Windsor Holiday Rentals

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Windsor holiday rentals

Property grounds

Holiday Home in Windsor

Waterfront Properties vacation rental
9.8 out of 10, Exceptional, (67 reviews)
"The house was perfect for our weekend. We appreciated that it was spotless and that the beds were super comfortable. Thank you! "
United States
Ronni
The price is HK$975
HK$2,449 total
includes taxes & fees
17 Feb - 18 Feb
Waterfront Properties vacation rental
Exterior detail

Cabin in Starlight

Handcrafted Riverfront Cabin on 10 acres
10.0 out of 10, Exceptional, (192 reviews)
"Excellent property and great location "
United States
Eric P.
The price is HK$674
HK$2,290 total
includes taxes & fees
25 Jan - 26 Jan
Handcrafted Riverfront Cabin on 10 acres
Interior

Cottage in Hancock

Charming 120-year-old farmhouse by the creek
8.8 out of 10, Excellent, (23 reviews)
"Our family had a lovely time on this charming home. From someone who grew up in the Catskills, this was a wonderful getaway from the usual hustle & bustle life."
United States
Liza G.
The price is HK$1,039
HK$2,446 total
includes taxes & fees
25 Jan - 26 Jan
Charming 120-year-old farmhouse by the creek
Exterior

Cabin in Binghamton

Cozy/Chic Cabin (ISOLATED RETREAT!) Binghamton NY
9.8 out of 10, Exceptional, (134 reviews)
"Really loved my stay at Kelly's place. Cozy and quiet, yet just a short ride into town. Kelly responded right away whenever I had a question and did everything possible to make the stay enjoyable. The kitchen and bathrooms have everything you need. Even had a full propane tank ready to go when the current one ran out. Will stay there again when I'm in the Binghamton area."
United States
frank g.
The price is HK$1,120
HK$2,570 total
includes taxes & fees
21 Jan - 22 Jan
Cozy/Chic Cabin (ISOLATED RETREAT!) Binghamton NY
TV

Holiday Home in Hancock

Angler and Nature's delight - West Branch Delaware
9.6 out of 10, Exceptional, (7 reviews)
"We enjoyed the weekend getaway with family. The house was very cozy and the hostess was very kind. Thank you very much. "
United States
Rosa P.
The price is HK$1,131
HK$2,826 total
includes taxes & fees
21 Jan - 22 Jan
Angler and Nature's delight - West Branch Delaware
Outdoor dining

Cabin in Thompson

King Cabin Secluded Romantic Space Near Elk Mountain. Hot Tub, Firepit & Views!
9.8 out of 10, Exceptional, (39 reviews)
"We had a lovely stay. The mountain and valley views from the cabin were spectacular. The property was beautifully landscaped and maintained. "
United States
duane r.
The price is HK$975
HK$1,568 total
includes taxes & fees
21 Jan - 22 Jan
King Cabin Secluded Romantic Space Near Elk Mountain. Hot Tub, Firepit & Views!
Terrace/patio

Residence in Equinunk

Equinunk
2.0 star property
The price is HK$1,364
HK$2,735 total
includes taxes & fees
22 Jan - 23 Jan
Equinunk
Smart TV, fireplace, books, music library

Cottage in Montrose

Quiet Lakefront Retreat nestled in the woods.
10.0 out of 10, Exceptional, (92 reviews)
"Beautiful place. We really enjoyed out stay."
United States
Tom B.
The price is HK$1,014
HK$1,483 total
includes taxes & fees
23 Jan - 24 Jan
Quiet Lakefront Retreat nestled in the woods.
Property grounds

Cottage in Pleasant Mount

2BR Premium Duplex • Close to Ski Adventures
9.0 out of 10, Wonderful, (2 reviews)
"Would've liked to have more to cook with than just a microwave, other than that the stay was commendable."
United States
Jeremy
The price is HK$1,076
HK$2,894 total
includes taxes & fees
24 Jan - 25 Jan
2BR Premium Duplex • Close to Ski Adventures
Smart TV

Cabin in Deposit

Cozy Cabin built 2024 in Deposit,NY Short walk to best Fly Fishing in Northeast
10.0 out of 10, Exceptional, (15 reviews)
"A couple of our crew stayed here for the last couple weeks while out of town working on a job, and the cabin felt like home, it was clean, the host was super responsive, and it was just the perfect place for us. "
United States
RHL C.
The price is HK$1,949
HK$2,719 total
includes taxes & fees
22 Jan - 23 Jan
Cozy Cabin built 2024 in Deposit,NY Short walk to best Fly Fishing in Northeast
Property grounds

