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Pet-friendly holiday rentals in Windsor County

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Windsor County

Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

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Home in Ludlow

4.87 out of 5 average rating, 137 reviews

1st floor, Okemo contemporary country 3 BR 2 BA

Family-friendly, pet-friendly, clean, comfortable, contemporary country ski cabin on Okema shuttle buss route in Ludlow, VT, a few minutes from mountain. Very easy access to outdoor activities: skiing, hiking, lakes, boating, hunting, snowmobiling, fly-fishing. Updated, comfortable, light filled ambiance. Great location, 10 minute walk to downtown (2 minute drive). Great for groups, couples, families. Recently renovated. New butcher block counter-tops and island, all new kitchen, new bathrooms.

Guest favourite

Tiny home in Clarendon

4.9 out of 5 average rating, 215 reviews

Secluded tiny house resort - DOG FRIENDLY

New tiny house, never lived in, but made to be comfortable. All amenities included: Air-condition, heat, WiFi, TV with cable, shower, tub, dry toilet, small full loft bed and full size couch futon, fire pit, river for swimming or fishing right out the door, small refrigerator, microwave, hot plate, toaster.ear three ski resorts (Killington, Okemo, Pico), Appalachian Long Trail two miles away, swinging bridge on trail beginning, White Rock hiking, lakes near for paddle boarding. Hot tub shared.

Guest favourite

Home in Mount Holly

4.92 out of 5 average rating, 115 reviews

Modern Farmhouse - 2 kings, minutes to Okemo!

Newly renovated property surrounded by picturesque mountains with views from every bedroom. Relax in our cozy 4 bedroom, 2 bath home, large enough for your whole family to come together. Sleeps 11. Dog friendly. Arcade games and firepit. Large yard. Excellent place to work remotely. Enjoy hiking, fishing, biking, kayaking, skiing & golf nearby. Explore nearby Ludlow, Woodstock, Manchester and Weston. Okemo & Jackson Gore resorts are less than 10 minutes away. Killington Mtn 30 min drive.

Guest favourite

Guest suite in Hartford

4.91 out of 5 average rating, 373 reviews

Sunny Side Airbnb (dog friendly)

Sunny Side Airbnb is located on a secluded 10+ acre property with plenty of outdoor space for dogs to run around and a short hiking trail with views. The Airbnb is located on the farther end of the house with a deck overlooking garden views, a fire pit, and an open field. Convenient location near shops and restaurants. Just over a mile from I-89 off Rt 4 in Quechee, Vt. A short drive to WRJ and W Lebanon, NH, 9.1 miles to Woodstock, VT, 11 miles to Hanover, NH, and 13.4 miles to DHMC.

Guest favourite

Flat in Royalton

4.98 out of 5 average rating, 178 reviews

Quiet Vermont Get Away

This space is ideal for a family or friends. This is a dog-friendly apartment located above our garage with stairs. Just 5 min off Exit 3 on I89. Full kitchen to make family meals. Cozy living/dining space. Come and stay for skiing, snowmobiling, hiking, biking, golf, local breweries and so much more depending on the season. Close to Vt Law School. 35-40 minutes to Killington, Pico, Stowe, Bolton and Sugarbush. 20 minutes to Quechee and Woodstock. Sleeps 5/6 with using a bunk bed.

Guest favourite

Apartment in Killington

4.96 out of 5 average rating, 116 reviews

Ski On/Ski Off - Dog-Friendly Mountainside Retreat

Experience year-round adventure at Sunrise Village at Killington, offering a true ski-in, ski-out location just steps from the Sun Dog Trail and Sunrise Village Triple Lift (488 ft away). After a day of skiing or exploring, unwind by the cozy electric fireplace. Outdoor enthusiasts will love the hiking, mountain biking, kayaking, and golfing nearby. The indoor sports complex, featuring a pool, hot tub, and gym, is just a short walk away. Come enjoy and make unforgettable memories!

Flat in Rutland

5 out of 5 average rating, 4 reviews

Mimi's Place - pets welcome!

Escape to this charming 1BR/1BA apartment in central Rutland Town! Perfectly located for outdoor adventures - it's a stone’s throw from skiing, hiking, and the vibrant Rutland City's scene. Enjoy a full kitchen, cozy living area, and the convenience of an in-unit washer/dryer. Bring your furry friends along! Whether you’re hitting the slopes or exploring local shops and dining, this is your ideal retreat for relaxation and adventure. Book now and experience the best of Vermont!

Townhouse in Killington

4.87 out of 5 average rating, 254 reviews

Renovated 2bd/2.5bath/Den + Pool Access (pets ok)

Recently updated ski condo - modern kitchen appliances and new furniture. Minutes away from Killington Ski base. Drive there or use a paid bus service, steps away from the condo. Part of the luxurious Woods Spa Resort and stay includes use of resort amenities including gym, pool, steam/sauna and hot tub. Spa service available but not included in fee (please check for open hours) Warm, cozy and welcoming-custom built for ski lovers to relax after a long day on the mountains.

