Windsor Vacation Rentals

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Vacation Rentals in Windsor

Vacation Home in Windsor

9.8 out of 10, Exceptional, (66)
"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
$285 nightly
The price is $322
Nov 30 - Dec 1
Total with taxes and fees
Waterfront Properties vacation rental

Cabin in Starlight

10.0 out of 10, Exceptional, (181)
"Enjoyed the cabin and made lots of memories and had some adventures for sure!"
United States
Tim S.
$267 nightly
The price is $290
Nov 30 - Dec 1
Total with taxes and fees
Handcrafted Riverfront Cabin on 10 acres

Apartment in Bainbridge

2.0 star property
$92 nightly
The price is $103
Dec 1 - Dec 2
Total with taxes and fees
Cozy 2b apt 25mins from All Star Village & 44mins from Cooperstown Dreams Park

Cabin in Thompson

10.0 out of 10, Exceptional, (12)
"This is the perfect place for you to come and relax. "
United States
Anabel P.
$159 nightly
The price is $173
Dec 3 - Dec 4
Total with taxes and fees
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!

Cottage in Hancock

8.8 out of 10, Excellent, (23)
"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.
$296 nightly
The price is $326
Nov 30 - Dec 1
Total with taxes and fees
Charming 120-year-old farmhouse by the creek

Cabin in Thompson

10.0 out of 10, Exceptional, (27)
"We enjoyed our short stay. Very clean. The view was great. We did wish that it had at least a window unit for air conditioning and an oven for making a frozen pizza."
United States
Denise B.
$159 nightly
The price is $173
Dec 3 - Dec 4
Total with taxes and fees
Queen Cabin Modern Cabin Near Skiing, Trails, Firepit, Hot Tub & Stargazing!

Cottage in Pleasant Mount

3.0 star property
$555 nightly
The price is $605
Nov 30 - Dec 1
Total with taxes and fees
Equestrian House Suites

Cottage in Montrose

10.0 out of 10, Exceptional, (90)
"Nice property & lake. Owners & family vert friendly & helpful"
United States
Nikki L.
$160 nightly
The price is $174
Dec 1 - Dec 2
Total with taxes and fees
Quiet Lakefront Retreat nestled in the woods.

Cottage in Pleasant Mount

$278 nightly
The price is $301
Dec 1 - Dec 2
Total with taxes and fees
Vacation Cottage Getaway • Close to Camps • Autumn Midweek - 35% OFF Promo!

Cottage in Pleasant Mount

9.0 out of 10, Wonderful, (2)
"Would've liked to have more to cook with than just a microwave, other than that the stay was commendable."
United States
Jeremy
$345 nightly
The price is $373
Nov 30 - Dec 1
Total with taxes and fees
2BR Premium Duplex • Autumn Midweek - 35% OFF Promo!

Cottage in Pleasant Mount

$278 nightly
The price is $301
Dec 1 - Dec 2
Total with taxes and fees
The Hideout Cottage • Autumn Midweek - 35% OFF Promo!

Vacation Home in Equinunk

2.0 star property
$467 nightly
The price is $495
Dec 1 - Dec 2
Total with taxes and fees
Equinunk

Apartment in Greene

10.0 out of 10, Exceptional, (7)
"Stayed for two nights. Apartment was clean and quiet. Plenty of towels and bed linens. "
United States
ANDREA K.
$128 nightly
The price is $143
Dec 3 - Dec 4
Total with taxes and fees
BRAND NEW! 1-bedroom apartment in the beautiful historic village of Greene, NY

Vacation Home in Thompson

10.0 out of 10, Exceptional, (11)
"Perfect place to bring the family for a quiet ski holiday. "
United States
Pamela S.
$265 nightly
The price is $288
Dec 3 - Dec 4
Total with taxes and fees
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!

Vacation Home in Johnson City

8.4 out of 10, Very Good, (13)
"Good place to stay for graduation weekend. "
United States
Steven
$101 nightly
The price is $114
Nov 29 - Nov 30
Total with taxes and fees
Cozy little house in Johnson City

Vacation Home in Nineveh

10.0 out of 10, Exceptional, (3)
"Beautiful location, clean, host was very helpful answering questions about the property / surrounding area."
United States
Kiel P.
$355 nightly
The price is $401
Nov 29 - Nov 30
Total with taxes and fees
Ska'no'ne -Peaceful Living 1-bedroom house with central HVAC & WiFi on 13+ acres

Cottage in Pleasant Mount

$212 nightly
The price is $229
Nov 29 - Nov 30
Total with taxes and fees
Deluxe Duplex • Farm Stay • Autumn Midweek - 35% OFF Promo!

Cabin in Binghamton

9.8 out of 10, Exceptional, (131)
"Location was great, host was very communicative and accommodating. Cabin was perfect for our needs for a weekend getaway and the place was stocked with anything you could think of. Like impossibly thoughtful in this way. Only challenge was getting into the driveway which is a bit precarious but very much a minor detail in the scheme of things. Would recommend and would visit again."
United States
Keith L Sherman S.
$301 nightly
The price is $340
Dec 1 - Dec 2
Total with taxes and fees
Cozy/Chic Cabin (ISOLATED RETREAT!) Binghamton NY

Apartment in Greene

10.0 out of 10, Exceptional, (14)
"Anniversary weekend getaway "
United States
Kayla M.
$135 nightly
The price is $151
Dec 1 - Dec 2
Total with taxes and fees
Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly

Chalet in Lakewood

9.6 out of 10, Exceptional, (122)
"We had a great stay. Very relaxing. House was so comfortable, slept like a rock. We enjoyed the critters, fishing and boating!"
United States
Lynda G.
$372 nightly
The price is $404
Dec 5 - Dec 6
Total with taxes and fees
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.
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

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $263 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, we have vacation rentals close to the most popular local attractions in Windsor, or you can choose 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 cafes and bars during your trip.

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

Waterfront Properties vacation rental: This Windsor vacation home rental is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind.

What’s there to see and do in Windsor?

Explore the area and cultural attractions such as Deposit Historical Museum, or visit a family-friendly sight such as Animal Adventure Park. Susquehanna River and Jimay's Flea Market are a couple of places you'll find in the larger area.

What’s a vacation rental in Windsor like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Windsor. Vacation rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for family gatherings.