Search Holiday Rentals in Windsor

    price find illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Save instantly and earn perks with One Key
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Top Holiday Rentals in Windsor

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

9.8 out of 10, Exceptional, (46)
"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, (179)
"The place was nice and the hosts looked out for us when a snow storm came through, would recommend."
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River

Handcrafted Riverfront Cabin on 10 acres

10.0 out of 10, Exceptional, (158)
"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 £277
includes taxes & fees
6 Jul - 7 Jul
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

Cozy 2-bedroom cabin in Vestal NY

10.0 out of 10, Exceptional, (1)
" Beautiful landcape, quiet and secluded."
The price is £194
includes taxes & fees
9 Jul - 10 Jul
Cozy 2-bedroom cabin in Vestal 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

Charming 120-year-old farmhouse by the creek

8.8 out of 10, Excellent, (18)
"Close to town ,clean just what we were looking for"
The price is £235
includes taxes & fees
31 Jul - 1 Aug
Charming 120-year-old farmhouse by the creek

Equestrian House Suites

2.5 star property
The price is £243
includes taxes & fees
2 Jul - 3 Jul
Equestrian House Suites

Charming & Private Delaware Riverfront Home near Callicoon NY

9.8 out of 10, Exceptional, (175)
"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

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

10.0 out of 10, Exceptional, (27)
"Loved the little cabin. Perfect for a great getaway to reset and relax. Close to great hiking trails and awesome views "
Brand New! Riverfront River Bend Cabin - Catskill fly fishing outside your door!

Modern Suite | Near BU, Hospitals & Downtown | NY

9.6 out of 10, Exceptional, (12)
"This was a very nice place to lay your head, which is what we did. The amenities were a bit lower quality than expected, however it met the immediate need."
The price is £384
includes taxes & fees
8 Jul - 9 Jul
Modern Suite | Near BU, Hospitals & Downtown | NY

Cozy ranch 3-bedroom house with WiFi, AC in brilliant Vestal

6.8 out of 10, (3)
"Our stay was great!"
Cozy ranch 3-bedroom house with WiFi, AC in brilliant Vestal

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 £266
includes taxes & fees
21 Jul - 22 Jul
Cozy/Chic Cabin (ISOLATED RETREAT!) Binghamton NY

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

Lakefront Gem: Hot Tub & Game Room in Hancock

9.8 out of 10, Exceptional, (43)
"Great host, great property, great stay. Secluded, big, well put together and comfortable. Would highly recommend and will 100% be staying again."
Lakefront Gem: Hot Tub & Game Room in Hancock

Indoor Pool,Largest Game Lodge,Sleeps 39

10.0 out of 10, Exceptional, (51)
"Amazing luxurious time,Everything was clean & well-maintained. Everyone in our family enjoyed it. Hope to return again in coming times!"
Indoor Pool,Largest Game Lodge,Sleeps 39

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

9.8 out of 10, Exceptional, (26)
"This was our 3rd year staying at this property and it never disappoints. The house is perfect for our large group and is always in excellent condition. The owner is very responsive and helpful. "
12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos

Breathtaking 44+ Acre Country Estate

10.0 out of 10, Exceptional, (32)
"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

!!LAKEFRONT house with baby goats!!

9.8 out of 10, Exceptional, (13)
"We loved the house. "
!!LAKEFRONT house with baby goats!!
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

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?

Indoor Pool,Largest Game Lodge,Sleeps 39: This holiday home rental outside of Windsor is located in the mountains, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 13 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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.