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Winsted Vacation Rentals

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Nov 14 - Nov 15
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Nov 21 - Nov 23

Vacation Rentals in Winsted

Interior
Peace and quiet on the lake

Peace and quiet on the lake

Sherwood Forest
9.6 out of 10, Exceptional, (228)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
United States
Anika J.
Peace and quiet on the lake
Dining
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Northwest Harwinton
8.6 out of 10, Excellent, (27)
"Clean, quite stores only 8 minutes away. "
United States
Mindy H.
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Exterior
The Blue Elm - A Historic Berkshire Cottage

The Blue Elm - A Historic Berkshire Cottage

Sheffield
10.0 out of 10, Exceptional, (14)
"If I could have given it more than 5 stars I would have. Beautiful, quiet area and the place is stunning. The gas fireplace in the dining area was great, has pretty much everything you could need and incredibly stylish (the retro fridge and microwave were very cool). Can’t speak to the pullout but the king in the master might have been the most comfortable bed I’ve ever slept in and the double shower is awesome. The hosts were friendly and responsive. Went to hike and the number of trails within...
United States
Marc R.
The Blue Elm - A Historic Berkshire Cottage
Fridge, microwave, oven, stovetop
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

Bloomfield
9.0 out of 10, Wonderful, (11)
"It was a comfortable stay "
United States
heidi L.
The price is ￥30,617
￥93,544 total
includes taxes & fees
Nov 17 - Nov 18
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Sherwood Forest
9.6 out of 10, Exceptional, (229)
"Very clean and well stocked cabin. Everything you need is there. Very quiet neighborhood. Perfect place to get away and relax. I would highly recommend this place especially if you like being close to nature. "
United States
Sharon Z.
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior
Beautiful retreat in a lake community to the enjoy the summer season.

Beautiful retreat in a lake community to the enjoy the summer season.

Tolland
10.0 out of 10, Exceptional, (44)
"It was a very nice home with a great sitting area. The screened in porch was another nice area."
United States
Susan D.
Beautiful retreat in a lake community to the enjoy the summer season.
Smart TV, fireplace, DVD player
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington
10.0 out of 10, Exceptional, (28)
"We had a wonderful time with family and friends. The location was great and it was helpful for everyone to have their own bathroom. Kitchen was well stocked and toys for kids was a bonus."
United States
Erin B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Interior
The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery

Plainville
8.8 out of 10, Excellent, (24)
"Pleasure staying here. "
United States
Jesse H.
The price is ￥12,834
￥42,480 total
includes taxes & fees
Nov 21 - Nov 22
The Sun Filled Cozy Creamery
Terrace/patio
Cozy Lakefront Bungalow w firepit/dock/kayaks

Cozy Lakefront Bungalow w firepit/dock/kayaks

Plymouth
9.8 out of 10, Exceptional, (39)
"Owners were there, helpful, all in all very good"
United States
Walter B.
Cozy Lakefront Bungalow w firepit/dock/kayaks
Terrace/patio
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Barkhamsted
10.0 out of 10, Exceptional, (3)
"It's a wonderful house, lots of space to visit with family and the bed rooms were confortable and cozy. The host was very helpful and accesible at all times."
Spain
Heather A.
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Exterior
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Egremont
9.8 out of 10, Exceptional, (25)
"Absolutely love this sweet home! There was plenty of room for all eight of us. Beds were comfortable and the kitchen was well stocked for a quick weekend away. We had tickets to Tanglewood and wished we had planned on a few more days to enjoy the house and surrounding are. The house in on a beautiful piece of land. Colon was very easy to work with- would recommend this stay without hesitation!"
United States
Laura S.
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
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)
"We enjoyed our stay in this beautiful old farmhouse. Plenty of room for everyone and kitchen and linens were fully stocked."
United States
Nicole K.
The price is ￥22,885
￥46,908 total
includes taxes & fees
Nov 17 - Nov 18
Big farmhouse in the foothills of the Berkshires
Interior
Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

2.0 star property
Bloomfield
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.
The price is ￥34,019
￥92,856 total
includes taxes & fees
Nov 25 - Nov 26
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Interior
Lakefront Fall Foliage in New England Just 2 Hours From NYC

Lakefront Fall Foliage in New England Just 2 Hours From NYC

Sharon
10.0 out of 10, Exceptional, (87)
"Wonderful time, beautiful lakeside view"
United States
Lianne S.
Lakefront Fall Foliage in New England Just 2 Hours From NYC
Exterior
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

Watertown
9.6 out of 10, Exceptional, (15)
"It was a great time. Loved it hear would come back again. Owner was very helpful."
United States
Nosa I.
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Interior
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

New Marlborough
9.6 out of 10, Exceptional, (17)
"House was adorable! Very clean and updated, perfect size for a family. Great location in the heart of the Berkshires."
United States
Laura B.
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Pool
Charming 1870 cape cottage in Litchfield

Charming 1870 cape cottage in Litchfield

Litchfield
10.0 out of 10, Exceptional, (65)
"So nice just to have peace and quiet "
United States
candice
Charming 1870 cape cottage in Litchfield
Fridge, microwave, oven, stovetop
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, (61)
"We had a perfect stay - the house is adorable and was just right for two of us. The river and neighborhood are great, as was the proximity to the center of town. We'll be back!"
United States
Courtney N.
The price is ￥40,219
￥70,259 total
includes taxes & fees
Nov 16 - Nov 17
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Property grounds
Quintessential 6-BR Berkshires Lodge

Quintessential 6-BR Berkshires Lodge

Becket
9.8 out of 10, Exceptional, (17)
"Nice. Quiet. The new pool is very nice."
United States
David T.
Quintessential 6-BR Berkshires Lodge
Exterior
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield
9.8 out of 10, Exceptional, (93)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
United States
Sharon S.
Antique Farmhouse Totally Restored
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
"Clean room but the ice machine outside had a loud hum which kept me awake "
Alexandra 1-night trip
Posted 15 hours ago
Holiday Inn Express & Suites Bradley Airport by IHG

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:

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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?

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, The Marina at Highland Lake and Burr Pond State Park 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.