Windsor Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21

Vacation Rentals in Windsor

Handcrafted Riverfront Cabin on 10 acres
Exterior

Handcrafted Riverfront Cabin on 10 acres

10.0 out of 10, Exceptional, (172)
"Beautiful property located on an excellent stretch of river. Love the cabin. Great fishing lodge. "
The price is ￥16,975
￥47,487 total
includes taxes & fees
Oct 14 - Oct 15
Handcrafted Riverfront Cabin on 10 acres
Cozy 2-bedroom cabin in Vestal NY
Property grounds

Cozy 2-bedroom cabin in Vestal NY

9.6 out of 10, Exceptional, (11)
" Beautiful landcape, quiet and secluded."
The price is ￥22,880
￥38,197 total
includes taxes & fees
Oct 6 - Oct 7
Cozy 2-bedroom cabin in Vestal NY
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River
Fridge, microwave, oven, stovetop

Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River

10.0 out of 10, Exceptional, (187)
"Very nice!"
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River
Spectacular Catskill Mountain River Front Custom Log Home
TV, DVD player

Spectacular Catskill Mountain River Front Custom Log Home

10.0 out of 10, Exceptional, (71)
"Great Location"
Spectacular Catskill Mountain River Front Custom Log Home
Quiet Lakefront Retreat nestled in the woods.
Property grounds

Quiet Lakefront Retreat nestled in the woods.

10.0 out of 10, Exceptional, (85)
"This cabin was just as advertised. The cabin was very clean, and all you would need for a comfortable stay was included. I very much enjoyed my two days there."
The price is ￥19,189
￥25,654 total
includes taxes & fees
Sep 29 - Sep 30
Quiet Lakefront Retreat nestled in the woods.
Cozy Cabin built 2024 in Deposit,NY Short walk to best Fly Fishing in Northeast
Interior

Cozy Cabin built 2024 in Deposit,NY Short walk to best Fly Fishing in Northeast

10.0 out of 10, Exceptional, (8)
"Charming cabin, newly built with outstanding attention to detail. Rachel was a wonderful host and very accommodating. We thoroughly enjoyed our stay and plan to return in the future."
Cozy Cabin built 2024 in Deposit,NY Short walk to best Fly Fishing in Northeast
Equestrian House Suites
Cabin (Cabin 4 bedroom) | Private kitchen

Equestrian House Suites

3.0 star property
The price is ￥13,701
￥43,656 total
includes taxes & fees
Sep 25 - Sep 26
Equestrian House Suites
Breathtaking 44+ Acre Country Estate
Fridge, microwave, oven, stovetop

Breathtaking 44+ Acre Country Estate

10.0 out of 10, Exceptional, (36)
"Great place, great setup and property "
Breathtaking 44+ Acre Country Estate
Rivers Edge of the West Branch Delaware River w Private Boat Launch
Interior

Rivers Edge of the West Branch Delaware River w Private Boat Launch

9.6 out of 10, Exceptional, (110)
"We stayed in the cabin for a weekend and used the boat launch to do an all day fishing trip. The cabin was great and the float was as well. Lovely place in a beautiful spot on the river!"
Rivers Edge of the West Branch Delaware River w Private Boat Launch
Riverfront Cabin West Branch Delaware River
Exterior

Riverfront Cabin West Branch Delaware River

9.8 out of 10, Exceptional, (115)
"Great lil place, great host, will stay again when visiting family who live in town. "
Riverfront Cabin West Branch Delaware River
Cozy/Chic Cabin (ISOLATED RETREAT!) Binghamton NY
Exterior

Cozy/Chic Cabin (ISOLATED RETREAT!) Binghamton NY

9.8 out of 10, Exceptional, (129)
"We love the cabin. Just as described. Host Kelly was very helpful and communicative. "
The price is ￥24,946
￥53,542 total
includes taxes & fees
Sep 29 - Sep 30
Cozy/Chic Cabin (ISOLATED RETREAT!) Binghamton NY
Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.
Outdoor dining

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

2.0 star property
8.8 out of 10, Excellent, (8)
"Wanted a quiet rural location for family conversation, a good view, and great food. This was a perfect location and truly enjoyed by all. "
The price is ￥31,736
￥54,035 total
includes taxes & fees
Sep 27 - Sep 28
Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.
12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos
Exterior

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

9.8 out of 10, Exceptional, (29)
"We really enjoyed our stay. The place is even better than the pictures and the host Julia was excellent."
12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos
Cabin on the Lake • Deck, Dock & Woods
Exterior

Cabin on the Lake • Deck, Dock & Woods

9.4 out of 10, Exceptional, (3)
"Nice place tucked away in the woods. Great place to read and watch nature."
Cabin on the Lake • Deck, Dock & Woods
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.
Exterior

Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.

9.6 out of 10, Exceptional, (118)
"Our second time coming back and it was fantastic. Fishing off the John boat was a highlight for the family."
The price is ￥33,212
￥58,236 total
includes taxes & fees
Sep 28 - Sep 29
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.
Cheerful 4 rooms Cabin with 2 bath near BU
Fridge, microwave, oven, stovetop

Cheerful 4 rooms Cabin with 2 bath near BU

9.4 out of 10, Exceptional, (23)
"Here for a college tour. Very convenient to Binghamton University. Host was quick to respond to all our needs and very gracious. "
Cheerful 4 rooms Cabin with 2 bath near BU
Steps from En-Joie Golf - 3BR Bungalow, Pet-Friendly w/ AC & WiFi
Exterior

Steps from En-Joie Golf - 3BR Bungalow, Pet-Friendly w/ AC & WiFi

9.8 out of 10, Exceptional, (10)
"We had a nice stay. The house was as described. "
Steps from En-Joie Golf - 3BR Bungalow, Pet-Friendly w/ AC & WiFi
Indoor Pool,Largest Game Lodge,Sleeps 39
Terrace/patio

Indoor Pool,Largest Game Lodge,Sleeps 39

10.0 out of 10, Exceptional, (54)
"A group of us stayed for two nights and the property absolutely exceeded our expectations. Leah was a great communicator and I would absolutely recommend this property for a group to get away and enjoy all of the activities it has to offer."
Indoor Pool,Largest Game Lodge,Sleeps 39
Secluded Summer Cabin Near Trails w/ Firepit, Hot Tub & Stargazing Views!
1 bedroom, iron/ironing board, free WiFi, bed sheets

Secluded Summer Cabin Near Trails w/ Firepit, Hot Tub & Stargazing Views!

10.0 out of 10, Exceptional, (26)
"These cabins are super cute and essentially like a studio cabin set up. Bedroom/Living Area is sufficient, Bathroom is really good size & outdoor areas are a bonus!"
The price is ￥14,623
￥25,511 total
includes taxes & fees
Sep 25 - Sep 26
Secluded Summer Cabin Near Trails w/ Firepit, Hot Tub & Stargazing Views!
Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing
Interior

Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing

10.0 out of 10, Exceptional, (44)
"Enjoyed our stay, unfortunately it rained so couldn’t enjoy the outside space. "
Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Tru by Hilton Binghamton Vestal

Tru by Hilton Binghamton Vestal

10/10 Excellent
"Business-friendly, gym, clean"
Rebecca 1-night trip
Posted 5 days ago
Tru by Hilton Binghamton Vestal

Find out more about Windsor

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?

Breathtaking 44+ Acre Country Estate: Visitors like this Windsor vacation home rental. It is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, 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.