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
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

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 ￥20,093
￥34,270 total
includes taxes & fees
Aug 19 - Aug 20
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 ￥19,788
￥35,900 total
includes taxes & fees
Sep 13 - Sep 14
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Exterior

3. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.4 out of 10, Exceptional, (6 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 ￥14,902
￥45,122 total
includes taxes & fees
Aug 16 - Aug 17
Cozy Attic 10 min to Llitchfield
Dining

4. 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 ￥22,423
￥69,237 total
includes taxes & fees
Sep 1 - Sep 2
Art House 3 Beds Close to Warner Theater
Property grounds

5. 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 ￥23,681
￥48,085 total
includes taxes & fees
Aug 17 - Aug 18
River Overlook - What a view from your deck!
Exterior

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 ￥20,596
￥53,763 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Modern Farmhouse Private Apt - 3 Beds
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 ￥27,110
￥46,366 total
includes taxes & fees
Sep 1 - Sep 2
Pristine Cozy Walkable Downtown 2BR Getaway
Property grounds

8. 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 ￥16,569
￥31,402 total
includes taxes & fees
Sep 10 - Sep 11
Peaceful Meadow Retreat
Property grounds

9. 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 ￥17,542
￥50,949 total
includes taxes & fees
Sep 9 - Sep 10
Sun Filled Lake House Living
Interior

10. 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 ￥11,003
￥40,462 total
includes taxes & fees
Aug 19 - Aug 20
The Sun Filled Cozy Creamery
Dining

11. 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 ￥37,281
￥83,004 total
includes taxes & fees
Sep 14 - Sep 15
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Outdoor dining

12. 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 ￥44,779
￥78,263 total
includes taxes & fees
Aug 17 - Aug 18
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
1 bedroom, desk, iron/ironing board, WiFi

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

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is ￥20,576
￥64,545 total
includes taxes & fees
Sep 15 - Sep 16
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Interior

14. 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 ￥12,279
￥44,084 total
includes taxes & fees
Aug 17 - Aug 18
The Historic Hideaway
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 ￥15,150
￥48,843 total
includes taxes & fees
Aug 16 - Aug 17
The Old Avon Village
Interior

16. 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, (14 reviews)
"The property was very clean and inviting and the owner was very welcoming and helpful!"
United States
Sarah
The price is ￥34,254
￥43,853 total
includes taxes & fees
Aug 26 - Aug 27
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Property grounds

17. 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 ￥27,244
￥52,710 total
includes taxes & fees
Sep 13 - Sep 14
Big farmhouse in the foothills of the Berkshires
Coffee/tea maker, fridge, microwave, oven

18. 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 ￥46,501
￥60,534 total
includes taxes & fees
Sep 3 - Sep 4
The Jefferson Guest House, Spacious, Special Views
Interior

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is ￥10,037
￥48,228 total
includes taxes & fees
Sep 13 - Sep 14
Real Estate: Therapy - Lake, Laundry, Love it
Outdoor spa tub

20. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ￥27,817
￥66,130 total
includes taxes & fees
Aug 26 - Aug 27
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
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

Delamar West Hartford

Delamar West Hartford

10/10 Excellent
"Beautiful hotel. Great location in West Hartford center. Plenty of restaurants and shopping surrounding it. Walking/bike path right there as well. The hotel itself is gorgeous, comfortable. The staff is excellent. The hotel restaurant is excellent as well. Highly recommend."
Sarah 1-night trip
Posted 4 hours ago
Delamar West Hartford

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:

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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.