Windsor Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Windsor

Waterfront Properties vacation rental
10.0 out of 10, Exceptional, (48)
"We enjoyed our stay. The accommodations were great!"
The price is NZ$366
includes taxes & fees
12 Jun - 13 Jun
Waterfront Properties vacation rental
Handcrafted Riverfront Cabin on 10 acres
10.0 out of 10, Exceptional, (108)
"Sean, We had the best year of fishing in over a decade. The property is awesome, and access to the water is easy. One silly item would be more hooks on the wall to hang clothing. Also, I wasn't sure how to turn on the baseboard heater in the bedroom. I turned on the bathroom and left the door open."
The price is NZ$637
includes taxes & fees
10 Jun - 11 Jun
Handcrafted Riverfront Cabin on 10 acres
Quiet Lakefront Retreat nestled in the woods.
10.0 out of 10, Exceptional, (50)
"The owners were great. Respected our privacy, answered any and all of our questions or needs. Property is beautiful, great fishing in the lake. Quiet surroundings, and other things to explore with a short drive. Just a really great experience!"
The price is NZ$281
includes taxes & fees
13 Jun - 14 Jun
Quiet Lakefront Retreat nestled in the woods.
Save an average of 15% on thousands of hotels when you're signed in
Cozy French Woods Cottage, Pond and Pool
10.0 out of 10, Exceptional, (4)
"The cottage was comfortable and well outfitted. “Uncle Joe” is a very generous host and made our stay special. Great fishing, swimming and bird watching in this bucollic spot. The kids had a ball and we loved the fire pit at night for campfire s’mores."
Cozy French Woods Cottage, Pond and Pool
Elk Mountain Ski Resort: Rustic Home on 21 Acres
10.0 out of 10, Exceptional, (32)
"This cabin was just what we were looking for! Beautiful views, lots and LOTS of space to run around, easy access to trails and so peaceful. We took the advice of the guide and visited Chet’s Place for dinner and visited the nearby lake. Both were great. My family and I had the most wonderful time and would love to return! 10/10 - would recommend!"
Elk Mountain Ski Resort: Rustic Home on 21 Acres
Beautiful and Cozy Home in Binghamton
8.0 out of 10, Very good, (7)
"It was a cute little older home. With nice updates on the inside. They are definitly doing work to the exterior. In the description it said there was a grill. Which there was unfortunately there was so many large black trash bags you could not get to it. The first step at the side walk was broken. And the railing inaide was very loose. Although there was some minor issues we enjoyed out atay."
The price is NZ$405
includes taxes & fees
10 Jun - 11 Jun
Beautiful and Cozy Home in Binghamton
Breathtaking 44+ Acre Country Estate
10.0 out of 10, Exceptional, (23)
"Gorgeous property and lovely pool. Home was spacious and comfortable. Had minor issues with check-in and hot water, both of which were resolved in a very timely manner. Adults and children had a wonderful time here."
Breathtaking 44+ Acre Country Estate
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River
10.0 out of 10, Exceptional, (156)
"Clean, quiet, comfy place. If you like nature this is for you! Got the best rest ever there. Owners are gems. Got to meet their fur family! Highly recommended if you want peace n quiet. Beautiful area"
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River
Indoor Pool + 3 Homes + Private Lodge/ Entertainment Clubhouse
10.0 out of 10, Exceptional, (39)
"We had the BEST experience!! Leah was extremely helpful!! It has great amenities if ur looking to stay and enjoy each others company without having to entertain anybody. There’s a great playroom with tons of toys for the babies and toddlers , loads of activities for teens and adults and a great pool to swim or just sunbathe!!! Would definitely consider going again!! The only issue we had were the mattress es, it’s not so comfortable…."
Indoor Pool + 3 Homes + Private Lodge/ Entertainment Clubhouse
New York Abode: 2 Mi to Binghamton University!
9.0 out of 10, Wonderful, (2)
"No AC that was weird but really didn’t need it fans in every room but not on living room,kitchen or dining room. House have a back yard but you can not access door is locked with wire. Tub is broken but they put a cover on it I thought it was not acceptable according to VRBO standards but in general was a good place for the value"
New York Abode: 2 Mi to Binghamton University!
!!LAKEFRONT!! 3 Bedroom house
10.0 out of 10, Exceptional, (5)
"The owner was extremely accommodating to everything. The lake was beautiful and the house was well kept and very cozy. Most definitely will be coming back"
!!LAKEFRONT!! 3 Bedroom house
Rivers Edge of the West Branch Delaware River w Private Boat Launch
9.6 out of 10, Exceptional, (93)
"We had a nice relaxing weekend with some great fishing. Andy was very kind and made sure we had what we needed. A great spot to visit again! Thanks Andy!"
Rivers Edge of the West Branch Delaware River w Private Boat Launch
Short Walk to Delaware River Access for Kayaking in a Quaint Large Hamlet Home
10.0 out of 10, Exceptional, (3)
"Property was exactly as listed. Older house, but well maintained. Would book again when in the area."
The price is NZ$745
includes taxes & fees
3 Jul - 4 Jul
Short Walk to Delaware River Access for Kayaking in a Quaint Large Hamlet Home
Family friendly cottage, covered deck, close to lake to fish, swim, and boat
Family friendly cottage, covered deck, close to lake to fish, swim, and boat
Tranquil river cottage w/hot tub, firepit , & 4 mins to a 18-holes golf course
10.0 out of 10, Exceptional, (15)
"We had a family gathering for our son’s graduation from Binghamton University. The river front home was a perfect place for our family get together. Thanks"
Tranquil river cottage w/hot tub, firepit , & 4 mins to a 18-holes golf course
Quiet Cabin 20 minutes from Elk Mountain/Dogs OK/Easy Drive from Philly and NYC
9.6 out of 10, Exceptional, (127)
"Great property for being close to nature, but difficult to find in the dark. "Cleaners" definitely need to do a better job in order to justify the cleaning fees."
Quiet Cabin 20 minutes from Elk Mountain/Dogs OK/Easy Drive from Philly and NYC
Cheerful 3 bed Cabin with 2 bath near BU
10.0 out of 10, Exceptional, (11)
"The cabin is very welcoming and the host goes above and beyond with amenities. I stayed here with my son to visit family in the area. I will stay here again and highly recommend."
Cheerful 3 bed Cabin with 2 bath near BU
Lakewood Cottage w/ Private Lake Access & Canoes!
10.0 out of 10, Exceptional, (11)
"The week we stayed there the homes near by appeared to be vacant so it felt like we had the lake all to ourselves. The cottage was clean, bright and comfortable. We had everything we needed to cook and BBQ. We had our morning coffee and evening glass of wine on the deck. I spent a couple days in the hammock reading while my husband fished off the dock. We took our dog on long hikes on nearby trails. I wished we could have stayed longer but we will come back and make use of the bikes, kayaks and...
Lakewood Cottage w/ Private Lake Access & Canoes!
DeerRidge Estate By Brophy
10.0 out of 10, Exceptional, (49)
"We are a group of college friends who have been getting together for over forty years. We’ve stayed at a variety of places over the years and now, with 3 generations attending, we need larger accommodations. I think we’ve found our place. Lovely setting. Clean, comfortable rooms. Plenty of bathrooms! We had perfect weather but even if there were rain, the front veranda offers lots of space to hang out. (A few rocking chairs would be nice for the babies and grandparents.) Overall, a lovely...
DeerRidge Estate By Brophy
RiverView Estate By Brophy
10.0 out of 10, Exceptional, (109)
"This estate provided a wonderful experience for our annual Family Reunion (four generations). The lodging was spacious, comfortable, and flowing. The back deck, off the main house, was the popular gathering spot. And the oversized kitchen and great-room in the entertainment house was fantastic for our dinners and post dinner gatherings. Lastly, the property manager (Walter) was great to engage with; very friendly, available, and responsive."
RiverView Estate By Brophy
Don't see what you're looking for?
See all available properties in Windsor
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.

