Windsor Holiday Rentals

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Holiday Rentals in Windsor

Interior
Waterfront Properties vacation rental
10.0 out of 10, Exceptional, (47)
"Immaculate everything you would need to have for a few days was supplied. It was a home away from home we enjoyed every minute! Thank you Bob and Amy"
The price is HK$625
HK$1,784 total
includes taxes & fees
11 Jun - 12 Jun
Waterfront Properties vacation rental
Exterior
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 HK$1,398
HK$3,181 total
includes taxes & fees
12 Jun - 13 Jun
Handcrafted Riverfront Cabin on 10 acres
Property grounds
Quiet Lakefront Retreat nestled in the woods.
10.0 out of 10, Exceptional, (49)
"Beautiful scenery all around. We went off season to enjoy the lake too much but the views are fantastic."
The price is HK$1,015
HK$1,357 total
includes taxes & fees
13 Jun - 14 Jun
Quiet Lakefront Retreat nestled in the woods.
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Fridge, microwave, oven, stovetop
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
Exterior
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
Property grounds
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
Fridge, microwave, oven, stovetop
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
Fridge, microwave, stovetop, dishwasher
New York Abode: 2 Mi to Binghamton University!
10.0 out of 10, Exceptional, (1)
"the only complait about this property, is there was only two bath towels. also there was only four forks"
New York Abode: 2 Mi to Binghamton University!
Outdoor dining
!!LAKEFRONT!! 3 Bedroom house
10.0 out of 10, Exceptional, (4)
"Wonderful time at this location! Perfect deck to sit by the lake on a gorgeous fall weekend & catch up with friends. Home was clean & perfect size for the 4 of us to eat, drink & talk & talk & talk!!!"
!!LAKEFRONT!! 3 Bedroom house
Interior
Tranquil river cottage w/hot tub, firepit , & 4 mins to a 18-holes golf course
10.0 out of 10, Exceptional, (14)
"This house is so cute!! We stayed with our family and enjoyed the house so much. It was cold during our visit but I imagine in the warmer months it is even more fun with the waterfront and outdoor areas! You can tell the owners put a lot of hard work into making this a cozy retreat for themselves and guests 😊"
Tranquil river cottage w/hot tub, firepit , & 4 mins to a 18-holes golf course
Fridge, microwave, oven, stovetop
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
Fridge, microwave, oven, stovetop
DeerRidge Estate By Brophy
10.0 out of 10, Exceptional, (48)
"We had the best time at this house. It was beautiful. Walter was the best. He came right away on any request we had. I highly recommend staying here. I think our family wants to make an annual thing. We had over 40 people stay and everyone slept comfortably. Our ages range from 2 to 74. Everyone had the best time."
DeerRidge Estate By Brophy
Exterior
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
TV, video games, books, music library
Luxurious Lakefront Estate - Pets Welcome!
10.0 out of 10, Exceptional, (32)
"Great place for our wedding party weekend. Scott was super accommodating and was an excellent host. Would recommend especially if you plan a small wedding. Just one note the entertainment room is not heated but this did not deter us and was fine even in January."
Luxurious Lakefront Estate - Pets Welcome!
Aerial view
LAKE FRONT WITH VIEWS TO DREAM OF
10.0 out of 10, Exceptional, (21)
"The house was clean and pictures were accurate. Easy to check in. The kitchen had many tools, cooking utensils and pots and pans but there was no basic pantry items just fyi. Easy to solve with a trip to a grocery store. There is only a Keurig coffee maker but pods are provided. My only issue was that we were only given the two trash bags in the trash can. The owner was quick to reply and provided additional bags very quickly. Overall a great place for a family of 4+, great view, comfy beds,...
LAKE FRONT WITH VIEWS TO DREAM OF
Fridge, microwave, stovetop, dishwasher
Family Home w/ Pool, Yard, Game Room, Deck & More!
10.0 out of 10, Exceptional, (16)
"What an amazing time we had in this well kept house. The pool was perfect, all outdoor spaces beautiful, and indoor room to stretchbout and so mich to do in the game room. Owners were super responsive and generous! Would love to come again"
Family Home w/ Pool, Yard, Game Room, Deck & More!
Property grounds
Peaceful Hancock Home w/ Patio, Deck & Grill!
10.0 out of 10, Exceptional, (13)
"We stay in the area often and first time at this house and we will be back again! Location was perfect. The house was awesome! Communication with PM was great! Woke up to fresh snow on Saturday! Overall great weekend."
Peaceful Hancock Home w/ Patio, Deck & Grill!
Fridge, microwave, stovetop, coffee/tea maker
Idyllic Poconos Cottage w/ Deck & Community Perks!
10.0 out of 10, Exceptional, (14)
"Great ski weekend! The cottage was very clean and close to the slopes!"
Idyllic Poconos Cottage w/ Deck & Community Perks!
Property grounds
Brand New! Riverfront River Bend Cabin - Catskill fly fishing outside your door!
10.0 out of 10, Exceptional, (11)
"The place was great had everything you need for a vacation."
Brand New! Riverfront River Bend Cabin - Catskill fly fishing outside your door!
TV, fireplace
Lakewood Cottage w/ Private Lake Access & Canoes!
9.8 out of 10, Exceptional, (10)
"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!
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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

Interior
Waterfront Properties vacation rental
10.0 out of 10, Exceptional, (47)
"Immaculate everything you would need to have for a few days was supplied. It was a home away from home we enjoyed every minute! Thank you Bob and Amy"
The price is HK$625
HK$1,784 total
includes taxes & fees
11 Jun - 12 Jun
Waterfront Properties vacation rental
Desk, iron/ironing board, free WiFi, bed sheets
Microtel Inn & Suites By Wyndham Binghamton
2.5 star property
9.0 out of 10, Wonderful, (1002)
"Quick overnight stay as part of a trip. Very clean, very nice. "
The price is HK$796
HK$900 total
includes taxes & fees
10 Jun - 11 Jun
Microtel Inn & Suites By Wyndham Binghamton
Meeting facility
DoubleTree by Hilton Hotel Binghamton
4.0 star property
8.8 out of 10, Excellent, (1000)
"The Double Tree Hilton in Binghamton was a lovely hotel to stay at. It was always clean and quiet and the staff were helpful. The restaurant and bar on site was great along with the small shop to buy snacks and medicines etc "
The price is HK$1,094
HK$1,236 total
includes taxes & fees
27 May - 28 May
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.

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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?

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.

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