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Top Holiday Rentals in Winsted

The Cottage at Highland Lake, year-round, waterfront with a boat dock

10.0 out of 10, Exceptional, (6)
"happen to get beautiful weather while staying at the cottage at highland lake. so nice to wake up with a view, and then at sunset to enjoy the glass like water."
The Cottage at Highland Lake, year-round, waterfront with a boat dock

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

9.2 out of 10, Wonderful, (17)
"We had a wonderful time at the cabin by the lake. Beautiful views in the Morning!! Loved it."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (41)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

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

10.0 out of 10, Exceptional, (39)
"Great house in the woods. We were there for a spotting event so didn't spend a lot of time at the house. There were great walks around there"
Beautiful retreat in a lake community to the enjoy the summer season.

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (13)
"Quick trip"
The price is £241
includes taxes & fees
20 Jul - 21 Jul
Tranquil Litchfield Connecticut Retreat".

Mountaintop Horse Farm with Heated Pool

10.0 out of 10, Exceptional, (27)
"This was a much needed haven! Frank was very helpful and hospitable. All of the animals were a definite plus! "
Mountaintop Horse Farm with Heated Pool

4 Mi to Great Barrington: Berkshires Retreat!

10.0 out of 10, Exceptional, (2)
"We had a great experience hiking the AT & enjoying the Berkshires and surrounding area. The home had everything we needed, was nicely decorated, and well stocked with all things from cookware to linens. Plenty of spaces in the home to gather as a group or family or separate for privacy. House is very convenient to Sheffield & Barrington where you’ll find plenty of restaurants & shopping. Brooks was great to quickly address any questions we had about the house or the area. Great home!"
4 Mi to Great Barrington: Berkshires Retreat!

Connecticut Retreat: Steps to Historic Downtown!

9.6 out of 10, Exceptional, (14)
"Everything was as described and updated we enjoyed our stay. "
Connecticut Retreat: Steps to Historic Downtown!

Rustic 3bd Lake Front Country Cottage

9.4 out of 10, Exceptional, (3)
"Enjoy our hikes and lake front view as well as kayaking around lake. Pretty area."
Rustic 3bd Lake Front Country Cottage

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (23)
"Clean, Cozy and Comfortable "
Charming 3BR Hilltop House, Newly Remodeled with Arcade

Cozy Modern 4 Bedroom Log Cabin on 45 Secluded Acres in the Berkshires

Cozy Modern 4 Bedroom Log Cabin on 45 Secluded Acres in the Berkshires

Peace and quiet on the lake

9.6 out of 10, Exceptional, (215)
"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! "
Peace and quiet on the lake

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

10.0 out of 10, Exceptional, (12)
"Host was extremely accommodating and house was as-advertised. Great spot to explore great Barrington and surrounding towns! Wood burning stove and fireplaces are a real highlight! Fire pit is not advertised on listing but there is one. Would recommend highly"
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.

Peaceful Meadow Retreat

2.0 star property
10.0 out of 10, Exceptional, (9)
"Quite and very clean"
The price is £163
includes taxes & fees
26 Jun - 27 Jun
Peaceful Meadow Retreat

Berkshire Lake at the Pillow, and EV!

9.4 out of 10, Exceptional, (15)
"Had a lovely time at this lake house. The lake access was a plus and the house was well stocked with water accessories and food items. Otis is a short distance from Lee and Lenox providing easy Berkshire access. Having a garage to park the car in was also nice. The only downside is the relatively poor condition of the driveway / shared road the house is on. The neighborhood is made up of single lane dirt roads that have suffered from some wet weather. All in all would definitely recommend."
Berkshire Lake at the Pillow, and EV!

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (7)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is £607
includes taxes & fees
30 Jun - 1 Jul
Guesthouse Cabin vacation rentals in Berkshire County

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (136)
"This was the perfect place to stay while we visited family in Massachusetts. The place was kept beautifully and had all of the amenities to make our visit comfortable. We will definitely book this place in the future."
The price is £272
includes taxes & fees
29 Jun - 30 Jun
Big farmhouse in the foothills of the Berkshires

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

9.6 out of 10, Exceptional, (24)
"Overall it was a great location for a relaxing girls trip. The hot tub and sunroom were great places to hang out. The pictures were very accurate of the house. We did have some issues with cleanliness and pests that we were not expecting. We would recommend it for a relaxing lakefront thing stay."
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

Lakefront Summer Spectacular in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (72)
"The host was great and the property had everything we wanted and more. We will be back."
Lakefront Summer Spectacular in New England Just 2 Hours From NYC
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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Frequently asked questions

Can I find holiday rentals in Winsted?

Yes, there are holiday rentals in Winsted close to Laurel Lanes, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winsted has to offer?

Mountaintop Horse Farm with Heated Pool: This holiday home rental outside of Winsted is located in the mountains, and has an outdoor pool, a balcony and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Winsted?

With 7 Expedia holiday rentals, you're guaranteed 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 Platt Hill State Park are other places worth a visit.

What are holiday rentals like in Winsted?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winsted. Holiday rentals feature extras like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a family getaway.