Windsor Vacation Rentals

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Vacation Rentals in Windsor

Handcrafted Riverfront Cabin on 10 acres
Exterior

Handcrafted Riverfront Cabin on 10 acres

10.0 out of 10, Exceptional, (172)
"Beautiful property located on an excellent stretch of river. Love the cabin. Great fishing lodge. "
$278 nightly
The price is $302
Oct 29 - Oct 30
Total with taxes and fees
Handcrafted Riverfront Cabin on 10 acres
Cozy 2-bedroom cabin in Vestal NY
Property grounds

Cozy 2-bedroom cabin in Vestal NY

9.6 out of 10, Exceptional, (12)
" Beautiful landcape, quiet and secluded."
$233 nightly
The price is $263
Sep 30 - Oct 1
Total with taxes and fees
Cozy 2-bedroom cabin in Vestal NY
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River
Fridge, microwave, oven, stovetop

Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River

10.0 out of 10, Exceptional, (187)
"Very nice!"
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River
Spectacular Catskill Mountain River Front Custom Log Home
TV, DVD player

Spectacular Catskill Mountain River Front Custom Log Home

10.0 out of 10, Exceptional, (71)
"Great Location"
Spectacular Catskill Mountain River Front Custom Log Home
Equestrian House Suites
Cabin (Cabin 4 bedroom) | Private kitchen

Equestrian House Suites

3.0 star property
$271 nightly
The price is $296
Sep 29 - Sep 30
Total with taxes and fees
Equestrian House Suites
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.
Exterior

Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.

9.6 out of 10, Exceptional, (118)
"Our second time coming back and it was fantastic. Fishing off the John boat was a highlight for the family."
$363 nightly
The price is $395
Oct 4 - Oct 5
Total with taxes and fees
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.
Quiet Lakefront Retreat nestled in the woods.
Property grounds

Quiet Lakefront Retreat nestled in the woods.

10.0 out of 10, Exceptional, (86)
"This cabin was just as advertised. The cabin was very clean, and all you would need for a comfortable stay was included. I very much enjoyed my two days there."
$160 nightly
The price is $174
Sep 30 - Oct 1
Total with taxes and fees
Quiet Lakefront Retreat nestled in the woods.
Riverfront Cabin West Branch Delaware River
Exterior

Riverfront Cabin West Branch Delaware River

9.8 out of 10, Exceptional, (115)
"Great lil place, great host, will stay again when visiting family who live in town. "
Riverfront Cabin West Branch Delaware River
Rivers Edge of the West Branch Delaware River w Private Boat Launch
Interior

Rivers Edge of the West Branch Delaware River w Private Boat Launch

9.6 out of 10, Exceptional, (110)
"We stayed in the cabin for a weekend and used the boat launch to do an all day fishing trip. The cabin was great and the float was as well. Lovely place in a beautiful spot on the river!"
Rivers Edge of the West Branch Delaware River w Private Boat Launch
Breathtaking 44+ Acre Country Estate
Fridge, microwave, oven, stovetop

Breathtaking 44+ Acre Country Estate

10.0 out of 10, Exceptional, (36)
"We had a great family vacation here, coming in from various parts of the country. The fire pit, fishing, pickle ball, pool, hot tub, bald eagles, shooting stars and scenic views were just a few of the highlights! Gorgeous property and very responsive answers to questions etc "
Breathtaking 44+ Acre Country Estate
Cozy/Chic Cabin (ISOLATED RETREAT!) Binghamton NY
Exterior

Cozy/Chic Cabin (ISOLATED RETREAT!) Binghamton NY

9.8 out of 10, Exceptional, (129)
"We love the cabin. Just as described. Host Kelly was very helpful and communicative. "
$292 nightly
The price is $330
Sep 29 - Sep 30
Total with taxes and fees
Cozy/Chic Cabin (ISOLATED RETREAT!) Binghamton NY
Elk Mountain Vacation Home on 21 Acres
Fridge, microwave, oven, stovetop

