Photo by Kim Knox Beckius

Winsted Holiday Rentals

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Holiday Rentals in Winsted

Newly Renovated Family House On Highland Lake with Dock
Fridge, microwave, oven, stovetop
Newly Renovated Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (19)
"The house was perfect for accommodating a large group of friends for a nice, relaxing break froze reality! It gave us space for cooking meals, playing games, and lounge around. The lake was perfect for a refreshing dip! It was overall an amazing experience!"
Newly Renovated Family House On Highland Lake with Dock
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Property grounds
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
9.4 out of 10, Exceptional, (34)
"Melissa was very easy to connect with, provided very clear directions for finding and entering the property. The property was just as described, very clean, nicely furnished and Melissa already had the AC running which both myself and little dog appreciated! It was perfect for our needs visiting with family in the area for the weekend."
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Interior
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
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Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (195)
"We’ve stayed at the cabin with our dog four times and always enjoy our peaceful stay. It’s cozy, clean and private. Also, the Sherwood Shoppe - just down the road - is a wonderful place for breakfast, homemade chili and much more."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Pristine Home In Becket Woods
Fridge, microwave, oven, stovetop
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (8)
"I really loved my stay at this beautiful property surrounded by nature and peacefulness in the Berkshire mountains. The owners were great too with communication and making things easy for check in and check out. Highly recommend this place!"
Pristine Home In Becket Woods
Spacious three bedroom house with pool and hot tub near Historic Suffield Center
Fridge, microwave, oven, stovetop
Spacious three bedroom house with pool and hot tub near Historic Suffield Center
10.0 out of 10, Exceptional, (3)
"Everything from check in to check out was a breeze. The house is clean, cozy and comfortable. Managers are very responsive and kind. We needed to extend our stay due to a medical issue, they were very gracious and were happy to help anyway possible. I would most definitely book again. Only thing i would like to share is the flight of stairs to get to main floor of the house could be difficult for some people, just keep that in mind. We were fine with it and were traveling with my mother in law...
Spacious three bedroom house with pool and hot tub near Historic Suffield Center
Peace and quiet on the lake
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (186)
"The house was clean and cozy. The kitchen was well stocked, especially important as we like to cook at home. Justin was responsive when I contacted him with questions. Love that the house was dog friendly with a fenced in back yard. The house has been updated inside but the deck needs some TLC, which I am sure are in the plans. A perfect get away!"
Peace and quiet on the lake
Mountaintop Horse Farm with Heated Pool
Outdoor pool, a heated pool
Mountaintop Horse Farm with Heated Pool
10.0 out of 10, Exceptional, (17)
"We enjoyed meeting and spending time with all the lovely animals on this quaint farm. Apartment was so lovely and spacious. Highly recommend stopping by for a stay."
Mountaintop Horse Farm with Heated Pool
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
7 bedrooms, iron/ironing board, cots/infant beds, travel cot
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Perfect Vacation Get Away - Historical New Marlborough
Property grounds
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, (49)
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is HK$1,171
per night
24 Jun - 25 Jun
Perfect Vacation Get Away - Historical New Marlborough
Serene Acreage - Pond - Hiking Trails Nearby
Property grounds
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (5)
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby
Tranquil 3-BR Waterfront Retreat
Exterior
Tranquil 3-BR Waterfront Retreat
10.0 out of 10, Exceptional, (7)
"The house is immaculate! One of the cleanest properties we've stayed in. The house was the perfect size for my family of 4 (2 adults, 2 teens) with room for more. The beds are comfortable, and there were plenty of linens and towels. The linens and towels are high quality, very soft. The kids had fun fishing in the pond and made good use of the kayak (they caught some bass, pickerel and sun fish). The neighborhood is nice and quiet, dirt roads, no traffic...great for taking walks. We used the...
Tranquil 3-BR Waterfront Retreat
Private Island - Largest Fresh Water Reservoir in Mass....
Property grounds
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, (3)
"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"
Private Island - Largest Fresh Water Reservoir in Mass....
Cozy & Chic Cabin by the Lake, with access to private Beach!
Exterior
Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, (8)
"We’d go back."
The price is HK$1,952
per night
1 Jul - 2 Jul
Cozy & Chic Cabin by the Lake, with access to private Beach!
Guest Cottage on Country Estate
Property grounds
Guest Cottage on Country Estate
9.2 out of 10, Wonderful, (33)
"My husband and son stayed here for 5 days. They had a fabulous time hiking in the state park nearby. Thanks for a great stay!"
Guest Cottage on Country Estate
Berkshires Cabin 2 Mi to Appalachian Trail!
Interior
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (6)
"My wife and I were looking for a nice little getaway within reasonable driving distance and came across this great property. As soon as we saw the big windows in the living room we were sold. Definitely getting added to our short list of places to go back to."
Berkshires Cabin 2 Mi to Appalachian Trail!
Beautiful retreat to the woods to enjoy the winter season.
Aerial view
Beautiful retreat to the woods to enjoy the winter season.
10.0 out of 10, Exceptional, (31)
"Very nice, well stocked and away from the hustle and bustle of city life. We had a great time."
Beautiful retreat to the woods to enjoy the winter season.
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
9.8 out of 10, Exceptional, (8)
"This is an immaculate guest suite with incredible views in a gorgeous setting. The owners were extremely responsive and communicative, enhancing our stay. The bed is very comfortable and the appliances and just about everything looks brand new. The grounds, pool area and views are amazing. If you’re looking for a comfortable and peaceful stay in a relaxing setting, this is the place! Your hosts will make sure you are well taken care of."
The price is HK$1,718
per night
15 Jul - 16 Jul
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
The Meadows House @ Otis Ridge w/ 7-person hot tub
Property grounds
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (21)
"The rental property was just as described online. We had a very relaxing time. We also enjoyed playing all the games provided. This is a beautiful location and very quiet area. We loved sitting out in the hot tub at night looking up at the stars. Really special experience."
The Meadows House @ Otis Ridge w/ 7-person hot tub
The Blue Elm - A Historic Berkshire Cottage
Exterior
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (2)
"If I could have given it more than 5 stars I would have. Beautiful, quiet area and the place is stunning. The gas fireplace in the dining area was great, has pretty much everything you could need and incredibly stylish (the retro fridge and microwave were very cool). Can’t speak to the pullout but the king in the master might have been the most comfortable bed I’ve ever slept in and the double shower is awesome. The hosts were friendly and responsive. Went to hike and the number of trails within...
The price is HK$1,952
per night
24 Jun - 25 Jun
The Blue Elm - A Historic Berkshire Cottage
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See all available properties in Winsted
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Winsted you may be interested in

