A wooden covered bridge over a river surrounded by lush greenery.

Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Windsor vacation rentals

Exterior

1. Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (98 reviews)
"Great location to enjoy some peaceful country living!"
United States
Jerry L.
$229 nightly
The price is $229
Sep 24 - Sep 25
Total with taxes and fees
Little house on the farm
Interior

2. Nestled Inn Mespo Modern & Cozy Apartment

Nestled Inn Mespo Modern & Cozy Apartment
Middlefield
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful place and very well taken care of."
United States
Andrew G.
$229 nightly
The price is $229
Sep 20 - Sep 21
Total with taxes and fees
Nestled Inn Mespo Modern & Cozy Apartment
Dining

3. 3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.

3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
Rome
10.0 out of 10, Exceptional, (53 reviews)
"Folks this cabin is amazing! Rustic in design, modern in amenities and so very comfortable. Exceptional detail was paid to decor and quality furnishings which round out one of the nicest VRBO I've stayed at."
United States
Amy P.
$206 nightly
The price is $214
Sep 22 - Sep 23
Total with taxes and fees
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
Property grounds

4. 2 bedroom apartment in the beautiful Middlefield countryside!

2 bedroom apartment in the beautiful Middlefield countryside!
Middlefield
8.4 out of 10, Very good, (5 reviews)
"It was good for us"
United States
Joyce A.
$186 nightly
The price is $186
Sep 20 - Sep 21
Total with taxes and fees
2 bedroom apartment in the beautiful Middlefield countryside!
Property grounds

5. The Thistle House off Chardon Square

The Thistle House off Chardon Square
Chardon
10.0 out of 10, Exceptional, (48 reviews)
"Totally charming, great kitchen. Excellent access to all that Chardon has to offer. We were there only a short time but the beach was stupendous. Felt welcoming and historic . . . Would recommend."
United States
Pamela
$533 nightly
The price is $533
Sep 21 - Sep 22
Total with taxes and fees
The Thistle House off Chardon Square
Exterior detail

6. Farmhouse of Stoneycreek Acres, our Family Farm

Farmhouse of Stoneycreek Acres, our Family Farm
Newbury
9.8 out of 10, Exceptional, (22 reviews)
"We had a great time at our stay! The house was so cute and cozy, it had everything we needed stocked, and the owner was so friendly through the whole process. Would absolutely stay here again!"
United States
Madison S.
$487 nightly
The price is $487
Sep 21 - Sep 22
Total with taxes and fees
Farmhouse of Stoneycreek Acres, our Family Farm
WiFi (free), bed sheets

7. Romantic Woodside Cabin | Hot Tub & Fire Pit

Romantic Woodside Cabin | Hot Tub & Fire Pit
Madison
9.6 out of 10, Exceptional, (5 reviews)
"This was an incredible stay for my wife and I. The cleanliness, quietness, and coziness was amazing. We will definitely be back for another anniversary stay. The multiple wineries around also help enhance the stay even more. You’re missing out if you don’t book this cabin. "
United States
Matthew
$181 nightly
The price is $200
Sep 30 - Oct 1
Total with taxes and fees
Romantic Woodside Cabin | Hot Tub & Fire Pit
Exterior

8. Storybook Cottage in the Woods

Storybook Cottage in the Woods
Geneva
10.0 out of 10, Exceptional, (4 reviews)
"We stayed here for my wedding and it was a great little cabin. Perfect location for where we needed to be with everything convenient nearby. The host was excellent, he had great communication and the check-in process was easy. The place itself was super cute and I would totally stay there again or recommend it to anyone!"
United States
Zoe N.
$360 nightly
The price is $406
Sep 22 - Sep 23
Total with taxes and fees
Storybook Cottage in the Woods
Exterior

9. Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Burton
10.0 out of 10, Exceptional, (68 reviews)
"Really nice place to stay."
United States
Phillip
$162 nightly
The price is $162
Sep 22 - Sep 23
Total with taxes and fees
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Smart TV, fireplace

10. Conveniently located 2 bedroom home only minutes from hiking and state park fun!

Conveniently located 2 bedroom home only minutes from hiking and state park fun!
Warren
10.0 out of 10, Exceptional, (142 reviews)
"Perfect location for us to stay while visiting family! Very clean and easy to find! Quiet location."
United States
Danielle
$163 nightly
The price is $163
Sep 27 - Sep 28
Total with taxes and fees
Conveniently located 2 bedroom home only minutes from hiking and state park fun!
Outdoor dining

11. Beautiful cabin situated on wooded land with nice yard clearing and small stream

Beautiful cabin situated on wooded land with nice yard clearing and small stream
Madison
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful stay :) "
United States
Jennifer S.
$157 nightly
The price is $161
Oct 9 - Oct 10
Total with taxes and fees
Beautiful cabin situated on wooded land with nice yard clearing and small stream
Dining

