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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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)
"This home was clean, affordable, and exactly as listed. Owners were very accommodating. Beautiful view of the river. Would book again."
United States
Michael B.
The price is ￥22,836
￥58,194 total
includes taxes & fees
Oct 31 - Nov 1
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 ￥19,686
￥25,804 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥34,268
￥56,631 total
includes taxes & fees
Nov 3 - Nov 4
Olivia House is a old farm house that has been updated!
A wooden cabin with a porch, a swing, and a view of the surrounding forest.

4. Modern Comforts Classic Cabin: Family/fish Escape!

Modern Comforts Classic Cabin: Family/fish Escape!
3.0 star property
Deposit
10.0 out of 10, Exceptional, (1 review)
"House was great, hosts were very helpful"
United States
Ronald
The price is ￥61,894
￥105,169 total
includes taxes & fees
Nov 3 - Nov 4
Modern Comforts Classic Cabin: Family/fish Escape!
A rustic cabin with a stone wall and a wooden deck.

5. Hilltop, relax and enjoy the Endless Mountains views

Hilltop, relax and enjoy the Endless Mountains views
Hallstead
9.2 out of 10, Wonderful, (14 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 ￥37,168
￥61,758 total
includes taxes & fees
Nov 5 - Nov 6
Hilltop, relax and enjoy the Endless Mountains views
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 ￥21,992
￥33,833 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥51,499
￥106,369 total
includes taxes & fees
Nov 2 - Nov 3
Modern Comforts Classic Cabin: Family/Fish Escape!
A rustic cabin with a stone facade, a wooden balcony, and a stone entrance.

8. Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY

Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
Binghamton
9.8 out of 10, Exceptional, (142 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 ￥24,030
￥58,932 total
includes taxes & fees
Oct 29 - Oct 30
Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
A hotel lounge with orange patterned sofas, a flat-screen TV, a fireplace, and a small table with a vase of flowers.

9. 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 traveler
The price is ￥14,542
￥16,432 total
includes taxes & fees
Oct 29 - Oct 30
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.

10. Hale Eddy

Hale Eddy
2.0 star property
Hancock
The price is ￥24,411
￥52,050 total
includes taxes & fees
Nov 2 - Nov 3
Hale Eddy
A compact living space with a sofa, a dining table, a kitchen area, and a bed with a sliding door.

11. 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 ￥13,224
￥24,544 total
includes taxes & fees
Oct 29 - Oct 30
BRAND NEW! 1-bedroom apartment in the beautiful historic village of Greene, NY
A wooden deck with a door and a utility box.

12. Cozy little house in Johnson City

Cozy little house in Johnson City
Johnson City
8.0 out of 10, Very good, (17 reviews)
"Place was convenient for dropping my daughter off at SUNY Binghamton. Was updated, very well laid out with all amenities, clean, organized, thoughtful. Had kitchen, living room, bedroom, bathroom all of a nice size for two people. Liked the auto soap dispenser. Easy parking. A bit woodsy if you are not into critters but otherwise quite fantastic for price and location."
United States
Lindsay
The price is ￥12,757
￥17,975 total
includes taxes & fees
Nov 1 - Nov 2
Cozy little house in Johnson City
Living area

13. 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 ￥62,996
￥97,685 total
includes taxes & fees
Nov 9 - Nov 10
Lakefront Home, Fast WiFi + Workspace, ideal for weeklong family friendly stays
A cozy living room with a wooden floor, a sofa, a coffee table, and a TV mounted on the wall.

14. 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 ￥19,749
￥25,658 total
includes taxes & fees
Nov 1 - Nov 2
Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly
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 ￥23,624
￥40,107 total
includes taxes & fees
Oct 29 - Oct 30
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!
A dining area with a wooden table and chairs, a kitchen with cabinets, a sofa with cushions, and a plant.

16. 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 ￥35,435
￥100,015 total
includes taxes & fees
Nov 2 - Nov 3
Peaceful 3-bedroom house close to Binghamton University/ UHS hospital.
A room with a bed, a nightstand, a window, and a ceiling fan.

17. Susquehanna Waterfall Haven

Susquehanna Waterfall Haven
Susquehanna
The price is ￥31,892
￥58,440 total
includes taxes & fees
Nov 4 - Nov 5
Susquehanna Waterfall Haven
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.

18. 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 ￥37,798
￥62,401 total
includes taxes & fees
Nov 9 - Nov 10
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
A hotel lounge with orange patterned sofas, a flat-screen TV, a fireplace, and a small table with a vase of flowers.

19. 1 King Bed | Non-Smoking, Mini Fridge

1 King Bed | Non-Smoking, Mini Fridge
Binghamton
10.0 out of 10, Exceptional, (3 reviews)
"We appreciated starting each day with coffee ready along with the large bed made for two people. Small things like free WiFi really boosted our experience."
United States
Anonymous traveler
The price is ￥13,776
￥15,567 total
includes taxes & fees
Oct 29 - Oct 30
1 King Bed | Non-Smoking, Mini Fridge
A hotel lounge with orange patterned sofas, a flat-screen TV, a fireplace, and a small table with a vase of flowers.

20. 2 Queen Beds | Non-Smoking, Mini Fridge

2 Queen Beds | Non-Smoking, Mini Fridge
Binghamton
10.0 out of 10, Exceptional, (2 reviews)
"Needed just a clean place near the highway, this fit fine for one night."
United States
Anonymous traveler
The price is ￥15,307
￥17,297 total
includes taxes & fees
Oct 29 - Oct 30
2 Queen Beds | Non-Smoking, Mini Fridge
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

8/10 Good
"It was a good budget place."
Tabinda 1-night trip
Posted 9 hours ago
Spark by Hilton Vestal Binghamton University Area

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 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.