Pet-friendly holiday rentals in Windsor County

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Windsor County pet-friendly home rentals

Pet-friendly house rentals

Top guest favourite
Home in Plymouth
4.96 out of 5 average rating, 52 reviews

Killington - Woodstock: Private Oasis w/ Hot-Tub

MichaelRating, 5 stars1 month ago
This home was perfect for our family including two young children. It was not too big, yet had plenty of space. sitting outside by the fire listing to the river was peaceful. Hot tub was an additional bonus. Showers were nice, mattresses were comfortable. Just a great place.
Guest favourite
Home in Plymouth
5 out of 5 average rating, 10 reviews

Escape to VT for hiking, biking, golfing, swimming

MorganRating, 5 stars2 months ago
This house is perfect for a family ski weekend getaway! Beautifully tucked away on a quiet road yet a super short drive from lots to do, skiing, etc. Beautiful and comfortable interior, our son and dogs were right at home too. Jeanne really thought of everything with the welcome basket! We have added this one to our favorites 😊👏🏻
Guest favourite
Home in Hartford
4.87 out of 5 average rating, 183 reviews

Beautiful Historic 1909 Library with a Fireplace

AmyRating, 5 stars2 months ago
We love the library! Stayed here 4 times now. It's a special place filled with history, in a beautiful area with quite a bit to do nearby. The fireplace is lovely and cozy, the bed is super comfortable, the kitchenette has everything you need, and we love that it's dog friendly too. There were even some toys for our pup to enjoy during our stay. Highly recommend for a unique and special getaway!
Guest favourite
Home in Rochester
4.97 out of 5 average rating, 144 reviews

Modern Farmhouse on 25 Acres - Superb Views

BrandonRating, 5 stars1 month ago
We had a quiet stay at the Farmhouse. Very peaceful and quiet location. Lots of space for our dog to roam. The house is very nice and clean. We enjoyed having coffee and looking out across the fields, reading, and cooking. It’s near the small village of Rochester with a few restaurants and otherwise we explored neighboring towns like Middlebury, Waitsfield, Stowe, and Montpelier.
Guest favourite
Home in Londonderry
4.99 out of 5 average rating, 135 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

GeorgiaRating, 5 stars1 day ago
We loved our stay here!! It was the perfect getaway for a long weekend. The property is beautiful and private but close to anything that you might need. The kitchen was super well stocked, beds were comfy, and we really appreciated the firewood supply. Nikki & Topher were great hosts - extremely responsive to all questions we had and proactive about check in/check out instructions. Would definitely come back!
Superhost
Home in Bridgewater
4.86 out of 5 average rating, 128 reviews

Blueberry Hill Escape | Pet Friendly | HotTub | Fi

AshleyRating, 5 stars2 weeks ago
We enjoyed our time at Chris's house. The house has everything you will need including coffee and kcups. We enjoyed the fireplace in the living room and the hot tub. The view from the hot tub was great! We didnt get to use the fire pit because it was raining the whole time but it looks like an awesome hang out area. Communication with Chris was great. We recommend a stay here and would definitely return in the future!
Guest favourite
Home in Rochester
4.91 out of 5 average rating, 295 reviews

Mountain Home ready for you!

ShannaRating, 5 stars3 months ago
My friends and I had a great stay at Jennifer’s home. We wanted a winter escape from the city and got exactly that! Jennifer was super friendly and communicative and left no questions unanswered. The home was so welcoming and cozy and had everything we needed for a fun weekend.
Guest favourite
Home in Reading
4.89 out of 5 average rating, 140 reviews

Greystone 1830

AlexandraRating, 5 stars1 week ago
Very special place - we loved it and hope to come back soon! It is everything wonderful about a stone home with a modernized kitchen and living areas. So cozy and beautiful!

Pet-friendly home rentals with a pool

Top guest favourite
Home in Mendon
4.89 out of 5 average rating, 247 reviews

Ranch at Mendon Mt Orchards

RobinRating, 5 stars3 weeks ago
We enjoyed our stay. we felt at home. very spacious and cozy. this house has everything you need for your stay. Very close to Rutland. The fresh baked apple pie was a bonus. It was so delicious. Everything was perfect for us! Thank you! We will definitely be back again!
Top guest favourite
Home in Killington
4.99 out of 5 average rating, 135 reviews

SugarBear- Pool, AC, Sauna, Gym, Tennis!

