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

Winsted Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Winsted holiday rentals

A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

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, (55 reviews)
"Clean property, very cute. Also very small. Cable/tv access was challenging, but all on all a good experience"
United States
traci
The price is HK$989
HK$1,867 total
includes taxes & fees
12 Oct - 13 Oct
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A wooden cabin interior with a bench, a rug, and a hanging plant.

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is HK$902
HK$1,654 total
includes taxes & fees
1 Nov - 2 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A two-story house with a front porch, a small balcony, and a white picket fence.

3. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.6 out of 10, Exceptional, (7 reviews)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
The price is HK$972
HK$3,090 total
includes taxes & fees
12 Oct - 13 Oct
Cozy Attic 10 min to Llitchfield
A balcony with a view of a lake, white railings, and outdoor furniture.

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

River Overlook - What a view from your deck!
Collinsville
10.0 out of 10, Exceptional, (27 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 HK$1,257
HK$2,464 total
includes taxes & fees
12 Oct - 13 Oct
River Overlook - What a view from your deck!
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

5. 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 HK$1,123
HK$3,433 total
includes taxes & fees
1 Nov - 2 Nov
Art House 3 Beds Close to Warner Theater
A two-story house with a front porch, a small balcony, and a white picket fence.

6. 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$1,244
HK$3,530 total
includes taxes & fees
28 Oct - 29 Oct
Cozy Modern Farmhouse Private Apt - 3 Beds
A modern kitchen with blue cabinets, a dining area with a glass table, and a living room with a brown leather sofa.

7. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
10.0 out of 10, Exceptional, (1 review)
"We loved the place, which feels like your own house in the woods. The setting is gorgeous especially with the leaves changing colors. We specifically chose the location so we could bike the Farmington Trail loop which starts at the bottom of the hill. The house is so well stocked with everything you could think of, especially coffee and there is plenty of space to relax inside and out. The host was very attentive to our needs. It couldn’t have been better for us."
United States
Margaret A.
The price is HK$1,434
HK$1,806 total
includes taxes & fees
29 Oct - 30 Oct
Collinsville River Escape / Fall Foliage, Deck & Yard
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

8. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (22 reviews)
"It was great!"
United States
Amanda T.
The price is HK$1,530
HK$2,507 total
includes taxes & fees
8 Nov - 9 Nov
Pristine Cozy Walkable Downtown 2BR Getaway
A square fire pit with flames, surrounded by a grassy field and a green chair.

9. 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 HK$816
HK$1,547 total
includes taxes & fees
26 Oct - 27 Oct
Peaceful Meadow Retreat
A patio with a table and chairs, a grill, and a view of a lake.

10. 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, (74 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is HK$2,448
HK$4,125 total
includes taxes & fees
19 Oct - 20 Oct
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

11. Sun Filled Lake House Living

Sun Filled Lake House Living
Avon
6.6 out of 10, (4 reviews)
"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 HK$565
HK$2,090 total
includes taxes & fees
26 Oct - 27 Oct
Sun Filled Lake House Living
A red door with a wicker basket hanging on it, leading to a laundry area with a brick wall and two large speakers.

12. 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 HK$573
HK$2,100 total
includes taxes & fees
12 Oct - 13 Oct
The Historic Hideaway
A wooden wall with a large mirror, a wooden console table, and two wall-mounted lanterns.

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

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is HK$1,096
HK$3,275 total
includes taxes & fees
13 Oct - 14 Oct
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
A historic building with red brick architecture, snow-covered roofs, and a prominent chimney.

14. 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 HK$573
HK$2,139 total
includes taxes & fees
14 Oct - 15 Oct
The Old Avon Village
A patio area with wicker furniture and a brick floor.

15. 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 traveller
The price is HK$1,428
HK$3,601 total
includes taxes & fees
12 Oct - 13 Oct
The Old Avon 1800 Manor
A lakeside view with a row of beach chairs and umbrellas.

16. Waterfront Lake Cottage - Lake Access -Kayaks

Waterfront Lake Cottage - Lake Access -Kayaks
Avon
The price is HK$2,472
HK$4,616 total
includes taxes & fees
27 Oct - 28 Oct
Waterfront Lake Cottage - Lake Access -Kayaks
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

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, (19 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is HK$1,687
HK$2,160 total
includes taxes & fees
12 Oct - 13 Oct
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

18. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 reviews)
"Everything about Jefferson House was perfect. It was located in a beautiful part of Connecticut adjoining a state park. The house was beautifully decorated. The kitchen was fully equipped and had a large island for dining. The bed, pillows and living room furnishings were very comfortable. The house was well up-to-date with two TVs, a charging device with multiple cords, a double oven (!), and countless thoughtful touches. I cannot recommend it highly enough!"
United States
genevieve
The price is HK$2,415
HK$3,098 total
includes taxes & fees
29 Oct - 30 Oct
The Jefferson Guest House, Spacious, Special Views
A deck with a white chair and a table, a sliding glass door, and a potted plant.

19. Bristol Condo Near Espn HQ & Lake Compounce!

Bristol Condo Near Espn HQ & Lake Compounce!
3.5 star property
Bristol
The price is HK$1,373
HK$2,463 total
includes taxes & fees
12 Oct - 13 Oct
Bristol Condo Near Espn HQ & Lake Compounce!
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

20. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (54 reviews)
"Quiet and peaceful"
United States
Michael S.
The price is HK$1,923
HK$4,427 total
includes taxes & fees
23 Oct - 24 Oct
Cozy Cottage-Sunset On The Lake
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

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol

8/10 Good
"Bed was not very comfortable."
Laura 1-night trip
Posted 1 day ago
Home2 Suites by Hilton Bristol

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!

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?

Waterfront House & Guest House Available in Winchester, CT!: This highly rated holiday home rental in Winsted is located on a lake, and offers a patio, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Winsted?

With 12 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 The Marina at Highland Lake 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.