
Pet-friendly vacation rentals in Windham
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Top-rated pet-friendly home rentals in Windham
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Pet-friendly house rentals

Catskills Mountaintop House w/ HOT TUB and VIEWS!
Absolutely stunning place, Kim and Russel are great hosts! Would surely be returning for another family stay!

Fantasy Cottage/Mountain Views/Trails/Fire pit
Martina’s cottage was fantastic. Everything was as advertised. Fantastic lighting, large space and, unbelievable views.
Woodstock Historic Artist Estate - The Pond House
No notes, incredible escape even in the pouring rain. The ambience, even down to the little things like walking through the door to classical music, was truly top notch.

Secluded 55 acre Windham Getaway w/ 6BRs + Hot Tub
Phil & Allan are great hosts, very responsive and clear. Their spot is the perfect cozy getaway with friends & family with amazing views and ample space. They supplied firewood for the fire pit and were flexible with check in times. A few minutes down the road is a great deli and a few other coffee shops, a brewery, and restaurants. The area is relaxed and perfect for hiking and other outdoor activities. We loved our stay!

Yanity House
We love this house! Every time we come here we feel right at home! It has now become a tradition for our family to come here at least once a year. Perfect place to relax. Pet friendly. Always looking forward to our next visit!

Modern Prefabricated Architectural Retreat
Adrian’s place was absolutely lovely. It’s beautiful, peaceful, and easy to relax into. The new “hedge” separating the driveway and the side yard is lovely. Having nature all around is gorgeous and restorative. We’ll definitely return!

Embrace nature in style @killercatmountainhouse
This is the perfect spot to stay and has everything you need to feel right at home. The beds are comfortable, linens are plush, kitchen is stocked. Dena spoiled us with the most delicious treats upon arrival and was so communicative, friendly, and helpful!

Mt. Wonder - Hot tub, sauna, wonderful view
Our favorite place to stay in the Catskills. Very private and peaceful.
Pet-friendly home rentals with a pool

Enchanting Upstate Cabin w Pool, Firepit
I spent a week at Fouz and Chris's place with my family (8 adults, a toddler and two dogs) and we had very relaxing, enjoyable, comfortable stay. The house is in a quiet, private area and a short distance from places of interest for hikes, restaurants, museums, historical sites, etc. We received great recommendations from the hosts.

Little owl Japanese teahouse: pool is OPEN
My husband and I had a wonderfully relaxing time at the Little Owl Teahouse. It’s a cozy and well-outfitted cabin with a super comfy bed and a great leather reading chair. Drank lots of the delicious mountain well water. Made breakfast in kitchen — love the pans and electric cooktop. Short drive to Woodstock for dinner. And oh the beauty of the surroundings - scenic views everywhere. Our two little doggies were happy to romp in the fenced in yard. Little too chilly when we were there but pool looks so appealing. Lisa is a proactive and super responsive host.

Modern Barn on 12 acres w Sauna, FirePit+swimming
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

Camp Fox Hollow: Heated Pool I Fire-Pit I Hot Tub
Absolute slice of heaven. Private, peaceful. Home itself modern and comfortable. Pool was absolutely amazing, comfortable in late May - in peak summer it must be amazing. Would love to stay again!

Modern Upstate Cabin, near Rhinebeck NY
Our second time staying at Maitopia with our cat, just as wonderful in a different warmer season. Tina was super responsive as usual and even accommodated a late checkout. We enjoyed feasting in the kitchen as well as grilling in the yard, floating around in the pool when it was warm enough out, "hiking" with our cat on a leash around the forest on the property, taking baths, streaming music. We didn't leave the property much, but it was a fun highlight to get a few local produce items at nearby Greig farm and meet the adorable goats. One tip- bring an eyemask if you're sensitive to light in the mornings- there aren't any window shades in the bedroom.

Mtn View Lux Dome w/ Heated Plunge Pool
We had a great time at the dome! Very peaceful and quiet. This dome was obviously saged or blessed by the pope himself because the vibes were immaculate. Felt like we were living inside a beautiful interior design Pinterest post. Cody was a great host and his Catskills guidebook was very helpful.