DoubleTree by Hilton Hartford - Bradley Airport
In-room safe, desk, blackout curtains, iron/ironing board
DoubleTree by Hilton Hartford - Bradley Airport
4.0 star property
8.0 out of 10, Very good, (1000)
"Great "
The price is HK$1,055
per night
1 Jul - 2 Jul
DoubleTree by Hilton Hartford - Bradley Airport
Holiday Inn Express & Suites Bradley Airport, an IHG Hotel
Exterior
Holiday Inn Express & Suites Bradley Airport, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (1006)
"Clean, comfortable room. Convenient to the airport, shuttle service and great price."
The price is HK$1,105
per night
23 Jun - 24 Jun
Holiday Inn Express & Suites Bradley Airport, an IHG Hotel
Sheraton Hartford Hotel at Bradley Airport
Executive lounge
Sheraton Hartford Hotel at Bradley Airport
3.5 star property
9.0 out of 10, Wonderful, (1000)
"The staff were all welcoming and helpful. We needed wheelchair assistance to the airport and staff was very helpful. Sunday night food service was thru bar /lounge, but good food and friendly team."
The price is HK$1,554
per night
1 Jul - 2 Jul
Sheraton Hartford Hotel at Bradley Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Search for holiday rentals in Winsted on Expedia! You can easily find your home rentals, villas, holiday apartments in Winsted using one of the methods below:

  • View our selection of featured holiday rentals in Winsted
  • Use the map to find apartments and other holiday homes in the Winsted neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winsted while they last

Look no further and take a look at our great range of rental properties in Winsted!

Frequently asked questions

Can I find holiday rentals in Winsted?

Yes, there are holiday rentals in Winsted close to Laurel Lanes, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winsted has to offer?

Pristine Home In Becket Woods: This holiday home rental outside of Winsted is located near skiing, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a private garden, 1 hot tub and a selection of books so that you can immerse yourself in your holiday.

How many holiday rentals are there in Winsted?

With 8 Expedia holiday rentals, you're guaranteed to find just the right place for your Winsted stay.

What’s there to see and do in Winsted?

Highland Lake and Burr Pond State Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Laurel Lanes. While here, Winchester Historical Society and Platt Hill State Park are other places worth a visit.

What are holiday rentals like in Winsted?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winsted. Holiday rentals feature extras like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a family getaway.

Recent reviews of Winsted properties
Expedia verified reviews

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

5/5 Excellent
"Over all was a good place to lay your head for a nice. Rooms cleans. Front desk was friendly. "
A verified traveller stayed at Days Inn by Wyndham Torrington
Posted 17 hours ago
Days Inn by Wyndham Torrington