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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

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
$197 nightly
The price is $223
Sep 13 - Sep 14
Total with taxes and fees
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A spacious kitchen with a large island, wooden beams, and pendant lighting.

2. 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.
$360 nightly
The price is $380
Sep 13 - Sep 14
Total with taxes and fees
Linny's - Private Dock - Lake Access - Firepit
A spacious living room with a brown leather sofa, a dining area with a wooden table and chairs, and a kitchen with stainless steel appliances.

3. #11 - 4 Bedrooms, 3 Baths! Sleeps up to 8

#11 - 4 Bedrooms, 3 Baths! Sleeps up to 8
Plainville
10.0 out of 10, Exceptional, (3 reviews)
"Great weekend with friends!"
United States
Neil R.
$563 nightly
The price is $611
Sep 13 - Sep 14
Total with taxes and fees
#11 - 4 Bedrooms, 3 Baths! Sleeps up to 8
A spacious living room with a brown leather sofa, a dining area with a wooden table and chairs, and a kitchen with stainless steel appliances.

4. #3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!

#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
Plainville
8.8 out of 10, Excellent, (15 reviews)
"Great place and good location."
United States
MARC S.
$360 nightly
The price is $388
Sep 12 - Sep 13
Total with taxes and fees
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
A hallway with a patterned wall, a wooden floor, a rug, a door with a wreath, and a bed visible through a glass door.

5. 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.
$227 nightly
The price is $242
Sep 21 - Sep 22
Total with taxes and fees
The Sun Filled Cozy Creamery
A patio area with wicker furniture and a brick floor.

6. 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
$441 nightly
The price is $483
Sep 14 - Sep 15
Total with taxes and fees
The Old Avon 1800 Manor
A historic building with red brick architecture, snow-covered roofs, and a prominent chimney.

7. 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.
$273 nightly
The price is $291
Sep 14 - Sep 15
Total with taxes and fees
The Old Avon Village
A red door with a wicker basket hanging on it, leading to a laundry area with a brick wall and two large speakers.

8. 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.
$253 nightly
The price is $269
Sep 23 - Sep 24
Total with taxes and fees
The Historic Hideaway
A loft-style room with a sloped ceiling, a wooden beam, a TV, a white entertainment unit, a black chair, a small table, and a lamp.

9. 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 11 - Sep 12
Total with taxes and fees
Bristol Condo Near Espn HQ & Lake Compounce!
A bedroom with a large bed, a wooden door, a mirror, and a wall-mounted light fixture.

10. Bristol Condo Near ESPN HQ & Lake Compounce!

Bristol Condo Near ESPN HQ & Lake Compounce!
Bristol
$273 nightly
The price is $310
Sep 11 - Sep 12
Total with taxes and fees
Bristol Condo Near ESPN HQ & Lake Compounce!
A square fire pit with flames, surrounded by a grassy field and a green chair.

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.
$167 nightly
The price is $190
Oct 5 - Oct 6
Total with taxes and fees
Peaceful Meadow Retreat
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

12. 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.
$263 nightly
The price is $283
Sep 16 - Sep 17
Total with taxes and fees
Sun Filled Lake House Living
A patio with a table and chairs, a grill, and a view of a lake.

13. 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, (71 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
$429 nightly
The price is $486
Sep 13 - Sep 14
Total with taxes and fees
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A balcony with a view of a lake, white railings, and outdoor furniture.

14. 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.
$279 nightly
The price is $316
Sep 20 - Sep 21
Total with taxes and fees
River Overlook - What a view from your deck!
A bunk bed with a ladder, a bedside table, a lamp, and a window with curtains.

15. Lakehaven • Hot Tub, Decks, Fires & More

Lakehaven • Hot Tub, Decks, Fires & More
Plymouth
$769 nightly
The price is $870
Oct 1 - Oct 2
Total with taxes and fees
Lakehaven • Hot Tub, Decks, Fires & More
A house with a porch, a garden with pink flowers, and a stone wall along the road.

16. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (150 reviews)
"Great location"
United States
Will G.
$312 nightly
The price is $330
Sep 13 - Sep 14
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
A two-story house with a front porch, a small balcony, and a white picket fence.

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.
$346 nightly
The price is $402
Sep 15 - Sep 16
Total with taxes and fees
Cozy Modern Farmhouse Private Apt - 3 Beds
A two-story house with a front porch, a small balcony, and a white picket fence.

18. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.4 out of 10, Exceptional, (6 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.
$322 nightly
The price is $370
Sep 14 - Sep 15
Total with taxes and fees
Cozy Attic 10 min to Llitchfield
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

19. 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.
$243 nightly
The price is $277
Sep 15 - Sep 16
Total with taxes and fees
Pristine Cozy Walkable Downtown 2BR Getaway
A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

20. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 reviews)
"Everything about Jefferson House was perfect. It was located in a beautiful part of Connecticut adjoining a state park. The house was beautifully decorated. The kitchen was fully equipped and had a large island for dining. The bed, pillows and living room furnishings were very comfortable. The house was well up-to-date with two TVs, a charging device with multiple cords, a double oven (!), and countless thoughtful touches. I cannot recommend it highly enough!"
United States
genevieve
$377 nightly
The price is $377
Sep 21 - Sep 22
Total with taxes and fees
The Jefferson Guest House, Spacious, Special Views
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

The Farmington Inn & Suites

The Farmington Inn & Suites

10/10 Excellent
"It looks a little dated but I think its part of the charm! Its like stepping back in time compared to contemporary looking hotels. Staff was very helpful and attentive and the room I was in was nice and clean! Definitely worth a look!"
Howard 1-night trip
Posted 2 hours ago
The Farmington Inn & Suites

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 $316 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?

The Meadows House @ Otis Ridge w/ 7-person hot tub: Visitors like this Winsted vacation home rental. It is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.