Vacation rentals in Winthrop

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Popular amenities for Winthrop vacation rentals

Stay near Winthrop's top sights

Hannaford Supermarket37 locals recommend
Fielder's Choice Ice Cream9 locals recommend
van der Brew9 locals recommend
FAST EDDIES DRIVE IN8 locals recommend
Lakeside Orchards7 locals recommend
Winthrop House of Pizza6 locals recommend

Other great vacation rentals in Winthrop

Top guest favorite
A covered entryway is situated beneath an upper porch, featuring a wooden bench beside a welcoming door. A stack of firewood is neatly arranged to the right, partially covered with a tarp. Soft lighting illuminates the space, accompanied by scattered autumn leaves.
Home in Greenwood
5 out of 5 average rating, 15 reviews

Cozy Greenwood Condo!

AnnieRating, 5 stars1 month ago
This condo, conveniently on the ground floor, and was clean and inviting. The wood stove provided warmth and ambiance. The furnishings included a modern well appointed coffee bar, ski themed decorations and two comfortable couches to gather around the wood stove after a day outside of adventuring. There was a mud room for outdoor clothing and boots and the bed was comfortable. The artwork in the bedroom is a fun ski-themed print. A lovely ski weekend.
Top guest favorite
An outdoor seating area is presented with a spacious sectional sofa made of dark wicker, positioned under a covered patio. The lawn extends towards the private sandy beach and dock by the lake, with a view of kayaks and trees in the background.
Cottage in Belgrade
5 out of 5 average rating, 103 reviews

Lakefront Home, Sandy Beach, Belgrade Lakes Maine

SarahRating, 5 stars5 months ago
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!
Top guest favorite
A sunlit porch features a natural wood ceiling with exposed beams and a cozy seating area. A round glass table is accompanied by black chairs, while a comfortable sofa is positioned nearby. A decorative wall of wood slices adds a rustic touch.
Home in Gray
4.97 out of 5 average rating, 63 reviews

cozy 3 bedroom ranch with deck and screen porch

MichaelRating, 5 stars4 months ago
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.
Superhost
A covered porch features a comfortable seating area with a wicker sofa and matching cushions, arranged around a low coffee table. A hammock is suspended for relaxation, and a striped outdoor rug adds texture to the wooden floor. Large windows provide views of the surrounding landscape.
Home in Otisfield
4.75 out of 5 average rating, 20 reviews

Log Cabin *15 acres*hunting* snowmobile*skiing

NinaRating, 5 stars3 months ago
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 !
Guest favorite
Home in Dallas Plantation
4.93 out of 5 average rating, 30 reviews

Ski/snowmobile retreat-hot tub

HeatherRating, 5 stars2 days ago
This home is absolutely beautiful and incredibly spacious!! The entire home is modern and the bedrooms were private and comfortable for each person. The showers were big, especially in the master bathroom! The shower heads felt absolutely amazing after a cold, wet day at the Snowmobile Races at Saddleback. Cyrus was a great host and fun to talk to when we would be outside in the backyard. He was also quick to get back in touch with us when we had a problem with the keys. This was definitely worth the money! I’d highly recommend this beautiful Airbnb!!
Superhost
The sun sets over Great Moose Lake, casting warm orange and golden hues across the water's surface. Reflections of the sunlight dance on the rippling waves, while silhouettes of trees mark the shore in the distance.
Home in Hartland
5 out of 5 average rating, 3 reviews

The Great Moose in Stunning Maine Swim, Fish & Ka

KevinRating, 5 stars7 months ago
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!
Top guest favorite
Two black Adirondack chairs are positioned around a stone fire pit on a stone patio. In the background, a serene view of Winnegance Creek is visible, framed by trees and a cloudy sky.
Home in Bath
5 out of 5 average rating, 101 reviews

Waterfront Farmhouse with Modern Flair!

Tony & KellyRating, 5 stars2 months ago
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.
Guest favorite
A spacious outdoor area features a circular arrangement of colorful chairs surrounding a stone fire pit. The lawn is bordered by trees, and the two-story home can be seen in the background, welcoming guests with its multiple decks and expansive layout.
Home in Freedom
4.9 out of 5 average rating, 94 reviews

Our Mountain Retreat – Lake Ossipee Access

FinRating, 5 stars1 month ago
Paula’s was the perfect spot for a weekend trip with a group of friends for my birthday! It had plenty of sleeping spots for us and was very comfortable, and we really loved the hot tub. They were such responsive and communicative hosts as well, and offered us a flexible late check-out. Thank you!

Quick stats about vacation rentals in Winthrop

  • Total rentals

    60 properties

  • Nightly prices starting at

    $40 before taxes and fees

  • Total number of reviews

    1.8K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Winthrop?

    Yes! Work meets play with ease at over 30 vacation rentals in Winthrop featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Winthrop?

    Four-legged friends are welcome in Winthrop. Choose from more than 20 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in cabin rentals in Winthrop?

    Experience the best of Winthrop with our cabin rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Winthrop have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Winthrop. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Winthrop have wireless internet?

    Absolutely! We offer over 10 cabin rentals with wireless internet in Winthrop. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winthrop have a bbq area?

    Absolutely! We offer over 20 house rentals with a bbq area in Winthrop. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly cabin rentals in Winthrop?

    Winthrop has more than 10 family-friendly cabin rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for House Rentals in Winthrop?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wireless internet, over 10 homes with air conditioning, over 20 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Kennebec County
  5. Winthrop