Winsted Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Winsted vacation rentals

Property grounds

Apartment in Granby

Peaceful Meadow Retreat
10.0 out of 10, Exceptional, (17 reviews)
"We stayed here as a quick overnight trip for events in the area. We really enjoyed the property, reading through the guestbook, and the local pizza place La Figata. "
United States
Kaleigh L.
$164 nightly
The price is $185
Jan 26 - Jan 27
Total with taxes and fees
Peaceful Meadow Retreat
Exterior

Apartment in Torrington

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
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.
$295 nightly
The price is $337
Jan 25 - Jan 26
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Exterior detail

Vacation Home in Goshen

CT Gate House Goshen CT, Gate House Goshen CT
9.4 out of 10, Exceptional, (9 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
$627 nightly
The price is $643
Jan 25 - Jan 26
Total with taxes and fees
CT Gate House Goshen CT, Gate House Goshen CT
Fridge, microwave, oven, stovetop

Vacation Home in East Granby

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
8.6 out of 10, Excellent, (4 reviews)
"Great Stay at the Olde Tobacco Barn. Was here for a work trip, and the place was perfect for our needs. House is set back really nicely and private. Host was super responsive and easy to deal with. Overall 5/5 stay. Thank you!"
United States
Sgt W.
$404 nightly
The price is $457
Jan 26 - Jan 27
Total with taxes and fees
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Exterior

Apartment in Torrington

Cozy Modern Farmhouse Private Apt - 3 Beds
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.
$341 nightly
The price is $392
Jan 25 - Jan 26
Total with taxes and fees
Cozy Modern Farmhouse Private Apt - 3 Beds
Interior

Cabin in Bethlehem

Cozy & Serene Cabin with Fireplace, Ski Nearby!
10.0 out of 10, Exceptional, (37 reviews)
"Very comfortable property. The host had thought of everything!"
United States
Jennifer Y.
$350 nightly
The price is $397
Jan 26 - Jan 27
Total with taxes and fees
Cozy & Serene Cabin with Fireplace, Ski Nearby!
Dining

Apartment in Torrington

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
$339 nightly
The price is $390
Jan 25 - Jan 26
Total with taxes and fees
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Smart TV, books

Vacation Home in Sherwood Forest

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
9.6 out of 10, Exceptional, (10 reviews)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
$339 nightly
The price is $379
Jan 25 - Jan 26
Total with taxes and fees
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
2 bedrooms, desk, free WiFi, bed sheets

Apartment in Torrington

Charming apartment 7 minute walk to downtown
10.0 out of 10, Exceptional, (16 reviews)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
United States
Kate B.
$211 nightly
The price is $239
Feb 2 - Feb 3
Total with taxes and fees
Charming apartment 7 minute walk to downtown
Interior

Vacation Home in Bloomfield

Stylish Townhome | Perfect for Family Gatherings & Events
10.0 out of 10, Exceptional, (4 reviews)
"The house was newer and the living room and kitchen had open layout that enabled to spend quality time with family."
United States
Muhammad G.
$629 nightly
The price is $713
Jan 25 - Jan 26
Total with taxes and fees
Stylish Townhome | Perfect for Family Gatherings & Events
Fridge, microwave, oven, stovetop

Vacation Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
$224 nightly
The price is $250
Jan 26 - Jan 27
Total with taxes and fees
Home in Great Barrington
Property grounds

Apartment in Collinsville

River Overlook - Check the view from your deck!
10.0 out of 10, Exceptional, (23 reviews)
"The place was perfect for the two of us. It was close to both our kids homes."
United States
Tomas M.
$235 nightly
The price is $266
Jan 25 - Jan 26
Total with taxes and fees
River Overlook - Check the view from your deck!
Property grounds

Vacation Home in Russell

Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
$283 nightly
The price is $299
Jan 26 - Jan 27
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Smart TV

Vacation Home in Bloomfield

Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
8.8 out of 10, Excellent, (5 reviews)
"I had a great time and I felt very welcome"
United States
Avis b.
$666 nightly
The price is $753
Jan 25 - Jan 26
Total with taxes and fees
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
Outdoor dining

Vacation Home in Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
10.0 out of 10, Exceptional, (61 reviews)
"Fabulous location. I can honestly say cleanest VRBO we’ve ever stayed!!"
United States
Jeanmarie G.
$346 nightly
The price is $391
Jan 25 - Jan 26
Total with taxes and fees
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Interior

Vacation Home in Goshen

Whispering Estate Guest House - A Romantic Countryside Getaway
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
$778 nightly
The price is $882
Jan 25 - Jan 26
Total with taxes and fees
Whispering Estate Guest House - A Romantic Countryside Getaway
Interior

Cabin in Sheffield

Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9 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.
$613 nightly
The price is $685
Jan 26 - Jan 27
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
Fridge, microwave, oven, stovetop

Apartment in Litchfield

The Jefferson Guest House, Spacious, Special Views
10.0 out of 10, Exceptional, (8 reviews)
"The place was absolutely spotless and magnificent in every way. Highly recommended."
United States
Robert A.
$375 nightly
The price is $375
Jan 26 - Jan 27
Total with taxes and fees
The Jefferson Guest House, Spacious, Special Views
Exterior

Vacation Home in Goshen

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
$444 nightly
The price is $504
Jan 25 - Jan 26
Total with taxes and fees
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Interior

Vacation Home in Bloomfield

Group-Friendly Townhouse Stay – Sleeps up to 20
8.0 out of 10, Very Good, (3 reviews)
"This was a terrific spot for our weekend plans to fly in and see a UCONN Husky basketball game in Hartford! Hope was comfortable and clean. Will definitely plan to stay here again. "
United States
Paul L.
$1,060 nightly
The price is $1,201
Jan 25 - Jan 26
Total with taxes and fees
Group-Friendly Townhouse Stay – Sleeps up to 20
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

Holiday Inn Express & Suites Bradley Airport by IHG

Holiday Inn Express & Suites Bradley Airport by IHG

10/10 Excellent
"Romm eas large and clean. The staff was excellent. Love the coffee/ tea station that is availability 24 hrs/ day."
Deborah 3-night trip
Posted 1 day ago
Holiday Inn Express & Suites Bradley Airport by IHG

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 $250 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?

Home in Great Barrington: Visitors like this Winsted vacation home rental. It is located in the city center and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Winsted?

With 7 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 Winchester Historical Society 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.