A tranquil lake with a stone tower, surrounded by autumn-colored trees and a clear sky.

Winsted Vacation Rentals

  • 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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Winsted vacation rentals

Terrace/patio

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

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (50 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is SAR 480
SAR 800 total
includes taxes & fees
10 Aug - 11 Aug
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
2 bedrooms, WiFi (free), bed sheets

2. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is SAR 466
SAR 839 total
includes taxes & fees
5 Aug - 6 Aug
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Dining

3. Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
The price is SAR 528
SAR 1,623 total
includes taxes & fees
4 Aug - 5 Aug
Art House 3 Beds Close to Warner Theater
Exterior

4. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
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 SAR 335
SAR 1,029 total
includes taxes & fees
1 Sep - 2 Sep
Cozy Attic 10 min to Llitchfield
Exterior

5. 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 SAR 485
SAR 1,251 total
includes taxes & fees
1 Sep - 2 Sep
Cozy Modern Farmhouse Private Apt - 3 Beds
Property grounds

6. Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (24 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
The price is SAR 419
SAR 777 total
includes taxes & fees
4 Aug - 5 Aug
Peaceful Meadow Retreat
Smart TV, fireplace

7. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (19 reviews)
"Wow what an enjoyable stay! Clean, fresh, relaxing, and wonderful to meet owners Corin and Jen… gracious and hospitable hosts. Very comfortable, great location, well appointed… everything we were looking for!"
United States
James M.
The price is SAR 601
SAR 1,034 total
includes taxes & fees
26 Aug - 27 Aug
Pristine Cozy Walkable Downtown 2BR Getaway
Property grounds

8. River Overlook - What a view from your deck!

River Overlook - What a view from your deck!
Collinsville
10.0 out of 10, Exceptional, (26 reviews)
"I only did a short stay (2 nights) but it was super adorable! I will definitely stay again when I'm back in the area."
United States
Mary S.
The price is SAR 620
SAR 1,200 total
includes taxes & fees
17 Aug - 18 Aug
River Overlook - What a view from your deck!
Dining

9. 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 SAR 879
SAR 1,945 total
includes taxes & fees
4 Aug - 5 Aug
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Interior

10. Linny's - Lakefront Retreat Private Dock & Firepit

Linny's - Lakefront Retreat Private Dock & Firepit
West Suffield
10.0 out of 10, Exceptional, (41 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
The price is SAR 675
SAR 1,396 total
includes taxes & fees
5 Aug - 6 Aug
Linny's - Lakefront Retreat Private Dock & Firepit
Outdoor dining

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

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (68 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is SAR 1,172
SAR 1,974 total
includes taxes & fees
10 Aug - 11 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
1 bedroom, desk, iron/ironing board, WiFi

12. Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is SAR 485
SAR 1,506 total
includes taxes & fees
6 Aug - 7 Aug
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Interior

13. The Historic Hideaway

The Historic Hideaway
Avon
6.0 out of 10, (4 reviews)
"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 SAR 327
SAR 1,076 total
includes taxes & fees
17 Aug - 18 Aug
The Historic Hideaway
Interior

14. The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (26 reviews)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
The price is SAR 259
SAR 949 total
includes taxes & fees
5 Aug - 6 Aug
The Sun Filled Cozy Creamery
Exterior

15. The Old Avon Village

The Old Avon Village
Avon
6.2 out of 10, (10 reviews)
"Great location. Alexander was very responsive to any requests. Met our needs. "
United States
Deborah S.
The price is SAR 406
SAR 1,202 total
includes taxes & fees
1 Sep - 2 Sep
The Old Avon Village
Coffee/tea maker, fridge, microwave, oven

16. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (8 reviews)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
United States
Jennifer A.
The price is SAR 1,095
SAR 1,414 total
includes taxes & fees
4 Aug - 5 Aug
The Jefferson Guest House, Spacious, Special Views
Interior

17. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (11 reviews)
"The property was very clean and inviting and the owner was very welcoming and helpful!"
United States
Sarah
The price is SAR 807
SAR 1,037 total
includes taxes & fees
5 Aug - 6 Aug
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Property grounds

18. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (148 reviews)
"Great location"
United States
Will G.
The price is SAR 714
SAR 1,314 total
includes taxes & fees
28 Aug - 29 Aug
Big farmhouse in the foothills of the Berkshires
Interior

19. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is SAR 312
SAR 1,221 total
includes taxes & fees
26 Aug - 27 Aug
Real Estate: Therapy - Lake, Laundry, Love it
Terrace/patio

20. The Old Avon 1800 Manor

The Old Avon 1800 Manor
Avon
7.0 out of 10, Good, (2 reviews)
"Wonderful place and host very responsive and friendly!"
United States
Anonymous traveler
The price is SAR 958
SAR 2,090 total
includes taxes & fees
17 Aug - 18 Aug
The Old Avon 1800 Manor
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

Holiday Inn Express & Suites Bradley Airport by IHG

Holiday Inn Express & Suites Bradley Airport by IHG

10/10 Excellent
"The staff was very helpful when we had to book an extra night."
Thomas 1-night trip
Posted 11 hours ago
Holiday Inn Express & Suites Bradley Airport by IHG

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?

Lakefront Summer Stunner in New England Just 2 Hours From NYC: You might want to consider this vacation home rental near Winsted, which is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a private yard and a selection of games.

How many vacation rentals are there in Winsted?

With 11 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, The Marina at Highland Lake and Platt Hill State Park 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.