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Top Holiday Rentals in Windsor

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

9.8 out of 10, Exceptional, (50)
"Was a nice quiet place to stay. "
Historic Main Street private 2 bedroom apartment with views and all amenities.

Cozy 2-bedroom cabin in Vestal NY

10.0 out of 10, Exceptional, (5)
" Beautiful landcape, quiet and secluded."
The price is £200
includes taxes & fees
18 Aug - 19 Aug
Cozy 2-bedroom cabin in Vestal NY

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

10.0 out of 10, Exceptional, (2)
"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

Handcrafted Riverfront Cabin on 10 acres

10.0 out of 10, Exceptional, (165)
"Great cabin exactly as advertised. Go ahead and book it you won’t be disappointed. "
The price is £242
includes taxes & fees
18 Aug - 19 Aug
Handcrafted Riverfront Cabin on 10 acres

Quiet Lakefront Retreat nestled in the woods.

10.0 out of 10, Exceptional, (80)
"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 £131
includes taxes & fees
21 Aug - 22 Aug
Quiet Lakefront Retreat nestled in the woods.

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

10.0 out of 10, Exceptional, (183)
"Very nice!"
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River

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

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

10.0 out of 10, Exceptional, (31)
"This is our 3rd year staying here. It’s a great property and a great location !! We’ll be back next year!!!"
Waterfront house on the upper most portion of the West Branch Delaware.

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

9.6 out of 10, Exceptional, (117)
"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.

Charming 120-year-old farmhouse by the creek

9.0 out of 10, Wonderful, (21)
"Close to town ,clean just what we were looking for"
The price is £247
includes taxes & fees
30 Aug - 31 Aug
Charming 120-year-old farmhouse by the creek

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

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

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

9.8 out of 10, Exceptional, (95)
"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

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

2.0 star property
9.6 out of 10, Exceptional, (4)
"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 £276
includes taxes & fees
18 Aug - 19 Aug
Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.

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

Peaceful and Private A-frame in the woods, not far from Elk Mountain Ski Resort!

2.0 star property
9.8 out of 10, Exceptional, (9)
"We had a wonderful stay at the A-frame! It was incredibly homey and clean. A perfect cabin in the woods and very close to Elk. Our host was extremely responsive and very accommodating. We will most definitely be back! "
Peaceful and Private A-frame in the woods, not far from Elk Mountain Ski Resort!

Equestrian House Suites

2.5 star property
The price is £238
includes taxes & fees
18 Aug - 19 Aug
Equestrian House Suites

Breathtaking 44+ Acre Country Estate

10.0 out of 10, Exceptional, (34)
"Great place, great setup and property "
Breathtaking 44+ Acre Country Estate

Spacious 7-bedroom House in Vestal

The price is £2,299
includes taxes & fees
21 Aug - 22 Aug
Spacious 7-bedroom House in Vestal

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
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?

Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.: This holiday home rental outside of Windsor is located in the mountains, and has a patio, a garden 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. 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 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.