Winsted Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Winsted vacation 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)
"It was a nice stay…worked well for the event we attended in town. The host was very nice to work with"
United States
Roberta S.
The price is CA $153
CA $295 total
includes taxes & fees
Nov 22 - Nov 23
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, (5 reviews)
The price is CA $146
CA $266 total
includes taxes & fees
Nov 15 - Nov 16
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

3. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (22 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 CA $244
CA $398 total
includes taxes & fees
Nov 16 - Nov 17
Pristine Cozy Walkable Downtown 2BR Getaway
A modern kitchen with a wooden dining table, blue chairs, and a decorative bowl centerpiece.

4. 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 CA $338
CA $807 total
includes taxes & fees
Nov 12 - Nov 13
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
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 CA $213
CA $609 total
includes taxes & fees
Nov 12 - Nov 13
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 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 CA $148
CA $504 total
includes taxes & fees
Nov 12 - Nov 13
Cozy Attic 10 min to Llitchfield
A two-story house with a front porch, a small balcony, and a white picket fence.

7. 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 CA $199
CA $578 total
includes taxes & fees
Nov 12 - Nov 13
Cozy Modern Farmhouse Private Apt - 3 Beds
A balcony with a view of a lake, white railings, and outdoor furniture.

8. 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 CA $251
CA $458 total
includes taxes & fees
Nov 16 - Nov 17
River Overlook - What a view from your deck!
A patio with a table and chairs, a grill, and a view of a lake.

9. 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, (76 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is CA $396
CA $658 total
includes taxes & fees
Nov 12 - Nov 13
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A modern kitchen with blue cabinets, a central island, and a dining area with a glass table and chairs.

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

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
9.6 out of 10, Exceptional, (4 reviews)
"Cute and cozy home away from home! We loved our stay and all the nice features there were!! Everything was neat and clean and host was super amazing and helpful! We definitely will choose this place again if we’re ever in the area."
United States
Leah H.
The price is CA $152
CA $181 total
includes taxes & fees
Nov 16 - Nov 17
Collinsville River Escape / Fall Foliage, Deck & Yard
A serene outdoor seating area with wooden chairs and a view of a pond surrounded by lush greenery.

11. Waterfront Lake Cottage - Lake Access -Kayaks

Waterfront Lake Cottage - Lake Access -Kayaks
Avon
10.0 out of 10, Exceptional, (1 review)
"The cottage is very cozy, private, and in a beatiful setting. We really appreciated the upgrades that made our stay comfortable. The fenced-in yard was great for our dog. Take a note of a stone floor on the lower level. We had to cover it to be not too cold for the dog to lie on (in late October). The location is right on the water for kayaking and close to some well maintained trails for biking and hiking."
United States
Victoria F.
The price is CA $447
CA $832 total
includes taxes & fees
Dec 8 - Dec 9
Waterfront Lake Cottage - Lake Access -Kayaks
A spacious kitchen with wooden cabinets, a large island with stools, and a clock on the wall.

12. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 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 CA $435
CA $533 total
includes taxes & fees
Nov 16 - Nov 17
The Jefferson Guest House, Spacious, Special Views
A square fire pit with flames, surrounded by a grassy field and a green chair.

13. Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (26 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
The price is CA $132
CA $250 total
includes taxes & fees
Nov 16 - Nov 17
Peaceful Meadow Retreat
A wooden wall with a large mirror, a wooden console table, and two wall-mounted lanterns.

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

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is CA $199
CA $573 total
includes taxes & fees
Dec 2 - Dec 3
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
A red door with a wicker basket hanging on it, leading to a laundry area with a brick wall and two large speakers.

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.
The price is CA $103
CA $348 total
includes taxes & fees
Nov 18 - Nov 19
The Historic Hideaway
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

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, (21 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is CA $304
CA $376 total
includes taxes & fees
Nov 12 - Nov 13
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

17. 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 CA $96
CA $354 total
includes taxes & fees
Nov 16 - Nov 17
Sun Filled Lake House Living
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

18. Escape to Bantam Lake- With Fireplace and Hot tub!

Escape to Bantam Lake- With Fireplace and Hot tub!
Morris
10.0 out of 10, Exceptional, (6 reviews)
"This house is a dream. First, the views are incredible. Second, it’s beautifully decorated and very cozy. Lastly, the property location is perfect. I can’t wait to stay again!"
United States
Shannon M.
The price is CA $333
CA $648 total
includes taxes & fees
Nov 18 - Nov 19
Escape to Bantam Lake- With Fireplace and Hot tub!
A historic building with red brick architecture, snow-covered roofs, and a prominent chimney.

19. 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 CA $103
CA $371 total
includes taxes & fees
Nov 16 - Nov 17
The Old Avon Village
A patio area with wicker furniture and a brick floor.

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 traveller
The price is CA $247
CA $586 total
includes taxes & fees
Nov 18 - Nov 19
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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Find vacation rentals that suit your style

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Top Winsted Hotel Reviews

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.
Blackberry River Inn

Blackberry River Inn

Blackberry River Inn
Norfolk

10/10 Excellent

Very nice place , staff was very nice also.
Canada
Mark
Reviewed July 21, 2026
Blackberry River Inn

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winsted vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winsted vacation rentals we have selected for you start as low as CA $1,264 per night. Entering your travel dates in the search wizard 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.

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?

Waterfront House & Guest House Available in Winchester, CT!: Visitors give good reviews to this Winsted vacation home rental, which 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 vacation rentals are there in Winsted?

With 12 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.

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