Windsor Vacation Rentals from $135: Search Short-Term Rentals

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

Center Strip | Pets OK | Wi-Fi | Near Wineries : This vacation home rental outside of Windsor is located on a lake and offers a barbecue grill, air-conditioning, and WiFi to help you feel perfectly comfortable in your new surroundings.

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Our top choices for Windsor vacation rentals

A two-story house with a front porch, a small garden, and a wooden deck.

1. Little house on the farm

Middlefield

Jerry L.

$218 nightly

Nov 5 - Nov 6

Total with taxes and fees

A rustic kitchen with wooden beams, a central island, bar stools, and a dining table with placemats.

2. 3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.

Rome

Amy P.

$204 nightly

Nov 9 - Nov 10

Total with taxes and fees

A covered porch with wicker chairs and a blue patterned rug.

3. 2 bedroom apartment in the beautiful Middlefield countryside!

Middlefield

Ashley B.

$178 nightly

Nov 8 - Nov 9

Total with taxes and fees

A staircase leading to a kitchen with dark wooden cabinets and a stainless steel refrigerator.

4. Nestled Inn Mespo Modern & Cozy Apartment

Middlefield

Abby M.

$218 nightly

Nov 5 - Nov 6

Total with taxes and fees

A wooden two-story building with a balcony, a front door, and a sign that says "OPEN".

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

Burton

Phillip

$154 nightly

Nov 9 - Nov 10

Total with taxes and fees

A compact kitchen with a sink, stove, microwave, and cabinets.

6. Cozy 1-bedroom Camper on the lake with AC in adorable Cortland.

Cortland

Robert K.

A living room with a brown leather sofa, two armchairs, a small table with a lamp, and a striped rug.

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

Warren

Carol D.

$163 nightly

Nov 9 - Nov 10

Total with taxes and fees

A square fire pit table with two metal chairs on a wooden deck.

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

Madison

Jennifer S.

$157 nightly

Nov 6 - Nov 7

Total with taxes and fees

A bedroom with a large bed, a wooden ceiling, and a view of a balcony with outdoor furniture.

9. Romantic Woodside Cabin | Hot Tub & Fire Pit

Madison

Matthew

$201 nightly

Nov 9 - Nov 10

Total with taxes and fees

A bedroom with a bed, a ceiling fan, a TV on a dresser, and two windows with blinds.

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

Geneva

frances f.

$189 nightly

Nov 5 - Nov 6

Total with taxes and fees

A covered outdoor deck with a black wicker sofa, a small table, and a chair.

11. On The Strip • Cozy GOTL Vacation Cottage

Geneva

Daniel M.

$229 nightly

Nov 8 - Nov 9

Total with taxes and fees

A living room with a brown sofa, a coffee table, a TV, and a ceiling fan.

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

Geneva

Daniel K.

$196 nightly

Nov 8 - Nov 9

Total with taxes and fees

A stone fire pit with burning logs, surrounded by a grassy area and two wooden chairs.

13. Center Strip | Pets OK | Wi-Fi | Near Wineries

Geneva

Patrick G.

$162 nightly

Nov 8 - Nov 9

Total with taxes and fees

A modern kitchen with stainless steel appliances, white cabinetry, and a wooden countertop.

14. Recently updated apartment in a Triplex close to Spire Wineries and the Lake.

Geneva

Devan M.

$175 nightly

Nov 5 - Nov 6

Total with taxes and fees

A compact living space with a kitchenette, a dining area with bar stools, a television, and a ceiling fan.

15. The Riesling Cottage - GOTL Strip - Cozy & Quaint

Geneva

Rebecca S.

$195 nightly

Nov 18 - Nov 19

Total with taxes and fees

A living room with a flat-screen TV mounted on the wall, a dark wood fireplace, and a brown leather sofa.

16. Quaint recently renovated apartment with AC in Geneva close to lake and wineries

Geneva

Donna G.

