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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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)
"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.
$305 nightly
The price is $345
Oct 8 - Oct 9
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
$218 nightly
The price is $262
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, (19 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 hotel room with two beds, a desk, and a chair. There is a door leading to another room and a wall-mounted phone.

4. 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
$93 nightly
The price is $105
Oct 8 - Oct 9
Total with taxes and fees
2 Full Beds | Non-Smoking, Mini Fridge
A wooden deck with a door and a utility box.

5. Cozy little house in Johnson City

Cozy little house in Johnson City
Johnson City
8.4 out of 10, Very good, (16 reviews)
"Second time staying here, everything was great!"
United States
Chad A.
$101 nightly
The price is $114
Oct 14 - Oct 15
Total with taxes and fees
Cozy little house in Johnson City
A campfire with four Adirondack chairs arranged around it in a forest setting.

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
9.6 out of 10, Exceptional, (5 reviews)
"Wonderful place to stay. Everything you need was provided in case you forgot to bring it with you. Living room comfortably sits 6 with YouTube tv provided. Property was quite and fire pit in rear added to country living experience. I have already recommended this property to several friends and plan to return in spring."
United States
paul
$180 nightly
The price is $202
Oct 8 - Oct 9
Total with taxes and fees
Peaceful 5-Acre Country Retreat with Cali~King Bed, Fire Pit & Near Oneonta
Property grounds

7. 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.
$355 nightly
The price is $401
Oct 8 - Oct 9
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.

8. 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.
$179 nightly
The price is $193
Oct 8 - Oct 9
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.

9. 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
$153 nightly
The price is $171
Oct 8 - Oct 9
Total with taxes and fees
BRAND NEW! 1-bedroom apartment in the beautiful historic village of Greene, NY
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
$145 nightly
The price is $162
Oct 19 - Oct 20
Total with taxes and fees
Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly
An outdoor bar area with a rustic wooden structure, a grill, and a sign that reads 'BAR-B-Q'.

11. 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.
$181 nightly
The price is $195
Oct 8 - Oct 9
Total with taxes and fees
Jack Cabin - Views, Hot Tub, Fire Pit & Outdoors!
A rustic cabin with a stone facade, a wooden balcony, and a stone entrance.

12. 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.
$337 nightly
The price is $381
Nov 4 - Nov 5
Total with taxes and fees
Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
A cozy living room with a stone fireplace, wooden walls, a television, and a coffee table with decorative items.

13. Quiet Lakefront Retreat nestled in the woods.

Quiet Lakefront Retreat nestled in the woods.
Montrose
10.0 out of 10, Exceptional, (107 reviews)
"It was very clean great area and the hosts were so nice!!"
United States
Grace D.
$175 nightly
The price is $190
Oct 9 - Oct 10
Total with taxes and fees
Quiet Lakefront Retreat nestled in the woods.
A hotel room with a bed, a desk, a chair, a television, a lamp, and a mirror.

14. 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
$88 nightly
The price is $99
Oct 8 - Oct 9
Total with taxes and fees
1 King Bed | Non-Smoking, Mini Fridge
A log cabin with a wooden door, a window, a bench, and a table.

15. Handcrafted Riverfront Cabin on 10 acres

Handcrafted Riverfront Cabin on 10 acres
Starlight
9.8 out of 10, Exceptional, (227 reviews)
"Awesome little cabin. Great river access and just the feeling of being remote and away without being too out of touch with amenities if needed."
United States
Joe M.
$336 nightly
The price is $365
Oct 13 - Oct 14
Total with taxes and fees
Handcrafted Riverfront Cabin on 10 acres
A brick building with a covered entrance and a clear sky.

16. 2 Full Beds | Mobility Access Tub Nsmk Fridge

2 Full Beds | Mobility Access Tub Nsmk Fridge
Binghamton
10.0 out of 10, Exceptional, (1 review)
"Quiet corridors ensured no interruptions from loud doors slamming or neighbors creating noise unlike other places I've recently visited"
United States
Anonymous traveler
$93 nightly
The price is $105
Nov 3 - Nov 4
Total with taxes and fees
2 Full Beds | Mobility Access Tub Nsmk Fridge
A hotel lounge with orange patterned sofas, a flat-screen TV, a fireplace, and a small table with a vase of flowers.

17. 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
$98 nightly
The price is $110
Oct 8 - Oct 9
Total with taxes and fees
2 Queen Beds | Non-Smoking, Mini Fridge
A rustic cabin with a stone wall and a wooden deck.

18. 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.
$349 nightly
The price is $379
Oct 19 - Oct 20
Total with taxes and fees
Hilltop, relax and enjoy the Endless Mountains views
A two-story house with a front deck, a small garden, and a wooden swing set.

19. 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.
$372 nightly
The price is $404
Nov 2 - Nov 3
Total with taxes and fees
Olivia House is a old farm house that has been updated!
A cozy living room with a sofa, a coffee table, and a lamp. There are large windows and a door leading to another room.

20. Hale Eddy

Hale Eddy
2.0 star property
Hancock
$322 nightly
The price is $338
Nov 3 - Nov 4
Total with taxes and fees
Hale Eddy
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

Motel 6 Binghamton, NY

Motel 6 Binghamton, NY

8/10 Good
"Ok"
Anna 2-night trip
Posted 9 hours ago
Motel 6 Binghamton, NY

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.