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Compare 143 Vacation Homes in Windsor with updated reviews, rates, and availability.

Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C

9.4 out of 10, Exceptional, (299)
"This was our second time staying at this property. Once again it was a great time. The house is super clean and comfortable. Matt is always responsive to my questions. We would definitely stay here again. "
Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C

Great Strip Location | Lake View | Pet Friendly | A/C | Sauna| Wine Country|WiFi

9.8 out of 10, Exceptional, (182)
"We had a great time! We had 8 adults and 6 kiddos and we had plenty of room! We had plenty of everything we needed. There is a regular drip coffee pot and one for k-cups. Many of the shops and restaurants in GOTL are closed in the winter. We would love to see how the city transforms in the summer! "
Great Strip Location | Lake View | Pet Friendly | A/C | Sauna| Wine Country|WiFi

Center of Strip |Pet Friendly|A/C|Wi-fi & Cable|Stately Home|Steps from Winery

9.4 out of 10, Exceptional, (224)
"House was great. Lots of room. Was perfect for adults, not too many bunk beds or single beds, that adults do not want to sleep in. Close to strip and easy drive to most of the wineries. Perfect for large group we had 11 adults and still had extra rooms. Has everything you could need!"
Center of Strip |Pet Friendly|A/C|Wi-fi & Cable|Stately Home|Steps from Winery

Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries

9.4 out of 10, Exceptional, (232)
"Took a trip with family and friends for my birthday. Location was perfect. Best part of this location was that everyone was able to have their own room. "
Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries

Great Strip Location | Walk to Lake|Wine Country|A/C|Fireplace|Family Friendly

9.6 out of 10, Exceptional, (93)
"Perfect size for group of eight."
Great Strip Location | Walk to Lake|Wine Country|A/C|Fireplace|Family Friendly

Great Strip Location|WalktoLake|Wine Country|AC|Grill&Firepit|FamilyFriendly

9.4 out of 10, Exceptional, (80)
"We stayed in the four bedroom cottage clean the arm and wonderful. Loved the ping pong table Thank you Matt "
Great Strip Location|WalktoLake|Wine Country|AC|Grill&Firepit|FamilyFriendly

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

9.8 out of 10, Exceptional, (14)
"This rental had everything we needed for our girls weekend. The property grounds are so cute and the hot tub was perfect in the cold! Highly recommend staying here!"
Hot Tub, Fire Pit, Private Backyard - Near Wineries & SPIRE

East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly

9.4 out of 10, Exceptional, (68)
"We are from Conneaut, but had a lot of business to take of in Mentor. My husband also needed to be able to get back to Conneaut as needed for other work projects. Instead of driving back and forth between the two we decided to get a place in Geneva.It worked out GREAT! It was so convenient and the cottage was clean, comfortable, pet friendly & well appointed with a perfect location. Lots of restaurants nearby and easy access to route 84. Matt is terrific!!!We'll be back - we highly...
East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly

Modern 2B Family Home Near Wine Country- 6m Walk to Lake +Pet Friendly

9.8 out of 10, Exceptional, (51)
"this place was very clean and had everything we needed. We will be back next year !"
Modern 2B Family Home Near Wine Country- 6m Walk to Lake +Pet Friendly

Large, family friendly, historic downtown Geneva. Lots of spaces for gathering.

10.0 out of 10, Exceptional, (75)
"We booked this property for Thanksgiving week. Three families for a total of 12 people stayed here. Because the house was so nice and spacious. We actually hosted Thanksgiving dinner for other family that live in the area. We had over 25 people total for dinner and easily had room for more. The house is exactly as shown in the pictures. It’s new, it’s clean and it actually had everything we needed in the kitchen. The hosts were wonderful from the moment we booked it. Beth reached out immediately...
Large, family friendly, historic downtown Geneva. Lots of spaces for gathering.

