Photo by Kim Knox Beckius

Winsted Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Winsted vacation rentals

Property grounds
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Apartment in winsted

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
9.2 out of 10, Wonderful, (46)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Fridge, microwave, oven, stovetop
The Birdsong Apt. | Game Room & Fire Pit

Apartment in Winchester

The Birdsong Apt. | Game Room & Fire Pit
2.0 star property
The price is ￥28,075
￥62,310 total
includes taxes & fees
Jan 12 - Jan 13, 2026
The Birdsong Apt. | Game Room & Fire Pit
Outdoor dining
The Historic Hideaway

Apartment in Avon

The Historic Hideaway
2.0 star property
7.0 out of 10, Good, (2)
"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "
United States
Nicole M.
The price is ￥8,611
￥38,162 total
includes taxes & fees
Jan 9 - Jan 10, 2026
The Historic Hideaway
Terrace/patio
Peaceful Meadow Retreat

Apartment in Granby

Peaceful Meadow Retreat
2.0 star property
10.0 out of 10, Exceptional, (16)
"Beautiful property comfy, cozy and clean little cottage."
United States
Denise T.
The price is ￥14,599
￥28,876 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Peaceful Meadow Retreat
Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Apartment in Torrington

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
9.6 out of 10, Exceptional, (4)
"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 ￥14,505
￥54,029 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

Vacation Home in Goshen

CT Gate House Goshen CT, Gate House Goshen CT
2.5 star property
9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is ￥13,856
￥97,195 total
includes taxes & fees
Jan 4 - Jan 5, 2026
CT Gate House Goshen CT, Gate House Goshen CT
Exterior
Cozy Modern Farmhouse Private Apt - 3 Beds

Apartment in Torrington

Cozy Modern Farmhouse Private Apt - 3 Beds
10.0 out of 10, Exceptional, (4)
"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 ￥20,980
￥63,727 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Cozy Modern Farmhouse Private Apt - 3 Beds
Fridge, microwave, oven, stovetop
#2 *Beautiful 1 BR Apartment - Central CT*

Apartment in Plainville

#2 *Beautiful 1 BR Apartment - Central CT*
9.0 out of 10, Wonderful, (2)
"I try to come up to Connecticut at least once a year if possible and this really worked out perfect for me first floor no steps easy to bring luggage in very comfortable. Would definitely come back and stay there again."
United States
Rodney L.
#2 *Beautiful 1 BR Apartment - Central CT*
Terrace/patio
Charming 1-bedroom in welcoming West Hartford with WiFi, AC

Vacation Home in West Hartford

Charming 1-bedroom in welcoming West Hartford with WiFi, AC
The price is ￥11,230
￥19,621 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Charming 1-bedroom in welcoming West Hartford with WiFi, AC
Smart TV, fireplace
Sun Filled Lake House Living

Vacation Home in Avon

Sun Filled Lake House Living
2.0 star property
6.0 out of 10, (3)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
The price is ￥9,394
￥39,113 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Sun Filled Lake House Living
Fridge, microwave, oven, stovetop
Home in Great Barrington

Vacation Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26)
"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 ￥23,583
￥40,105 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Home in Great Barrington
Exterior detail
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Apartment in Torrington

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
10.0 out of 10, Exceptional, (1)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
The price is ￥21,607
￥65,113 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Property grounds
Big farmhouse in the foothills of the Berkshires

Vacation Home in Russell

Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (143)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is ￥31,194
￥56,712 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Big farmhouse in the foothills of the Berkshires
Property grounds
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

Vacation Home in East Granby

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
8.6 out of 10, Excellent, (4)
"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 ￥31,314
￥80,007 total
includes taxes & fees
Jan 2 - Jan 3, 2026
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Outdoor dining
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥22,740
￥58,677 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Fridge, microwave, oven, stovetop
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Vacation Home in Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
10.0 out of 10, Exceptional, (61)
"Fabulous location. I can honestly say cleanest VRBO we’ve ever stayed!!"
United States
Jeanmarie G.
The price is ￥48,663
￥81,113 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Fridge, microwave, oven, stovetop
Charming apartment 7 minute walk to downtown

Apartment in Torrington

Charming apartment 7 minute walk to downtown
10.0 out of 10, Exceptional, (16)
"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 ￥22,405
￥40,484 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Charming apartment 7 minute walk to downtown
Exterior
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Vacation Home in Sherwood Forest

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is ￥24,986
￥61,533 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Interior
The Sun Filled Cozy Creamery

Apartment in Plainville

The Sun Filled Cozy Creamery
8.8 out of 10, Excellent, (25)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
The Sun Filled Cozy Creamery
Dining
Guesthouse Cabin vacation rentals in Berkshire County

Cabin in Sheffield

Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9)
"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 ￥61,296
￥106,970 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Guesthouse Cabin vacation rentals in Berkshire County
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winsted Hotel Reviews

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent
"Basic, clean, well-kept. "
Justin 3-night trip
Posted 10 hours ago
DoubleTree by Hilton Hotel Bristol, Connecticut

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
  • 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!

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Winsted?

Yes, we have vacation rentals in Winsted close to Laurel Lanes, or you can go with a more secluded option if you're looking for extra privacy while you relax.

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

Peace and quiet on the lake: Visitors like this Winsted vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Winsted?

With 7 Expedia vacation rentals, you're sure 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 The Marina at Highland Lake are other places worth a visit.

What are vacation rentals like in Winsted?

Vacation rentals are private properties you can stay in for several days or longer in Winsted. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from shared hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family gatherings.