Elk Mountain Vacation Home on 21 Acres

9.8 out of 10, Exceptional, (44)
"It’s our 4th year at Union Dales at this property. Simply amazing, rustic clean house, nature, privacy, beautiful trails, peace and quiet. "
Elk Mountain Vacation Home on 21 Acres
Steps from En-Joie Golf - 3BR Bungalow, Pet-Friendly w/ AC & WiFi
Exterior

Steps from En-Joie Golf - 3BR Bungalow, Pet-Friendly w/ AC & WiFi

9.8 out of 10, Exceptional, (10)
"We had a nice stay. The house was as described. "
Steps from En-Joie Golf - 3BR Bungalow, Pet-Friendly w/ AC & WiFi
Cozy Cabin built 2024 in Deposit,NY Short walk to best Fly Fishing in Northeast
Interior

Cozy Cabin built 2024 in Deposit,NY Short walk to best Fly Fishing in Northeast

10.0 out of 10, Exceptional, (8)
"Charming cabin, newly built with outstanding attention to detail. Rachel was a wonderful host and very accommodating. We thoroughly enjoyed our stay and plan to return in the future."
Cozy Cabin built 2024 in Deposit,NY Short walk to best Fly Fishing in Northeast
12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos
Exterior

12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos

9.8 out of 10, Exceptional, (29)
"We really enjoyed our stay. The place is even better than the pictures and the host Julia was excellent."
12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos
Cabin on the Lake • Deck, Dock & Woods
Exterior

Cabin on the Lake • Deck, Dock & Woods

9.4 out of 10, Exceptional, (3)
"Nice place tucked away in the woods. Great place to read and watch nature."
Cabin on the Lake • Deck, Dock & Woods
Indoor Pool,Largest Game Lodge,Sleeps 39
Terrace/patio

Indoor Pool,Largest Game Lodge,Sleeps 39

10.0 out of 10, Exceptional, (56)
"Love the place! Plenty of space both inside and out. Beautiful log cabins. Would highly recommend! "
Indoor Pool,Largest Game Lodge,Sleeps 39
Binghamton's Beautiful Riverside Drive Living!
Microwave, oven, stovetop, dishwasher

Binghamton's Beautiful Riverside Drive Living!

10.0 out of 10, Exceptional, (13)
"We had a family group of 7 ranging in age from 13 to 80 in town for a high school graduation. The house was perfect for us snd the hosts provided many extras to make it feel like a home away from home.visiting"
Binghamton's Beautiful Riverside Drive Living!
Cabin on 4 acres near Elk Mountain/Dogs OK/Easy Drive from Philly and NYC
Exterior

Cabin on 4 acres near Elk Mountain/Dogs OK/Easy Drive from Philly and NYC

9.6 out of 10, Exceptional, (142)
"Absolutely wonderful place to stay. Our dogs loved it"
Cabin on 4 acres near Elk Mountain/Dogs OK/Easy Drive from Philly and NYC
DISCOUNT LAST MINUTE Elk Mountain Estate Manor in beautiful PA-Groups and Events
Fridge, microwave, oven, stovetop

DISCOUNT LAST MINUTE Elk Mountain Estate Manor in beautiful PA-Groups and Events

9.8 out of 10, Exceptional, (95)
"We booked at the last minute due to another rental falling through. The booking process was smooth and Laura was a gracious and amazing host. The property is beautiful and spacious! We can’t wait to visit again "
DISCOUNT LAST MINUTE Elk Mountain Estate Manor in beautiful PA-Groups and Events
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
"Clean room and great staff"
Robert 2-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Vestal by IHG

Find out more about Windsor

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 $174 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Breathtaking 44+ Acre Country Estate: Visitors like this Windsor vacation home rental. It is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a hot tub so you can immerse yourself in your vacation.

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 West Branch Delaware River 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.