Woodstock Romantic Mountain Studio w/ Pool
We loved this cute studio cabin at the end of a quiet lane in the woods. The host was accommodating and left a welcome basket with tea & muffins for our arrival. The whole unit was clean and well maintained with basic equipment for cooking. We enjoyed sitting on the veranda watching the wildlife. Convenient location for Woodstock for coffee and food, & Ashokan reservoir for walking and cycling. There were a few potholes on the access road to the property which deer use to drink from (☺️). We loved that the cabin was bug free and did not have any trace of bug spray! (We get very bad reactions to that stuff). Thank you for hosting & being respive. Recommend for a weekend 👍🏼

Private Waterfront w/Swimming, Boats & Hot Tub+
This comfortable, cozy, magical piece of Catskill paradise was the perfect place to gather to mourn the loss of my father and make some new family memories for a lifetime. Photography is a hobby of mine and the picturesque landscape allowed me to get lost in my passion. We cooked all our meals together in the well-appointed kitchen, challenged each other in the PacMan arcade game and cuddled up together to watch the stars shine and a movie on the comfy couch. We took long walks and met two local farm horses grazing freely in the local fields. The wonderful host was very accommodating and fast to respond. We loved her thorough recommendations for local dining, fun activities and nearby shopping. Book this cabin in the Catskills! You will not be disappointed! We will be back! ". . . there are deeper gorges, greater streams and higher mountains but in no other place is the combination so blended into a harmony so perfect as to form such tempting bits for the camera or the brush.”
Private, pet-friendly home rentals

Moritz - Cozy Modern with a Perfect View
Wonderful place to stay in Hunter! Loved the view from this super comfortable and spacious (for one or a couple) modern cabin. The hosts have great taste in design and were very responsive and friendly when I needed help with something. Great WiFi, great kitchen and bath and comfortable bed. There’s a lovely view of the mountains through a large window but it’s so cleverly designed that you never feel a lack of privacy. I highly recommend a stay here.

"Your Country Getaway at Beulah Land Farm."
We had a lovely stay here. The apartment was spotless, well stocked and comfortable. It suited our needs for a location in the Catskills.

Modern & Chic Log Home-Spectacular Mountain Views!
Had a beautiful stay with my parents and sibling -- we loved watching movies on the large projector, cooking meals together in the lovely kitchen and taking in the serenity of the area. Michael was very responsive, and we couldn't have asked for a more pleasant stay in the Catskills!

Mtn Views • Firepit • 5 Min to Hiking + Brewery
The house was beautiful and had everything we needed, even instructions in case of bad weather. We felt so comfortable and relaxed during our stay. We would absolutely recommend staying here for a weekend getaway! Thanks so much to Kelsey for everything!

Stunning 2-Bedoom A-Frame in the Woods with Sauna
Nicolas was amazing! He responded very quickly to all our messages, and the house was absolutely beautiful. My family felt very comfortable throughout our stay. Thank you, Nicolas, for an incredible staycation,we truly enjoyed every moment!

Brand New Outdoor Hot Tub - Luxury 2 Bedroom Suite
Just a short stay but all was seamless. Beds comfy, bathrooms clean and updated. I would stay again.

Your Windham Mtn Getaway•Hot Tub•BBQ•1mi to Main
Joanna’s place was one of my Top AirBNB experiences, and she is a dream host. Immaculately clean, incredible communication, well-stocked, great location (minutes from Main Street and ski resort) l. Her place truly felt like a home away from home, and we cannot wait to return!

5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
everything was amazing. she helped with all during our stay. super recommended!!
Quick stats about vacation rentals that are pet-friendly in Windham
Total rentals
50 properties
Nightly prices starting at
R1,604 ZAR before taxes and fees
Total number of reviews
2.3K reviews
Family-friendly rentals
50 properties are a good fit for families
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Howe Caverns
- The Kartrite Resort & Indoor Waterpark
- John Boyd Thacher State Park
- Glimmerglass State Park
- Albany Center Gallery
- Taconic State Park
- Resorts World Catskills
- Catamount Mountain Ski Resort
- Zoom Flume
- Windham Mountain
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Hancock Shaker Village
- Hunter Mountain Resort
- Opus 40
- Naumkeag
- Pineridge Cross Country Ski Area
- Thaddeus Hait Farm
- Butternut Ski Area and Tubing Center
- Plattekill Mountain