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
$190 nightly
The price is $215
Aug 11 - Aug 12
Total with taxes and fees
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
$198 nightly
The price is $224
Aug 30 - Aug 31
Total with taxes and fees
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Interior

3. Bristol Condo Near ESPN HQ & Lake Compounce!

Bristol Condo Near ESPN HQ & Lake Compounce!
Bristol
$273 nightly
The price is $310
Sep 1 - Sep 2
Total with taxes and fees
Bristol Condo Near ESPN HQ & Lake Compounce!
Apartment (1 Bedroom) | Interior

4. Bristol Condo Near Espn HQ & Lake Compounce!

Bristol Condo Near Espn HQ & Lake Compounce!
3.5 star property
Bristol
$273 nightly
The price is $314
Sep 1 - Sep 2
Total with taxes and fees
Bristol Condo Near Espn HQ & Lake Compounce!
Interior

5. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
$309 nightly
The price is $345
Aug 24 - Aug 25
Total with taxes and fees
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Exterior

6. 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.
$230 nightly
The price is $273
Aug 11 - Aug 12
Total with taxes and fees
Cozy Attic 10 min to Llitchfield
Dining

7. 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.
$388 nightly
The price is $448
Sep 1 - Sep 2
Total with taxes and fees
Art House 3 Beds Close to Warner Theater
1 bedroom, desk, iron/ironing board, WiFi

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

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
$352 nightly
The price is $405
Aug 11 - Aug 12
Total with taxes and fees
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Smart TV, fireplace

9. 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.
$232 nightly
The price is $263
Sep 2 - Sep 3
Total with taxes and fees
Pristine Cozy Walkable Downtown 2BR Getaway
Property grounds

10. 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.
$268 nightly
The price is $303
Aug 13 - Aug 14
Total with taxes and fees
River Overlook - What a view from your deck!
Property grounds

11. 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.
$174 nightly
The price is $197
Sep 8 - Sep 9
Total with taxes and fees
Peaceful Meadow Retreat
Exterior

12. 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.
$267 nightly
The price is $284
Aug 11 - Aug 12
Total with taxes and fees
The Old Avon Village
Interior

13. Linny's - Private Dock - Lake Access - Firepit

Linny's - Private Dock - Lake Access - Firepit
West Suffield
10.0 out of 10, Exceptional, (43 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
Linny's - Private Dock - Lake Access - Firepit
Property grounds

14. 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.
$297 nightly
The price is $321
Sep 9 - Sep 10
Total with taxes and fees
Sun Filled Lake House Living
Interior

15. 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.
$277 nightly
The price is $297
Aug 16 - Aug 17
Total with taxes and fees
The Historic Hideaway
Outdoor dining

16. 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
$434 nightly
The price is $491
Aug 19 - Aug 20
Total with taxes and fees
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Exterior

17. 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.
$284 nightly
The price is $337
Sep 1 - Sep 2
Total with taxes and fees
Cozy Modern Farmhouse Private Apt - 3 Beds
Dining

18. 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.
$439 nightly
The price is $521
Aug 11 - Aug 12
Total with taxes and fees
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Interior

19. The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (26 reviews)
$239 nightly
The price is $254
Aug 12 - Aug 13
Total with taxes and fees
The Sun Filled Cozy Creamery
Property grounds

20. 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.
$316 nightly
The price is $334
Aug 23 - Aug 24
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
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

Simsbury 1820 House

Simsbury 1820 House

10/10 Excellent
"The room was very clean and spacious. Bathroom a little dated. Room was very comfortable. We stayed in the carriage house, which we like very much. The breakfast was very good for a continental breakfast. We appreciated the bottled water provided each day. Thank you for a nice stay."
Harvey 5-night trip
Posted 10 hours ago
Simsbury 1820 House

Find out more about Winsted

Everything you need to know about Winsted vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winsted vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winsted vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winsted vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winsted. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winsted in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $224 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winsted rentals

At Expedia, we put the best Winsted vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winsted rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winsted vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winsted. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

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.