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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

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.
The price is ￥19,201
￥48,949 total
includes taxes & fees
Sep 27 - Sep 28
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 ￥22,273
￥62,662 total
includes taxes & fees
Sep 17 - Sep 18
Ska'no'ne-Peaceful escape; Sunrise coffee on the covered porch, sun set Fire pit
A wooden cabin with a porch, a swing, and a view of the surrounding forest.

3. 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 ￥49,002
￥90,074 total
includes taxes & fees
Sep 21 - Sep 22
Modern Comforts Classic Cabin: Family/fish Escape!
A two-story house with a front deck, a small garden, and a wooden swing set.

4. 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 ￥36,961
￥59,454 total
includes taxes & fees
Sep 23 - Sep 24
Olivia House is a old farm house that has been updated!
A cozy cabin with wooden walls, a sofa, a desk with a computer, a refrigerator, and two windows.

5. Fireside Cabin at Osborne Creek

Fireside Cabin at Osborne Creek
Port Crane
10.0 out of 10, Exceptional, (15 reviews)
"Great location, great host, and great property. "
United States
Matthew A.
The price is ￥19,201
￥23,780 total
includes taxes & fees
Oct 12 - Oct 13
Fireside Cabin at Osborne Creek
A kitchen with white cabinetry, a washing machine, a microwave, and shelves with kitchenware.

6. 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.
The price is ￥19,201
￥29,682 total
includes taxes & fees
Sep 14 - Sep 15
1st floor Farmhouse Apartment at Osborne Creek!
A rustic cabin with a stone facade, a wooden balcony, and a stone entrance.

7. 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 ￥23,483
￥57,938 total
includes taxes & fees
Sep 13 - Sep 14
Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
A rustic cabin with a stone wall and a wooden deck.

8. Hilltop, relax and enjoy the Endless Mountains views

Hilltop, relax and enjoy the Endless Mountains views
Hallstead
9.2 out of 10, Wonderful, (13 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 ￥34,738
￥58,201 total
includes taxes & fees
Sep 13 - Sep 14
Hilltop, relax and enjoy the Endless Mountains views
A wooden cabin interior with a staircase, leather sofa, and a coffee table.

9. 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 ￥40,296
￥91,538 total
includes taxes & fees
Sep 15 - Sep 16
Modern Comforts Classic Cabin: Family/Fish Escape!
A cozy living room with a stone fireplace, wooden walls, a television, and a coffee table with decorative items.

10. Quiet Lakefront Retreat nestled in the woods.

Quiet Lakefront Retreat nestled in the woods.
Montrose
10.0 out of 10, Exceptional, (106 reviews)
"It was very clean great area and the hosts were so nice!!"
United States
Grace D.
The price is ￥19,969
￥29,209 total
includes taxes & fees
Sep 16 - Sep 17
Quiet Lakefront Retreat nestled in the woods.
A room with wooden ceiling beams, a skylight, a framed picture, and a window with a snowy forest view.

11. 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 ￥20,046
￥47,734 total
includes taxes & fees
Sep 13 - Sep 14
Charming 120-year-old farmhouse by the creek
A natural landscape with a pond, a wooden bridge, and a forested area.

12. Susquehanna Waterfall Haven

Susquehanna Waterfall Haven
Susquehanna
The price is ￥31,106
￥57,000 total
includes taxes & fees
Sep 13 - Sep 14
Susquehanna Waterfall Haven
A log cabin with a wooden porch, a bench, and a door with a window.

13. Handcrafted Riverfront Cabin on 10 acres

Handcrafted Riverfront Cabin on 10 acres
Starlight
9.8 out of 10, Exceptional, (223 reviews)
"Great little cabin in a great location. "
United States
Michael M.
The price is ￥19,592
￥52,817 total
includes taxes & fees
Sep 23 - Sep 24
Handcrafted Riverfront Cabin on 10 acres
A compact living space with a sofa, a dining table, a kitchen area, and a bed with a sliding door.

14. 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 ￥12,367
￥23,360 total
includes taxes & fees
Sep 14 - Sep 15
BRAND NEW! 1-bedroom apartment in the beautiful historic village of Greene, NY
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.

15. 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 ￥30,722
￥53,352 total
includes taxes & fees
Sep 13 - Sep 14
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
A cozy living room with a wooden floor, a sofa, a coffee table, and a TV mounted on the wall.

16. 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 ￥19,201
￥24,946 total
includes taxes & fees
Sep 13 - Sep 14
Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly
A campfire with four Adirondack chairs arranged around it in a forest setting.

17. 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
9.6 out of 10, Exceptional, (4 reviews)
"Loved being in the woods! It was so quiet! We needed the peaceful stay!"
United States
Joy S.
The price is ￥16,467
￥24,465 total
includes taxes & fees
Sep 14 - Sep 15
Peaceful 5-Acre Escape Near Animal Adventure Park with Cali~King Bed & 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.

18. 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 ￥15,207
￥29,602 total
includes taxes & fees
Sep 23 - Sep 24
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!
A brick building with a covered entrance and a clear sky.

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

1 King Bed | Non-Smoking, Mini Fridge
Binghamton
The price is ￥13,962
￥15,778 total
includes taxes & fees
Oct 1 - Oct 2
1 King Bed | Non-Smoking, Mini Fridge

20. 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 ￥95,238
￥135,859 total
includes taxes & fees
Sep 16 - Sep 17
Lakefront Home, Fast WiFi + Workspace, ideal for weeklong family friendly stays
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

Colonial Brick Inn & Suites

Colonial Brick Inn & Suites

10/10 Excellent
"Awesome"
Vishalkumar 1-night trip
Posted 10 hours ago
Colonial Brick Inn & Suites

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
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • 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 Oquaga Lake 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.