Windsor Holiday Rentals

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Holiday Rentals in Windsor

Historic Main Street private 2 bedroom apartment with views and all amenities.

9.8 out of 10, Exceptional, (49)
"Was a nice quiet place to stay. "
Historic Main Street private 2 bedroom apartment with views and all amenities.

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

10.0 out of 10, Exceptional, (182)
"Very nice!"
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River

Cozy 2-bedroom cabin in Vestal NY

10.0 out of 10, Exceptional, (3)
"Love the cabin and its location!"
The price is AU$416
includes taxes & fees
6 Aug - 7 Aug
Cozy 2-bedroom cabin in Vestal NY

Handcrafted Riverfront Cabin on 10 acres

10.0 out of 10, Exceptional, (164)
"Great cabin exactly as advertised. Go ahead and book it you won’t be disappointed. "
The price is AU$520
includes taxes & fees
4 Aug - 5 Aug
Handcrafted Riverfront Cabin on 10 acres

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

9.6 out of 10, Exceptional, (108)
"Cabin was in a great location and very cozy with great appliances. Would definitely recommend. "
Rivers Edge of the West Branch Delaware River w Private Boat Launch

Charming & Private Delaware Riverfront Home near Callicoon NY

9.8 out of 10, Exceptional, (179)
"Love this place would come here again with family"
Charming & Private Delaware Riverfront Home near Callicoon NY

Indoor Pool,Largest Game Lodge,Sleeps 39

10.0 out of 10, Exceptional, (52)
"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

Riverfront Cabin West Branch Delaware River

9.8 out of 10, Exceptional, (113)
"This place is clean and host is great, I recommend "
Riverfront Cabin West Branch Delaware River

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

9.6 out of 10, Exceptional, (115)
"My family rented this cabin for a short ski trip to Elk mtn. The cabin was really nice and described nicely in summary. We couldn’t do much exploring of propety due to amount of snow but we are already looking forward to renting this in summer. It’s right on lake with a dock, couldn’t ask for anything better. We really enjoyed our visit. "
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.

Equestrian House Suites

2.5 star property
The price is AU$532
includes taxes & fees
5 Aug - 6 Aug
Equestrian House Suites

Charming 120-year-old farmhouse by the creek

8.8 out of 10, Excellent, (20)
"Close to town ,clean just what we were looking for"
The price is AU$485
includes taxes & fees
13 Aug - 14 Aug
Charming 120-year-old farmhouse by the creek

Modern Suite | Near BU, Hospitals & Downtown | NY

9.6 out of 10, Exceptional, (13)
"Traveling with a dog, so we really appreciated being able to walk her through the neighborhood. Sweet little apartment, comfortable bed, nicely furnished. If we're passing through again, we'll definitely rebook."
The price is AU$807
includes taxes & fees
5 Aug - 6 Aug
Modern Suite | Near BU, Hospitals & Downtown | NY

Brand New! Riverfront River Bend Cabin - Catskill fly fishing outside your door!

9.8 out of 10, Exceptional, (29)
"Perfect getaway and a lot of fishing opportunities in the area. "
Brand New! Riverfront River Bend Cabin - Catskill fly fishing outside your door!

Cheerful 4 rooms Cabin with 2 bath near BU

9.8 out of 10, Exceptional, (21)
"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

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

9.8 out of 10, Exceptional, (30)
"We stayed for a long weekend and the place was great. It was clean and the location was perfect. Close to town and very relaxing by the river. Ron was a great host, communication was top notch, easy to work with. Highly recommend staying here."
Waterfront house on the upper most portion of the West Branch Delaware.

Lakeside Gem: Hot Tub & Game Room in Hancock

9.8 out of 10, Exceptional, (45)
"Great host, great property, great stay. Secluded, big, well put together and comfortable. Would highly recommend and will 100% be staying again."
Lakeside Gem: Hot Tub & Game Room in Hancock

Spectacular Catskill Mountain River Front Custom Log Home

10.0 out of 10, Exceptional, (66)
"Great Location"
Spectacular Catskill Mountain River Front Custom Log Home

Cozy/Chic Cabin (ISOLATED RETREAT!) Binghamton NY

9.8 out of 10, Exceptional, (127)
"Very nice property with everything you would ever need. Super host. "
The price is AU$559
includes taxes & fees
11 Aug - 12 Aug
Cozy/Chic Cabin (ISOLATED RETREAT!) Binghamton NY

DISCOUNT LAST MINUTE Elk Mountain Estate Manor in beautiful PA-Groups and Events

9.8 out of 10, Exceptional, (94)
"We booked at the last minute due to another rental falling through. The booking process was smooth and Laura was a gracious and amazing host. The property is beautiful and spacious! We can’t wait to visit again "
DISCOUNT LAST MINUTE Elk Mountain Estate Manor in beautiful PA-Groups and Events

Breathtaking 44+ Acre Country Estate

10.0 out of 10, Exceptional, (33)
"The house was great. Clean, cozy and spacious. There was room for everyone in our large group snowboarding at elk mountain (a little over 20 min away). "
Breathtaking 44+ Acre Country Estate
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

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?

Charming & Private Delaware Riverfront Home near Callicoon NY: This holiday home rental outside of Windsor is located on the waterfront, and has a fireplace, a patio and a BBQ 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 that 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 one of the family-friendly sights such as Animal Adventure Park. Susquehanna River and West Branch Delaware River 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.