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

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.
The price is AED 569
AED 841 total
includes taxes & fees
24 Sep - 25 Sep
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.
The price is AED 624
AED 841 total
includes taxes & fees
21 Sep - 22 Sep
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, (54 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.
The price is AED 529
AED 851 total
includes taxes & fees
22 Sep - 23 Sep
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.
The price is AED 367
AED 683 total
includes taxes & fees
2 Oct - 3 Oct
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
The price is AED 1,230
AED 1,958 total
includes taxes & fees
21 Sep - 22 Sep
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.
The price is AED 1,157
AED 1,803 total
includes taxes & fees
21 Sep - 22 Sep
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
The price is AED 587
AED 736 total
includes taxes & fees
30 Sep - 1 Oct
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.
The price is AED 1,157
AED 1,493 total
includes taxes & fees
22 Sep - 23 Sep
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, (69 reviews)
"Really nice place to stay."
United States
Phillip
The price is AED 393
AED 595 total
includes taxes & fees
22 Sep - 23 Sep
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
The price is AED 331
AED 602 total
includes taxes & fees
27 Sep - 28 Sep
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.
The price is AED 477
AED 598 total
includes taxes & fees
9 Oct - 10 Oct
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.
The price is AED 731
AED 1,330 total
includes taxes & fees
21 Sep - 22 Sep
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.
The price is AED 459
AED 837 total
includes taxes & fees
20 Oct - 21 Oct
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.
The price is AED 1,102
AED 1,469 total
includes taxes & fees
29 Sep - 30 Sep
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.
The price is AED 981
AED 1,816 total
includes taxes & fees
21 Sep - 22 Sep
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, (22 reviews)
"Good stay"
Canada
Corey
The price is AED 360
AED 772 total
includes taxes & fees
21 Sep - 22 Sep
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.
The price is AED 533
AED 984 total
includes taxes & fees
21 Sep - 22 Sep
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.
The price is AED 1,157
AED 1,322 total
includes taxes & fees
22 Sep - 23 Sep
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
The price is AED 327
AED 706 total
includes taxes & fees
21 Sep - 22 Sep
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.
The price is AED 514
AED 624 total
includes taxes & fees
21 Sep - 22 Sep
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

Pete's Lakefront Motel

Pete's Lakefront Motel

8/10 Good
"The room could have been cleaner specially the shower and above the window. It was very loud at night when the water from the A/C above dripped on our unit. Otherwise all went well. Overall the stay was good."
Carrie 2-night trip
Posted 1 hour ago
Pete's Lakefront Motel

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.