Pet-friendly vacation 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

Guest favorite

Home in Cavendish

4.94 out of 5 average rating, 78 reviews

Close to Okemo, 25 Acre Mountain Playground

PatriciaRating, 5 stars2 months ago
Wonderful place. Cozy, clean, peaceful, kitchen had everything you could ask for, comfortable beds. I would definitely recommend this place. Sheryl was very responsive. Hope to go back next year.
Superhost

Home in Killington

4.83 out of 5 average rating, 84 reviews

Killington Racquetball House

CoreyRating, 5 stars9 months ago
We had a great stay at the racquetball house. It’s even better and bigger than it appears in pictures. Couldn’t be closer to the access road with all of the skiing and amenities. We were there during a snow storm (2+ feet) and the driveway was plowed routinely and there were shovels/sand on the property ready for use. Owner was very generous in supplying a welcome basket. Easy in/out with keypad entry. I highly recommend the property for a great time in Killington.
Superhost

Home in Bridgewater

4.77 out of 5 average rating, 115 reviews

The Buddah House

AshleiRating, 5 stars2 weeks ago
This location was incredibly well stocked and incredibly gorgeous. The view from the back deck simply cannot be beat.
Guest favorite

Home in Woodstock

4.98 out of 5 average rating, 41 reviews

Sweet retreat in South Woodstock near GMHA

LisaRating, 5 stars3 months ago
Bright, comfortable, well-appointed house in a beautiful setting! Town and outdoor activities easily accessible! Loved our stay!
Superhost

Home in Pittsfield

4.84 out of 5 average rating, 70 reviews

Green Mountain/Killington Getaway

WendyRating, 5 stars2 months ago
The house was everything we needed it to be - peaceful and quiet in the Kingdom of the North in Vermont. The beds were super comfortable. The Leaves from the deck with a cup of coffee were a perfect way to start the day. We were within reasonable driving distance to everything we needed to get to. We will totally be back!! Thank you Paula!!
Guest favorite

Home in Londonderry

4.97 out of 5 average rating, 130 reviews

Wild Blossom Farmhouse - a lovely family getaway

AlexRating, 5 stars2 months ago
Very cute, cozy house in rural Vermont. Grocery store close by, kitchen stocked with everything you’d need to cook, and the yard is perfect (kids loved the tree house and fire pit! House is centrally located in southern Vermont and within an hours drive to Rutland, Manchester, Springfield, and Brattleboro. Chester is also worth a stop!
Superhost

Home in Bridgewater

4.84 out of 5 average rating, 114 reviews

Blueberry Hill Escape Pet Friendly HotTub Fire pit

ArianaRating, 5 stars3 weeks ago
Amazing stay. Great views. Remote enough but still close to towns. The house was very cozy inside with the fireplace and comfortable couch, and cozy outside with the great hot tub and pretty fire pit area. Only thing was that a lot of dishware in the kitchen were still dirty with dried food on it. Overall, really great stay and definitely worth a visit. Host was very communicative and helpful when we had questions during our visit.
Guest favorite

Home in Cavendish

4.84 out of 5 average rating, 142 reviews

Okemo-Ludlow, fireplace, hottub, sleeps 13

KiaraRating, 5 stars2 weeks ago
Our stay was awesome! We felt right at home. There were games for us to play and a cozy fireplace which were our favorite things we enjoyed. It was a perfect home to enjoy a nice weekend getaway together as a family!

Pet-friendly home rentals with a pool

Guest favorite

Home in Mendon

4.88 out of 5 average rating, 231 reviews

Ranch at Mendon Mt Orchards

PatrickRating, 5 stars6 days ago
Great location and property! Close to Killington (~20 min) with plenty of grocery stores and restaurants nearby. But the best part of our stay was the fantastic apple pie!!
Guest favorite

Home in Killington

4.98 out of 5 average rating, 124 reviews

SugarBear Pool, Hot Tub, 2 En Suite BRs, FirePlace

AngiaRating, 5 stars6 days ago
The place is clean and comfy and it is close to the slopes. Dan&Holly are responsive and friendly. I would love to go back soon.
Superhost

Home in Landgrove

4.75 out of 5 average rating, 28 reviews

Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths!

JadeRating, 5 stars3 months ago
Beautiful home and cottage with stunning surrounding scenery. Came here on a getaway from NYC and it was exactly what we needed. The jumbo jet bathtubs and fireplaces give this cozy space a luxurious feel, and the kitchen was downright impressive (brought a chef friend for us who was very impressed). Had to call the host with some questions when I arrived but they were answered immediately. Very clear check in instructions from the host and once we pulled up to the property it was very seamless to get inside and begin unpacking. We had an stress-free stay and checkout thanks to the intention with which these hosts set up their space and rental process. We will be coming back next year!
Guest favorite

