A flooded dock with a covered boat, surrounded by dense greenery and trees.

Winsted Holiday Rentals

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Our top choices for Winsted holiday rentals

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.
The price is NZ$965
includes taxes & fees
18 Oct - 19 Oct
Lakefront 3BR | Hot Tub, Pool Table!

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 NZ$481
includes taxes & fees
25 Oct - 26 Oct
Pet-Friendly 4BR Home, Walk to Downtown

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 NZ$650
includes taxes & fees
16 Nov - 17 Nov
Cozy, convenient, pet friendly, wifi, covered porch, firepit & yard! Sleeps 6

4. Cozy Lakeside Cabin w/ Fireplace & Great Views

Cozy Lakeside Cabin w/ Fireplace & Great Views
Maple Lake Township
10.0 out of 10, Exceptional, (30 reviews)
"Absolutely loved this place. Was perfect for our girls getaway. "
United States
Heidi H.
The price is NZ$750
includes taxes & fees
16 Nov - 17 Nov
Cozy Lakeside Cabin w/ Fireplace & Great Views

5. Historic 2-bedroom apartment in charming downtown Glencoe

Historic 2-bedroom apartment in charming downtown Glencoe
Glencoe
10.0 out of 10, Exceptional, (1 review)
The price is NZ$382
includes taxes & fees
21 Oct - 22 Oct
Historic 2-bedroom apartment in charming downtown Glencoe

6. Cozy lake cabin with your own private dock. Secluded lot close to the city!

Cozy lake cabin with your own private dock. Secluded lot close to the city!
Buffalo
9.2 out of 10, Wonderful, (63 reviews)
"The spot on the lake was great, very comfy beds, and is just want you need for a cabin weekend!"
United States
Savannah G.
The price is NZ$426
includes taxes & fees
24 Oct - 25 Oct
Cozy lake cabin with your own private dock. Secluded lot close to the city!

7. The Shiloh House - a peaceful retreat

The Shiloh House - a peaceful retreat
Rockford Township
10.0 out of 10, Exceptional, (11 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 NZ$659
includes taxes & fees
15 Nov - 16 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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Top Winsted Hotel Reviews

Find out more about Winsted

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winsted holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winsted. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winsted. Seeing all the best attractions is bound to make you fall in love with Winsted. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winsted short-term rentals, that won’t be hard to do.

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.