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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Windsor vacation rentals

Property grounds

Waterfront Properties vacation rental

Waterfront Properties vacation rental
Windsor
9.8 out of 10, Exceptional, (69 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.
$282 nightly
The price is $319
Jul 28 - Jul 29
Total with taxes and fees
Waterfront Properties vacation rental
Fridge, microwave, oven, stovetop

2-bed historic Lustron home newly remodeled, modern interior. Nearby shopping!

2-bed historic Lustron home newly remodeled, modern interior. Nearby shopping!
Vestal
$244 nightly
The price is $275
Jul 20 - Jul 21
Total with taxes and fees
2-bed historic Lustron home newly remodeled, modern interior. Nearby shopping!
1 bedroom, iron/ironing board, WiFi, bed sheets

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, (12 reviews)
"Very nice clean, right in the center of town, convenient to shops on restaurants. "
United States
Laura P.
$139 nightly
The price is $155
Jul 8 - Jul 9
Total with taxes and fees
BRAND NEW! 1-bedroom apartment in the beautiful historic village of Greene, NY
Exterior detail

Cozy little house in Johnson City

Cozy little house in Johnson City
Johnson City
8.6 out of 10, Excellent, (14 reviews)
"Second time staying here, everything was great!"
United States
Chad A.
$101 nightly
The price is $114
Jul 8 - Jul 9
Total with taxes and fees
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, (18 reviews)
"The host was very responsive. The property was very clean, cozy and had many amenities. "
United States
Anonymous traveler
$120 nightly
The price is $134
Jul 8 - Jul 9
Total with taxes and fees
Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly
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, (17 reviews)
"This is the perfect place for you to come and relax. "
United States
Anabel P.
$188 nightly
The price is $204
Jul 9 - Jul 10
Total with taxes and fees
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!
Smart TV, video games

Fireside Cabin at Osborne Creek

Fireside Cabin at Osborne Creek
Port Crane
10.0 out of 10, Exceptional, (5 reviews)
"Our host was just wonderful! He was attentive to our needs and went above and beyond by even bringing my grandson an air mattress & showing us his horses. The cabin was beautiful and the outdoor fireplace and hammock was great. The only problem we had was the television service was spotty even after our host tried to fix it. All in all, a wonderful visit."
United States
Heidi
$109 nightly
The price is $123
Jul 19 - Jul 20
Total with taxes and fees
Fireside Cabin at Osborne Creek
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, (43 reviews)
"Great stay especially for a wedding for family vacation "
United States
Catherine P.
$188 nightly
The price is $204
Jul 8 - Jul 9
Total with taxes and fees
King Cabin Secluded Romantic Space Near Elk Mountain. Hot Tub, Firepit & Views!
Fridge, microwave, oven, stovetop

Peaceful 5-Acre Family Retreat with a King Bed

Peaceful 5-Acre Family Retreat with a King Bed
Afton
10.0 out of 10, Exceptional, (2 reviews)
"What an absolutely amazing experience. So cute, small, cozy just perfect for a little family getaway with nature."
United States
april
$150 nightly
The price is $168
Jul 21 - Jul 22
Total with taxes and fees
Peaceful 5-Acre Family Retreat with a King Bed
Exterior detail

Handcrafted Riverfront Cabin on 10 acres

Handcrafted Riverfront Cabin on 10 acres
Starlight
10.0 out of 10, Exceptional, (212 reviews)
"Great little cabin in a great location. "
United States
Michael M.
$352 nightly
The price is $382
Jul 10 - Jul 11
Total with taxes and fees
Handcrafted Riverfront Cabin on 10 acres
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, (11 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.
$349 nightly
The price is $379
Jul 28 - Jul 29
Total with taxes and fees
Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.
Property grounds

Queen Cabin Modern Cabin Near Skiing, Trails, Firepit, Hot Tub & Stargazing!

Queen Cabin Modern Cabin Near Skiing, Trails, Firepit, Hot Tub & Stargazing!
Thompson
10.0 out of 10, Exceptional, (35 reviews)
"The surrounding area is beautiful for nice walks. Had a great weekend in this charming little cabin. The police was clean and we were able to bring our dog. Will definitely return. "
United States
Mayra M.
$175 nightly
The price is $190
Jul 12 - Jul 13
Total with taxes and fees
Queen Cabin Modern Cabin Near Skiing, Trails, Firepit, Hot Tub & Stargazing!
Exterior

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.
$352 nightly
The price is $398
Jul 13 - Jul 14
Total with taxes and fees
Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
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, (102 reviews)
"It was very quiet and beautiful"
United States
Timothy G.
$175 nightly
The price is $190
Jul 13 - Jul 14
Total with taxes and fees
Quiet Lakefront Retreat nestled in the woods.
Interior

Charming 120-year-old farmhouse by the creek

Charming 120-year-old farmhouse by the creek
Hancock
9.0 out of 10, Wonderful, (26 reviews)
"This is really a beautiful place to stay, we definitely will return in summer. "
United States
Paul C.
$309 nightly
The price is $340
Jul 14 - Jul 15
Total with taxes and fees
Charming 120-year-old farmhouse by the creek
Property grounds

Susquehanna Waterfall Haven

Susquehanna Waterfall Haven
Susquehanna
$345 nightly
The price is $374
Jul 8 - Jul 9
Total with taxes and fees
Susquehanna Waterfall Haven
TV, fireplace

Lake View Log Cabin with amazing views

Lake View Log Cabin with amazing views
Hancock
$636 nightly
The price is $700
Jul 8 - Jul 9
Total with taxes and fees
Lake View Log Cabin with amazing views
Property grounds

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.
$355 nightly
The price is $401
Jul 10 - Jul 11
Total with taxes and fees
Ska'no'ne-Peaceful escape; Sunrise coffee on the covered porch, sun set Fire pit
Property grounds

Jack Cabin Modern Cabin for Families Close to Skiing with Hot Tub and Firepit

Jack Cabin Modern Cabin for Families Close to Skiing with Hot Tub and Firepit
Thompson
9.4 out of 10, Exceptional, (13 reviews)
"Cool place to chilaxx"
United States
Luis R.
$192 nightly
The price is $209
Jul 14 - Jul 15
Total with taxes and fees
Jack Cabin Modern Cabin for Families Close to Skiing with Hot Tub and Firepit
House, Private Bathroom, Mountain View (Angler & Nature's Delight) | Lounge

Hale Eddy

Hale Eddy
2.0 star property
Hancock
$351 nightly
The price is $370
Jul 22 - Jul 23
Total with taxes and fees
Hale Eddy
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
"Very comfortable room."
Robert 1-night trip
Posted 5 hours ago
Microtel Inn & Suites By Wyndham Binghamton

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

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

Windsor vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $123 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation 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 vacation.

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 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?

Charming & Private Delaware Riverfront Home near Callicoon NY: Visitors like this Windsor vacation home rental. It is located on the waterfront and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.