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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Winsted vacation rentals

A spacious living room with a dark leather sofa, a wooden coffee table, and a patterned rug.

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

Pet-Friendly 4BR Home, Walk to Downtown
Glencoe
9.4 out of 10, Exceptional, (13 reviews)
"Great stay! Very clean, everything we needed. Hope to stay again."
United States
Melissa M.
$274 nightly
The price is $278
Oct 18 - Oct 19
Total with taxes and fees
Pet-Friendly 4BR Home, Walk to Downtown
A modern kitchen with a central island, bar stools, and a built-in refrigerator.

2. 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)
$186 nightly
The price is $200
Oct 5 - Oct 6
Total with taxes and fees
Historic 2-bedroom apartment in charming downtown Glencoe
A lakeside deck with Adirondack chairs, a swing, and a dock extending into the water.

3. 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.
$421 nightly
The price is $424
Oct 25 - Oct 26
Total with taxes and fees
Cozy Lakeside Cabin w/ Fireplace & Great Views
A wooden deck with a table and two chairs, overlooking a body of water and trees.

4. 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, (61 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.
$229 nightly
The price is $246
Oct 11 - Oct 12
Total with taxes and fees
Cozy lake cabin with your own private dock. Secluded lot close to the city!
A bedroom with a large bed, a fireplace, and a view of trees through the windows.

5. The Shiloh House - a peaceful retreat

The Shiloh House - a peaceful retreat
Rockford Township
9.8 out of 10, Exceptional, (10 reviews)
"Beautiful property, new/modern build, very clean and comfortable. Seems like they thought of everything that a guest could possibly need. The hosts were quite accommodating when I had a special request. Perfect for our family of 4 with 2 older children. We plan to stay there again next time we are in the area."
United States
Miranda K.
$358 nightly
The price is $376
Oct 27 - Oct 28
Total with taxes and fees
The Shiloh House - a peaceful retreat
A modern kitchen with stainless steel appliances, granite countertops, and wooden cabinets.

6. 3 bed 2 bath luxury home next to crow river private.

3 bed 2 bath luxury home next to crow river private.
Hutchinson
10.0 out of 10, Exceptional, (5 reviews)
"Awesome Host! Fantastic, clean, modern property."
United States
Michael W.
$423 nightly
The price is $454
Oct 15 - Oct 16
Total with taxes and fees
3 bed 2 bath luxury home next to crow river private.
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

Budget Host Inn Buffalo

Budget Host Inn Buffalo

10/10 Excellent
"Great place to stay. Staff were very personable and helpful. Recommended."
Ward 4-night trip
Posted 1 day ago
Budget Host Inn Buffalo

Find out more about Winsted

Everything you need to know about Winsted vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winsted vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winsted vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winsted in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $246 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winsted rentals

At Expedia, we put the best Winsted vacation 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 vacation.

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.

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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.