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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Winsted vacation rentals

A wooden cabin interior with a bench, a rug, and a hanging plant.

1. 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, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
$174 nightly
The price is $197
Nov 8 - Nov 9
Total with taxes and fees
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.

2. 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.
$251 nightly
The price is $284
Oct 28 - Oct 29
Total with taxes and fees
Pristine Cozy Walkable Downtown 2BR Getaway
A modern kitchen with a wooden dining table, blue chairs, and a decorative bowl centerpiece.

3. 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.
$511 nightly
The price is $594
Oct 27 - Oct 28
Total with taxes and fees
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

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.
$387 nightly
The price is $447
Oct 27 - Oct 28
Total with taxes and fees
Art House 3 Beds Close to Warner Theater
A balcony with a view of a lake, white railings, and outdoor furniture.

5. 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.
$277 nightly
The price is $314
Oct 27 - Oct 28
Total with taxes and fees
River Overlook - What a view from your deck!
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.
$323 nightly
The price is $371
Oct 27 - Oct 28
Total with taxes and fees
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.
$369 nightly
The price is $425
Oct 27 - Oct 28
Total with taxes and fees
Cozy Modern Farmhouse Private Apt - 3 Beds
A patio with a table and chairs, a grill, and a view of a lake.

8. 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, (75 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
$464 nightly
The price is $526
Oct 29 - Oct 30
Total with taxes and fees
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.

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

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
9.4 out of 10, Exceptional, (3 reviews)
"This was a great weekend away in CT! The house was comfortable and clean. Very cozy setup and good communication with the host. The weather wasn’t amazing but we still enjoyed our stay for the weekend."
United States
Brandon R.
$185 nightly
The price is $209
Nov 2 - Nov 3
Total with taxes and fees
Collinsville River Escape / Fall Foliage, Deck & Yard
A square fire pit with flames, surrounded by a grassy field and a green chair.

10. 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.
$164 nightly
The price is $185
Oct 28 - Oct 29
Total with taxes and fees
Peaceful Meadow Retreat
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.
$251 nightly
The price is $266
Nov 16 - Nov 17
Total with taxes and fees
Sun Filled Lake House Living
A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

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.
$395 nightly
The price is $395
Oct 27 - Oct 28
Total with taxes and fees
The Jefferson Guest House, Spacious, Special Views
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
$363 nightly
The price is $419
Oct 29 - Oct 30
Total with taxes and fees
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.

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.
$252 nightly
The price is $268
Nov 4 - Nov 5
Total with taxes and fees
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.

15. 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.
$244 nightly
The price is $276
Oct 27 - Oct 28
Total with taxes and fees
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

16. 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.
$477 nightly
The price is $540
Nov 16 - Nov 17
Total with taxes and fees
Escape to Bantam Lake- With Fireplace and Hot tub!
A historic building with red brick architecture, snow-covered roofs, and a prominent chimney.

17. 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.
$257 nightly
The price is $273
Nov 4 - Nov 5
Total with taxes and fees
The Old Avon Village
A lakeside view with a row of beach chairs and umbrellas.

18. Waterfront Lake Cottage - Lake Access -Kayaks

Waterfront Lake Cottage - Lake Access -Kayaks
Avon
$520 nightly
The price is $588
Oct 27 - Oct 28
Total with taxes and fees
Waterfront Lake Cottage - Lake Access -Kayaks
A two-story house with a well-maintained lawn and mature trees.

19. Sharon Retreat w/ Private Yard

Sharon Retreat w/ Private Yard
Sharon
9.2 out of 10, Wonderful, (37 reviews)
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"
United States
Heidi F.
$398 nightly
The price is $451
Oct 28 - Oct 29
Total with taxes and fees
Sharon Retreat w/ Private Yard
A hallway with a patterned wall, a wooden floor, a rug, a door with a wreath, and a bed visible through a glass door.

20. The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (27 reviews)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
$238 nightly
The price is $253
Nov 16 - Nov 17
Total with taxes and fees
The Sun Filled Cozy Creamery
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"We love staying at this hotel every fall. It is in an easy access location with plenty of parking and very clean. The staff are very friendly and the breakfast is fantastic. We’ll be back!!"
Patricia 2-night trip
Posted 2 hours ago
Quality Inn Great Barrington

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 $150 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?

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.