JennRating, 5 stars1 month ago
Dan & Holly are amazing hosts. They provided everything needed to make our week great. They left dining recommendations and all of the information we needed for the property. It was the perfect space for our family. The on-site amenities were great. The pool space was super clean and the staff was amazing. The property is well maintained and we had everything we needed to feel at home. We would definitely recommend this property to friends and family. Downtown Rutland was a short drive, and there was so much to see just minutes from the property. Dan & Holly are extremely responsive and truly think of everything. We had no questions and checking in and out was a breeze because they are so thorough. It was a wonderful experience from start to finish.
Guest favourite
Home in Hartford
5 out of 5 average rating, 26 reviews

The Fairway House - Premier Golf Course 3 BR Home

KarenRating, 5 stars3 months ago
Jenna' place was great! Nice open and comfy feel to the living room and dining room. The kitchen was well stocked and really clean. The beds were comfortable and the bedrooms were cozy. I would definitely recommend Jenna's home.
Superhost
Flat in Mendon
4.91 out of 5 average rating, 58 reviews

Charming Killington get away with pool, sleeps 4

JackRating, 5 stars2 months ago
Great place to stay for the weekend! Super close to Pico and Kilington mountains. Would highly recommend!
Superhost
Townhouse in Killington
4.86 out of 5 average rating, 99 reviews

SKI ON/OFF Spruce Glen C | AC | Sauna| Fireplace

LynneRating, 5 stars3 weeks ago
Ryan communication was impeccable. He communicated within two hours. He accommodated my husband myself and my two dogs. The renter was clean and outside area was fun to explore and have adventures in the woods. The river outback with the landscaping with his natural habitat was a plus. I would truly recommend this to anyone all seasons
Guest favourite
Home in Hartford
4.95 out of 5 average rating, 19 reviews

Farmhouse, Fireplace & Office | Wheelock Hideaway

HeidiRating, 5 stars8 months ago
Very quiet and cozy. Comfortable beds. Lots of room for everyone.
Superhost
Apartment in Killington
4.89 out of 5 average rating, 245 reviews

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

IanRating, 5 stars4 months ago
The place was great, clean, nice bathrooms. The oven seemed like it wouldn't go up to temperature at one point so I messaged the host and they responded right away to get the maintenance folks over. But it turned out that it was just set to Celsius and I was able to look up how to change it online (Hold down the broil button!). There were PLENTY of towels/linens which was nice.
Superhost
Home in Hartford
4.88 out of 5 average rating, 16 reviews

Elegance Meets Rustic Charm: Vermont 3-Bed Retreat

JulieRating, 5 stars10 months ago
Our stay was a family group of six adults and my two grandchildren who are ages seven and eight. We decided to spend the week in Queechee with the second weekend being a family wedding. We loved the peace and comfort of a private home and especially enjoyed the backyard deck playing cornhole and barbecuing. Being tucked away up off of Willard Road was worth the very slight inconvenience of an extra five minutes or so drive to get back into Queechee proper. The owners were very responsive to any concerns or questions I had about the property during our stay. The home is spacious and lovely with attractive and comfortable furnishings. The kitchen is open to the main level and very well equipped for cooking all your meals if you choose. our granddaughters enjoyed the games that are stashed away in the front closet Highly recommended!

Private, pet-friendly home rentals

Guest favourite
Cabin in Plymouth
4.99 out of 5 average rating, 112 reviews

~The ClubHaus~

KatelynRating, 5 stars1 week ago
The clubhaus was absolutely incredible for our little family getaway. It was clean, well stocked, and conveniently located close to everything we wanted to do! Vermont has always been a special place to us, but this house made our getaway that much better! We will definitely be back.
Guest favourite
Cabin in Ludlow
4.96 out of 5 average rating, 100 reviews

