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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Windsor vacation rentals

A round table with a red umbrella, two white chairs, and a grassy area near a body of water with trees in the background.

1. Waterfront Properties vacation rental

Waterfront Properties vacation rental
Windsor
10.0 out of 10, Exceptional, (76 reviews)
"My family and I had a perfect weekend getaway at this beautiful property. Amy and her husband were extremely nice and helpful. We would definitely stay there again."
United States
KURT N.
The price is CA $203
CA $499 total
includes taxes & fees
Nov 8 - Nov 9
Waterfront Properties vacation rental
A cozy cabin with wooden walls, a sofa, a desk with a computer, a refrigerator, and two windows.

2. Fireside Cabin at Osborne Creek

Fireside Cabin at Osborne Creek
Port Crane
9.8 out of 10, Exceptional, (21 reviews)
"Great location, great host, and great property. "
United States
Matthew A.
The price is CA $158
CA $197 total
includes taxes & fees
Nov 8 - Nov 9
Fireside Cabin at Osborne Creek
A two-story house with a front deck, a small garden, and a wooden swing set.

3. Olivia House is a old farm house that has been updated!

Olivia House is a old farm house that has been updated!
Susquehanna
10.0 out of 10, Exceptional, (54 reviews)
"We have now stayed a few times here. Every time has been nothing short of perfect!!"
United States
Anna E.
The price is CA $324
CA $508 total
includes taxes & fees
Nov 18 - Nov 19
Olivia House is a old farm house that has been updated!
A rustic cabin with a stone wall and a wooden deck.

4. Hilltop, relax and enjoy the Endless Mountains views

Hilltop, relax and enjoy the Endless Mountains views
Hallstead
9.2 out of 10, Wonderful, (15 reviews)
"We needed a place to stay for the 6 of us attending the funeral of our mother and this vintage home was the perfect place for us. It offered tranquil views which was just what we needed. "
United States
Paula M.
The price is CA $331
CA $523 total
includes taxes & fees
Nov 9 - Nov 10
Hilltop, relax and enjoy the Endless Mountains views
A rustic cabin with a stone facade, a wooden balcony, and a stone entrance.

5. Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY

Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
Binghamton
9.8 out of 10, Exceptional, (144 reviews)
"A delightful weekend getaway.Kelly the owner went out of her way to make us comfortableAs soon as you walk in the front door you can smell the cleanliness and the essential oils.We loved the sunken jacuzzi, hot tub, multiple swings and all the twinkle lightsThe free continental breakfast was a bonus "
United States
Dawn N.
The price is CA $223
CA $515 total
includes taxes & fees
Nov 9 - Nov 10
Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
A campfire with chairs around it, a brick fire pit, and a house in the background.

6. Peaceful 5-Acre Country Retreat with Cali~King Bed, Fire Pit & Near Oneonta

Peaceful 5-Acre Country Retreat with Cali~King Bed, Fire Pit & Near Oneonta
Afton
9.4 out of 10, Exceptional, (6 reviews)
"Clean and cozy. Well-stocked and private. Really enjoyed the location and stay. Heat/air was amazing."
United States
Wes
The price is CA $195
CA $284 total
includes taxes & fees
Nov 9 - Nov 10
Peaceful 5-Acre Country Retreat with Cali~King Bed, Fire Pit & Near Oneonta
A wooden cabin interior with a staircase, leather sofa, and a coffee table.

7. Modern Comforts Classic Cabin: Family/Fish Escape!

Modern Comforts Classic Cabin: Family/Fish Escape!
Deposit
10.0 out of 10, Exceptional, (3 reviews)
"I would give this property 100 stars if I could. We were so grateful when we arrived and found this house to be even better than we expected. It is super cute, extremely clean and the perfect amount of space for our family of 5.This home met every need, and more! It was pristine, had the most adorable decorations, and was very comfortable and cozy. It was also well cared for (it was not beat up like many other properties we have stayed in). We had plenty of towels, coffee pods, toilet...
United States
Kristin G.
The price is CA $458
CA $908 total
includes taxes & fees
Nov 10 - Nov 11
Modern Comforts Classic Cabin: Family/Fish Escape!
A hotel lounge with orange patterned sofas, a flat-screen TV, a fireplace, and a small table with a vase of flowers.

8. 2 Full Beds | Non-Smoking, Mini Fridge

2 Full Beds | Non-Smoking, Mini Fridge
Binghamton
8.8 out of 10, Excellent, (3 reviews)
"A calm vibe filled the room with gentle heating that wasn't harsh or chilly, just right. Internet worked steadily during my visit without interruptions or slowdowns."
United States
Anonymous traveller
The price is CA $127
CA $144 total
includes taxes & fees
Dec 8 - Dec 9
2 Full Beds | Non-Smoking, Mini Fridge
A cozy living room with a sofa, a coffee table, and a lamp. There are large windows and a door leading to another room.

9. Hale Eddy

Hale Eddy
2.0 star property
Hancock
The price is CA $217
CA $463 total
includes taxes & fees
Nov 8 - Nov 9
Hale Eddy
A cozy living room with a wooden floor, a sofa, a coffee table, and a TV mounted on the wall.

10. Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly

Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly
Greene
10.0 out of 10, Exceptional, (21 reviews)
"Well appointed with all you could need. Great communication with the host."
United States
Brian
The price is CA $175
CA $215 total
includes taxes & fees
Nov 8 - Nov 9
Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly
Exterior

11. Horse Motel • RV Camping • Tent Camping • Horse Experiences PET FRIENDLY!

Horse Motel • RV Camping • Tent Camping • Horse Experiences PET FRIENDLY!
Port Crane
10.0 out of 10, Exceptional, (2 reviews)
"We pitched our tent in a beautiful, grassy field on the height of land with a breathtaking view of the valley below. No road noise or light pollution. The sunset and night stars were stunning. Our dog loved the field. Terrific value. Highly recommended."
United States
Wendy W.
The price is CA $71
CA $99 total
includes taxes & fees
Nov 30 - Dec 1
Horse Motel • RV Camping • Tent Camping • Horse Experiences PET FRIENDLY!
A spacious cabin interior with a fireplace, wooden floors, and large windows overlooking a lake.

12. Lakefront Home, Fast WiFi + Workspace, ideal for weeklong family friendly stays

Lakefront Home, Fast WiFi + Workspace, ideal for weeklong family friendly stays
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful setting"
United States
Gerald L.
The price is CA $561
CA $828 total
includes taxes & fees
Nov 9 - Nov 10
Lakefront Home, Fast WiFi + Workspace, ideal for weeklong family friendly stays
A room with a bed, a nightstand, a window, and a ceiling fan.

13. Susquehanna Waterfall Haven

Susquehanna Waterfall Haven
Susquehanna
The price is CA $284
CA $501 total
includes taxes & fees
Nov 9 - Nov 10
Susquehanna Waterfall Haven
A wooden deck with a door and a utility box.

14. Cozy little house in Johnson City

Cozy little house in Johnson City
Johnson City
8.0 out of 10, Very good, (17 reviews)
"Second time staying here, everything was great!"
United States
Chad A.
The price is CA $114
CA $147 total
includes taxes & fees
Nov 9 - Nov 10
Cozy little house in Johnson City
A log cabin with a wooden deck, a cozy bedroom with a bed and a sofa, and a dining area with a table and chairs.

15. Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!

Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!
Thompson
10.0 out of 10, Exceptional, (18 reviews)
"This is the perfect place for you to come and relax. "
United States
Anabel P.
The price is CA $227
CA $347 total
includes taxes & fees
Nov 9 - Nov 10
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!
A compact living space with a sofa, a dining table, a kitchen area, and a bed with a sliding door.

16. BRAND NEW! 1-bedroom apartment in the beautiful historic village of Greene, NY

BRAND NEW! 1-bedroom apartment in the beautiful historic village of Greene, NY
Greene
10.0 out of 10, Exceptional, (15 reviews)
"Property was beautiful would t change anything. Will definitely book again when we are in town."
United States
Lori
The price is CA $113
CA $201 total
includes taxes & fees
Nov 10 - Nov 11
BRAND NEW! 1-bedroom apartment in the beautiful historic village of Greene, NY
A dining area with a wooden table and chairs, a kitchen with cabinets, a sofa with cushions, and a plant.

17. Peaceful 3-bedroom house close to Binghamton University/ UHS hospital.

Peaceful 3-bedroom house close to Binghamton University/ UHS hospital.
Johnson City
The price is CA $315
CA $852 total
includes taxes & fees
Nov 9 - Nov 10
Peaceful 3-bedroom house close to Binghamton University/ UHS hospital.
A cozy living room with a stone fireplace, wooden walls, a television, and a coffee table with decorative items.

18. Quiet Lakefront Retreat nestled in the woods.

Quiet Lakefront Retreat nestled in the woods.
Montrose
10.0 out of 10, Exceptional, (110 reviews)
"It was very clean great area and the hosts were so nice!!"
United States
Grace D.
The price is CA $182
CA $256 total
includes taxes & fees
Nov 9 - Nov 10
Quiet Lakefront Retreat nestled in the woods.
An open patio with a wooden pergola, two chairs, a small table with a bottle and glasses, and a view of a grassy yard with trees and a house in the distance.

19. Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!

Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
Thompson
10.0 out of 10, Exceptional, (17 reviews)
"We loved our stay here! Great place, beautiful views, wished we could’ve stayed longer. Thank you!!"
United States
T.J. E.
The price is CA $363
CA $541 total
includes taxes & fees
Nov 9 - Nov 10
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
A lakeside cabin with a wooden deck and a stone pathway leading to the entrance.

20. Cozy 2-bedroom cabin in Vestal NY

Cozy 2-bedroom cabin in Vestal NY
Vestal
9.6 out of 10, Exceptional, (21 reviews)
"Location was great, definitely amazing way to disconnect for a couple days with the family. Only had 1 problem which was the stove top not working but besides that everything else was great."
United States
Omar
The price is CA $189
CA $315 total
includes taxes & fees
Nov 8 - Nov 9
Cozy 2-bedroom cabin in Vestal NY
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

Spark by Hilton Vestal Binghamton University Area

Spark by Hilton Vestal Binghamton University Area

10/10 Excellent
"The staff was very nice- letting me know that there were college kids there and if they were disruptive to let him know and he would take care of it. Also the room was huge, very clean and surprisingly quiet. I would definitely book another stay there"
Debra 1-night trip
Posted 6 hours ago
Spark by Hilton Vestal Binghamton University Area

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor vacation rentals we have selected for you start as low as CA $147 per night. Entering your travel dates in the search wizard 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 Ross Park Zoo. 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.