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
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 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 AED 408
AED 1,852 total
includes taxes & fees
5 Nov - 6 Nov
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 AED 392
AED 968 total
includes taxes & fees
8 Nov - 9 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 AED 551
AED 1,286 total
includes taxes & fees
5 Nov - 6 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 AED 367
AED 765 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 AED 634
AED 1,490 total
includes taxes & fees
16 Nov - 17 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, (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 AED 803
AED 1,301 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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Top Winsted Hotel Reviews

The Shoreline Hotel

The Shoreline Hotel

10/10 Excellent
"It’s very nice. Nice view. Everything closes at 10pm which isn’t great. Not their fault"
Bryan 2-night trip
Posted 1 day ago
The Shoreline Hotel

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.