Pet-friendly holiday rentals in Windham

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Windham pet-friendly home rentals

Pet-friendly house rentals

Top Guest favourite
Home in Jefferson
5 out of 5 average rating, 121 reviews

Catskills Mountaintop House w/ HOT TUB and VIEWS!

Hisham AhmedRating, 5 stars2 days ago
Absolutely stunning place, Kim and Russel are great hosts! Would surely be returning for another family stay!
Guest favourite
Home in Germantown
4.97 out of 5 average rating, 336 reviews

Fantasy Cottage/Mountain Views/Trails/Fire pit

DenzeylRating, 5 stars2 weeks ago
Martina’s cottage was fantastic. Everything was as advertised. Fantastic lighting, large space and, unbelievable views.
Guest favourite
Home in Woodstock
4.94 out of 5 average rating, 338 reviews

Woodstock Historic Artist Estate - The Pond House

CodyRating, 5 stars1 month ago
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.
Guest favourite
Home in Windham
4.96 out of 5 average rating, 149 reviews

Secluded 55 acre Windham Getaway w/ 6BRs + Hot Tub

MarisaRating, 5 stars1 month ago
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!
Guest favourite
Home in Prattsville
4.91 out of 5 average rating, 315 reviews

Yanity House

Ana CarolinaRating, 5 stars2 weeks ago
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!
Top Guest favourite
Home in Catskill
4.97 out of 5 average rating, 187 reviews

Modern Prefabricated Architectural Retreat

AdamRating, 5 stars1 week ago
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!
Top Guest favourite
Home in Hunter
4.99 out of 5 average rating, 181 reviews

Embrace nature in style @killercatmountainhouse

SarahRating, 5 stars3 weeks ago
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!
Guest favourite
Home in Mount Tremper
4.93 out of 5 average rating, 225 reviews

Mt. Wonder - Hot tub, sauna, wonderful view

DianeRating, 5 stars2 days ago
Wonderful views and lots of space to explore your surroundings. We enjoyed the eco-friendly hot tub the most!

Pet-friendly home rentals with a pool

Superhost
Chalet in Ruby
4.91 out of 5 average rating, 118 reviews

Enchanting Upstate Cabin w Pool, Firepit

KimberlyRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Woodstock
4.92 out of 5 average rating, 244 reviews

Little owl Japanese teahouse: pool is OPEN

JaneRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Ghent
4.88 out of 5 average rating, 318 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

JasonRating, 5 stars3 weeks ago
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.
Guest favourite
Cabin in Shandaken
4.95 out of 5 average rating, 197 reviews

Camp Fox Hollow: Heated Pool I Fire-Pit I Hot Tub

DeirdreRating, 5 stars2 weeks ago
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!
Top Guest favourite
Cabin in Red Hook
4.96 out of 5 average rating, 353 reviews

Modern Upstate Cabin, near Rhinebeck NY

JenniferRating, 5 stars1 week ago
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.
Guest favourite
Dome in Hobart
4.93 out of 5 average rating, 155 reviews

Mtn View Lux Dome w/ Heated Plunge Pool

ShaneRating, 5 stars4 days ago
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.
Guest favourite
Home in Woodstock
4.91 out of 5 average rating, 201 reviews

Woodstock Romantic Mountain Studio w/ Pool

JannineRating, 5 stars8 months ago
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 👍🏼
Guest favourite
Cabin in Prattsville
4.83 out of 5 average rating, 172 reviews

Private Waterfront w/Swimming, Boats & Hot Tub+

KRating, 5 stars3 weeks ago
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

Superhost
Cabin in Hunter
4.86 out of 5 average rating, 7 reviews

Moritz - Cozy Modern with a Perfect View

CharlesRating, 5 stars2 weeks ago
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.
Top Guest favourite
Apartment in Roxbury
4.94 out of 5 average rating, 289 reviews

"Your Country Getaway at Beulah Land Farm."

LisaRating, 5 stars3 weeks ago
We had a lovely stay here. The apartment was spotless, well stocked and comfortable. It suited our needs for a location in the Catskills.
Top Guest favourite
Cabin in Margaretville
4.98 out of 5 average rating, 404 reviews

Modern & Chic Log Home-Spectacular Mountain Views!

HemanginiRating, 5 stars4 days ago
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!
Guest favourite
Cabin in West Kill
4.97 out of 5 average rating, 124 reviews

Mtn Views • Firepit • 5 Min to Hiking + Brewery

MarisaRating, 5 stars1 week ago
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!
Guest favourite
Cabin in Saugerties
4.98 out of 5 average rating, 203 reviews

Stunning 2-Bedoom A-Frame in the Woods with Sauna

Shawn FayeRating, 5 stars1 month ago
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!
Superhost
Condo in Windham
4.9 out of 5 average rating, 10 reviews

Brand New Outdoor Hot Tub - Luxury 2 Bedroom Suite

MarcyRating, 5 stars2 months ago
Just a short stay but all was seamless. Beds comfy, bathrooms clean and updated. I would stay again.
Top Guest favourite
Townhouse in Windham
5 out of 5 average rating, 9 reviews

Your Windham Mtn Getaway•Hot Tub•BBQ•1mi to Main

FeliciaRating, 5 stars3 months ago
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!
Top Guest favourite
Cabin in Windham
4.97 out of 5 average rating, 95 reviews

5 Min to Skiing | Hot Tub | Fire Pit | Pool Table

PabloRating, 5 stars4 weeks ago
everything was amazing. she helped with all during our stay. super recommended!!

Quick stats about holiday rentals that are pet-friendly in Windham

  • Total rentals

    50 properties

  • Nightly prices starting at

    $139 AUD 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

  • Wi-Fi availability

    50 properties include access to Wi-Fi

Destinations to explore

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  4. Greene County
  5. Windham
  6. Pet-friendly rentals