Windsor Holiday Rentals

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

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$977
HK$2,518 total
includes taxes & fees
7 Mar - 8 Mar
Waterfront Properties vacation rental
Property grounds

Cabin in Thompson

Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!
10.0 out of 10, Exceptional, (12 reviews)
"This is the perfect place for you to come and relax. "
United States
Anabel P.
The price is HK$977
HK$1,572 total
includes taxes & fees
8 Mar - 9 Mar
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!
Exterior detail

Cabin in Starlight

Handcrafted Riverfront Cabin on 10 acres
10.0 out of 10, Exceptional, (196 reviews)
"Excellent property and great location "
United States
Eric P.
The price is HK$1,020
HK$2,664 total
includes taxes & fees
18 Mar - 19 Mar
Handcrafted Riverfront Cabin on 10 acres
Property grounds

Cabin in Thompson

Queen Cabin Modern Cabin Near Skiing, Trails, Firepit, Hot Tub & Stargazing!
10.0 out of 10, Exceptional, (31 reviews)
"Very very beautiful sites and the hot tub was a must "
United States
Ethan F.
The price is HK$977
HK$1,572 total
includes taxes & fees
10 Mar - 11 Mar
Queen Cabin Modern Cabin Near Skiing, Trails, Firepit, Hot Tub & Stargazing!
Exterior

Cottage in Pleasant Mount

Equestrian House Suites
3.0 star property
The price is HK$1,575
HK$4,657 total
includes taxes & fees
14 Mar - 15 Mar
Equestrian House Suites
Fridge, microwave, oven, stovetop

Cottage in Pleasant Mount

The Hideout Cottage • The Velvet Slopes of Romance
The price is HK$844
HK$2,360 total
includes taxes & fees
8 Mar - 9 Mar
The Hideout Cottage • The Velvet Slopes of Romance
Terrace/patio

Residence in Equinunk

Equinunk
2.0 star property
The price is HK$1,540
HK$2,929 total
includes taxes & fees
6 Apr - 7 Apr
Equinunk
Interior

Cottage in Hancock

Charming 120-year-old farmhouse by the creek
9.0 out of 10, Wonderful, (24 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$1,154
HK$2,559 total
includes taxes & fees
8 Mar - 9 Mar
Charming 120-year-old farmhouse by the creek
Property grounds

Cottage in Pleasant Mount

Deluxe Duplex • Heart Runs & Ski Runs
The price is HK$1,313
HK$3,222 total
includes taxes & fees
9 Mar - 10 Mar
Deluxe Duplex • Heart Runs & Ski Runs
Exterior

Cabin in Binghamton

Cozy/Chic Cabin (ISOLATED RETREAT!) Binghamton NY
9.8 out of 10, Exceptional, (136 reviews)
"Excellent host. Very accommodating. House is bigger then it looks. Very cozy and highly recommend. Warm and welcoming feeling all throughout the house "
United States
Thomas N.
The price is HK$1,259
HK$2,748 total
includes taxes & fees
8 Mar - 9 Mar
Cozy/Chic Cabin (ISOLATED RETREAT!) Binghamton NY
Smart TV

Cabin in Deposit

Seasons on Oak Short walk to best Fly Fishing in Northeast Cozy Cabin Deposit NY
10.0 out of 10, Exceptional, (16 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$2,033
HK$2,820 total
includes taxes & fees
9 Mar - 10 Mar
Seasons on Oak Short walk to best Fly Fishing in Northeast Cozy Cabin Deposit NY
Property grounds

Cottage in Pleasant Mount

2BR Premium Duplex • The Velvet Slopes of Romance
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$985
HK$2,782 total
includes taxes & fees
8 Mar - 9 Mar
2BR Premium Duplex • The Velvet Slopes of Romance
Smart TV, fireplace, books, music library

Cottage in Montrose

Quiet Lakefront Retreat nestled in the woods.
10.0 out of 10, Exceptional, (93 reviews)
"Great clean, comfortable place, attentive hosts, beautiful location. "
United States
David A.
The price is HK$1,016
HK$1,486 total
includes taxes & fees
8 Mar - 9 Mar
Quiet Lakefront Retreat nestled in the woods.
Interior

Holiday Home in Thompson

Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
10.0 out of 10, Exceptional, (14 reviews)
"Perfect place to bring the family for a quiet ski holiday. "
United States
Pamela S.
The price is HK$1,251
HK$2,259 total
includes taxes & fees
11 Mar - 12 Mar
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
Dining

Apartment in Bainbridge

Cozy 2b apt 25mins from All Star Village & 44mins from Cooperstown Dreams Park
10.0 out of 10, Exceptional, (2 reviews)
"They had everything you need and the space was very clean. would stay again 100%."
United States
Nicholas
The price is HK$625
HK$1,138 total
includes taxes & fees
15 Mar - 16 Mar
Cozy 2b apt 25mins from All Star Village & 44mins from Cooperstown Dreams Park
Dining

Cottage in Pleasant Mount

Vacation Cottage Getaway • Crystal Peaks, Timeless Love
The price is HK$844
HK$2,360 total
includes taxes & fees
7 Mar - 8 Mar
Vacation Cottage Getaway • Crystal Peaks, Timeless Love
Smart TV, stereo

Apartment in Greene

Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly
10.0 out of 10, Exceptional, (16 reviews)
"Anniversary weekend getaway "
United States
Kayla M.
The price is HK$899
HK$1,182 total
includes taxes & fees
9 Mar - 10 Mar
Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly
Outdoor dining

Cabin in Thompson

King Cabin Secluded Romantic Space Near Elk Mountain. Hot Tub, Firepit & Views!
9.6 out of 10, Exceptional, (40 reviews)
"Great stay especially for a wedding for family vacation "
United States
Catherine P.
The price is HK$977
HK$1,597 total
includes taxes & fees
17 Mar - 18 Mar
King Cabin Secluded Romantic Space Near Elk Mountain. Hot Tub, Firepit & Views!
TV, fireplace

Holiday Home in Hancock

Lake View Log Cabin with amazing views
The price is HK$3,127
HK$5,822 total
includes taxes & fees
24 Mar - 25 Mar
Lake View Log Cabin with amazing views
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$782
HK$2,491 total
includes taxes & fees
8 Mar - 9 Mar
Ska'no'ne - WINTER BEAUTY. Skiing, Ice Skating all within a short drive,
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

Holiday Inn Express Hotel & Suites Vestal by IHG

Holiday Inn Express Hotel & Suites Vestal by IHG

10/10 Excellent
"Smooth check, got a later check out at my request without any problem, room was very clean and everything worked well. It looks like the owners are gradually trying to upgrade things. The indoor pool was closed (and drained), but it didn't affect my stay at all. The breakfast (included) was slightly better than most places, and the staff did a great job keeping the area clean and well-stocked. The seating area for breakfast was clean and had very comfortable seating options. Housekeeping staff on my floor was very friendly and professional.I'd definitely stay here again!"
Jaime 1-night trip
Posted 10 hours ago
Holiday Inn Express Hotel & Suites Vestal by IHG

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
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • 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?

Indoor Pool, Luxury Log Estate, 2 Story Game Room : This holiday home rental outside of Windsor is located in the mountains, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 13 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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.