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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 homes

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 CA $173
CA $446 total
includes taxes & fees
Sep 15 - Sep 16
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 CA $201
CA $569 total
includes taxes & fees
Sep 14 - Sep 15
Ska'no'ne-Peaceful escape; Sunrise coffee on the covered porch, sun set Fire pit
A two-story house with a front deck, a small garden, and a wooden swing set.

3. 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 CA $331
CA $536 total
includes taxes & fees
Sep 23 - Sep 24
Olivia House is a old farm house that has been updated!
A campfire with four Adirondack chairs arranged around it in a forest setting.

4. 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 CA $148
CA $220 total
includes taxes & fees
Sep 14 - Sep 15
Peaceful 5-Acre Escape Near Animal Adventure Park with Cali~King Bed & Fire Pit
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, (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 CA $112
CA $158 total
includes taxes & fees
Sep 14 - Sep 15
Cozy little house in Johnson City
A natural landscape with a pond, a wooden bridge, and a forested area.

6. Susquehanna Waterfall Haven

Susquehanna Waterfall Haven
Susquehanna
The price is CA $280
CA $519 total
includes taxes & fees
Sep 14 - Sep 15
Susquehanna Waterfall Haven
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
9.2 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 CA $311
CA $525 total
includes taxes & fees
Sep 14 - Sep 15
Hilltop, relax and enjoy the Endless Mountains views
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.

8. 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 CA $277
CA $486 total
includes taxes & fees
Sep 16 - Sep 17
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
A cozy living room with a sofa, a coffee table, and a lamp. There are large windows and a door leading to another room.

9. Hale Eddy

Hale Eddy
2.0 star property
Hancock
The price is CA $240
CA $486 total
includes taxes & fees
Oct 6 - Oct 7
Hale Eddy
A kitchen with wooden cabinets, a stainless steel stove, a dishwasher, a sink, and a window with a view of trees.

10. 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, (1 review)
"We enjoyed an overdue getaway at this unique property. The host was helpful and the place was very clean. The bedrooms are a little bit small but well appointed, and the convenience of the washer and dryer was a plus, as we stayed 9 nights. The metal architectural elements were an intriguing blast from the past, and there were deer in the back almost every evening. We ideally would have preferred less traffic noise (construction at the shopping center across the street during our stay), but it...
United States
Ross M.
The price is CA $156
CA $381 total
includes taxes & fees
Sep 16 - Sep 17
2-bed historic Lustron home newly remodeled, modern interior. Nearby shopping!

11. 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 CA $858
CA $1,237 total
includes taxes & fees
Sep 15 - Sep 16
Lakefront Home, Fast WiFi + Workspace, ideal for weeklong family friendly stays
A dining area with a wooden table and chairs, a kitchen with cabinets, a sofa with cushions, and a plant.

12. 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 CA $311
CA $885 total
includes taxes & fees
Sep 14 - Sep 15
Peaceful 3-bedroom house close to Binghamton University/ UHS hospital.
A spacious wooden cabin with a high ceiling, a staircase leading to an upper level, a cozy living area with a sofa, chairs, and a dining table.

13. Lake View Log Cabin with amazing views

Lake View Log Cabin with amazing views
Hancock
The price is CA $553
CA $1,044 total
includes taxes & fees
Oct 1 - Oct 2
Lake View Log Cabin with amazing views
A two-story house with a well-lit front porch and a dock extending into a body of water.

14. 12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos

12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos
Montrose
9.8 out of 10, Exceptional, (35 reviews)
"We really enjoyed our stay. The place is even better than the pictures and the host Julia was excellent."
United States
Blake T.
The price is CA $1,734
CA $2,652 total
includes taxes & fees
Oct 1 - Oct 2
12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos
A sunroom with a wooden table, two chairs, a sofa, and a view of a green landscape.

15. Equinunk

Equinunk
3.0 star property
Equinunk
The price is CA $258
CA $503 total
includes taxes & fees
Sep 16 - Sep 17
Equinunk
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 18 hours ago
Colonial Brick Inn & Suites

Find out more about Windsor

Windsor Vacation Homes information

Number of reviews
221
Accommodation
110 Vacation Homes
Lowest Price
CA $158
Highest Price
CA $2,652

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