Townhouse in Killington

4.96 out of 5 average rating, 47 reviews

SKI IN and SKI OUT at Sunrise

BrendanRating, 5 stars9 months ago
Radha’s condo was perfect for my annual college buddies reunion killington ski trip. We were very impressed and she was the most gracious host we’ve ever had bar none. Communicative, detailed and caring. The search is over, we’ll be staying here until our skiing days are over.
Superhost

Townhouse in Killington

4.68 out of 5 average rating, 71 reviews

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

JohnRating, 5 stars2 months ago
what a beautiful home in the mountains of Vermont.
Superhost

Condo in Killington

4.9 out of 5 average rating, 240 reviews

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

RitaRating, 5 stars1 month ago
Great, comfortable place to stay. Place was beautiful. Th David was quick to respond to my questions, always checked in to make sure everything was satisfactory and up to standards.
Guest favorite

Home in Chittenden

4.91 out of 5 average rating, 87 reviews

Comfortable, relaxing large country home

KarenRating, 5 stars4 months ago
Beautiful home, great location Danielle was very responsive We had a very enjoyable vacation
Guest favorite

Apartment in Clarendon

4.92 out of 5 average rating, 146 reviews

Vermont Horse Farm

ChristineRating, 5 stars3 months ago
One word that comes to mind is "Soul-Full!" Waking up here, felt like heaven on earth. The breathtaking views were filled with nature and animals!

Private, pet-friendly home rentals

Guest favorite

Home in Londonderry

4.97 out of 5 average rating, 66 reviews

Londonderry Vermont Vacation Lodge

NunzioRating, 5 stars2 months ago
The house is in a perfectl location: immerse in the green but just 5 Min drive from grocery stores and restaurants. The house is cozy, with many options to spend nice time: board games, videogames, pool/hockey table, barbecue, 2 indoor fireplaces and 1 outdoor firepit. Ideal for pets as there is a big garden. Mary is a great host, very responsive and always nice. We had a great time and I strongly recommend this place.
Guest favorite

Guest suite in Lebanon

4.91 out of 5 average rating, 101 reviews

Convenient and chic private suite with 2 bedrooms!

GretchenRating, 5 stars3 weeks ago
Great stay! Had everything we needed, beautifully decorated, very comfortable beds. It was walking distance to the relatives we were visiting for Thanksgiving, so location was perfect for us. We didn't need a full kitchen, so this place worked well, but the kitchenette with fridge and sink and dishes was great to have for breakfasts, coffee, etc.
Guest favorite

Barn in Woodstock

5 out of 5 average rating, 11 reviews

Green Mountain retreat: The Skyland Duplex

JoshRating, 5 stars2 months ago
This is the second time we stayed at Jeffrey's place. We love the location and Jeffrey makes it easy.
Guest favorite

Cabin in Mount Holly

4.97 out of 5 average rating, 225 reviews

Private Cabin/PetsOK/Minutes to Okemo/AC/Fast Wifi

YosraRating, 5 stars1 month ago
I absolutely loved this place, it was everything I needed for this weekend. It was cozy, peaceful and very clean. Darrin was super responsive and has an instruction book with lot of food and activities recommendations. I wish I could stay longer but I will definitely go back!
Guest favorite

Cabin in West Windsor

4.97 out of 5 average rating, 242 reviews

Sunset Cabin - your private romantic hideaway

SallyRating, 5 stars1 month ago
We *LOVED* our time in the Cabin in the Woods. Sondra and Daniel were very responsive in responding to questions about the property. The layout of the cabin was sensible and comfortable and the bed was very comfortable. We would love to go back! The cabin location is perfect and is sweet and romantic. Sondra and Daniel have thought through every detail. Thanks again for a splendid vacation spot!
Guest favorite

Cottage in Londonderry

4.85 out of 5 average rating, 53 reviews

Vermont Country Cottage (Near Village)

AgnesRating, 5 stars2 months ago
Loved our stay at the cottage! Perfect for a family of 3 + the puppy. Quiet and cozy, Rachel was super responsive and helpful. The place is at the same time in the middle of nowhere (in a perfect way) and close to a lot of spots to visit (nature, hikes, farms, route 100). Would definitely like to visit again!
Guest favorite

Apartment in Bridgewater

4.93 out of 5 average rating, 76 reviews

Nana's House

JanetRating, 5 stars2 months ago
Ellen‘s home was a wonderful place to stay and we wish we could’ve stayed longer! It was out of town a little ways on a beautiful quiet road but very easy to get to. The house was roomy and very comfortable. The kitchen was very well supplied and we were able to do some cooking with the supplies that were already there. That was very much appreciated. Ellen was available when questions came up and she also provided information on local places to go. All in all it was a wonderful Airbnb.
Guest favorite

Campsite in Shrewsbury

5 out of 5 average rating, 15 reviews

Private Campsite 37 Acres (Pet-Friendly!)

AnnRating, 5 stars2 months ago
This was a lovely 3 min hike-in hike-out very private excellent campsite. All the amenities Youn described matched and he is wonderfully responsive and generous to help carry our tent and things with his atv. He is an exceptional host :)

Destinations to explore