Photo by Kim Knox Beckius

Winsted Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Winsted

CT Gate House Goshen CT, Gate House Goshen CT
2.5 star property
9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is AU$1,025
includes taxes & fees
2 Nov - 3 Nov
CT Gate House Goshen CT, Gate House Goshen CT
Peaceful Meadow Retreat
2.0 star property
10.0 out of 10, Exceptional, (13)
"Quite and very clean"
United States
Craig M.
The price is AU$320
includes taxes & fees
20 Oct - 21 Oct
Peaceful Meadow Retreat
The Sun Filled Cozy Creamery
8.8 out of 10, Excellent, (22)
"Nice,cozy and a reasonable rate."
United States
Rachelle B.
The price is AU$427
includes taxes & fees
20 Oct - 21 Oct
The Sun Filled Cozy Creamery
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
9.6 out of 10, Exceptional, (4)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
The price is AU$425
includes taxes & fees
20 Oct - 21 Oct
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
J Suite on John Smith
2.0 star property
6.0 out of 10, (3)
"Did not stay even one night. Was charged anyway. The driveway, walkway and stairs were dangerously icy and poorly treated considering the weather. Moved to a hotel."
United States
Kae V.
The price is AU$387
includes taxes & fees
26 Oct - 27 Oct
J Suite on John Smith
Sun Filled Lake House Living
2.0 star property
6.0 out of 10, (3)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
The price is AU$443
includes taxes & fees
28 Oct - 29 Oct
Sun Filled Lake House Living
The Historic Hideaway
2.0 star property
7.0 out of 10, Good, (2)
"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "
United States
Nicole M.
The price is AU$440
includes taxes & fees
20 Oct - 21 Oct
The Historic Hideaway
The Jefferson Guest House, Spacious, Special Views
10.0 out of 10, Exceptional, (7)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
United States
Jennifer A.
The price is AU$586
includes taxes & fees
26 Oct - 27 Oct
The Jefferson Guest House, Spacious, Special Views
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
2.0 star property
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 AU$1,266
includes taxes & fees
27 Oct - 28 Oct
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Charming apartment 7 minute walk to downtown
10.0 out of 10, Exceptional, (15)
"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 AU$416
includes taxes & fees
27 Oct - 28 Oct
Charming apartment 7 minute walk to downtown
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
10.0 out of 10, Exceptional, (2)
"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 AU$766
includes taxes & fees
20 Oct - 21 Oct
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$621
includes taxes & fees
28 Oct - 29 Oct
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
10.0 out of 10, Exceptional, (61)
"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. "
United States
Amanda W.
The price is AU$694
includes taxes & fees
20 Oct - 21 Oct
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (11)
"Everything was great...and beautiful!"
United States
Nicole L.
The price is AU$628
includes taxes & fees
20 Oct - 21 Oct
The Blue Elm - A Historic Berkshire Cottage
River Overlook - Check the view from your deck!
10.0 out of 10, Exceptional, (23)
"I only did a short stay (2 nights) but it was super adorable! I will definitely stay again when I'm back in the area."
United States
Mary S.
The price is AU$469
includes taxes & fees
27 Oct - 28 Oct
River Overlook - Check the view from your deck!
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
9.6 out of 10, Exceptional, (8)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is AU$612
includes taxes & fees
27 Oct - 28 Oct
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Private Classy 2nd Flr 3 Bed Apt Near Downtown
Private Classy 2nd Flr 3 Bed Apt Near Downtown
Cozy. Clean. Free bagel shop.
10.0 out of 10, Exceptional, (10)
"The perfect location for a stay in Great Barrington. The house is so well done and very comfortable!"
United States
Carly F.
The price is AU$1,032
includes taxes & fees
4 Nov - 5 Nov
Cozy. Clean. Free bagel shop.
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (39)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AU$704
includes taxes & fees
9 Nov - 10 Nov
Cheerful 3-bedroom cottage with woodstove
KING BED, Affordable Classic Bristol Home Sleep 8+
The price is AU$437
includes taxes & fees
26 Oct - 27 Oct
KING BED, Affordable Classic Bristol Home Sleep 8+
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winsted Hotel Reviews

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$427 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, 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.