$190 nightly

Nov 5 - Nov 6

Total with taxes and fees

A wooden deck with two metal chairs and a small round table.

17. Cozy Country Apartment in Heart of Geauga County

Newbury

Phillip R.

$264 nightly

Nov 5 - Nov 6

Total with taxes and fees

A modern kitchen with a wooden countertop, stainless steel sink, and a black refrigerator.

18. Peaceful private apartment in the charming Hiram countryside

Garrettsville

Matthew W.

$180 nightly

Nov 17 - Nov 18

Total with taxes and fees

A compact living space with a kitchenette, a dining area, and a sofa with cushions.

19. Little oasis a short walk from GOTL strip

Geneva-on-the-Lake

Jared M.

$196 nightly

Nov 5 - Nov 6

Total with taxes and fees

A small house with solar panels, a porch with outdoor furniture, and a wooden deck.

20. Cozy Shed-Teau in Geneva + Firepit

Geneva

William M B.

$138 nightly

Nov 9 - Nov 10

Total with taxes and fees

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Top Windsor Hotel Reviews

Holiday Inn Express & Suites Painesville - Concord by IHG

10/10 Excellent

"Everything was fantastic. Breakfast bar was great and had lots of options. Room was clean and comfy and big enough for our family of 5. Lots of parking, well-lit lot, Everything was sparkling clean. Would absolutely stay here again!"

The Lodge at Geneva-on-the-Lake

8/10 Good

"This was an excellent place to stay. The rooms were nice and the amenities were great. The trees were at peak and walking through the trails was a great experience. They even provide free basic bikes for use for those who have rooms. The only thing I was surprised by was the extent of dead bugs sitting on beams and ledges in the foyer. I understand that the mayflies cause lots of issues at certain times of the year and would require lots of cleaning for a period of time, but it doesn't present the idea of cleanliness for the property. However, our actual room was very clean. Overall we had a very good experience and I still rate this a 4/5 stars. I just think this presentation and impression is important and should have a higher priority. Cleanliness is a very important aspect of any property."

Residence Inn By Marriott Cleveland Mentor

10/10 Excellent

"I and my wife stayed here for her Birthday weekend and I surprised her with an extra day. Thur-Sun we stayed and the stay was fantastic. The Staff was very helpful and friendly. The Room was very clean and fresh. We love the fact the kitchen area has dish detergent and actual dish ware for use. The complimentary breakfast was actually great. Overall great and wonderful stay. We will be making reservations again soon. There’s also a tennis court, basketball court and pool!"

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 $135 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.

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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?

Center Strip | Pets OK | Wi-Fi | Near Wineries: This vacation home rental outside of Windsor is located on a lake and offers a barbecue grill, air-conditioning, and WiFi to help you feel perfectly comfortable in your new surroundings.

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 Middlefield Village Center 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.

Windsor Vacation Rentals

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Check prices for these dates

Our top choices for Windsor vacation rentals

1. Little house on the farm

2. 3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.

3. 2 bedroom apartment in the beautiful Middlefield countryside!

4. Nestled Inn Mespo Modern & Cozy Apartment

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

6. Cozy 1-bedroom Camper on the lake with AC in adorable Cortland.

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

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

9. Romantic Woodside Cabin | Hot Tub & Fire Pit

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

11. On The Strip • Cozy GOTL Vacation Cottage

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

13. Center Strip | Pets OK | Wi-Fi | Near Wineries

14. Recently updated apartment in a Triplex close to Spire Wineries and the Lake.

15. The Riesling Cottage - GOTL Strip - Cozy & Quaint

16. Quaint recently renovated apartment with AC in Geneva close to lake and wineries

17. Cozy Country Apartment in Heart of Geauga County

18. Peaceful private apartment in the charming Hiram countryside

19. Little oasis a short walk from GOTL strip

20. Cozy Shed-Teau in Geneva + Firepit

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

Holiday Inn Express & Suites Painesville - Concord by IHG

Find out more about Windsor

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