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Holiday Rentals in Winsted

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Holiday Rentals in Winsted

Home in the Woods

10.0 out of 10, Exceptional, (2)
"We liked the property very much. Great yard, shady and private. Nice that the grill was new. My only wish is that there was a window a/c unit in the bedrooms. We were hot! The fans provided were not enough. Other than that it was a very nice stay. Thank you. "
The price is €277
includes taxes & fees
27 Jul - 28 Jul
Home in the Woods

Cozy Pet Friendly Lake Cottage!

The price is €165
includes taxes & fees
23 Jul - 24 Jul
Cozy Pet Friendly Lake Cottage!

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

The price is €368
includes taxes & fees
28 Jul - 29 Jul
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

This is Room sharing property we only listed the master bedroom and bathroom

The price is €185
includes taxes & fees
18 Jul - 19 Jul
This is Room sharing property we only listed the master bedroom and bathroom

The Jefferson Guest House, Spacious, Special Views

10.0 out of 10, Exceptional, (5)
"The lighting is warm and inviting as you step up the stairs into a large open concept room. Every detail is beyond modern from the giant marble counter equipped with the comfiest and largest leather barstools, to the kitchen whose colors and appliances are so beautifully designed; cabinets stocked with every item you need to cook a homemade meal.The king size bed was like a cloud, swallowing us in the fluffiest duvets and sheets, comfortable pillows, making it an easy switch to use the TV in the...
The price is €288
includes taxes & fees
20 Jul - 21 Jul
The Jefferson Guest House, Spacious, Special Views

Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

9.2 out of 10, Wonderful, (5)
"Beautiful new spacious property in a great safe neighborhood. Very nice for groups. Common Living space s conducive for gathering. Property still under construction as there were other homes still being built. Near busy street but monimal noise. Would stay again."
The price is €733
includes taxes & fees
23 Jul - 24 Jul
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

2.0 star property
10.0 out of 10, Exceptional, (2)
"There were 7 of us staying for a Wedding near by. The home was bright, clean and very roomy. I would 100% stay here again. Host was on top of everything!! "
The price is €733
includes taxes & fees
20 Jul - 21 Jul
Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Old Avon Village

2.0 star property
6.0 out of 10, (7)
"We had a nice stay while visiting our son at AOF. There were a couple of small issues which the owner remedied IMMEDIATELY. Things happen in life which are unforeseen, we appreciated the owner jumping on the issues quickly."
The price is €322
includes taxes & fees
11 Aug - 12 Aug
Old Avon Village

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
The price is €737
includes taxes & fees
27 Jul - 28 Jul
CT Gate House Goshen CT, Gate House Goshen CT

Home in Great Barrington

9.8 out of 10, Exceptional, (21)
"Our family had a wonderful experience and stay. "
The price is €366
includes taxes & fees
6 Aug - 7 Aug
Home in Great Barrington

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

10.0 out of 10, Exceptional, (5)
"My wife, two kids, and chocolate lab spent a few days at the cottage to enjoy the snow and hot tub. Everything was set up exactly as described and Nicole was very friendly and proactive. We had a great time and would do it again "
The price is €457
includes taxes & fees
6 Aug - 7 Aug
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

The price is €442
includes taxes & fees
20 Jul - 21 Jul
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (14)
"My friends and stayed for a night. The house is nice and the owners is very communicative. "
The price is €284
includes taxes & fees
23 Jul - 24 Jul
Tranquil Litchfield Connecticut Retreat".

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

10.0 out of 10, Exceptional, (57)
"We had a great time and I would highly recommend for your next stay. Very clean and had everything to make your vacation enjoyable."
The price is €404
includes taxes & fees
20 Jul - 21 Jul
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (38)
"The property was centrally located for skiing, and was a comfortable stay."
The price is €440
includes taxes & fees
30 Jul - 31 Jul
Cheerful 3-bedroom cottage with woodstove

Charming 3-bedroom Modern cottage with lakeside views

2.0 star property
The price is €1,314
includes taxes & fees
19 Jul - 20 Jul
Charming 3-bedroom Modern cottage with lakeside views

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (138)
"The house is so charming. Beautifully decorated and very clean, with everything you could need easy to find. Plenty of space for 8 people. The hosts are very helpful and communicative. Would definitely stay here again."
The price is €316
includes taxes & fees
27 Jul - 28 Jul
Big farmhouse in the foothills of the Berkshires

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
The price is €649
includes taxes & fees
21 Jul - 22 Jul
Great Barrington Get Away

Premium 3-Story Townhome | Perfect for Large Groups

2.0 star property
9.0 out of 10, Wonderful, (4)
"Property as advertised & convenient - nice location. Great communication; appreciate the hospitality! "
The price is €724
includes taxes & fees
21 Jul - 22 Jul
Premium 3-Story Townhome | Perfect for Large Groups
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.
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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?

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT: This holiday home rental outside of Winsted is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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 Rowley Fields are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Laurel Lanes. While here, Burr Pond State Park 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.