12. Country Cottage Farm Stay at Stoneycreek Acres

Country Cottage Farm Stay at Stoneycreek Acres
Newbury
10.0 out of 10, Exceptional, (76 reviews)
"Excellent communication with host and extremely clean, peaceful and beautiful place to stay "
United States
Jennifer T.
$359 nightly
The price is $359
Sep 21 - Sep 22
Total with taxes and fees
Country Cottage Farm Stay at Stoneycreek Acres
Terrace/patio

13. Tiny Haven

Tiny Haven
Kinsman
10.0 out of 10, Exceptional, (33 reviews)
"Absolutely a lovely place to stay! Felt like home from the minute we walked in the door. The owners amazing cookies are to die for!!! Would love to go back and stay again!"
United States
Amy M.
$217 nightly
The price is $217
Sep 29 - Sep 30
Total with taxes and fees
Tiny Haven
Smart TV, fireplace

14. Hot Tub - Luxury 3BR Authentic Log Cabin Retreat Near Wineries, GOTL & Spire.

Hot Tub - Luxury 3BR Authentic Log Cabin Retreat Near Wineries, GOTL & Spire.
Geneva
10.0 out of 10, Exceptional, (21 reviews)
"Great Stay. "
United States
Sam K.
$400 nightly
The price is $400
Sep 29 - Sep 30
Total with taxes and fees
Hot Tub - Luxury 3BR Authentic Log Cabin Retreat Near Wineries, GOTL & Spire.
Smart TV

15. Hot Tub, Fire Pit, Private Backyard - Near Wineries & SPIRE

Hot Tub, Fire Pit, Private Backyard - Near Wineries & SPIRE
Geneva
9.8 out of 10, Exceptional, (29 reviews)
"Amazing stay! Host was super responsive, property had all the amenities amd was located in a good area."
United States
Jamie L.
$453 nightly
The price is $474
Sep 20 - Sep 21
Total with taxes and fees
Hot Tub, Fire Pit, Private Backyard - Near Wineries & SPIRE
Living area

16. A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!

A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
Geneva
10.0 out of 10, Exceptional, (21 reviews)
"Good stay"
Canada
Corey
$210 nightly
The price is $210
Sep 20 - Sep 21
Total with taxes and fees
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
Outdoor dining

17. Cozy Country Apartment in Heart of Geauga County

Cozy Country Apartment in Heart of Geauga County
Newbury
10.0 out of 10, Exceptional, (33 reviews)
"The apartment was clean, well maintained, and family friendly. Molly was a great host!"
United States
Phillip R.
$266 nightly
The price is $266
Sep 21 - Sep 22
Total with taxes and fees
Cozy Country Apartment in Heart of Geauga County
Exterior

18. Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.

Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.
Burton
10.0 out of 10, Exceptional, (8 reviews)
"My friends and I had a great stay at the cabins in newberry axel is very kind and the property is very nice"
United States
David H.
$341 nightly
The price is $341
Sep 21 - Sep 22
Total with taxes and fees
Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.
2 bedrooms, WiFi (free), bed sheets

19. A great stay, close to Spire, GOTL, & Wineries....King Bed!

A great stay, close to Spire, GOTL, & Wineries....King Bed!
Geneva
10.0 out of 10, Exceptional, (46 reviews)
"Cute rental in a great location not far from shopping and the lake !!! Our family had a great stay here we made so many memories. The arcade was a big hit!"
United States
ceberio68
$192 nightly
The price is $192
Sep 21 - Sep 22
Total with taxes and fees
A great stay, close to Spire, GOTL, & Wineries....King Bed!
Terrace/patio

20. Cabin 1 The Sunrise Patio

Cabin 1 The Sunrise Patio
Geneva
9.4 out of 10, Exceptional, (18 reviews)
"It's private and rustic. Nice relaxing time . Very friendly hosts as well"
United States
Ann Irene D.
$160 nightly
The price is $170
Sep 20 - Sep 21
Total with taxes and fees
Cabin 1 The Sunrise Patio
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 Windsor Hotel Reviews

Hampton Inn Ashtabula

Hampton Inn Ashtabula

8/10 Good
"We did have to move rooms due to pet odor. New room was great and staff very accommodating."
Christine 1-night trip
Posted 1 hour ago
Hampton Inn Ashtabula

Find out more about Windsor

Everything you need to know about Windsor 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 Windsor 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 Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. 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 Windsor 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 $148 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 Windsor rentals

At Expedia, we put the best Windsor 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 Windsor 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 Windsor 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 Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Windsor?

Yes, we have vacation rentals near top local attractions in Windsor, or you can select a secluded option if you're looking for relaxation.

What are some of the best vacation home rentals in Windsor?

Walk to Lake • Strip • Wineries • Firepit: This vacation home rental outside of Windsor is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What can I see and do in Windsor?

While exploring the area, visit family-friendly sights like Pioneer Waterland & Dry Fun Park, or get outside and enjoy nature at Punderson Lake. Windsor Mills Covered Bridge and Geauga County Fairgrounds are a couple of places you'll find in the larger area.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned accommodations you can reserve for a short or long stay in Windsor. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people 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 a great option for a family getaway.