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

Winsted Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Winsted vacation 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.
The price is ￥17,489
￥79,426 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥16,812
￥41,539 total
includes taxes & fees
Nov 8 - Nov 9
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 ￥23,634
￥55,155 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥15,756
￥32,821 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥27,179
￥61,059 total
includes taxes & fees
Nov 2 - Nov 3
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, (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 ￥34,427
￥55,822 total
includes taxes & fees
Nov 11 - Nov 12
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

The Shoreline Hotel

The Shoreline Hotel

10/10 Excellent
"Hands down, one of the most exceptional properties I’ve ever had the pleasure of staying at! From the moment I arrived, the staff went above and beyond to make my stay feel truly special. Their warmth, attentiveness, and genuine hospitality made the entire experience unforgettable. The restaurant is equally impressive, offering delicious food, fantastic cocktails, and a welcoming atmosphere. The staff are incredibly personable and always happy to answer questions, offer recommendations, or simply share a friendly conversation, something I especially appreciated as a solo traveler. And the views! The lakefront rooms and restaurant offer absolutely breathtaking scenery. The rooms themselves are just as stunning, with incredibly comfortable beds, spacious covered patios furnished to take in the views, and thoughtful touches throughout. From the plush robes perfect for lounging to the oversized showers and wonderfully fragrant bath products, every detail feels luxurious and inviting. It’s rare to find a property that delivers so beautifully on every level, but this one truly does. I can’t say enough wonderful things about my experience and am already looking forward to my next visit!"
Elizabeth 1-night trip
Posted 5 days ago
The Shoreline Hotel

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 vacation rental in Winsted?

Yes, we offer vacation rentals close to well known sights in Winsted, or you can go with a secluded option if you'd like a relaxing place to stay.

What's the top vacation rental in Winsted?

Just a mile from the Winstock Country Music Festival and blocks from downtown.: Visitors give good reviews to this Winsted vacation home rental, which is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, an oven, and a microwave. Make the most of the selection 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 vacation rental in Winsted like?

Vacation rentals are privately owned properties you can book for several days or longer in Winsted. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.