Holiday Rentals in Windsor

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Windsor

Waterfront Properties vacation rental

Windsor
9.8 out of 10, Exceptional, (65)
"This property is perfect for a quiet get away. The river views are lovely. The house was clean and well appointed. The location was in a quiet area but close enough to the town to meet basic needs."
United States
Marisa P.
The price is €281
includes taxes & fees
23 Nov - 24 Nov
Waterfront Properties vacation rental

Equestrian House Suites

3.0 star property
Pleasant Mount
The price is €530
includes taxes & fees
20 Nov - 21 Nov
Equestrian House Suites

Handcrafted Riverfront Cabin on 10 acres

Starlight
10.0 out of 10, Exceptional, (177)
"Beautiful cabin on very nice property. Great place to just relax. "
United States
Mary P.
The price is €252
includes taxes & fees
16 Nov - 17 Nov
Handcrafted Riverfront Cabin on 10 acres

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

Montrose
9.8 out of 10, Exceptional, (29)
"I can not recommend this property enough, it had everything a large group could need. We thoroughly enjoyed our time at this property and look forward to returning next year. The owners were helpful and responsive, the lake was beautiful and the time there was lovely!"
United States
Tamara J.
12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos

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

Lakewood
9.6 out of 10, Exceptional, (122)
"We loved the privacy and enjoyed all the kayaks, boat and canoe. Perfect lake vacation, plan on making it a yearly trip."
United States
CINDY M.
The price is €358
includes taxes & fees
15 Nov - 16 Nov
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.

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

Deposit
10.0 out of 10, Exceptional, (12)
"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."
United States
Rick M.
The price is €307
includes taxes & fees
11 Dec - 12 Dec
Cozy Cabin built 2024 in Deposit,NY Short walk to best Fly Fishing in Northeast

Cozy little house in Johnson City

Johnson City
8.4 out of 10, Very good, (13)
"A great one night stay close to the hospital in which I was working. It snowed overnight and my host finished shoveling the walk way as I was heading to work. I was happy from check in to check out. Thanks for a great stay!"
United States
Kristel R.
The price is €102
includes taxes & fees
14 Nov - 15 Nov
Cozy little house in Johnson City

Your Tranquil Oasis on the Susquehanna River

Kirkwood
9.8 out of 10, Exceptional, (10)
"Everything was great! Very comfortable home! Suited our out of town work needs perfectly!"
United States
jeff
Your Tranquil Oasis on the Susquehanna River

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

Endicott
10.0 out of 10, Exceptional, (12)
"Wonderful house and location. The house was truly perfect for us! "
United States
Piper O.
Steps from En-Joie Golf - 3BR Bungalow, Pet-Friendly w/ AC & WiFi

Riverfront Cabin West Branch Delaware River

Deposit
9.8 out of 10, Exceptional, (118)
"This place is clean and host is great, I recommend "
United States
David R.
Riverfront Cabin West Branch Delaware River

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

Lake Como
10.0 out of 10, Exceptional, (189)
"We really enjoyed our stay! Jim and Tracy were fantastic and very nice! The cabin is so peaceful. If, you are looking for a peaceful getaway this is the place to go to! You will love it!"
United States
Alexis M.
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River

Breathtaking 44+ Acre Country Estate

Pleasant Mount
10.0 out of 10, Exceptional, (36)
"Jennifer was a great host, very communicative. The property is really beautiful and the sunsets/sunrises were wonderful to watch from the porch and the fire pit! The pictures from the listing were accurate. Overall a great stay"
United States
Michael S.
Breathtaking 44+ Acre Country Estate

Spectacular Catskill Mountain River Front Custom Log Home

hancock
10.0 out of 10, Exceptional, (73)
"Great Location"
United States
David S.
Spectacular Catskill Mountain River Front Custom Log Home

Waterfront house on the upper most portion of the West Branch Delaware.

Deposit
10.0 out of 10, Exceptional, (35)
"Best spot for Stylesville area flyfishing."
United States
Patrick O.
Waterfront house on the upper most portion of the West Branch Delaware.

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

Conklin
10.0 out of 10, Exceptional, (49)
"Beautiful, clean property. Loved being on the river. House had everything we needed. "
United States
Hayley R.
Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing

Binghamton's Beautiful Riverside Drive Living!

Binghamton
10.0 out of 10, Exceptional, (16)
"The host was wonderful and the property far exceeded our expectations in terms of cleanliness, amenities, decor, being in an inviting neighborhood and proximity to downtown Binghamton. We recommend it to anyone looking for a beautiful place to stay. You will not be disappointed. Five Stars"
United States
Charles G.
Binghamton's Beautiful Riverside Drive Living!

Elk Mountain Vacation Home on 21 Acres

Union Dale
9.8 out of 10, Exceptional, (47)
"Family and friends Elk Mountain getaway. Cabin is very nicely situated on the large property. Cabin was very cozy and warm. The wood stove is a great touch. Kitchen was well stocked with cook and dinner ware. Everything met our needs and was to our liking. We would definitely recommend this property."
United States
Michael R.
Elk Mountain Vacation Home on 21 Acres

Hip Dtwn Apt W/ Arcade & Gym

Binghamton
9.0 out of 10, Wonderful, (2)
"Overall, my family had a nice stay at the apartment. The space was clean, comfortable with a modern vibe. The arcade game in the apartment was a plus. It’s convenient to some of the local dining options. It’s ideal for a family of four with the two bedrooms with double beds. It’s a walk up but the stairs are wide and easy to navigate. The owner was very responsive when we requested additional towels, and someone parked in the apartment’s designated spot (not his fault but was a little annoying,...
United States
William
The price is €220
includes taxes & fees
16 Nov - 17 Nov
Hip Dtwn Apt W/ Arcade & Gym

Western Catskills Paradise - Four-Season Mountaintop Retreat

Bainbridge
9.8 out of 10, Exceptional, (61)
"Our family had a lovely time at the property. Karen and Don are responsive hosts and very lovely people. The grandkids did not want to leave!"
United States
Kimberly M.
Western Catskills Paradise - Four-Season Mountaintop Retreat

Fully Loaded Riverfront Cabin on West Branch of the Delaware River, Deposit, NY

Deposit
10.0 out of 10, Exceptional, (3)
"The place is beautifully outfitted and decorated. A/C, induction stove top, beverage fridge in addition. Perfectly set up for someone with a disability. Will visit again, no question. "
United States
Bob P.
Fully Loaded Riverfront Cabin on West Branch of the Delaware River, Deposit, NY
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

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

Windsor holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as €102 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday 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 holiday.

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 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 Animal Adventure Park. Susquehanna River and Jimay's Flea Market 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.