Winsted Holiday Rentals from €353: Search Short-Term Rentals

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

Peace and quiet on the lake : This holiday home rental outside of Winsted is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

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Holiday Rentals in Winsted

"The cabin was great! Exactly as described and pictured. The kitchen was well stocked with all the basic cooking instruments and utensils. We had a blast and would absolutely come back."

"Everything was great...and beautiful!"

includes taxes & fees

30 Sept - 1 Oct

"Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. "

"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."

"Beautiful property and great location. A true retreat. "

includes taxes & fees

5 Oct - 6 Oct

"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"

"The house has rustic charm and sits right on the lake. It is a beautiful peaceful spot. "

"The chalet was great. Plenty of room, very cozy and in a very quiet neighborhood community. "

"Spacious, welcoming, so well stocked, we felt lucky to find the property."

"We had a wonderful time, the property is lovely and the house is delightful."

"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "

includes taxes & fees

30 Sept - 1 Oct

"Pleasure staying here. "

includes taxes & fees

30 Sept - 1 Oct

"There is a lot of fun things to do close by. The house was spotless and it was nice to relax on the sofa or outside patio and look at the river. "

includes taxes & fees

8 Oct - 9 Oct

"Enjoyed the property, location and charming house that was well stocked with everything we needed."

"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."

"Beautiful new spacious property in a great safe neighborhood. Very nice for groups. Common Living space s conducive for gathering. Property still under construction as there were other homes still being built. Near busy street but monimal noise. Would stay again."

includes taxes & fees

30 Sept - 1 Oct

"Clean and quiet location, great place for a relaxing stay."

"The house is huge with plenty of room and tons of features! Pool and hot tubs were lots of fun and the game room is full of games and tables to keep the kids happy.The location is very secluded and private, with easy access to stores and restaurants right down the street if needed.Brian was very responsive and easy to work with before and during our stay."

"I spent my 60th birthday with a few friends at Mountain House and it was even better than I dreamed. The comfort and simplicity of the decor along with the mountain views. A must for those who like simple elegance."

"We had a great time. The owner Bill was a great host."

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Top Winsted Hotel Reviews

Hampton Inn Westfield

10/10 Excellent

"Room was clean and very spacious. "

Holiday Inn Express & Suites Bradley Airport by IHG

10/10 Excellent

"We have stayed at this location several times and have another stay here booked in November. This hotel is clean, the rooms are spacious and the beds are very comfortable. It would be nice if the breakfast had a few more non dairy options, but aside from that I have no complaints. "

Find out more about Winsted

Everything you need to know about Winsted holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winsted holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winsted holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winsted holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winsted holiday rentals we have selected for you start as low as €353 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winsted rentals

At Expedia, we put the best Winsted holiday 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 holiday.

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.

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?

Peace and quiet on the lake: This holiday home rental outside of Winsted is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

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 Winchester Historical Society 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.

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Holiday Rentals in Winsted

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Holiday Rentals in Winsted

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

The Blue Elm - A Historic Berkshire Cottage

Peace and quiet on the lake

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Whispering Estate Guest House - A Romantic Countryside Getaway

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Summer Lake Cottage, private beach, Berkshire Hills, small village

The Goshen Glass Chalet

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

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Guesthouse Cabin vacation rentals in Berkshire County

The Sun Filled Cozy Creamery

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Antique Farmhouse Totally Restored

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

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

Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi

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

The Race Mountain House

Private Island - Largest Fresh Water Reservoir in Mass

Top Winsted Hotel Reviews

Hampton Inn Westfield

The Farmington Inn & Suites

Fairfield Inn & Suites by Marriott Plainville

Sheraton Hartford Hotel at Bradley Airport

Holiday Inn Express & Suites Bradley Airport by IHG

Homewood Suites by Hilton Hartford-Farmington

Simsbury 1820 House

Hampton Inn Hartford/Airport

Hampton Inn & Suites Hartford/Farmington

Find out more about Winsted

Frequently asked questions

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