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, (180)
"Very nice!"
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River

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

Handcrafted Riverfront Cabin on 10 acres

10.0 out of 10, Exceptional, (162)
"Very lovely and quant log home near a beautiful view of the Delaware river! Has all the amenities you’d need for a getaway! Would highly recommend for anyone look for a little serenity in the middle of the woods!"
The price is NZ$602
includes taxes & fees
20 July - 21 July
Handcrafted Riverfront Cabin on 10 acres

Cozy 2-bedroom cabin in Vestal NY

10.0 out of 10, Exceptional, (1)
" Beautiful landcape, quiet and secluded."
The price is NZ$445
includes taxes & fees
20 July - 21 July
Cozy 2-bedroom cabin in Vestal NY

Charming & Private Delaware Riverfront Home near Callicoon NY

9.8 out of 10, Exceptional, (177)
"Photos are somewhat deceiving- house is more “worn out” than I expected. Owner Joe was great, helpful, very gracious bring us breakfast treats and credit at local bakery. Location on the Delaware is spectacular !!!"
Charming & Private Delaware Riverfront Home near Callicoon NY

Riverfront Cabin West Branch Delaware River

9.8 out of 10, Exceptional, (112)
"This place is clean and host is great, I recommend "
Riverfront Cabin West Branch Delaware River

Equestrian House Suites

2.5 star property
The price is NZ$569
includes taxes & fees
21 July - 22 July
Equestrian House Suites

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

9.6 out of 10, Exceptional, (114)
"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.

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

9.8 out of 10, Exceptional, (28)
"Beautiful place and thought full owners experience was great "
Brand New! Riverfront River Bend Cabin - Catskill fly fishing outside your door!

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

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 NZ$537
includes taxes & fees
17 July - 18 July
Charming 120-year-old farmhouse by the creek

Cheerful 4 rooms Cabin with 2 bath near BU

10.0 out of 10, Exceptional, (19)
"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, (27)
"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.

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

Lakeside Gem: Hot Tub & Game Room in Hancock

9.8 out of 10, Exceptional, (44)
"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

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 NZ$596
includes taxes & fees
31 July - 1 Aug
Cozy/Chic Cabin (ISOLATED RETREAT!) Binghamton NY

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

Angler and Nature's delight - West Branch Delaware

9.6 out of 10, Exceptional, (7)
"We enjoyed the weekend getaway with family. The house was very cozy and the hostess was very kind. Thank you very much. "
The price is NZ$778
includes taxes & fees
17 July - 18 July
Angler and Nature's delight - West Branch Delaware

Quiet Lakefront Retreat nestled in the woods.

10.0 out of 10, Exceptional, (77)
"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 NZ$237
includes taxes & fees
26 July - 27 July
Quiet Lakefront Retreat nestled in the woods.
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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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.