Windsor Holiday Rentals

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Check prices for these dates

Tonight
25 Aug - 26 Aug
Tomorrow
26 Aug - 27 Aug
This weekend
29 Aug - 31 Aug
Next weekend
5 Sept - 7 Sept

Holiday Rentals in Windsor

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

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

10.0 out of 10, Exceptional, (5)
Cozy Cabin built 2024 in Deposit,NY Short walk to best Fly Fishing in Northeast
Cozy 2-bedroom cabin in Vestal NY
Property grounds

Cozy 2-bedroom cabin in Vestal NY

10.0 out of 10, Exceptional, (7)
" Beautiful landcape, quiet and secluded."
The price is HK$1,211
HK$2,058 total
includes taxes & fees
27 Aug - 28 Aug
Cozy 2-bedroom cabin in Vestal NY
Handcrafted Riverfront Cabin on 10 acres
Exterior

Handcrafted Riverfront Cabin on 10 acres

10.0 out of 10, Exceptional, (167)
"Great cabin exactly as advertised. Go ahead and book it you won’t be disappointed. "
The price is HK$950
HK$2,628 total
includes taxes & fees
28 Aug - 29 Aug
Handcrafted Riverfront Cabin on 10 acres
Spectacular Catskill Mountain River Front Custom Log Home
TV, DVD player

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
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (184)
"Very nice!"
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River
Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.
Outdoor dining

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

2.0 star property
8.0 out of 10, Very good, (5)
"It was the perfect place for our small group. We just needed a place to sleep and shower overnight. The property was beautiful and we had a great time exploring. "
The price is HK$1,680
HK$2,853 total
includes taxes & fees
27 Aug - 28 Aug
Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.
Riverfront Cabin West Branch Delaware River
Exterior

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
Quiet Lakefront Retreat nestled in the woods.
Property grounds

Quiet Lakefront Retreat nestled in the woods.

10.0 out of 10, Exceptional, (81)
"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 HK$1,016
HK$1,358 total
includes taxes & fees
1 Sept - 2 Sept
Quiet Lakefront Retreat nestled in the woods.
Waterfront house on the upper most portion of the West Branch Delaware.
Outdoor dining

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

10.0 out of 10, Exceptional, (33)
"4 rainy days of fishing. "
Waterfront house on the upper most portion of the West Branch Delaware.
Charming 120-year-old farmhouse by the creek
Property grounds

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 HK$1,391
HK$2,596 total
includes taxes & fees
14 Sept - 15 Sept
Charming 120-year-old farmhouse by the creek
Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing
Interior

Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing

10.0 out of 10, Exceptional, (38)
"Enjoyed our stay, unfortunately it rained so couldn’t enjoy the outside space. "
Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing
Peaceful and Private A-frame in the woods, not far from Elk Mountain Ski Resort!
Exterior

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)
"Perfect little rustic cabin. Has all the amenities you will need with the backwoods feel. Sharief is lightning fast with his responses and even gives excellent food recommendations! Will definitely look at this place again next year. "
Peaceful and Private A-frame in the woods, not far from Elk Mountain Ski Resort!
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.
Exterior

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.
Binghamton's Beautiful Riverside Drive Living!
Microwave, oven, stovetop, dishwasher

Binghamton's Beautiful Riverside Drive Living!

10.0 out of 10, Exceptional, (11)
"This was the perfect house for our trip! This house was meant for entertaining for sure. We were comfortable and able to actually host a family dinner! Everyone loved the house and space! This is a definite stay again! "
Binghamton's Beautiful Riverside Drive Living!
12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos
Exterior

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

9.8 out of 10, Exceptional, (29)
"We really enjoyed our stay. The place is even better than the pictures and the host Julia was excellent."
12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos
Indoor Pool,Largest Game Lodge,Sleeps 39
Terrace/patio

Indoor Pool,Largest Game Lodge,Sleeps 39

10.0 out of 10, Exceptional, (54)
"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
2 Story Loft House With Massage Chair
Interior

2 Story Loft House With Massage Chair

2.0 star property
9.0 out of 10, Wonderful, (2)
"Great place. Clean and quiet. "
2 Story Loft House With Massage Chair
Cheerful 4 rooms Cabin with 2 bath near BU
Fridge, microwave, oven, stovetop

Cheerful 4 rooms Cabin with 2 bath near BU

9.8 out of 10, Exceptional, (22)
"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
Breathtaking 44+ Acre Country Estate
Fridge, microwave, oven, stovetop

Breathtaking 44+ Acre Country Estate

10.0 out of 10, Exceptional, (35)
"Great place, great setup and property "
Breathtaking 44+ Acre Country Estate
Charming & Private Delaware Riverfront Home near Callicoon NY
Dining

Charming & Private Delaware Riverfront Home near Callicoon NY

9.8 out of 10, Exceptional, (182)
"Once again we thoroughly enjoyed our stay at Joe's. The owner and property manager are very nice people. I highly recommend this property if you enjoy the river and other outdoor opportunities. Thanks again!"
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

Hampton Inn & Suites Binghamton/Vestal

Hampton Inn & Suites Binghamton/Vestal

10/10 Excellent
"Nice rooms, very clean, good breakfast and good pool"
Stefania 1-night trip
Posted 21 hours ago
Hampton Inn & Suites Binghamton/Vestal

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.