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Compare 98 Vacation Homes in Windsor with updated reviews, rates, and availability.

Indoor Pool, 13 BR, Sleeps 39, 3 Luxury Homes

10.0 out of 10, Exceptional, (44)
"We have a group of 25 that have been celebrating New Year’s together for the past 30 years. This worked great as everyone had their own bedroom and there was plenty to do on-site. The clubhouse and pool were enjoyed by all! We look forward to staying there again next year."
Indoor Pool, 13 BR, Sleeps 39, 3 Luxury Homes

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 SAR 469
SAR 1,180 total
includes taxes & fees
23 Jan - 24 Jan
Waterfront Properties vacation rental

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

7.0 out of 10, Good, (12)
"Cute little home felt very comfortable "
The price is SAR 514
SAR 966 total
includes taxes & fees
23 Jan - 24 Jan
Beautiful and Cozy Home in Binghamton

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

Lakefront Gem: Hot Tub & Game Room in Hancock

10.0 out of 10, Exceptional, (40)
"It’s a good space for a large group. Enough rooms for everyone. Beautiful lake nearby. Scott was very helpful. House has two kitchens, three refrigerators which was great. Kitchens weee stocked with pantry essentials which was very convenient. Over all, a good stay. "
Lakefront Gem: Hot Tub & Game Room in Hancock

Your Own Personal Ski - Skate - Fishing LODGE!

9.8 out of 10, Exceptional, (32)
"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!

Poconos Home w/ Private Hot Tub & Fireplace

9.8 out of 10, Exceptional, (24)
"We were happy with our stay, the hot tub was a nice perk!"
Poconos Home w/ Private Hot Tub & Fireplace

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

Cozy 3 bedroom log cabin in a scenic country setting. Very private

10.0 out of 10, Exceptional, (26)
"My friend and I were excited to get away during the New years week. We got everything from warm mid 40s to 6 inches of snow and low 20s. We were looking for a cozy cabin with a fireplace/stove and some outdoors for our dog. This was exactly what we wanted. I was able to do some excellent trout fishing nearby and some great hikes on DEC trails in State Forests, which were right up the road. The kitchen worked great and the cabin has a cozy feel with an open concept. The owner, Angelo was super...
Cozy 3 bedroom log cabin in a scenic country setting. Very private

Steam Punk Steamer Trunk

10.0 out of 10, Exceptional, (5)
"We stayed over the holiday. The house has thoughtful touches that we really enjoyed. All appliances worked well, beds comfortable and the house was clean upon arrival. Our host replied quickly for any questions. Thanks! "
Steam Punk Steamer Trunk

Tranquil, Stylish Elk Mountain Home with Lake Access

9.8 out of 10, Exceptional, (9)
"Excellent experience, clean and well maintained property."
Tranquil, Stylish Elk Mountain Home with Lake Access

Historic former bed and breakfast - 15 min to Elk Mountain Ski Resort

10.0 out of 10, Exceptional, (4)
"We had a great stay! The house was the perfect size for our family trip. We had a problem with the door lock but Brenda was very quick to assist us! She was very quick to respond to our messages. We enjoyed our stay at Smiley Hollow!"
Historic former bed and breakfast - 15 min to Elk Mountain Ski Resort

Riverside Retreat in The Catskill Mountains

Riverside Retreat in The Catskill Mountains

Grand Monarch! Luxury Boutique Living! Best for Extended Stays.

2.5 star property
10.0 out of 10, Exceptional, (1)
"Great place to stay very clean and secured"
The price is SAR 619
SAR 953 total
includes taxes & fees
23 Jan - 24 Jan
Grand Monarch! Luxury Boutique Living! Best for Extended Stays.

Charming & Historic 3-bedroom house in sleepy Gibson with Wifi, AC & hot tub

Charming & Historic 3-bedroom house in sleepy Gibson with Wifi, AC & hot tub

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, (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
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 property types 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 SAR 469
SAR 1,180 total
includes taxes & fees
23 Jan - 24 Jan
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, (140)
"Property was clean and just the right size for our group of 2 people and 2 dogs. Had a great time disconnecting from our everyday and walking the property. Hosts were responsive and helpful. "
The price is SAR 450
SAR 1,259 total
includes taxes & fees
27 Jan - 28 Jan
Handcrafted Riverfront Cabin on 10 acres
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.