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Compare 96 Vacation Homes in Windsor with updated reviews, rates, and availability.

Charming & Private Delaware Riverfront Home near Callicoon NY
Exterior

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
Waterfront Properties vacation rental
Property grounds

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 470
SAR 1,181 total
includes taxes & fees
26 Dec - 27 Dec
Waterfront Properties vacation rental
Your Own Personal Ski - Skate - Fishing LODGE!
Living Room as you walk-in. New Couches and PA Live Edge Wood Coffee Table.

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!
1 Mi to Dtwn: Colorful Binghamton Home
Binghamton Vacation Rental | 4BR | 1.5BA | 1,680 Sq Ft | Stairs Required

1 Mi to Dtwn: Colorful Binghamton Home

1 Mi to Dtwn: Colorful Binghamton Home
Beautiful and Cozy Home in Binghamton
Private kitchen

Beautiful and Cozy Home in Binghamton

7.6 out of 10, Good, (11)
"Cute little home felt very comfortable "
The price is SAR 515
SAR 971 total
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
Outdoor spa tub

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

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
New York Abode: 2 Mi to Binghamton University!
Binghamton Vacation Rental | 3BR | 1BA | Steps Required | 1,452 Sq Ft

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!
On the Delaware River, beautiful views, fishing, kayaking, floating, swimming
River view/access from front yard

On the Delaware River, beautiful views, fishing, kayaking, floating, swimming

10.0 out of 10, Exceptional, (6)
"The house was perfect, it had everything we needed. The beds and bedding were very comfortable. The view was gorgeous and relaxing. The fishing was great. Dawn is a wonderful host and Jordan was extremely helpful during our stay. We will definitely be back. "
On the Delaware River, beautiful views, fishing, kayaking, floating, swimming
LARGE RUSTIC BRICK SCHOOL HOUSE WITH MUSIC JAMSPACE /RECORDING STUDIO
Exterior

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
Pet-Friendly Hancock Home on the Delaware River!
Hancock Vacation Rental | 2BR | 1BA | 2 Steps Required | 1,200 Sq Ft

Pet-Friendly Hancock Home on the Delaware River!

9.8 out of 10, Exceptional, (19)
"Couldnt ask for a better location or a house better situated to enjoy it. Watching eagles, deer, ducks, fishermen and we think a bear. We are 3 eomen in town for a high school reunion, could have used a second bath."
Pet-Friendly Hancock Home on the Delaware River!
Cozy little house in Johnson City
Room

Cozy little house in Johnson City

9.4 out of 10, Exceptional, (9)
"A great one night stay close to the hospital in which I was working. It snowed overnight and my host finished shoveling the walk way as I was heading to work. I was happy from check in to check out. Thanks for a great stay!"
The price is SAR 338
SAR 430 total
includes taxes & fees
24 Dec - 25 Dec
Cozy little house in Johnson City
Tranquil, Stylish Elk Mountain Home with Lake Access
Exterior

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
Riverside Retreat in The Catskill Mountains
Exterior

Riverside Retreat in The Catskill Mountains

Riverside Retreat in The Catskill Mountains
Grand Monarch! Luxury Boutique Living! Best for Extended Stays.
Private kitchen

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"
Grand Monarch! Luxury Boutique Living! Best for Extended Stays.
Indoor Pool + 3 Homes + Private Lodge/ Entertainment Clubhouse
Part of the expansive patio at the Eagle Manor

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
DeerRidge Estate By Brophy
Exterior

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
All 3 dwellings and pool

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
Breathtaking 44+ Acre Country Estate
Pool

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
LAKE HOUSE WITH PRIVATE DOCK TO CANNON BALL OFF!
Exterior

LAKE HOUSE WITH PRIVATE DOCK TO CANNON BALL OFF!

9.6 out of 10, Exceptional, (4)
"We had a wonderful time, Hanna was great and her property was beautiful. It has everything you need for outdoor fun & fun if you enjoy the water. We caught so many fish, enjoyed swimming & the boats that was available to use. Just a little tip, take swimming shoes because the bottom of the lake in some parts have small rocks. Would definitely go back and have already recommended family & friends. Thank for having us Hanna :)"
LAKE HOUSE WITH PRIVATE DOCK TO CANNON BALL OFF!
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
Property grounds

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 470
SAR 1,181 total
includes taxes & fees
26 Dec - 27 Dec
Waterfront Properties vacation rental
Historic Main Street private 2 bedroom apartment with views and all amenities.
Property grounds

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
Exterior

Handcrafted Riverfront Cabin on 10 acres

10.0 out of 10, Exceptional, (137)
"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 SAR 537
SAR 1,367 total
includes taxes & fees
7 Jan - 8 January 2025
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.