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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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, (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 HK$1,137
HK$2,924 total
includes taxes & fees
28 Oct - 29 Oct
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
Rustic 3-bedroom cottage in Windsor.
Two horses grazing in a grassy field with a fence in the background.

3. Fireside Cabin at Osborne Creek

Fireside Cabin at Osborne Creek
Port Crane
10.0 out of 10, Exceptional, (20 reviews)
"Great location, great host, and great property. "
United States
Matthew A.
The price is HK$980
HK$1,285 total
includes taxes & fees
27 Oct - 28 Oct
Fireside Cabin at Osborne Creek
A hotel lounge with orange patterned sofas, a flat-screen TV, a fireplace, and a small table with a vase of flowers.

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 traveller
The price is HK$727
HK$821 total
includes taxes & fees
27 Oct - 28 Oct
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
8.0 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 HK$635
HK$895 total
includes taxes & fees
27 Oct - 28 Oct
Cozy little house in Johnson City
A two-story house with a front deck, a small garden, and a wooden swing set.

6. 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 HK$1,736
HK$2,800 total
includes taxes & fees
2 Nov - 3 Nov
Olivia House is a old farm house that has been updated!
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
The price is HK$699
HK$1,266 total
includes taxes & fees
27 Oct - 28 Oct
BRAND NEW! 1-bedroom apartment in the beautiful historic village of Greene, NY
A campfire with four Adirondack chairs arranged around it in a forest setting.

8. 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 HK$1,365
HK$2,020 total
includes taxes & fees
2 Nov - 3 Nov
Peaceful 5-Acre Country Retreat with Cali~King Bed, Fire Pit & Near Oneonta
A rustic cabin with a stone facade, a wooden balcony, and a stone entrance.

9. Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY

Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
Binghamton
9.8 out of 10, Exceptional, (141 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 HK$1,193
HK$2,943 total
includes taxes & fees
27 Oct - 28 Oct
Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
A room with three framed portraits on the wall, a window with a view of greenery, and a table with a lamp.

10. 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 HK$1,851
HK$3,075 total
includes taxes & fees
27 Oct - 28 Oct
Hilltop, relax and enjoy the Endless Mountains views
A hotel lounge with orange patterned sofas, a flat-screen TV, a fireplace, and a small table with a vase of flowers.

11. 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 traveller
The price is HK$688
HK$778 total
includes taxes & fees
27 Oct - 28 Oct
1 King Bed | 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.

12. Hale Eddy

Hale Eddy
2.0 star property
Hancock
The price is HK$1,216
HK$2,592 total
includes taxes & fees
27 Oct - 28 Oct
Hale Eddy
A hotel lounge with orange patterned sofas, a flat-screen TV, a fireplace, and a small table with a vase of flowers.

13. 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 traveller
The price is HK$727
HK$821 total
includes taxes & fees
27 Oct - 28 Oct
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.

14. 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 traveller
The price is HK$765
HK$864 total
includes taxes & fees
27 Oct - 28 Oct
2 Queen Beds | Non-Smoking, Mini Fridge
A lakeside cabin with a wooden deck and a stone pathway leading to the entrance.

15. Cozy 2-bedroom cabin in Vestal NY

Cozy 2-bedroom cabin in Vestal NY
Vestal
9.6 out of 10, Exceptional, (21 reviews)
"Location was great, definitely amazing way to disconnect for a couple days with the family. Only had 1 problem which was the stove top not working but besides that everything else was great."
United States
Omar
The price is HK$1,059
HK$1,861 total
includes taxes & fees
27 Oct - 28 Oct
Cozy 2-bedroom cabin in Vestal NY
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 HK$980
HK$1,274 total
includes taxes & fees
1 Nov - 2 Nov
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.

17. 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 HK$1,176
HK$1,997 total
includes taxes & fees
27 Oct - 28 Oct
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!
A natural landscape with a pond, a wooden bridge, and a forested area.

18. Susquehanna Waterfall Haven

Susquehanna Waterfall Haven
Susquehanna
The price is HK$1,588
HK$2,910 total
includes taxes & fees
30 Oct - 31 Oct
Susquehanna Waterfall Haven
A kitchen with white cabinets, a stove, and a dining area with a round table and chairs.

19. Cozy 2b apt 25mins from All Star Village & 44mins from Cooperstown Dreams Park

Cozy 2b apt 25mins from All Star Village & 44mins from Cooperstown Dreams Park
Bainbridge
9.6 out of 10, Exceptional, (5 reviews)
"Quick, easy,, very nice and welcoming. Great place to rest, relax and enjoy some peace of life."
United States
Christopher F.
The price is HK$776
HK$1,397 total
includes taxes & fees
27 Oct - 28 Oct
Cozy 2b apt 25mins from All Star Village & 44mins from Cooperstown Dreams Park
A cozy living room with a stone fireplace, wooden walls, a television, and a coffee table with decorative items.

20. Quiet Lakefront Retreat nestled in the woods.

Quiet Lakefront Retreat nestled in the woods.
Montrose
10.0 out of 10, Exceptional, (108 reviews)
"It was very clean great area and the hosts were so nice!!"
United States
Grace D.
The price is HK$1,020
HK$1,491 total
includes taxes & fees
27 Oct - 28 Oct
Quiet Lakefront Retreat nestled in the woods.
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

Hampton Inn Binghamton/Johnson City

Hampton Inn Binghamton/Johnson City

10/10 Excellent
"Staff was friendly and fantastic!"
Karen 2-night trip
Posted 3 hours ago
Hampton Inn Binghamton/Johnson City

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 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 West Branch Delaware River 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.