Search Vacation Homes in Windsor

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 140 Vacation Homes in Windsor with updated reviews, rates, and availability.

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

9.4 out of 10, Exceptional, (222)
"We had an amazing family reunion at one of Matt Caudill's properties on Geneva-on-the-Lake. Matt was incredibly accommodating, ensuring all our needs were met. The location of the property was perfect—close to restaurants, entertainment, and everything we needed for a fun and relaxing stay. The home itself was exceptionally well-stocked, making our stay comfortable and hassle-free. Overall, we had a wonderful experience and would highly recommend Matt's property to anyone looking for a great...
Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries

Heart of the Strip, Lakefront, Private Beach!

10.0 out of 10, Exceptional, (109)
"What a beautiful slice of heaven on earth! Pretty lake views and relaxing and comfortable home away from home. We appreciated the cleanliness, switch labels on all the lights/fans, and also the thoughtfulness of all the details and amenities the place had to offer! Thanksso much!"
Heart of the Strip, Lakefront, Private Beach!

Great Strip Location |WalktoLake|Wine Country|Brewing Company|A/C|Grill&Firepit

9.2 out of 10, Wonderful, (61)
"Location is very good Very cold with no real heating source"
Great Strip Location |WalktoLake|Wine Country|Brewing Company|A/C|Grill&Firepit

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

9.4 out of 10, Exceptional, (295)
"This was the perfect landing spot for our fall wine weekend to NE Ohio. We had a great time and would recommend. "
Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C

GENEVA-ON-LAKE Center Strip - Sunsets, happy hour & morning coffee ON the lake!

9.4 out of 10, Exceptional, (60)
"The property was just as described We had a great time Thank you"
GENEVA-ON-LAKE Center Strip - Sunsets, happy hour & morning coffee ON the lake!

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

10.0 out of 10, Exceptional, (87)
"Perfect little home for our stay. Grocery store right across the street and gas station. Also next to police station. Some traffic noise during the day, but quiet at night. Furniture and beds very comfortable. Would definitely stay here again!"
The price is SAR 375
SAR 638 total
includes taxes & fees
3 Dec - 4 Dec
Conveniently located 2 bedroom home only minutes from hiking and state park fun!

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

9.6 out of 10, Exceptional, (90)
"Beds are a bit on the hard side, but otherwise was all good. "
Great Strip Location | Walk to Lake|Wine Country|A/C|Fireplace|Family Friendly

Pet Friendly | A/C | Wi-Fi & Cable | Grill |Walk to Lake| Firepit | Wine Country

9.6 out of 10, Exceptional, (176)
"Very nice place and affordable for us I appreciate it Thank you "
Pet Friendly | A/C | Wi-Fi & Cable | Grill |Walk to Lake| Firepit | Wine Country

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

9.4 out of 10, Exceptional, (79)
"Was very nice, would like to stay there again. Would like to recommend to everyone "
Great Strip Location|WalktoLake|Wine Country|AC|Grill&Firepit|FamilyFriendly

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

9.4 out of 10, Exceptional, (222)
"Our second stay - accommodations exactly what we need, location is perfect! Thanks Matt!"
Center of Strip |Pet Friendly|A/C|Wi-fi & Cable|Stately Home|Steps from Winery

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

9.4 out of 10, Exceptional, (66)
"The house was super Duper clean and very well organized! Definitely would like to stay there again!"
East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly

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. "
The price is SAR 751
SAR 1,074 total
includes taxes & fees
27 Nov - 28 Nov
House 1 mile from Geneva on Lake. We have several wineries in the area.

East End of The Strip. A/C Wifi Cable TV Firepit Walk to Park/Lake Wineries

9.6 out of 10, Exceptional, (71)
"The house was exactly as described and the host had excellent communication. It was an easy 15 min drive to Spire. Would like to come back again to enjoy the lake!"
East End of The Strip. A/C Wifi Cable TV Firepit Walk to Park/Lake Wineries

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

Ezmeralda's ~ Classic 1920's Renovated Bungalow ~ "A Hidden Gem of Geneva"

10.0 out of 10, Exceptional, (181)
"Very nice property enjoyed relaxing by the fire at the wine shack great company and host"
Ezmeralda's ~ Classic 1920's Renovated Bungalow ~ "A Hidden Gem of Geneva"

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

9.8 out of 10, Exceptional, (46)
"The place we was in was very nice. It was very clean and relaxing. The property was very clean. Everything worked very well. It was super close to Everything we wanted to do. Overall the location and the place was 10/10. The only negative thing i have to say that the front door blind was broken when we arrivedwe got there is that"
Modern 2B Family Home Near Wine Country- 6m Walk to Lake +Pet Friendly

Wooded Luxury Home

9.8 out of 10, Exceptional, (53)
"We had stayed here once before and absolutely loved it and made plans to come back. The house was still beautiful and the pool and hot tub were absolutely perfect! Overall it was a great weekend getaway with family! The only things I wish were better were the quality of the internet and we were not able to get any of the fireplaces to work. We were unable to utilize any of the televisions for the majority of the trip due to poor internet quality. We messaged the host via the VRBO app and did not...
Wooded Luxury Home

Melodic Forest~Hot Tub, Music Studio, Close to Wineries, Erie & Cleveland

10.0 out of 10, Exceptional, (19)
"The property was amazing. Enjoyed a walk on the trail behind the house. Hot tub was very relaxing. Steakhouse down the street was an additional bonus. "
Melodic Forest~Hot Tub, Music Studio, Close to Wineries, Erie & Cleveland

Rosko Ridge Cottage located minutes from GOTL and wineries

9.4 out of 10, Exceptional, (16)
"Great place with good coffee maker, refrigerator/freezer, televisions and good beds. We did run out of toilet paper and we had to fix the door handle to keep it working but minor issues compared to great rental overall."
Rosko Ridge Cottage located minutes from GOTL and wineries

Lakefront - Winery - GOTL Oasis- Sunset Vacation Rentals

9.4 out of 10, Exceptional, (50)
"Couples weekend with friends. Place was right on the lake, so clean, well kept and quaint. Close to many attractions and strip."
Lakefront - Winery - GOTL Oasis- Sunset Vacation Rentals
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.
Don't see what you're looking for?
See all available properties in Windsor
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Windsor

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

9.4 out of 10, Exceptional, (222)
"We had an amazing family reunion at one of Matt Caudill's properties on Geneva-on-the-Lake. Matt was incredibly accommodating, ensuring all our needs were met. The location of the property was perfect—close to restaurants, entertainment, and everything we needed for a fun and relaxing stay. The home itself was exceptionally well-stocked, making our stay comfortable and hassle-free. Overall, we had a wonderful experience and would highly recommend Matt's property to anyone looking for a great...
Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries

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

9.4 out of 10, Exceptional, (295)
"This was the perfect landing spot for our fall wine weekend to NE Ohio. We had a great time and would recommend. "
Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C

Heart of the Strip, Lakefront, Private Beach!

10.0 out of 10, Exceptional, (109)
"What a beautiful slice of heaven on earth! Pretty lake views and relaxing and comfortable home away from home. We appreciated the cleanliness, switch labels on all the lights/fans, and also the thoughtfulness of all the details and amenities the place had to offer! Thanksso much!"
Heart of the Strip, Lakefront, Private 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.