Windsor Holiday Rentals

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Holiday Rentals in Windsor

Peaceful Eagle One is nestled in a quaint small town near many attractions

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay. Very close to where my son lives in Cortland. It was perfect for us to go slowly in the mornings, then head to the their house after they chored. Good for my husband (only a couple steps) with mobility issues. We will definitely stay there again! Oh yes, the Greene Eagle Winery was great too!"
The price is AU$323
includes taxes & fees
16 July - 17 July
Peaceful Eagle One is nestled in a quaint small town near many attractions

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

10.0 out of 10, Exceptional, (111)
"Charming, clean and comfortable. The relics take you back in time leaving pleasant thoughts of the past."
The price is AU$270
includes taxes & fees
22 July - 23 July
Conveniently located 2 bedroom home only minutes from hiking and state park fun!

Ledgestone Farms- Cozy Hideaway

The price is AU$261
includes taxes & fees
14 July - 15 July
Ledgestone Farms- Cozy Hideaway

Ledgestone Farms-Rustic Western Getaway

8.4 out of 10, Very good, (26)
"I enjoyed my stay the place was clean, quiet and peaceful. Would recommend that you give a try. DJ"
The price is AU$261
includes taxes & fees
14 July - 15 July
Ledgestone Farms-Rustic Western Getaway

Ledgestone Farms-Quiet Country Apartment

9.0 out of 10, Wonderful, (32)
"Very clean place, loved the seclusion and the host is the nicest person you will ever meet."
The price is AU$306
includes taxes & fees
14 July - 15 July
Ledgestone Farms-Quiet Country Apartment

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

10.0 out of 10, Exceptional, (5)
"Every bit of this property was great. They went above and beyond to make sure anyone that stays feels like they are at home with all they need. They are also the owners that put money into their house and it shows. They don't just rent out a house and collect money, they really care and upgrade the property. "
The price is AU$358
includes taxes & fees
15 July - 16 July
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.

Peaceful 3BR Cabin Retreat w/Hot Tub-Near Wineries, Geneva-on-the-Lake & Spire

10.0 out of 10, Exceptional, (5)
"Gorgeous cabin with space to visit together or spread out. We enjoyed the rocking chairs on the front porch, playing games, and watching movies. Kitchen and bathrooms were stocked with everything we needed. Weather was hot while we were there, and the a/c kept us comfortably cool. Great location for visiting wineries, hiking, and kayaking. Check in and check out were simple."
The price is AU$528
includes taxes & fees
29 July - 30 July
Peaceful 3BR Cabin Retreat w/Hot Tub-Near Wineries, Geneva-on-the-Lake & Spire

Little house on the farm

10.0 out of 10, Exceptional, (90)
"This is our 2nd time staying here. We love the property and all it has to offer!"
The price is AU$329
includes taxes & fees
14 July - 15 July
Little house on the farm

Erieview Lakehouse - Lakeside Retreat in GOTL

10.0 out of 10, Exceptional, (28)
"Enjoyed my stay here. Big house with amazing views."
The price is AU$1,083
includes taxes & fees
27 July - 28 July
Erieview Lakehouse - Lakeside Retreat in GOTL

Sun Retreats GOTL Cozy campground in lovely Geneva with AC, WiFi, fitness room

The price is AU$375
includes taxes & fees
20 July - 21 July
Sun Retreats GOTL Cozy campground in lovely Geneva with AC, WiFi, fitness room

Ultimate Wine Country Retreat | Hot Tub, Arcade, and Mins to Spire and Winery!

10.0 out of 10, Exceptional, (58)
"Definitely can't recommend this property highly enough. Clean, comfortable, had everything we needed, and the hot tub was amazing! Thanks for a perfect place to stay on our mini vacation!"
The price is AU$497
includes taxes & fees
16 July - 17 July
Ultimate Wine Country Retreat | Hot Tub, Arcade, and Mins to Spire and Winery!

Modern Home, Next to SPIRE, Near Wineries, Geneva-On-The-Lake

10.0 out of 10, Exceptional, (14)
"It was such an easy process. Host was very attentive, and the place was adorable and very clean. They had a really nice layout of coffee, drinks and snacks as a nice touch. Would definitely stay there again!"
The price is AU$784
includes taxes & fees
14 July - 15 July
Modern Home, Next to SPIRE, Near Wineries, Geneva-On-The-Lake

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

10.0 out of 10, Exceptional, (28)
"Great place to stay while in Geneva and it's close to everything plus the host was very attentive!"
The price is AU$525
includes taxes & fees
31 July - 1 Aug
House 1 mile from Geneva on Lake. We have several wineries in the area.

Welcome To Wine Country - Relaxed Luxury!

9.8 out of 10, Exceptional, (9)
"The house was beautiful and in a great location. We thoroughly enjoyed our girls trip to Geneva and would definitely recommend this property to our friends."
The price is AU$678
includes taxes & fees
14 July - 15 July
Welcome To Wine Country - Relaxed Luxury!

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

9.6 out of 10, Exceptional, (189)
"It was a convenient location to the strip and the parks. "
The price is AU$390
includes taxes & fees
27 July - 28 July
Pet Friendly | A/C | Wi-Fi & Cable | Grill |Walk to Lake| Firepit | Wine Country

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

9.8 out of 10, Exceptional, (63)
"The best I have ever stayed in."
The price is AU$475
includes taxes & fees
21 July - 22 July
Modern 2B Family Home Near Wine Country- 6m Walk to Lake +Pet Friendly

Linny's GOTL Cottages "Lazy Days" Charming 2-bedroom bungalow with AC, GOTL.

10.0 out of 10, Exceptional, (5)
The price is AU$327
includes taxes & fees
30 July - 31 July
Linny's GOTL Cottages "Lazy Days" Charming 2-bedroom bungalow with AC, GOTL.

Linny's GOTL Cottages "Blue Pearl" 3-bedroom house on the strip in GOTL, spire

10.0 out of 10, Exceptional, (3)
"This house is in a great location with just about a 30 second walk to the strip. Clean house, great space for multiple couples and friendly host. **Highly recommended**"
The price is AU$476
includes taxes & fees
27 July - 28 July
Linny's GOTL Cottages "Blue Pearl" 3-bedroom house on the strip in GOTL, spire

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

9.2 out of 10, Wonderful, (69)
"We really enjoyed it, had a great time We always enjoy Eagle Cliff Inn "
The price is AU$306
includes taxes & fees
17 July - 18 July
Great Strip Location |WalktoLake|Wine Country|Brewing Company|A/C|Grill&Firepit

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

9.4 out of 10, Exceptional, (91)
"This is a great place, great location, very clean. "
The price is AU$398
includes taxes & fees
3 Aug - 4 Aug
Great Strip Location|WalktoLake|Wine Country|AC|Grill&Firepit|FamilyFriendly
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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Frequently asked questions

Are there holiday rentals in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Windsor has to offer?

Pet Friendly | A/C | Wi-Fi & Cable | Grill |Walk to Lake| Firepit | Wine Country: This holiday home rental outside of Windsor is located on a lake, and offers a BBQ, air conditioning and free WiFi to help you feel perfectly comfortable 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 Middlefield Cheese Chalet Shop, or get outside and enjoy nature at Punderson Lake. Windsor Mills Covered Bridge and Pioneer Waterland & Dry Fun Park are a couple of places you'll find in the wider area.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family trips.