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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, (74 reviews)
"We enjoyed our stay. The accommodations were great!"
United States
Terri R.
$270 nightly
The price is $305
Oct 5 - Oct 6
Total with taxes and fees
Waterfront Properties vacation rental
An outdoor seating area with a fire pit, chairs, and a table.

2. Rustic 3-bedroom cottage in Windsor.

Rustic 3-bedroom cottage in Windsor.
Windsor
$225 nightly
The price is $270
Oct 19 - Oct 20
Total with taxes and fees
Rustic 3-bedroom cottage in Windsor.
A cozy cabin with wooden walls, a sofa, a desk with a computer, a refrigerator, and two windows.

3. Fireside Cabin at Osborne Creek

Fireside Cabin at Osborne Creek
Port Crane
10.0 out of 10, Exceptional, (18 reviews)
"Great location, great host, and great property. "
United States
Matthew A.
$145 nightly
The price is $164
Oct 13 - Oct 14
Total with taxes and fees
Fireside Cabin at Osborne Creek
A kitchen with white cabinetry, a washing machine, a microwave, and shelves with kitchenware.

4. 1st floor Farmhouse Apartment at Osborne Creek!

1st floor Farmhouse Apartment at Osborne Creek!
Port Crane
10.0 out of 10, Exceptional, (18 reviews)
"Great place to stay, host was super friendly. Definitely will stay again!!"
United States
Sharon M.
1st floor Farmhouse Apartment at Osborne Creek!
Property grounds

5. Ska'no'ne-Peaceful escape; Sunrise coffee on the covered porch, sun set Fire pit

Ska'no'ne-Peaceful escape; Sunrise coffee on the covered porch, sun set Fire pit
Nineveh
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful location, clean, host was very helpful answering questions about the property / surrounding area."
United States
Kiel P.
$255 nightly
The price is $288
Sep 30 - Oct 1
Total with taxes and fees
Ska'no'ne-Peaceful escape; Sunrise coffee on the covered porch, sun set Fire pit
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.

6. 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.
$178 nightly
The price is $192
Sep 30 - Oct 1
Total with taxes and fees
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.

7. 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
$145 nightly
The price is $162
Sep 30 - Oct 1
Total with taxes and fees
BRAND NEW! 1-bedroom apartment in the beautiful historic village of Greene, NY
A hotel room with two beds, a desk, and a chair. There is a door leading to another room and a wall-mounted phone.

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

2 Full Beds | Non-Smoking, Mini Fridge
Binghamton
$94 nightly
The price is $106
Oct 5 - Oct 6
Total with taxes and fees
2 Full Beds | Non-Smoking, Mini Fridge
An outdoor bar area with a rustic wooden structure, a grill, and a sign that reads 'BAR-B-Q'.

9. Jack Cabin - Views, Hot Tub, Fire Pit & Outdoors!

Jack Cabin - Views, Hot Tub, Fire Pit & Outdoors!
Thompson
9.4 out of 10, Exceptional, (13 reviews)
"Diamond in the rough!!! Excellent "
United States
Tasha M.
$178 nightly
The price is $192
Sep 30 - Oct 1
Total with taxes and fees
Jack Cabin - Views, Hot Tub, Fire Pit & Outdoors!
A wooden deck with a door and a utility box.

10. Cozy little house in Johnson City

Cozy little house in Johnson City
Johnson City
8.4 out of 10, Very good, (16 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
$101 nightly
The price is $114
Sep 30 - Oct 1
Total with taxes and fees
Cozy little house in Johnson City
A rustic cabin with a stone facade, a wooden balcony, and a stone entrance.

11. Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY

Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
Binghamton
9.8 out of 10, Exceptional, (138 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.
$312 nightly
The price is $353
Sep 30 - Oct 1
Total with taxes and fees
Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
A cozy living room with a wooden floor, a sofa, a coffee table, and a TV mounted on the wall.

12. 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
$145 nightly
The price is $162
Sep 30 - Oct 1
Total with taxes and fees
Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly
A two-story house with a front deck, a small garden, and a wooden swing set.

13. 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.
$329 nightly
The price is $358
Oct 12 - Oct 13
Total with taxes and fees
Olivia House is a old farm house that has been updated!
A log cabin with a wooden door, a window, a bench, and a table.

14. Handcrafted Riverfront Cabin on 10 acres

Handcrafted Riverfront Cabin on 10 acres
Starlight
9.8 out of 10, Exceptional, (227 reviews)
"Great little cabin in a great location. "
United States
Michael M.
$315 nightly
The price is $343
Sep 30 - Oct 1
Total with taxes and fees
Handcrafted Riverfront Cabin on 10 acres
A room with wooden ceiling beams, a skylight, a framed picture, and a window with a snowy forest view.

15. Charming 120-year-old farmhouse by the creek

Charming 120-year-old farmhouse by the creek
Hancock
9.0 out of 10, Wonderful, (28 reviews)
"This is really a beautiful place to stay, we definitely will return in summer. "
United States
Paul C.
$273 nightly
The price is $301
Sep 30 - Oct 1
Total with taxes and fees
Charming 120-year-old farmhouse by the creek
A natural landscape with a pond, a wooden bridge, and a forested area.

16. Susquehanna Waterfall Haven

Susquehanna Waterfall Haven
Susquehanna
$323 nightly
The price is $351
Sep 30 - Oct 1
Total with taxes and fees
Susquehanna Waterfall Haven
A kitchen with wooden cabinets, a stainless steel stove, a dishwasher, a sink, and a window with a view of trees.

17. 2-bed historic Lustron home newly remodeled, modern interior. Nearby shopping!

2-bed historic Lustron home newly remodeled, modern interior. Nearby shopping!
Vestal
10.0 out of 10, Exceptional, (2 reviews)
"The check-in went smoothly and we were able to reach the host easily and quickly. The house was perfect for us and had everything that we needed. We highly recommend this location."
United States
Micheline L.
$265 nightly
The price is $299
Sep 30 - Oct 1
Total with taxes and fees
2-bed historic Lustron home newly remodeled, modern interior. Nearby shopping!
A wooden cabin interior with a staircase, leather sofa, and a coffee table.

18. 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.
$579 nightly
The price is $637
Sep 30 - Oct 1
Total with taxes and fees
Modern Comforts Classic Cabin: Family/Fish Escape!
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.
$305 nightly
The price is $329
Sep 30 - Oct 1
Total with taxes and fees
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
A rustic cabin with a stone wall and a wooden deck.

20. 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.
$327 nightly
The price is $356
Oct 19 - Oct 20
Total with taxes and fees
Hilltop, relax and enjoy the Endless Mountains views
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 Binghamton Downtown by IHG

Holiday Inn Binghamton Downtown by IHG

8/10 Good
"Ok"
jose R 1-night trip
Posted 7 hours ago
Holiday Inn Binghamton Downtown by IHG

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 $114 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 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.