Peaceful- SPIRE, GOTL, Wine Country, Beach

9.8 out of 10, Exceptional, (16)
"“Thank you, Rebekah, for a great stay! The house was spotless, and your thoughtful touches made us feel right at home. The wine shuttle was perfect! "
Peaceful- SPIRE, GOTL, Wine Country, Beach

GOTL Joe’s Bungalow - Sunset Vacation Rental

9.0 out of 10, Wonderful, (7)
"Property was nice. Description was accurate."
GOTL Joe’s Bungalow - Sunset Vacation Rental

House 1 mile from Geneva on Lake. We have several wineries in the area.

10.0 out of 10, Exceptional, (28)
"Overnight stay on the way home from Cleveland concert. Everything was clean, modern and perfect. "
House 1 mile from Geneva on Lake. We have several wineries in the area.

Madison Lakehouse – Spectacular Sunsets, Triple Lot.

10.0 out of 10, Exceptional, (55)
"Our family came up to celebrate Thanksgiving. The house is stunning and it is so well equipped in the kitchen, that we didn’t need half the things that we brought. The cleanliness is outstanding! My 88-year-old mother said it was the best Thanksgiving she ever had and we hope to come back next year! Thank you so much!"
Madison Lakehouse – Spectacular Sunsets, Triple Lot.

The Champion House

2.0 star property
10.0 out of 10, Exceptional, (6)
"Warm and roomy for this family of 4. We enjoyed our stay here while visiting family in Warren. Everything we needed was provided and house was spotless. "
The price is AED 533
AED 958 total
includes taxes & fees
5 Mar - 6 Mar
The Champion House

Geauga Maple Cottage

10.0 out of 10, Exceptional, (170)
"We only needed extra bedrooms and beds and did most of our activities with family in Chardon. This place was perfect! While the bed situation was a little different (a twin room and a twin bed on the upstairs landing), it is exactly what we expected based on the posted pictures. The house was clean, uncluttered, very comfortable bedsheets and towels, and coffee machines. Also, a nice sized living room and parking. Just what we needed! AND some good books and movies for those who had some extra...
Geauga Maple Cottage

Rosko Ridge Cottage located minutes from GOTL and wineries

9.4 out of 10, Exceptional, (17)
"Nice little place close to all amenities."
Rosko Ridge Cottage located minutes from GOTL and wineries

Lakefront - Winery - GOTL Oasis- Sunset Vacation Rentals

9.4 out of 10, Exceptional, (51)
"Beautiful views of the lake and all the stacking ice was amazing ! Over all a great stay. Only issues was dog hair left by a previous guest and a patio door wouldn’t lock. Would love to come back in the summer. "
Lakefront - Winery - GOTL Oasis- Sunset Vacation Rentals

GOTL - Hot Tub - Wine Tours - Sunset Vacation Rentals

10.0 out of 10, Exceptional, (12)
"Very good space for a gathering. "
GOTL - Hot Tub - Wine Tours - Sunset Vacation Rentals

Central Location- SPIRE, Wineries, GOTL, Beach

9.6 out of 10, Exceptional, (19)
"The host was very responsive to questions. Great location to wineries and great food in downtown Ashtabula. Beds were comfortable and large table was great for games and cards after visiting wineries. Would definitely stay again. "
Central Location- SPIRE, Wineries, GOTL, Beach
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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Other property types in Windsor

Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C

9.4 out of 10, Exceptional, (299)
"This was our second time staying at this property. Once again it was a great time. The house is super clean and comfortable. Matt is always responsive to my questions. We would definitely stay here again. "
Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C

Strip Location | Pet Friendly | A/C | Wi-Fi & Cable | Fire Pit | Wine Country

9.6 out of 10, Exceptional, (209)
"This was a cute cottage ! On the smaller side but was cute and had everything we needed ! Nice bedding and towels ! "
Strip Location | Pet Friendly | A/C | Wi-Fi & Cable | Fire Pit | Wine Country

Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries

9.4 out of 10, Exceptional, (232)
"Took a trip with family and friends for my birthday. Location was perfect. Best part of this location was that everyone was able to have their own room. "
Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries
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.