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Winsted Holiday Rentals

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Holiday Rentals in Winsted

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 AU$1,244
includes taxes & fees
20 July - 21 July
Modern Family Retreat | Near Downtown Hartford | Sleeps 10

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 AU$1,264
includes taxes & fees
24 July - 25 July
Premium 3-Story Townhome | Perfect for Large Groups

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 AU$935
includes taxes & fees
17 July - 18 July
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

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

The price is AU$769
includes taxes & fees
13 July - 14 July
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

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 AU$583
includes taxes & fees
6 Aug - 7 Aug
Old Avon Village

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 AU$698
includes taxes & fees
13 July - 14 July
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

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 AU$552
includes taxes & fees
27 July - 28 July
Big farmhouse in the foothills of the Berkshires

Home in the Woods

10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay at the Home in the Woods. We stayed for 1 night on the way to Amherst for a graduation. The home is very cozy and clean. Jessica was easy to communicate with and the check-in/check out process was simple. Highly recommend!"
The price is AU$494
includes taxes & fees
14 July - 15 July
Home in the Woods

Charming 3-bedroom Modern cottage with lakeside views

2.0 star property
The price is AU$2,285
includes taxes & fees
15 July - 16 July
Charming 3-bedroom Modern cottage with lakeside views

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 AU$487
includes taxes & fees
23 July - 24 July
Tranquil Litchfield Connecticut Retreat".

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

The price is AU$322
includes taxes & fees
13 July - 14 July
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 AU$503
includes taxes & fees
14 July - 15 July
The Jefferson Guest House, Spacious, Special Views

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 AU$742
includes taxes & fees
13 July - 14 July
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

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

The price is AU$621
includes taxes & fees
28 July - 29 July
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
The price is AU$1,185
includes taxes & fees
13 July - 14 July
CT Gate House Goshen CT, Gate House Goshen CT

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."
Cheerful 3-bedroom cottage with woodstove

Home in Great Barrington

9.8 out of 10, Exceptional, (21)
"Our family had a wonderful experience and stay. "
The price is AU$640
includes taxes & fees
6 Aug - 7 Aug
Home in Great Barrington

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 AU$1,128
includes taxes & fees
13 July - 14 July
Great Barrington Get Away
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.