Windsor Holiday Rentals

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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 NZ$561
includes taxes & fees
23 Nov - 24 Nov
Waterfront Properties vacation rental

Equestrian House Suites

3.0 star property
Pleasant Mount
The price is NZ$1,044
includes taxes & fees
17 Nov - 18 Nov
Equestrian House Suites

Handcrafted Riverfront Cabin on 10 acres

Starlight
10.0 out of 10, Exceptional, (180)
"Beautiful cabin on very nice property. Great place to just relax. "
United States
Mary P.
The price is NZ$515
includes taxes & fees
17 Nov - 18 Nov
Handcrafted Riverfront Cabin on 10 acres

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 NZ$612
includes taxes & fees
17 Nov - 18 Nov
Cozy Cabin built 2024 in Deposit,NY Short walk to best Fly Fishing in Northeast

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

Lake Como
10.0 out of 10, Exceptional, (190)
"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

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

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 NZ$201
includes taxes & fees
17 Nov - 18 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

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 NZ$433
includes taxes & fees
18 Nov - 19 Nov
Hip Dtwn Apt W/ Arcade & Gym

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

Our Rustic Serenity Camp is 190 sq ft and over looks the river valley

Unadilla
10.0 out of 10, Exceptional, (3)
"Beautiful property, super helpful host. Can't wait to go back"
United States
Katie T.
Our Rustic Serenity Camp is 190 sq ft and over looks the river valley

Quiet Lakefront Retreat nestled in the woods.

Montrose
10.0 out of 10, Exceptional, (90)
"Wish we had time to enjoy all the features… esp the lake!"
United States
Wendy N.
The price is NZ$306
includes taxes & fees
17 Nov - 18 Nov
Quiet Lakefront Retreat nestled in the woods.

Spectacular Catskill Mountain River Front Custom Log Home

hancock
10.0 out of 10, Exceptional, (74)
"Great Location"
United States
David S.
Spectacular Catskill Mountain River Front Custom Log Home

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 NZ$711
includes taxes & fees
18 Nov - 19 Nov
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.

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

Deposit
9.6 out of 10, Exceptional, (112)
"Great home base for fishing the West Branch. It was nice getting to show up and all you need is food drink and fishing gear. "
United States
Gregory S.
Rivers Edge of the West Branch Delaware River w Private Boat Launch

Welcoming 2-bedrooms cute house in Vestal.

2.0 star property
Vestal
8.0 out of 10, Very good, (1)
"This was a last minute booking due to another rental not having heat. The host did meet us upon arrival which was a pleasant surprise. She communicated quickly and clearly. The place was clean and cozy. It is in a basement so the ceiling is low. I’m 6’3” and I was always stooped over. We were the host’s first guests. We could have used 1 more towel and the kitchen could use some dinnerware and silverware as well as some coffee filters for the coffee machine. The bathroom is a bit small but...
United States
T F.
Welcoming 2-bedrooms cute house in Vestal.

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

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

Charming & Private Delaware Riverfront Home near Callicoon NY

Equinunk
9.8 out of 10, Exceptional, (187)
"Beautiful stay "
United States
Lisa H.
Charming & Private Delaware Riverfront Home near Callicoon 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.
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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, 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 NZ$201 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.