Winsted Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Winsted vacation rentals

Exterior detail

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
Goshen
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.
The price is ￥14,421
￥96,025 total
includes taxes & fees
Feb 15 - Feb 16
CT Gate House Goshen CT, Gate House Goshen CT
Property grounds

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
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.
The price is ￥14,299
￥28,284 total
includes taxes & fees
Feb 23 - Feb 24
Peaceful Meadow Retreat
Interior

#31 - Downtown Terryville- 1 Br

#31 - Downtown Terryville- 1 Br
Plymouth
10.0 out of 10, Exceptional, (1 review)
"In convenient safe area. Os is easy to contact"
United States
Gina P.
#31 - Downtown Terryville- 1 Br
Interior

The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
8.8 out of 10, Excellent, (25 reviews)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
The Sun Filled Cozy Creamery
Exterior

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
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 ￥12,229
￥50,476 total
includes taxes & fees
Feb 16 - Feb 17
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Interior

Cozy & Serene Cabin with Fireplace, Ski Nearby!

Cozy & Serene Cabin with Fireplace, Ski Nearby!
Bethlehem
10.0 out of 10, Exceptional, (39 reviews)
"Very comfortable property. The host had thought of everything!"
United States
Jennifer Y.
The price is ￥30,554
￥64,851 total
includes taxes & fees
Feb 16 - Feb 17
Cozy & Serene Cabin with Fireplace, Ski Nearby!
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 ￥18,447
￥59,571 total
includes taxes & fees
Feb 16 - Feb 17
Cozy Modern Farmhouse Private Apt - 3 Beds
Property grounds

River Overlook - Check the view from your deck!

River Overlook - Check the view from your deck!
Collinsville
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.
The price is ￥20,486
￥40,861 total
includes taxes & fees
Feb 15 - Feb 16
River Overlook - Check the view from your deck!
Fridge, microwave, oven, stovetop

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
East Granby
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.
The price is ￥33,151
￥81,358 total
includes taxes & fees
Feb 14 - Feb 15
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
2 bedrooms, desk, free WiFi, bed sheets

Charming apartment 7 minute walk to downtown

Charming apartment 7 minute walk to downtown
Torrington
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.
The price is ￥25,818
￥44,815 total
includes taxes & fees
Mar 11 - Mar 12
Charming apartment 7 minute walk to downtown
Smart TV, books

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.8 out of 10, Exceptional, (11 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is ￥24,474
￥60,271 total
includes taxes & fees
Feb 23 - Feb 24
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
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, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is ￥30,554
￥55,549 total
includes taxes & fees
Feb 15 - Feb 16
Big farmhouse in the foothills of the Berkshires
Smart TV

Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield

Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
Bloomfield
9.0 out of 10, Wonderful, (6 reviews)
"I had a great time and I felt very welcome"
United States
Avis b.
The price is ￥47,198
￥115,459 total
includes taxes & fees
Feb 15 - Feb 16
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
Interior

#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10

#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10
Plainville
10.0 out of 10, Exceptional, (3 reviews)
"Great weekend with friends!"
United States
Neil R.
The price is ￥34,326
￥77,632 total
includes taxes & fees
Mar 11 - Mar 12
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10
Interior

Stylish Townhome | Perfect for Family Gatherings & Events

Stylish Townhome | Perfect for Family Gatherings & Events
Bloomfield
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.
The price is ￥47,053
￥108,879 total
includes taxes & fees
Feb 15 - Feb 16
Stylish Townhome | Perfect for Family Gatherings & Events
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (27 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.
The price is ￥23,786
￥40,219 total
includes taxes & fees
Feb 23 - Feb 24
Home in Great Barrington
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 ￥60,039
￥105,971 total
includes taxes & fees
Feb 16 - Feb 17
Guesthouse Cabin vacation rentals in Berkshire County
Exterior

Dugway Hideaway Walking Distance to Lime Rock Park

Dugway Hideaway Walking Distance to Lime Rock Park
Salisbury
9.2 out of 10, Wonderful, (15 reviews)
"Super clean, great communication and Super location if you are going to the track. Love my stay there, will definitely do it again and definitely recommend."
United States
Brig
The price is ￥30,554
￥47,664 total
includes taxes & fees
Mar 1 - Mar 2
Dugway Hideaway Walking Distance to Lime Rock Park
Exterior

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Goshen
10.0 out of 10, Exceptional, (1 review)
"Without a doubt, we will be back! Your home was so beautiful, warm and comfortable. Our host was so helpful and friendly. We can't thank you enough for providing such a wonderful experience to our trip. "
United States
Linda D.
The price is ￥40,484
￥84,405 total
includes taxes & fees
Feb 24 - Feb 25
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
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)
"The place was absolutely spotless and magnificent in every way. Highly recommended."
United States
Robert A.
The price is ￥44,548
￥55,700 total
includes taxes & fees
Feb 22 - Feb 23
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

Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

10/10 Excellent
"Comfortable for a before or after flight. Very close to Bradley Airport."
Penelope 1-night trip
Posted 18 hours ago
Hampton Inn Hartford/Airport

Find out more about Winsted

Search for holiday rentals in Winsted on Expedia! You can easily find your home rentals, villas, holiday apartments in Winsted using one of the methods below:

  • View our selection of featured holiday rentals in Winsted
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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?

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: Visitors like this Winsted vacation home rental. It offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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, The Marina at Highland Lake and Ledgebrook Plaza 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.