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
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Winsted vacation rentals

Terrace/patio

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
9.2 out of 10, Wonderful, (47 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is AED 579
AED 908 total
includes taxes & fees
22 Jun - 23 Jun
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Exterior

Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.2 out of 10, Wonderful, (5 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 AED 316
AED 992 total
includes taxes & fees
29 Jun - 30 Jun
Cozy Attic 10 min to Llitchfield
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 545
AED 1,376 total
includes taxes & fees
23 Jun - 24 Jun
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Property grounds

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (23 reviews)
The price is AED 455
AED 808 total
includes taxes & fees
12 Jul - 13 Jul
Peaceful Meadow Retreat
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (147 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is AED 698
AED 1,305 total
includes taxes & fees
2 Jul - 3 Jul
Big farmhouse in the foothills of the Berkshires
Interior

The Historic Hideaway

The Historic Hideaway
Avon
6.0 out of 10, (4 reviews)
"Once we found the house it was very warm & cozy. The mini- muffins on the counter was a bonus. House mailbox was 87 but address was 89 that you only see if door is closed which it wasn't on 1st 2 passes. Limited exterior lights made coming back at night a challenge. "
United States
Kim C.
The price is AED 268
AED 990 total
includes taxes & fees
23 Jun - 24 Jun
The Historic Hideaway
Property grounds

River Overlook - What a view from your deck!

River Overlook - What a view from your deck!
Collinsville
10.0 out of 10, Exceptional, (23 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 AED 606
AED 1,185 total
includes taxes & fees
24 Jun - 25 Jun
River Overlook - What a view from your deck!
1 bedroom, iron/ironing board, free WiFi, bed sheets

#2 *Beautiful 1 BR Apartment - Central CT*

#2 *Beautiful 1 BR Apartment - Central CT*
Plainville
9.0 out of 10, Wonderful, (2 reviews)
"I try to come up to Connecticut at least once a year if possible and this really worked out perfect for me first floor no steps easy to bring luggage in very comfortable. Would definitely come back and stay there again."
United States
Rodney L.
The price is AED 330
AED 729 total
includes taxes & fees
28 Jun - 29 Jun
#2 *Beautiful 1 BR Apartment - Central CT*
Exterior

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 AED 353
AED 1,115 total
includes taxes & fees
5 Jul - 6 Jul
The Old Avon Village
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (32 reviews)
"Perfect space for an overnight stay. Very clean and well appointed. Communication from host was great and check in was a breeze. 2 minute drive from downtown Great Barrington."
United States
Anonymous traveler
The price is AED 876
AED 1,348 total
includes taxes & fees
22 Jun - 23 Jun
Home in Great Barrington
Exterior

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 AED 486
AED 1,487 total
includes taxes & fees
29 Jun - 30 Jun
Cozy Modern Farmhouse Private Apt - 3 Beds
Smart TV, fireplace

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 AED 716
AED 1,166 total
includes taxes & fees
23 Jun - 24 Jun
Pristine Cozy Walkable Downtown 2BR Getaway
Terrace/patio

The Old Avon 1800 Manor

The Old Avon 1800 Manor
Avon
10.0 out of 10, Exceptional, (1 review)
"Wonderful place and host very responsive and friendly!"
United States
Anonymous traveler
The price is AED 643
AED 1,651 total
includes taxes & fees
24 Jun - 25 Jun
The Old Avon 1800 Manor
Dining

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 AED 785
AED 1,883 total
includes taxes & fees
8 Jul - 9 Jul
Art House 3 Beds Close to Warner Theater
Outdoor dining

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, (66 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is AED 1,031
AED 1,784 total
includes taxes & fees
22 Jun - 23 Jun
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Outdoor spa tub

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, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AED 787
AED 1,699 total
includes taxes & fees
29 Jun - 30 Jun
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Bloomfield
7.6 out of 10, Good, (4 reviews)
"There were 7 of us staying for a Wedding near by. The home was bright, clean and very roomy. I would 100% stay here again. Host was on top of everything!! "
United States
Joslynn T.
The price is AED 889
AED 2,321 total
includes taxes & fees
22 Jun - 23 Jun
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is AED 959
AED 1,461 total
includes taxes & fees
22 Jun - 23 Jun
Litchfield Retreat, Wineries, Foliage & Skiing
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is AED 1,469
AED 2,536 total
includes taxes & fees
23 Jun - 24 Jun
Guesthouse Cabin vacation rentals in Berkshire County
Fridge, microwave, oven, stovetop

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 AED 1,071
AED 1,387 total
includes taxes & fees
5 Jul - 6 Jul
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"best location possible. so convenient and easy. not a luxury property but perfect for what we need. have stayed multiple times"
Carrie 1-night trip
Posted 2 hours ago
Quality Inn Great Barrington

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?

Lakefront Retreat with Stunning Views | Forget-Me-Not by AvantStay: You might want to consider this vacation home rental near Winsted, which is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 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 8 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?

Rowley Fields and Highland Lake 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 Northwestern Connecticut Community College Library 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.