Photo by Kim Knox Beckius

Winsted Holiday Rentals

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Holiday Rentals in Winsted

Our top choices for Winsted holiday rentals

Family House On Highland Lake with Dock

10.0 out of 10, Exceptional, (26)
"Awesome location, plenty of space in the house, clean, and the host was very responsive. Will definitely stay here again when in Connecticut. "
Family House On Highland Lake with Dock

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (220)
"Cabin was exactly what we were looking for in a weekend away. Great location, quiet, and had everything we needed. Hope to go back again soon! "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

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

9.4 out of 10, Exceptional, (81)
"Wonderful lake retreat 🥾"
Summer Lake Cottage, private beach, Berkshire Hills, small village

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

10.0 out of 10, Exceptional, (8)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

10.0 out of 10, Exceptional, (14)
"Beautiful lake, traditional charming cottage- great get-away"
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

Peace and quiet on the lake

9.6 out of 10, Exceptional, (218)
"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. "
Peace and quiet on the lake

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (32)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is AU$1,051
includes taxes & fees
4 Sept - 5 Sept
Guesthouse Cabin vacation rentals in Berkshire County

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

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

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (10)
"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "
The price is AU$623
includes taxes & fees
1 Oct - 2 Oct
The Blue Elm - A Historic Berkshire Cottage

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (91)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
Antique Farmhouse Totally Restored

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

10.0 out of 10, Exceptional, (27)
"Spacious, welcoming, so well stocked, we felt lucky to find the property."
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

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

9.4 out of 10, Exceptional, (6)
"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."
The price is AU$1,223
includes taxes & fees
11 Sept - 12 Sept
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

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

10.0 out of 10, Exceptional, (54)
"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!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Cozy 2-bedroom Cottage with Access to Bantam Lake

9.6 out of 10, Exceptional, (18)
"Even with horrible weather, we had a wonderful stay!"
Cozy 2-bedroom Cottage with Access to Bantam Lake

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (139)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
The price is AU$561
includes taxes & fees
16 Sept - 17 Sept
Big farmhouse in the foothills of the Berkshires

Lakefront Fall Foliage in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (80)
"Great place! Loved waking up to a water view. Very peaceful."
Lakefront Fall Foliage in New England Just 2 Hours From NYC

Charming Retreat at Stone Hill Estate – Nature Meets Luxury

10.0 out of 10, Exceptional, (2)
"Beautiful property and great location. A true retreat. "
The price is AU$1,089
includes taxes & fees
8 Sept - 9 Sept
Charming Retreat at Stone Hill Estate – Nature Meets Luxury

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

8.8 out of 10, Excellent, (23)
"We love being there do we extended our stay. Would have liked to stay even longer. Very relaxing and peaceful."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

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

10.0 out of 10, Exceptional, (59)
"We were visiting University of Hartford and this was the perfect place to stay outside of the city. Great space with all the conveniences of home. Wonderful food options within walking distance. "
The price is AU$689
includes taxes & fees
4 Sept - 5 Sept
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
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

Find out more about Winsted

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, 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 favourite 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 depend 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 AU$561 per night. Entering your travel dates in the search wizard might find you 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, Platt Hill State Park and Burr Pond 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.