitchen had everything we needed to make dinner. Views of the lake were stunning. We all enjoyed a swim and paddle in the kayaks.
Quick stats about vacation rentals in Winslow
Total rentals
80 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Frequently Asked Questions
Do house rentals in Winslow have free parking?
Absolutely! We offer over 30 house rentals with free parking in Winslow. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Winslow?
Winslow has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Winslow have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Winslow. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Winslow?
Yes! Work meets play with ease at over 20 vacation rentals in Winslow featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Winslow have wifi?
Absolutely! We offer over 30 house rentals with wifi in Winslow. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Winslow?
Four-legged friends are welcome in Winslow. Choose from more than 10 vacation rentals for guests traveling with pets.
What are the most popular amenities for House Rentals in Winslow?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with free parking, over 20 homes with air conditioning, over 30 homes with a kitchen, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in house rentals in Winslow?
Experience the best of Winslow with our house rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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- Fox Ridge Golf Club
- Brunswick Golf Club
- Belgrade Lakes Golf Club
- Pemaquid Beach
- Samoset Resort
- Pemaquid Point Lighthouse
- Maine Maritime Museum
- Dragonfly Farm & Winery
- Pinnacle Park
- Spragues Beach
- Coastal Maine Botanical Gardens
- Sugarloaf Golf Club
- Narrow Place Beach
- Hermon Mountain Ski Area
- Bear Island Beach
- Martindale Country Club
- Lost Valley Ski Area
- Black Mountain of Maine
- Eaton Mountain Ski Resort
- Farnsworth Art Museum
- Rockland Breakwater Light
- The Camden Snow Bowl
- Titcomb Mountain
- Pebble Beach
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