Windsor Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Windsor vacation rentals

Property grounds

Waterfront Properties vacation rental

Waterfront Properties vacation rental
Windsor
9.8 out of 10, Exceptional, (67 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 ￥19,649
￥50,090 total
includes taxes & fees
May 31 - Jun 1
Waterfront Properties vacation rental
Exterior

Equestrian House Suites

Equestrian House Suites
3.0 star property
Pleasant Mount
The price is ￥23,015
￥84,197 total
includes taxes & fees
May 15 - May 16
Equestrian House Suites
Property grounds

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, (16 reviews)
"This is the perfect place for you to come and relax. "
United States
Anabel P.
The price is ￥15,562
￥27,148 total
includes taxes & fees
May 19 - May 20
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!
Property grounds

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, (16 reviews)
"Excellent and just as advertised. Lisa was wonderful. Highly recommend!"
United States
David R.
The price is ￥25,150
￥45,262 total
includes taxes & fees
May 20 - May 21
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
Outdoor dining

King Cabin Secluded Romantic Space Near Elk Mountain. Hot Tub, Firepit & Views!

King Cabin Secluded Romantic Space Near Elk Mountain. Hot Tub, Firepit & Views!
Thompson
9.8 out of 10, Exceptional, (41 reviews)
"Great stay especially for a wedding for family vacation "
United States
Catherine P.
The price is ￥15,562
￥27,148 total
includes taxes & fees
May 17 - May 18
King Cabin Secluded Romantic Space Near Elk Mountain. Hot Tub, Firepit & Views!
Exterior

Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY

Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
Binghamton
9.8 out of 10, Exceptional, (137 reviews)
"Warm, comfortable, welcoming house. The owner was very helpful and communicative. The hot tub was glorious. we loved it!"
United States
sandra s.
The price is ￥24,993
￥59,682 total
includes taxes & fees
May 17 - May 18
Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
House, Private Bathroom, Courtyard View (Equinunk) | Exterior

Equinunk

Equinunk
2.0 star property
Equinunk
The price is ￥32,466
￥60,604 total
includes taxes & fees
Jun 1 - Jun 2
Equinunk
Interior

Charming 120-year-old farmhouse by the creek

Charming 120-year-old farmhouse by the creek
Hancock
9.0 out of 10, Wonderful, (25 reviews)
"Close to town ,clean just what we were looking for"
United States
Anonymous traveler
The price is ￥22,411
￥51,696 total
includes taxes & fees
May 20 - May 21
Charming 120-year-old farmhouse by the creek
1 bedroom, free WiFi, bed sheets

Fireside Cabin at Osborne Creek

Fireside Cabin at Osborne Creek
Port Crane
The price is ￥12,591
￥17,780 total
includes taxes & fees
May 17 - May 18
Fireside Cabin at Osborne Creek
TV, fireplace

Lake View Log Cabin with amazing views

Lake View Log Cabin with amazing views
Hancock
The price is ￥56,588
￥109,278 total
includes taxes & fees
May 14 - May 15
Lake View Log Cabin with amazing views
Smart TV, Netflix, Hulu, books

The Hideout Cottage • Awaken With Spring

The Hideout Cottage • Awaken With Spring
Pleasant Mount
The price is ￥17,021
￥47,575 total
includes taxes & fees
May 14 - May 15
The Hideout Cottage • Awaken With Spring
Exterior detail

Handcrafted Riverfront Cabin on 10 acres

Handcrafted Riverfront Cabin on 10 acres
Starlight
10.0 out of 10, Exceptional, (205 reviews)
"Everything was clean, tidy, and comfortable. Very nice, cozy property."
United States
M C.
The price is ￥23,482
￥58,045 total
includes taxes & fees
Jun 5 - Jun 6
Handcrafted Riverfront Cabin on 10 acres
Exterior detail

Cozy little house in Johnson City

Cozy little house in Johnson City
Johnson City
8.6 out of 10, Excellent, (14 reviews)
"Good place to stay for graduation weekend. "
United States
Steven
The price is ￥12,732
￥17,940 total
includes taxes & fees
May 17 - May 18
Cozy little house in Johnson City
Smart TV, stereo

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, (16 reviews)
"Anniversary weekend getaway "
United States
Kayla M.
The price is ￥15,719
￥21,126 total
includes taxes & fees
May 20 - May 21
Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly
Smart TV, fireplace, books, music library

Quiet Lakefront Retreat nestled in the woods.

Quiet Lakefront Retreat nestled in the woods.
Montrose
10.0 out of 10, Exceptional, (97 reviews)
"Great clean, comfortable place, attentive hosts, beautiful location. "
United States
David A.
The price is ￥20,435
￥30,223 total
includes taxes & fees
May 17 - May 18
Quiet Lakefront Retreat nestled in the woods.
Property grounds

Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.

Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.
Hallstead
9.0 out of 10, Wonderful, (9 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 ￥35,368
￥59,423 total
includes taxes & fees
May 28 - May 29
Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.
Property grounds

Susquehanna Waterfall Haven

Susquehanna Waterfall Haven
Susquehanna
The price is ￥31,831
￥58,329 total
includes taxes & fees
May 14 - May 15
Susquehanna Waterfall Haven
Dining

Vacation Cottage Getaway • Fields in Bloom

Vacation Cottage Getaway • Fields in Bloom
Pleasant Mount
The price is ￥17,354
￥47,899 total
includes taxes & fees
May 14 - May 15
Vacation Cottage Getaway • Fields in Bloom
Property grounds

2BR Premium Duplex • A Season of Renewal

2BR Premium Duplex • A Season of Renewal
Pleasant Mount
9.0 out of 10, Wonderful, (2 reviews)
"Would've liked to have more to cook with than just a microwave, other than that the stay was commendable."
United States
Jeremy
The price is ￥19,858
￥56,248 total
includes taxes & fees
May 14 - May 15
2BR Premium Duplex • A Season of Renewal
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

Microtel Inn & Suites By Wyndham Binghamton

Microtel Inn & Suites By Wyndham Binghamton

10/10 Excellent
"Our room was very clean, the staff was nice & it was located in a convenient spot (easy on/off the interstate). Breakfast was basic, but good for what it was. The waffles were good. They kept the breakfast area clean & well stocked. Also, there was plenty of parking."
Robert 1-night trip
Posted 10 hours ago
Microtel Inn & Suites By Wyndham Binghamton

Find out more about Windsor

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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?

Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!: Visitors like this Windsor vacation home rental. It is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 Animal Adventure Park. 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.