Other types of properties in Windsor you may be interested in

Waterfront Properties vacation rental
10.0 out of 10, Exceptional, (48)
"We enjoyed our stay. The accommodations were great!"
The price is NZ$366
includes taxes & fees
12 Jun - 13 Jun
Waterfront Properties vacation rental
Microtel Inn & Suites By Wyndham Binghamton
2.5 star property
9.0 out of 10, Wonderful, (1009)
"The room and breakfast were clean and good. When checking in we asked the woman at the desk where our room was. Thinking she was kidding, she said "I am not allowed to tell you" and proceeded to not tell us other than handing us the keys. We then asked which side of the building we should park and she said any side. Not a good first meeting with a place you haven't been before. The checkout gentleman was very nice. "
The price is NZ$192
includes taxes & fees
17 Jun - 18 Jun
Microtel Inn & Suites By Wyndham Binghamton
DoubleTree by Hilton Hotel Binghamton
4.0 star property
8.8 out of 10, Excellent, (1002)
"The hotel was clean and well maintained. The staff was friendly and there were a lot of restaurants in walking distance and one on the property. The only draw back was the hotel bar was only open until 10pm."
The price is NZ$247
includes taxes & fees
16 Jun - 17 Jun
DoubleTree by Hilton Hotel Binghamton
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Windsor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Windsor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Windsor. Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Windsor short-term rentals, that won’t be hard to do.

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?

Waterfront Properties vacation rental: This highly rated holiday home rental in Windsor is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

What’s there to see and do in Windsor?

Endless Mountains and Susquehanna River are a couple of lovely local spots to get outside and enjoy nature. Animal Adventure Park 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.

Recent reviews of Windsor properties
Expedia verified reviews