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Winsted Vacation Rentals

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Dec 2 - Dec 3
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Dec 12 - Dec 14

Vacation Rentals in Winsted

Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Apartment in Torrington

9.6 out of 10, Exceptional, (4)
"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.
$230 nightly
The price is $274
Dec 3 - Dec 4
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Terrace/patio
Peaceful Meadow Retreat

Apartment in Granby

2.0 star property
10.0 out of 10, Exceptional, (16)
"The place is beautiful and very quiet and relaxing"
United States
Marian
$176 nightly
The price is $200
Dec 4 - Dec 5
Total with taxes and fees
Peaceful Meadow Retreat
Exterior
Cozy Modern Farmhouse Private 2 Bdrm Apartment

Apartment in Torrington

10.0 out of 10, Exceptional, (4)
"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.
$273 nightly
The price is $324
Dec 4 - Dec 5
Total with taxes and fees
Cozy Modern Farmhouse Private 2 Bdrm Apartment
Fridge, microwave, oven, stovetop
#2 *Beautiful 1 BR Apartment - Central CT*

Apartment in Plainville

9.0 out of 10, Wonderful, (2)
"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.
$185 nightly
The price is $198
Dec 7 - Dec 8
Total with taxes and fees
#2 *Beautiful 1 BR Apartment - Central CT*
Interior
#31 - Downtown Terryville- 1 Br

Apartment in Plymouth

10.0 out of 10, Exceptional, (1)
"In convenient safe area. Os is easy to contact"
United States
Gina P.
$349 nightly
The price is $381
Dec 31 - Jan 1, 2026
Total with taxes and fees
#31 - Downtown Terryville- 1 Br
Interior
The Sun Filled Cozy Creamery

Apartment in Plainville

8.8 out of 10, Excellent, (24)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
$384 nightly
The price is $426
Dec 22 - Dec 23
Total with taxes and fees
The Sun Filled Cozy Creamery
Private kitchen
Home in the Woods

Vacation Home in Russell

10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at the Home in the Woods. We stayed for 1 night on the way to Amherst for a graduation. The home is very cozy and clean. Jessica was easy to communicate with and the check-in/check out process was simple. Highly recommend!"
United States
Travis H.
$304 nightly
The price is $321
Dec 3 - Dec 4
Total with taxes and fees
Home in the Woods
Fridge, microwave, oven, stovetop
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!

Apartment in Plainville

8.4 out of 10, Very Good, (12)
"We enjoyed staying here. Great place, good communication, and a good rate for the space."
United States
Daniel F.
$273 nightly
The price is $291
Dec 18 - Dec 19
Total with taxes and fees
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
Property grounds
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

Vacation Home in East Granby

8.6 out of 10, Excellent, (4)
"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.
$387 nightly
The price is $439
Dec 3 - Dec 4
Total with taxes and fees
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$338 nightly
The price is $377
Dec 3 - Dec 4
Total with taxes and fees
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Outdoor dining
The Historic Hideaway

Apartment in Avon

2.0 star property
7.0 out of 10, Good, (2)
"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.
$233 nightly
The price is $245
Dec 6 - Dec 7
Total with taxes and fees
The Historic Hideaway
Exterior
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Vacation Home in Sherwood Forest

9.6 out of 10, Exceptional, (10)
"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.
$338 nightly
The price is $378
Dec 3 - Dec 4
Total with taxes and fees
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Fridge, microwave, oven, stovetop
Charming apartment 7 minute walk to downtown

Apartment in Torrington

10.0 out of 10, Exceptional, (15)
"Well equipped, lovely home, extremely clean and comfortable!"
United States
Sally V.
$218 nightly
The price is $247
Dec 3 - Dec 4
Total with taxes and fees
Charming apartment 7 minute walk to downtown
Smart TV, fireplace
Sun Filled Lake House Living

Vacation Home in Avon

2.0 star property
6.0 out of 10, (3)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
$238 nightly
The price is $251
Dec 11 - Dec 12
Total with taxes and fees
Sun Filled Lake House Living
Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

Vacation Home in Goshen

2.5 star property
9.8 out of 10, Exceptional, (7)
"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
Dec 7 - Dec 8
Total with taxes and fees
CT Gate House Goshen CT, Gate House Goshen CT
Fridge, microwave, oven, stovetop
Home in Great Barrington

Vacation Home in Great Barrington

9.8 out of 10, Exceptional, (25)
"Enjoyed our stay!!!"
United States
Fred W.
$243 nightly
The price is $271
Dec 15 - Dec 16
Total with taxes and fees
Home in Great Barrington
Fridge, microwave, oven, stovetop
River Overlook - Check the view from your deck!

Apartment in Collinsville

10.0 out of 10, Exceptional, (23)
"The place was perfect for the two of us. It was close to both our kids homes."
United States
Tomas M.
$253 nightly
The price is $286
Dec 3 - Dec 4
Total with taxes and fees
River Overlook - Check the view from your deck!
Interior
Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Vacation Home in Bloomfield

2.0 star property
9.4 out of 10, Exceptional, (3)
"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.
$607 nightly
The price is $688
Dec 7 - Dec 8
Total with taxes and fees
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Exterior
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Vacation Home in Goshen

2.0 star property
$459 nightly
The price is $520
Dec 3 - Dec 4
Total with taxes and fees
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Property grounds
Big farmhouse in the foothills of the Berkshires

Vacation Home in Russell

10.0 out of 10, Exceptional, (143)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
United States
Jon O.
$344 nightly
The price is $364
Dec 3 - Dec 4
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
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
"Staff was great in every way. Room was very nice and clean. Breakfast was good with lots of options."
Charles 1-night trip
Posted 2 days 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 $364 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?

Peace and quiet on the lake: Visitors like this Winsted vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

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 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.