Cozy Log Cabin with Hot Tub | 1/2 mile to Okemo

VirginiaRating, 5 stars3 months ago
The perfect place for our family’s ski trip. The cabin is exactly what you picture for a winter VT trip. Charming log cabin with a wood burning stove, but with all the modern comforts. We were only 5 minutes from Okemo and the hot tub was amazing after long ski days. Locked ski locker on the porch was convenient. Great kitchen so we could cook breakfast and hit the slopes early. The host gave clear instructions and lots of helpful recommendations - very friendly and quick to respond. Fire wood and log starters made the cabin cozy at night. Despite all the snow, the driveway was well plowed. It’s a quiet dead end road without traffic. We will definitely be back!
Guest favourite
Cabin in Fairlee
4.95 out of 5 average rating, 140 reviews

Fairlee Log Cabin

JackieRating, 5 stars2 weeks ago
I was so happy staying at Brooke's cabin. There was so much to be happy with, I'll do my best to list them all! 1. Brooke was well responsive - I ran into 2 small problems and she was proactive and fixed them fast. 2. The whole place is super dog friendly! I am often worried where my dog is and isn't allowed in Airbnbs, not here! Brooke even left out dog toys, bowls,and beds as well! 3. All linens were cleaned, even the throw blankets! 4. the trail in the backyard is a nice touch! unfortunately I didn't have many non rainy days so only got to explore some of it, but it is a different world back there! 5. The kitchen is incredible: 3 different ways to make coffee along with a frother and a grinder! the pots and pans are chef's choice! and the knives aren't dull! I was well equipped to cook and theres plenty of space to do so. 6. the bathtub is a godsend! 7. incredible library! I cannot recommend this place enough!
Superhost
Chalet in Stockbridge
4.84 out of 5 average rating, 158 reviews

Vermont Chalet

JugoRating, 5 stars3 weeks ago
Great little cabin. My wife and I had an amazing time. We really enjoyed both decks and the fire pit by the pond. We will be back for sure. It’s located in between some great Vermont towns.
Guest favourite
Townhouse in Fairlee
4.99 out of 5 average rating, 256 reviews

Garden Retreat, Lake Fairlee, Dartmouth & Ski-way

AndrewRating, 5 stars2 days ago
I was fortunate enough to spend a very life changing trip here. Words can’t express my gratitude.❤️🥹🙏
Guest favourite
Cabin in Mount Holly
4.92 out of 5 average rating, 151 reviews

Camp Mt. Holly - modern cabin by Okemo & Ludlow

AngelaRating, 5 stars1 month ago
Wow! This cabin literally felt like a slice of heaven in the Green Mountains. While being close to town, and easy enough to find and access, we were secluded and nestled amongst the trees and a flowing creek. We felt safe and secure. The wifi was fast and we were able to make calls and send texts. We were thrilled to find a Vermont Country Store just ten minutes down the street, and would highly recommend going! Shaw's grocery store in Ludlow was also surprisingly good, and we enjoyed many unexpected finds. This is notable as many of the businesses in Ludlow appear to be seasonal, and you may end up cooking back at the cabin. This is thankfully easily accomplished as the kitchen is pretty large, with ample cabinet space and new stainless appliances. The cabin had a nice outdoor fire pit and indoor wood stove, which both made for a wonderful ambiance. Also, of note, the water out of the sink was delicious, and cold. No need to buy bottled water while you are staying. Thank you!
Guest favourite
Guest house in Cavendish
4.95 out of 5 average rating, 151 reviews

Cozy Cavendish Bunkhouse

AdamRating, 5 stars3 weeks ago
Great space and extremely comfortable. Easy and pleasant communication with the hosts. Would definitely stay again. Make sure you stop at Singletons General Store, it’s amazing. Short drive to the town of Ludlow, Buttermilk Falls and other areas.
Guest favourite
Barn in Bridgewater
5 out of 5 average rating, 78 reviews

Breathtaking Riverfront Farmhouse w/Mountain Views

MargaretRating, 5 stars1 month ago
The house is beautifully decorated and immaculately clean. It is well equipped very peaceful to view the river flowing right out the large windows of the kitchen/dining/living room area and also from the master bedroom. The only negative is that there is street noise because it is close to the road, but they told us about that and we got used to it. The host was very easy to work with and I highly recommend this rental to others. We hope to come again.

Destinations to explore