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Winsted Holiday Rentals

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Holiday Rentals in Winsted

Newly Renovated Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, 19 reviews
"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.
9.4 out of 10, Exceptional, 33 reviews
"Very positive."
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
9.8 out of 10, Exceptional, 32 reviews
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, 195 reviews
"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
10.0 out of 10, Exceptional, 8 reviews
"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
10.0 out of 10, Exceptional, 3 reviews
"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
9.6 out of 10, Exceptional, 186 reviews
"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
10.0 out of 10, Exceptional, 16 reviews
"How fun to stay above a hose barn in such a spectaular spot. The apartment was much more spacious than we expected and really fun! As we sat poolside for a little bit we watched Frank driving his tractor, heard animals chatting and played with the dogs. It was the perfect spot to call home during our high school reunion. Loved it and hope to return again some day!"
Mountaintop Horse Farm with Heated Pool
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, 49 reviews
"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 AU$409
per night
8 July - 9 July
Perfect Vacation Get Away - Historical New Marlborough
Tranquil 3-BR Waterfront Retreat
10.0 out of 10, Exceptional, 7 reviews
"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
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, 29 reviews
"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
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, 4 reviews
"Perfect place to relax and have dogs as part of a mini vacation. Very clean, organized, and provided helpful local information. Will definitely stay there again."
Serene Acreage - Pond - Hiking Trails Nearby
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, 3 reviews
"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!
10.0 out of 10, Exceptional, 8 reviews
"We’d go back."
The price is AU$745
per night
8 July - 9 July
Cozy & Chic Cabin by the Lake, with access to private Beach!
Guest Cottage on Country Estate
9.2 out of 10, Wonderful, 33 reviews
"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!
9.8 out of 10, Exceptional, 6 reviews
"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.
10.0 out of 10, Exceptional, 31 reviews
"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!
9.8 out of 10, Exceptional, 8 reviews
"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 AU$452
per night
8 July - 9 July
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, 2 reviews
"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 AU$632
per night
16 June - 17 June
The Blue Elm - A Historic Berkshire Cottage
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, 21 reviews
"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
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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
4.0 star property
8.0 out of 10, Very good, 1,002 reviews
"Great experience in all areas! Thank you so much. "
The price is AU$234
per night
2 July - 3 July
DoubleTree by Hilton Hartford - Bradley Airport
Holiday Inn Express & Suites Bradley Airport, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, 1,006 reviews
"Very clean and modern! Quiet. Good breakfast. "
The price is AU$245
per night
17 June - 18 June
Holiday Inn Express & Suites Bradley Airport, an IHG Hotel
Sheraton Hartford Hotel at Bradley Airport
3.5 star property
9.0 out of 10, Wonderful, 1,000 reviews
"It was really easy to get to the airport from the hotel"
The price is AU$359
per night
1 July - 2 July
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.

Everything you need to know about Winsted holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winsted holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winsted holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winsted holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winsted. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winsted holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winsted holiday rentals we have selected for you start as low as AU$409 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winsted rentals

At Expedia, we put the best Winsted holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winsted rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winsted holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winsted. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 7 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
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