A wooden covered bridge with an American flag, surrounded by autumn foliage.

Windsor Vacation 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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Dates

November 2026

December 2026

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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.

AED 801 total

includes taxes & fees

5 Nov - 6 Nov

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

2. Nestled Inn Mespo Modern & Cozy Apartment

Middlefield

Abby M.

AED 801 total

includes taxes & fees

5 Nov - 6 Nov

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

3. 2 bedroom apartment in the beautiful Middlefield countryside!

Middlefield

Ashley B.

AED 654 total

includes taxes & fees

8 Nov - 9 Nov

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

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

Burton

Phillip

AED 566 total

includes taxes & fees

9 Nov - 10 Nov

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

5. 3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.

Rome

Amy P.

AED 786 total

includes taxes & fees

9 Nov - 10 Nov

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

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

Warren

Carol D.

AED 599 total

includes taxes & fees

9 Nov - 10 Nov

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

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

Madison

Jennifer S.

AED 591 total

includes taxes & fees

6 Nov - 7 Nov

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

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

Geneva

frances f.

AED 696 total

includes taxes & fees

5 Nov - 6 Nov

A modern kitchen with dark cabinets, a white stove, and a granite countertop.

9. Chardonnay Cottage - GOTL Strip - Cozy & Quaint

Geneva

James

AED 732 total

includes taxes & fees

5 Nov - 6 Nov

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

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

Geneva

Daniel K.

AED 718 total

includes taxes & fees

8 Nov - 9 Nov

A bedroom with a bed, nightstands, a lamp, and curtains.

11. The Blue Grape: Dog-Friendly Wine Country Home, King Bed & Private Deck

Madison

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

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

Geneva

Patrick G.

AED 637 total

includes taxes & fees

8 Nov - 9 Nov

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

13. Romantic Woodside Cabin | Hot Tub & Fire Pit

Madison

Matthew

AED 805 total

includes taxes & fees

18 Nov - 19 Nov

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.

AED 622 total

includes taxes & fees

10 Nov - 11 Nov

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

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

Geneva

Donna G.

AED 716 total

includes taxes & fees

5 Nov - 6 Nov

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

16. Little oasis a short walk from GOTL strip

Geneva-on-the-Lake

Jared M.

AED 718 total

includes taxes & fees

5 Nov - 6 Nov

A bedroom with a bed, a ceiling fan, a window with patterned curtains, and a door.

17. Quaint cottage a short walk from the GTOL strip!

Geneva-on-the-Lake

Rita D.

AED 646 total

includes taxes & fees

5 Nov - 6 Nov

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

18. On The Strip • Cozy GOTL Vacation Cottage

Geneva

Daniel M.

AED 899 total

includes taxes & fees

8 Nov - 9 Nov

A two-story house with a covered porch and a landscaped garden.

19. 1 Bed 1 Bath Suite On Strip

Geneva on the Lake

Mark B.

AED 682 total

includes taxes & fees

5 Nov - 6 Nov

A sunset over a calm sea with a clear horizon.

20. "The Beach Hive" unit 1; lower-level apartment on the Lake

Geneva

Nicholas

AED 590 total

includes taxes & fees

7 Nov - 8 Nov

View all properties

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

A Holiday Inn Express & Suites hotel with a modern design, featuring a well-lit entrance and clear signage.

Holiday Inn Express & Suites Painesville - Concord by IHG

Painesville

10/10 Excellent

Alicia

A Holiday Inn Express & Suites hotel with a modern design, featuring a covered entrance and a well-lit facade.

Holiday Inn Express & Suites Madison by IHG

Madison

10/10 Excellent

Vicki

An outdoor patio with a fire pit, seating, and string lights.

Hampton Inn Madison

Madison

10/10 Excellent

John M

An indoor swimming pool with clear views of the sunset through large windows.

Hampton Inn Ashtabula

Austinburg

10/10 Excellent

Anonymous traveler

A modern hotel with a fire pit in the courtyard, outdoor seating, and a covered patio area.

Towneplace Suites By Marriott Geneva

Geneva

10/10 Excellent

Mary

A buffet with various food items, including omelets and other dishes, served in metal containers.

Holiday Inn Express Hotel & Suites Ashtabula-Geneva by IHG

Austinburg

10/10 Excellent

Anonymous traveler

Best Western Plus Mentor-Cleveland Northeast

Mentor

10/10 Excellent

Matt

A large resort with multiple buildings, a swimming pool, and a tennis court.

The Lodge at Geneva-on-the-Lake

Geneva-on-the-Lake

10/10 Excellent

Tom

A white house with a gravel driveway, surrounded by lush greenery and flowering bushes.

The Lost Pearl

Madison

10/10 Excellent

This was a great two night stay in a themed "Pirate" room. The Inn is conveniently located in wine country. Southing music was playing in the room on a Kindle upon arrival and two coffee mugs etched with the Inn's logo were ours to keep. Our room was clean and relaxing. The breakfast was gourmet served in he kitchen while seated at the island. Goats, ducks, and kitties are on the property to see. We will return and recommend to others.

John

An indoor swimming pool with a wooden ceiling, clear skylights, and a tiled floor.

Comfort Inn Painesville - Concord

Painesville

10/10 Excellent

Anonymous traveler

A modern dining area with high tables and booths, a kitchen in the background, and a large window providing natural light.

Hampton Inn & Suites Cleveland Mentor

Mentor

10/10 Excellent

Lette

A kitchenette with a coffee maker, toaster, and a milk frother.

Americas Best Value Inn Austinburg

Austinburg

10/10 Excellent

MARLA

A breakfast area with a sign for Express Start Breakfast, a bakery section, and a display of hot food, cereal, and fruit.

Holiday Inn Express Mentor Banquet Center by IHG

Mentor

10/10 Excellent

Shonna

A hotel reception area with a counter, beverage dispensers, a painting, and a toaster.

Austinburg Hotel

Austinburg

10/10 Excellent

sharon

A lodge with a large building and a covered deck area.

Tall Oaks Resort

Willoughby

10/10 Excellent

This place is brand new and beautiful. The staff and owners were super welcoming and made my boring, Wednesday night stay feel like an event to celebrate. The room was extremely comfortable and there's a wooded area in the back with swings and chairs for relaxing. There are sidewalks and a few dining options in walking distance, as well as a park and multi-use path into a natural area. I recommend Tall Oaks wholeheartedly.

Laura

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

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor vacation rentals

1. Little house on the farm

2. Nestled Inn Mespo Modern & Cozy Apartment

3. 2 bedroom apartment in the beautiful Middlefield countryside!

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

5. 3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.

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

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

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

9. Chardonnay Cottage - GOTL Strip - Cozy & Quaint

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

11. The Blue Grape: Dog-Friendly Wine Country Home, King Bed & Private Deck

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

13. Romantic Woodside Cabin | Hot Tub & Fire Pit

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

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

16. Little oasis a short walk from GOTL strip

17. Quaint cottage a short walk from the GTOL strip!

18. On The Strip • Cozy GOTL Vacation Cottage

19. 1 Bed 1 Bath Suite On Strip

20. "The Beach Hive" unit 1; lower-level apartment on the Lake

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

Holiday Inn Express & Suites Painesville - Concord by IHG

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Windsor?

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

What can I see and do in Windsor?

What are vacation rentals like in Windsor?