Winsted Holiday Rentals

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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Winsted holiday rentals

Fridge, microwave, oven, stovetop

The Birdsong Apt. | Game Room & Fire Pit

The Birdsong Apt. | Game Room & Fire Pit
Winchester
10.0 out of 10, Exceptional, (1 review)
"Very well kept, decorated very beautifully, wonderful location! The team was extremely attentive and communicative! The neighbors were also very pleasant and friendly!"
United States
Stephanie
The Birdsong Apt. | Game Room & Fire Pit
Interior

Cozy & Serene Cabin with Fireplace, Ski Nearby!

Cozy & Serene Cabin with Fireplace, Ski Nearby!
Bethlehem
10.0 out of 10, Exceptional, (39 reviews)
"Very comfortable property. The host had thought of everything!"
United States
Jennifer Y.
The price is HK$1,563
HK$3,295 total
includes taxes & fees
17 Feb - 18 Feb
Cozy & Serene Cabin with Fireplace, Ski Nearby!
Property grounds

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (17 reviews)
"We stayed here as a quick overnight trip for events in the area. We really enjoyed the property, reading through the guestbook, and the local pizza place La Figata. "
United States
Kaleigh L.
The price is HK$732
HK$1,447 total
includes taxes & fees
23 Feb - 24 Feb
Peaceful Meadow Retreat
Exterior detail

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
Goshen
9.4 out of 10, Exceptional, (9 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is HK$738
HK$4,913 total
includes taxes & fees
17 Feb - 18 Feb
CT Gate House Goshen CT, Gate House Goshen CT
Property grounds

River Overlook - Check the view from your deck!

River Overlook - Check the view from your deck!
Collinsville
10.0 out of 10, Exceptional, (23 reviews)
"The place was perfect for the two of us. It was close to both our kids homes."
United States
Tomas M.
The price is HK$1,048
HK$2,106 total
includes taxes & fees
17 Feb - 18 Feb
River Overlook - Check the view from your deck!
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is HK$1,407
HK$2,611 total
includes taxes & fees
2 Mar - 3 Mar
Big farmhouse in the foothills of the Berkshires
Smart TV, books

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.8 out of 10, Exceptional, (11 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is HK$1,252
HK$3,084 total
includes taxes & fees
23 Feb - 24 Feb
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Exterior

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Torrington
9.2 out of 10, Wonderful, (5 reviews)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
The price is HK$624
HK$2,575 total
includes taxes & fees
17 Feb - 18 Feb
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
2 bedrooms, desk, free WiFi, bed sheets

Pristine, Walkable downtown, Entire 2 Bedroom apartment

Pristine, Walkable downtown, Entire 2 Bedroom apartment
Torrington
10.0 out of 10, Exceptional, (16 reviews)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
United States
Kate B.
The price is HK$1,321
HK$2,293 total
includes taxes & fees
17 Feb - 18 Feb
Pristine, Walkable downtown, Entire 2 Bedroom apartment
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (27 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is HK$1,217
HK$2,058 total
includes taxes & fees
23 Feb - 24 Feb
Home in Great Barrington
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is HK$3,072
HK$5,422 total
includes taxes & fees
22 Feb - 23 Feb
Guesthouse Cabin vacation rentals in Berkshire County
Fridge, microwave, oven, stovetop

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

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
East Granby
8.6 out of 10, Excellent, (4 reviews)
"Great Stay at the Olde Tobacco Barn. Was here for a work trip, and the place was perfect for our needs. House is set back really nicely and private. Host was super responsive and easy to deal with. Overall 5/5 stay. Thank you!"
United States
Sgt W.
The price is HK$1,696
HK$4,194 total
includes taxes & fees
17 Feb - 18 Feb
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Exterior

Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
The price is HK$944
HK$3,048 total
includes taxes & fees
17 Feb - 18 Feb
Cozy Modern Farmhouse Private Apt - 3 Beds
Interior

Stylish Townhome | Perfect for Family Gatherings & Events

Stylish Townhome | Perfect for Family Gatherings & Events
Bloomfield
10.0 out of 10, Exceptional, (4 reviews)
"The house was newer and the living room and kitchen had open layout that enabled to spend quality time with family."
United States
Muhammad G.
The price is HK$2,408
HK$5,571 total
includes taxes & fees
17 Feb - 18 Feb
Stylish Townhome | Perfect for Family Gatherings & Events
Exterior

Dugway Hideaway Walking Distance to Lime Rock Park

Dugway Hideaway Walking Distance to Lime Rock Park
Salisbury
9.2 out of 10, Wonderful, (15 reviews)
"Super clean, great communication and Super location if you are going to the track. Love my stay there, will definitely do it again and definitely recommend."
United States
Brig
The price is HK$1,563
HK$2,439 total
includes taxes & fees
1 Mar - 2 Mar
Dugway Hideaway Walking Distance to Lime Rock Park
Fridge, microwave, oven, stovetop

The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (8 reviews)
"The place was absolutely spotless and magnificent in every way. Highly recommended."
United States
Robert A.
The price is HK$2,279
HK$2,928 total
includes taxes & fees
17 Feb - 18 Feb
The Jefferson Guest House, Spacious, Special Views
Dining

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Torrington
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
The price is HK$1,001
HK$3,118 total
includes taxes & fees
1 Mar - 2 Mar
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Dining

Spacious, cozy 3BR Home-Near CCSU, UConn Health

Spacious, cozy 3BR Home-Near CCSU, UConn Health
New Britain
The price is HK$1,567
HK$3,240 total
includes taxes & fees
1 Mar - 2 Mar
Spacious, cozy 3BR Home-Near CCSU, UConn Health
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is HK$2,040
HK$3,038 total
includes taxes & fees
28 Feb - 1 Mar
Litchfield Retreat, Wineries, Foliage & Skiing
Interior

#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10

#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10
Plainville
10.0 out of 10, Exceptional, (3 reviews)
"Great weekend with friends!"
United States
Neil R.
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10
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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Top Winsted Hotel Reviews

Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

10/10 Excellent
"Rooms are always clean and the staff friendly."
Betty 1-night trip
Posted 2 days ago
Hampton Inn Hartford/Airport

Find out more about Winsted

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
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  • 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?

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: This holiday home rental outside of Winsted offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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, The Marina at Highland Lake and Ledgebrook Plaza 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.