Vacation rentals in Winsted, Winchester

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Popular amenities for Winsted, Winchester vacation rentals

Stay near Winsted, Winchester's top sights

Gilson Cinema & Cafe14 locals recommend
Mario's Tuscany Grill11 locals recommend
Stop & Shop8 locals recommend
Noujaim's Food & Catering5 locals recommend
Little Red Barn Brewers5 locals recommend
The American Museum of Tort Law4 locals recommend

Other great vacation rentals in Winsted, Winchester

Top guest favorite
Home in Hillsdale
5 out of 5 average rating, 56 reviews

Lakefront close to ski & shopping

KathyRating, 5 stars2 months ago
A beautiful home and the views were breathtaking on the lake. Although, it was frozen. All the amenities we needed and more. Close to skiing and tubing. Owner Sara was very attentive to respond quickly. We just wanted a getaway place for a family weekend. The road was narrow and very icy. Would go back but not in the winter. Summer and the Fall I think would be best. Lots more things to do in the nicer weather months. Thank you Sara for your hospitality.
Top guest favorite
Home in Granby
5 out of 5 average rating, 7 reviews

Lake house retreat Granby CT

DianeRating, 5 stars1 week ago
We were in the area to meet our son's fiance's extended family. Nathania's home was perfect! We had 7 adults and 5 little boys ages 9, 7, 5, 2, and 2 months. There was plenty of space to spread out and enjoy the time together. The hot tub, kayaks, and foosball table were especially popular! We were able to host a family dinner with guests which was wonderful. Everything we needed for preparation was readily available. Lots of beautiful parks, playgrounds, hiking areas. Plenty to keep everyone entertained! Nathania was extremely kind, gracious, and responsive to questions. We had absolutely zero issues. So grateful for a wonderful vacation. Thank you for sharing your idyllic home with us. We hope to visit again!!!
Top guest favorite
Home in Millerton
4.97 out of 5 average rating, 181 reviews

Vacation Home In Millerton

SarahRating, 5 stars1 week ago
We had a wonderful week at Corina's house while out for a family event! The house was spotless and the kitchen was stocked with everything we could need. The outside space was just as amazing. We had a great campfire one night, enjoyed using the grill, and our dog loved being able to run around the large yard. I'm sure we'll be back next year!
Guest favorite
Home in Great Barrington
4.96 out of 5 average rating, 26 reviews

Perfect Nature Retreat In Great Barrington

TriciaRating, 5 stars2 days ago
Wonderful home, 2 min drive from town. Everything was very cozy and comfortable from the beds to the big cozy couch in the living room. Our family of four and my mother-in-law enjoyed all of the space and amenities like the bbq and big tub in the master. We had a wonderful stay and will be back soon!
Top guest favorite
Cabin in Cornwall
5 out of 5 average rating, 48 reviews

Beautiful Cabin in Cornwall CT.

JanRating, 5 stars2 weeks ago
Henry's beautiful home and yard provided the perfect getaway for 5 friends who try to get together at least once a year, coming from 3 different states. The large rooms, clean/fresh bed linens and towels, two full bathrooms and spacious living room adjacent to the kitchen gave us jus t the right setting in which to enjoy each other's company. Breakfast at the kitchen table overlooking the backyard was bright and sunny first thing in the morning. We especially liked the backyard patio, which gets sun all day long. After a cold rainy start to our stay, we were able to enjoy a warm afternoon on the patio - sunshine, blue skies, birds, budding trees and the soothing sound of the water fountain and small pond . We found great restaurants in both Kent and in Litchfield. As an avid gardener, I can just picture Henry's beautiful landscaping when all is in bloom later in the season. Very comfortable place to hang out! We wouldn't hesitate to give others a recommendation for Henry's home.
Guest suite in Goshen
4.73 out of 5 average rating, 249 reviews

Rural Litchfield County Apartment Goshen CT

KennethRating, 5 stars2 weeks ago
Wonderful stay and reasonably priced. We were attending a concert at the Warner Theater in the area so we made a weekend of it. There was a Vineyard and a farm that made their own chocolate nearby that we visited during our stay. The scenery was countryside side farm with Mohawk mountain nearby for a view. The accommodations were clean and comfortable and the host Pauline was available for any concerns.
Guest favorite
Home in New Fairfield
4.95 out of 5 average rating, 79 reviews

The Lakeside Nook

MarisaRating, 5 stars3 weeks ago
A perfect place for our family trip. Nestled in a peaceful beautiful area, close to the pond/lake. The home was so cozy and Monika was so responsive to our messages. Definitely would stay there again
Top guest favorite
Home in Great Barrington
5 out of 5 average rating, 13 reviews

Great Barrington Ranch. Sleeps 10,Hot Tub, 5 acres

JuanRating, 5 stars1 month ago
We loved this airbnb! The location was perfect very close to Catamount where we went skiing. The house had plenty of space for 9 people. The best part was the host though. Alyssa’s communication is great and she was very flexible and helpful. Would definitely stay again!

Destinations to explore

  1. Airbnb
  2. United States
  3. Connecticut
  4. Litchfield County
  5. Winchester
  6. Winsted