Holiday Rentals in Windsor

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Holiday Rentals in Windsor

Waterfront Properties vacation rental

9.8 out of 10, Exceptional, (59)
"We stayed here and it was a true paradise, very quiet and very very pretty. The cottage is on a really nice bend in the river, you can sit on the front porch and just watch it go by. The place is newly updated, very clean and presentable. We would stay here again. Also, check out Animal Adventure Park 5 min away."
The price is €311
includes taxes & fees
21 Dec - 22 Dec
Waterfront Properties vacation rental

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

9.6 out of 10, Exceptional, (41)
"Had another outstanding stay at this location everything I expected was at hand."
Historic Main Street private 2 bedroom apartment with views and all amenities.

Handcrafted Riverfront Cabin on 10 acres

10.0 out of 10, Exceptional, (136)
"This cabin was very charming, clean and a great spot to getaway from the everyday grind. The cabin was the perfect size for me, my husband and our dog. Everything we needed was at the cabin and our host was accommodating. We will be back in the future "
The price is €345
includes taxes & fees
22 Dec - 23 Dec
Handcrafted Riverfront Cabin on 10 acres

Elk Mountain Ski Resort: Rustic Home on 21 Acres

9.8 out of 10, Exceptional, (35)
"I’ve stayed at many places. Let me tell you this is at the top of the list. The house is beautiful, clean (top to bottom) and the location and views are breathtaking. The house has everything you need on site and in kitchen etc. We absolutely loved the place and my teenage boys are already asking when we’re going back Again overall an amazing place and we”ll definitely be booking again !!!"
Elk Mountain Ski Resort: Rustic Home on 21 Acres

Quiet Lakefront Retreat nestled in the woods.

10.0 out of 10, Exceptional, (67)
"Wish we had time to enjoy all the features… esp the lake!"
The price is €141
includes taxes & fees
3 Jan - 4 Jan 2025
Quiet Lakefront Retreat nestled in the woods.

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

10.0 out of 10, Exceptional, (173)
"Great Inside/Outside"
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River

Your Own Personal Ski - Skate - Fishing LODGE!

9.8 out of 10, Exceptional, (31)
"I booked this property for a birthday weekend for my adult children and I. I wanted a house close to a lake and also hiking, and this was perfect! The home had everything we needed to relax, enjoy the outdoors, and have a great stay. The fishing was excellent and the sup was used by everyone! We met lovely people at the beach and ended each day at the firepit. The property was pet friendly, and there were even dog treats for us upon arrival! I would recommend this property for its location,...
Your Own Personal Ski - Skate - Fishing LODGE!

Indoor Pool + 3 Homes + Private Lodge/ Entertainment Clubhouse

10.0 out of 10, Exceptional, (43)
"We had an absolute BLAST at this house!!!! Honestly, the pictures did not do it justice. The beautiful views around, waking up to morning fog, the amount of sprawling space across all 4 properties. I can’t say enough great things. It was so clean and had everything we needed. We WILL be back!"
Indoor Pool + 3 Homes + Private Lodge/ Entertainment Clubhouse

Rivers Edge of the West Branch Delaware River w Private Boat Launch

9.6 out of 10, Exceptional, (102)
"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

Charming & Private Delaware Riverfront Home near Callicoon NY

9.8 out of 10, Exceptional, (171)
"Really a spectacular place to stay, beautiful and peaceful, comfortable and well-maintained. Hosts very responsive, even stopped by with a delicious apple pie and new cords for the internet! Would stay here again in a heartbeat. "
Charming & Private Delaware Riverfront Home near Callicoon NY

Beautiful and Cozy Home in Binghamton

7.6 out of 10, Good, (11)
"Cute little home felt very comfortable "
The price is €256
includes taxes & fees
27 Dec - 28 Dec
Beautiful and Cozy Home in Binghamton

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

9.8 out of 10, Exceptional, (27)
" "
Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing

Quiet Cabin 20 minutes from Elk Mountain/Dogs OK/Easy Drive from Philly and NYC

9.6 out of 10, Exceptional, (135)
"House was located off the beaten path and it was great. Great to sit on the deck and watch the rain while drinking coffee."
Quiet Cabin 20 minutes from Elk Mountain/Dogs OK/Easy Drive from Philly and NYC

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

9.8 out of 10, Exceptional, (22)
"I booked this stay to celebrate my mom's 60th birthday, in which she wanted nothing more than a big family reunion. It was such a beautiful property with amazing amenities. We were lucky with good weather in November to kayak on the lake. Everyone was so pleased with the stay and it was exactly what my mom wanted for her birthday. It provided us with unforgettable memories. Julia was very responsive and was an amazing host that helped with any question that I have. We will definitely be staying...
11 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos

Breathtaking 44+ Acre Country Estate

10.0 out of 10, Exceptional, (26)
"We had an amazing time. The house is really nice & views are incredible. The kids went sledding in backyard which was awesome. Jennifer was really quick to respond and help with anything needed. One thing that should be disclosed in the listing is that two of the top floor bedrooms are railroad style. "
Breathtaking 44+ Acre Country Estate

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

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

9.6 out of 10, Exceptional, (106)
"My husband and I stayed for our anniversary week in early September and the place could not have been more perfect! The photos in the listening don't do the property justice. The lake was spectacular. Perfect location with rustic cabin charm!"
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.

RiverView Estate By Brophy

10.0 out of 10, Exceptional, (113)
"We had a wonderful gathering of friends for two nights here. The big kitchen was a centerpiece in the main house and we enjoyed the beautiful entertainment lodge. The kids had a wonderful time. I highly recommend tubing in town at OARS. The river was pristine and it was a highlight for us. Thank you for hosting our group."
RiverView Estate By Brophy

New York Abode: 2 Mi to Binghamton University!

9.0 out of 10, Wonderful, (4)
"It was well situated for the activites we had planned. They said they would be fixing windows & AC this summer which would be a great imporvement. Good communication, Very clean. Thanks!"
New York Abode: 2 Mi to Binghamton University!

LARGE RUSTIC BRICK SCHOOL HOUSE WITH MUSIC JAMSPACE /RECORDING STUDIO

9.6 out of 10, Exceptional, (47)
"Lovely space with lots of character and a great place for enjoying music, loved how each room had a CD collection and speakers. "
LARGE RUSTIC BRICK SCHOOL HOUSE WITH MUSIC JAMSPACE /RECORDING STUDIO
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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Other types of properties in Windsor you may be interested in

Waterfront Properties vacation rental

9.8 out of 10, Exceptional, (59)
"We stayed here and it was a true paradise, very quiet and very very pretty. The cottage is on a really nice bend in the river, you can sit on the front porch and just watch it go by. The place is newly updated, very clean and presentable. We would stay here again. Also, check out Animal Adventure Park 5 min away."
The price is €311
includes taxes & fees
21 Dec - 22 Dec
Waterfront Properties vacation rental

Holiday Inn Binghamton Downtown, an IHG Hotel

3.0 star property
8.4 out of 10, Very good, (1003)
"Nice Holiday Inn."
The price is €115
includes taxes & fees
25 Dec - 26 Dec
Holiday Inn Binghamton Downtown, an IHG Hotel

Microtel Inn & Suites By Wyndham Binghamton

2.5 star property
9.0 out of 10, Wonderful, (1035)
"our place to stay in binghamton"
The price is €97
includes taxes & fees
22 Dec - 23 Dec
Microtel Inn & Suites By Wyndham 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.

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.