Cabin in Thompson

Jack Cabin Modern Cabin for Families Close to Skiing with Hot Tub and Firepit
9.4 out of 10, Exceptional, (11 reviews)
"Cool place to chilaxx"
United States
Luis R.
The price is HK$975
HK$1,568 total
includes taxes & fees
22 Jan - 23 Jan
Jack Cabin Modern Cabin for Families Close to Skiing with Hot Tub and Firepit
Exterior

Holiday Home in Nineveh

Ska'no'ne - WINTER BEAUTY. Skiing, Ice Skating all within a short drive,
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful location, clean, host was very helpful answering questions about the property / surrounding area."
United States
Kiel P.
The price is HK$1,053
HK$3,084 total
includes taxes & fees
18 Feb - 19 Feb
Ska'no'ne - WINTER BEAUTY. Skiing, Ice Skating all within a short drive,
Dining

Apartment in Bainbridge

Cozy 2b apt 25mins from All Star Village & 44mins from Cooperstown Dreams Park
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"They had everything you need and the space was very clean. would stay again 100%."
United States
Nicholas
The price is HK$624
HK$1,135 total
includes taxes & fees
21 Jan - 22 Jan
Cozy 2b apt 25mins from All Star Village & 44mins from Cooperstown Dreams Park
Interior

Holiday Home in Thompson

Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
10.0 out of 10, Exceptional, (11 reviews)
"Perfect place to bring the family for a quiet ski holiday. "
United States
Pamela S.
The price is HK$1,247
HK$2,253 total
includes taxes & fees
21 Jan - 22 Jan
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
Interior

Holiday Home in Equinunk

Angler and Hunter's delight - Upper Delaware River
9.4 out of 10, Exceptional, (3 reviews)
"We absolutely loved our stay. The place was clean, warm, spacious, and suited our needs perfectly. We will definitely look to rent it again if we are welcomed back! 😊"
United States
Brian H.
The price is HK$1,364
HK$3,115 total
includes taxes & fees
28 Jan - 29 Jan
Angler and Hunter's delight - Upper Delaware River
Lounge

Holiday Home in Hancock

Hale Eddy
2.0 star property
The price is HK$1,131
HK$2,491 total
includes taxes & fees
21 Jan - 22 Jan
Hale Eddy
Dining

Cottage in Pleasant Mount

Vacation Cottage Getaway • Close to Ski Mountain
The price is HK$842
HK$2,354 total
includes taxes & fees
21 Jan - 22 Jan
Vacation Cottage Getaway • Close to Ski Mountain
Fridge, microwave, oven, stovetop

Cottage in Pleasant Mount

The Hideout Cottage • Near Camps & ELK Ski
The price is HK$842
HK$2,354 total
includes taxes & fees
21 Jan - 22 Jan
The Hideout Cottage • Near Camps & ELK Ski
TV

Holiday Home in Johnson City

3-bedroom pet friendly house in centrally located Johnson City. 1 mi. from SUNY.
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"This home was a perfect choice for us. My adult sons all live several hours away from me. We all were able to meet here and have our Christmas celebration, with just a couple of hours of driving for all. The location was very convenient and nearby several restaurants and shopping areas. The house was a good size, and tastefully decorated. Brian stopped by to say hello and to see if we needed anything. "
United States
Deborah J.
The price is HK$1,154
HK$1,859 total
includes taxes & fees
21 Jan - 22 Jan
3-bedroom pet friendly house in centrally located Johnson City. 1 mi. from SUNY.
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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Top Windsor Hotel Reviews

Comfort Inn Binghamton I-81

Comfort Inn Binghamton I-81

10/10 Excellent
"Everything is great! Perfect for a quick snooze!"
Steven 1-night trip
Posted 3 days ago
Comfort Inn Binghamton I-81

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
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  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find a holiday rental 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. Windsor is known for its parks and basketball games. Make sure you have time to check out the cafés and bars during your trip.

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

3-bedroom pet friendly house in centrally located Johnson City. 1 mi. from SUNY.: This holiday home rental outside of Windsor offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What’s there to see and do in Windsor?

Explore the area and cultural attractions such as Deposit Historical Museum, or visit one of the family-friendly sights such as Animal Adventure Park. Susquehanna River and West Branch Delaware River are a couple of places you'll find in the wider area.

What’s a holiday rental in Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windsor. Holiday rentals offer amenities such as hot tubs, fire pits and patios 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 privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.