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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Windsor holiday 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)
"The owners were very attentive and willing to answer any question we had with very quick responses. The owners gave many recommendations for food in the area when asked. The place fit our needs perfectly. Will rent this place again if in the area again."
United States
Tyler J.
The price is NZ$526
includes taxes & fees
1 Sept - 2 Sept
Waterfront Properties vacation rental

2. 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.
The price is NZ$683
includes taxes & fees
21 Sept - 22 Sept
Ska'no'ne-Peaceful escape; Sunrise coffee on the covered porch, sun set Fire pit
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, (14 reviews)
"Great location, great host, and great property. "
United States
Matthew A.
The price is NZ$226
includes taxes & fees
30 Aug - 31 Aug
Fireside Cabin at Osborne Creek
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 NZ$985
includes taxes & fees
31 Aug - 1 Sept
Modern Comforts Classic Cabin: Family/fish Escape!
A wooden cabin interior with a staircase, leather sofa, and a coffee table.

5. 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 NZ$998
includes taxes & fees
23 Sept - 24 Sept
Modern Comforts Classic Cabin: Family/Fish Escape!
A rustic cabin with a stone facade, a wooden balcony, and a stone entrance.

6. Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY

Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
Binghamton
9.8 out of 10, Exceptional, (137 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 NZ$662
includes taxes & fees
1 Sept - 2 Sept
Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
A rustic cabin with a stone wall and a wooden deck.

7. Hilltop, relax and enjoy the Endless Mountains views

Hilltop, relax and enjoy the Endless Mountains views
Hallstead
9.0 out of 10, Wonderful, (12 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 NZ$622
includes taxes & fees
30 Aug - 31 Aug
Hilltop, relax and enjoy the Endless Mountains views
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, (17 reviews)
"This is the perfect place for you to come and relax. "
United States
Anabel P.
The price is NZ$322
includes taxes & fees
30 Aug - 31 Aug
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!

9. Peaceful 5-Acre Escape Near Animal Adventure Park with Cali~King Bed & Fire Pit

Peaceful 5-Acre Escape Near Animal Adventure Park with Cali~King Bed & Fire Pit
Afton
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful!! Very comfortable, we felt very much at home.."
United States
Alfred M.
The price is NZ$268
includes taxes & fees
2 Sept - 3 Sept
Peaceful 5-Acre Escape Near Animal Adventure Park with Cali~King Bed & Fire Pit
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.

10. 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 NZ$573
includes taxes & fees
30 Aug - 31 Aug
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
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, (14 reviews)
"Property was beautiful would t change anything. Will definitely book again when we are in town."
United States
Lori
The price is NZ$281
includes taxes & fees
23 Sept - 24 Sept
BRAND NEW! 1-bedroom apartment in the beautiful historic village of Greene, NY
A log cabin with a wooden porch, a bench, and a door with a window.

12. Handcrafted Riverfront Cabin on 10 acres

Handcrafted Riverfront Cabin on 10 acres
Starlight
9.8 out of 10, Exceptional, (221 reviews)
"Great little cabin in a great location. "
United States
Michael M.
The price is NZ$540
includes taxes & fees
6 Sept - 7 Sept
Handcrafted Riverfront Cabin on 10 acres
A cozy living room with a wooden floor, a sofa, a coffee table, and a TV mounted on the wall.

13. 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 NZ$226
includes taxes & fees
30 Aug - 31 Aug
Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly

14. 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)
"Cool place to chilaxx"
United States
Luis R.
The price is NZ$322
includes taxes & fees
31 Aug - 1 Sept
Jack Cabin - Views, Hot Tub, Fire Pit & Outdoors!
A natural landscape with a pond, a wooden bridge, and a forested area.

15. Susquehanna Waterfall Haven

Susquehanna Waterfall Haven
Susquehanna
The price is NZ$618
includes taxes & fees
4 Sept - 5 Sept
Susquehanna Waterfall Haven
A cozy living room with a sofa, a coffee table, and a lamp. There are large windows and a door leading to another room.

16. Hale Eddy

Hale Eddy
2.0 star property
Hancock
The price is NZ$574
includes taxes & fees
1 Sept - 2 Sept
Hale Eddy
A room with wooden ceiling beams, a skylight, a framed picture, and a window with a snowy forest view.

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

Charming 120-year-old farmhouse by the creek
Hancock
9.0 out of 10, Wonderful, (27 reviews)
"This is really a beautiful place to stay, we definitely will return in summer. "
United States
Paul C.
The price is NZ$555
includes taxes & fees
4 Sept - 5 Sept
Charming 120-year-old farmhouse by the creek
A wooden deck with a door and a utility box.

18. Cozy little house in Johnson City

Cozy little house in Johnson City
Johnson City
8.4 out of 10, Very good, (15 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 NZ$192
includes taxes & fees
31 Aug - 1 Sept
Cozy little house in Johnson City
A cozy living room with a stone fireplace, wooden walls, a television, and a coffee table with decorative items.

19. Quiet Lakefront Retreat nestled in the woods.

Quiet Lakefront Retreat nestled in the woods.
Montrose
10.0 out of 10, Exceptional, (106 reviews)
"Such a sweet space in a beautiful setting. Definitely will be back! "
United States
Rachel F.
The price is NZ$319
includes taxes & fees
3 Sept - 4 Sept
Quiet Lakefront Retreat nestled in the woods.
A dining area with a wooden table and chairs, a kitchen with cabinets, a sofa with cushions, and a plant.

20. 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 NZ$1,027
includes taxes & fees
20 Sept - 21 Sept
Peaceful 3-bedroom house close to Binghamton University/ UHS hospital.
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

Comfort Inn Binghamton I-81

Comfort Inn Binghamton I-81

8/10 Good
"The 3rd shift front desk lady. CC I think her name was Janine was amazing. Her customer service is above any I have experienced at a hotel. Now thee wed hotel was great except they allow the construction workers to park in the handi cap spots and rent the accessible rooms while not disabled"
Michelle 3-night trip
Posted 11 hours ago
Comfort Inn Binghamton I-81

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as NZ$192 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 holiday 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 holiday.

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 holiday rental in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select 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 cafés and bars during your trip.

What are some of the best holiday rentals that Windsor has to offer?

Waterfront Properties vacation rental: This highly rated holiday home rental in Windsor is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most 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 one of the family-friendly sights such as Ross Park Zoo. Susquehanna River and Oquaga Lake are a couple of places you'll find in the wider area.

What’s a holiday rental in Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windsor. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.