Winsted Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Winsted holiday rentals

A wooden deck with a railing, overlooking a frozen body of water with bare trees and a cloudy sky.

1. Lakefront 3BR | Hot Tub, Pool Table!

Lakefront 3BR | Hot Tub, Pool Table!
Howard Lake
9.8 out of 10, Exceptional, (6 reviews)
"Great location "
United States
Paul V.
Lakefront 3BR | Hot Tub, Pool Table!
A spacious living room with a dark leather sofa, a wooden coffee table, and a patterned rug.

2. Pet-Friendly 4BR Home, Walk to Downtown

Pet-Friendly 4BR Home, Walk to Downtown
Glencoe
9.4 out of 10, Exceptional, (15 reviews)
"Nice house! There is a small bathroom (no shower) on the main floor, which is helpful! Thank you for the lovely house to stay in!"
United States
Jennie
The price is HK$836
HK$2,067 total
includes taxes & fees
10 Nov - 11 Nov
Pet-Friendly 4BR Home, Walk to Downtown
A bedroom with a bed, two bedside lamps, a bookshelf, a door leading to a balcony, and a painting on the wall.

3. Cozy, convenient, pet friendly, wifi, covered porch, firepit & yard! Sleeps 6

Cozy, convenient, pet friendly, wifi, covered porch, firepit & yard! Sleeps 6
Norwood Young America
9.6 out of 10, Exceptional, (14 reviews)
"We were looking for a pet friendly house to stay while in the area for a family gathering.This property was very clean, quiet & safe."
United States
Patrick O.
The price is HK$1,881
HK$3,568 total
includes taxes & fees
7 Nov - 8 Nov
Cozy, convenient, pet friendly, wifi, covered porch, firepit & yard! Sleeps 6
A modern kitchen with a central island, bar stools, and a built-in refrigerator.

4. Historic 2-bedroom apartment in charming downtown Glencoe

Historic 2-bedroom apartment in charming downtown Glencoe
Glencoe
9.0 out of 10, Wonderful, (2 reviews)
"The stairs were a real issue. It would have made a difference to us if this had been up front about the lack of a elevator."
United States
Theresa
The price is HK$784
HK$1,633 total
includes taxes & fees
9 Nov - 10 Nov
Historic 2-bedroom apartment in charming downtown Glencoe
A lakeside cabin with a sandy path leading to blue Adirondack chairs, surrounded by large rocks and trees.

5. Cozy Lakeside Cabin w/ Fireplace & Great Views

Cozy Lakeside Cabin w/ Fireplace & Great Views
Maple Lake Township
10.0 out of 10, Exceptional, (31 reviews)
"Absolutely loved this place. Was perfect for our girls getaway. "
United States
Heidi H.
The price is HK$1,352
HK$3,038 total
includes taxes & fees
17 Nov - 18 Nov
Cozy Lakeside Cabin w/ Fireplace & Great Views
A bedroom with a large bed, a fireplace, and a view of trees through the windows.

6. The Shiloh House - a peaceful retreat

The Shiloh House - a peaceful retreat
Rockford Township
10.0 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay at the Shiloh House very much! It is beautifully decorated, beds are super comfy, and the kitchen has everything we needed. We would recommend!"
United States
Haley S.
The price is HK$1,713
HK$2,777 total
includes taxes & fees
8 Nov - 9 Nov
The Shiloh House - a peaceful retreat
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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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 a holiday rental in Winsted?

Yes, there are holiday rentals close to the most popular sights in Winsted, 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?

Just a mile from the Winstock Country Music Festival and blocks from downtown.: This highly rated holiday home rental in Winsted is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, an oven and a microwave. Make the most of games in this rental home to help you unwind.

What’s there to see and do in Winsted?

Explore the area and family-friendly sights such as Big Stone Mini-golf and Sculpture Garden, or get out into nature at a spot like Howard Lake. While here, Winsted City Hall and Winsted Public Library are other places worth a visit.

What’s a holiday rental in Winsted like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winsted. Holiday rentals offer extras like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for families.