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

Winsted Vacation Rentals

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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 AED 466
AED 786 total
includes taxes & fees
18 Aug - 19 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 AED 507
AED 882 total
includes taxes & fees
24 Aug - 25 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 AED 540
AED 1,609 total
includes taxes & fees
2 Sep - 3 Sep
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 AED 339
AED 1,024 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 AED 505
AED 1,265 total
includes taxes & fees
2 Sep - 3 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 AED 410
AED 756 total
includes taxes & fees
16 Aug - 17 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 AED 573
AED 990 total
includes taxes & fees
2 Sep - 3 Sep
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 AED 606
AED 1,174 total
includes taxes & fees
13 Aug - 14 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 AED 859
AED 1,892 total
includes taxes & fees
9 Aug - 10 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, (42 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
The price is AED 671
AED 1,365 total
includes taxes & fees
16 Aug - 17 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 AED 1,146
AED 1,931 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 AED 474
AED 1,473 total
includes taxes & fees
9 Aug - 10 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 AED 309
AED 1,036 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 AED 253
AED 921 total
includes taxes & fees
12 Aug - 13 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 AED 279
AED 1,018 total
includes taxes & fees
11 Aug - 12 Aug
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 AED 1,071
AED 1,376 total
includes taxes & fees
18 Aug - 19 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 AED 790
AED 1,000 total
includes taxes & fees
18 Aug - 19 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 AED 698
AED 1,285 total
includes taxes & fees
2 Sep - 3 Sep
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
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 AED 856
AED 1,935 total
includes taxes & fees
18 Aug - 19 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.
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Top Winsted Hotel Reviews

Springhill Suites Marriott Airport

Springhill Suites Marriott Airport

8/10 Good
"the complementary breakfast was very good and the attendant kept it clean and refilled. Rooms are refurbished and generally nice though the bathroom plumbing reflected the age and use of the aged building."
Ray 1-night trip
Posted 5 hours ago
Springhill Suites Marriott Airport

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?

Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR: Visitors give good reviews to this Winsted vacation home rental, which is located on a lake and has a balcony, a garden, and air-conditioning to put you at ease in your new surroundings.

How many vacation rentals are there in Winsted?

With 10 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.