Guest favourite

Cabin in Killington

4.96 out of 5 average rating, 27 reviews

Luxury Ski Cabin, 2 bedrooms, den & 3 bathrooms

This luxury residence on Killington Mountain is a 400-yard walk to the closest ski trail or a short 5-minute drive to the principal ski bases, along with the resort's array of bars, eateries, and retail outlets. It features an indoor jacuzzi, a spacious living/kitchen area bathed in natural light. A variety of summer pursuits, including golf, hiking, mountain biking, and canoeing, are conveniently accessible within minutes from the home. Plus, the property welcomes pets.

Guest favourite

Home in Plymouth

4.95 out of 5 average rating, 245 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

Welcome to one of the most unique "retreats" in Vermont! Located on top of a private mountain, beautiful 100 mile views of the White Mountains. Ideally located between Killington (7 miles) and Okemo resorts, near Woodstock and Long Trail Brewery. Relax in the Jacuzzi hot tub while enjoying the views and stars. Private hiking trails, waterfalls, with trail maps! 7 miles to the beach at Camp Plymouth State Park. Secluded yet close to everything. New ventilation system.

Guest favourite

Cottage in Hartland

4.93 out of 5 average rating, 111 reviews

Adorable Dog Friendly Cottage w/FIOS

Bright and clean 2-story cottage on a shared 20-acre sanctuary. With a view of the hills, flanked by woods and open pastures, the cottage includes 2 bedrooms (1 up w/Queen, 1 down w/full bed, 1 bathroom (2nd floor - shower only), kitchen/living/dining area (2nd floor), and laundry. 10% discount for guests using only one bedroom (cannot be combined with other discounts). See details in property description. Pet sitting available - please inquire for rates & info.

Home in Mendon

4.92 out of 5 average rating, 12 reviews

Cute & cozy 2 bedroom home.

Updated 2 bedroom home in Mendon, VT. Convenient location; 6 minutes from Pico, 10 minutes from Rutland, and 13 minutes to Killington. I’m sharing my place with others so they can vacation with their dogs and children. (While I like cats, we're allergic). We recommend snow tires, or 4-wheel drive to get up the small hill to the house. Finally, be careful as it is on the main highway. If you're looking for comfort & convenience, this is it.

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Flats

Convenient locations with everyday essentials

Popular amenities for Windsor County pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Home in Ludlow

4.88 out of 5 average rating, 43 reviews

Hillside Haven Victorian! Hot Tub Firepit 5m-Okemo

Guest favourite

Home in Woodstock

4.89 out of 5 average rating, 53 reviews

Beautiful Village of Woodstock home near the Inn

Guest favourite

Home in Cavendish

4.94 out of 5 average rating, 81 reviews

Close to Okemo, 25 Acre Mountain Playground

Home in Bridgewater

4.76 out of 5 average rating, 119 reviews

The Buddah House

Guest favourite

Home in Woodstock

4.98 out of 5 average rating, 42 reviews

Sweet retreat in South Woodstock near GMHA

Home in Pittsfield

4.84 out of 5 average rating, 76 reviews

Green Mountain/Killington Getaway

Guest favourite

Home in Londonderry

4.97 out of 5 average rating, 137 reviews

Wild Blossom Farmhouse - a lovely family getaway

Guest favourite

Home in Bridgewater

4.85 out of 5 average rating, 119 reviews

Blueberry Hill Escape Pet Friendly HotTub Fire pit

Pet-friendly home rentals with a pool

Guest favourite

Home in Mendon

4.88 out of 5 average rating, 237 reviews

Ranch at Mendon Mt Orchards

Guest favourite

Home in Killington

4.98 out of 5 average rating, 129 reviews

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

Guest favourite

Home in Rutland

5 out of 5 average rating, 5 reviews

Entire Home, Near Slopes, Hot Tub, EV Charger

Guest favourite

Apartment in Killington

5 out of 5 average rating, 6 reviews

Stunning Slopeside Condo at Mountain Green: 1BR

Home in Landgrove

4.71 out of 5 average rating, 7 reviews

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

Apartment in Killington

4.89 out of 5 average rating, 245 reviews

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

Guest favourite

Home in Chittenden

4.91 out of 5 average rating, 88 reviews

Comfortable, relaxing large country home

Guest favourite

Apartment in Killington

4.97 out of 5 average rating, 143 reviews

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!

Private, pet-friendly home rentals

Guest favourite

Guest suite in Lebanon

4.91 out of 5 average rating, 105 reviews

Convenient and chic private suite with 2 bedrooms!

Home in Ludlow

4.9 out of 5 average rating, 69 reviews

Updated 6BR Home 4 min to Okemo w fenced in yard!

Guest favourite

Barn in Woodstock

5 out of 5 average rating, 11 reviews

Green Mountain retreat: The Skyland Duplex

Guest favourite

Cabin in West Windsor

4.97 out of 5 average rating, 242 reviews

Sunset Cabin - your private romantic hideaway

Guest favourite

Cottage in Londonderry

4.85 out of 5 average rating, 61 reviews

Vermont Country Cottage (Near Village)

Guest favourite

Cabin in Hartland

4.95 out of 5 average rating, 22 reviews

Private Log Cabin near Quechee

Guest favourite

Flat in Bridgewater

4.94 out of 5 average rating, 81 reviews

Nana's House

Guest favourite

Campsite in Shrewsbury

5 out of 5 average rating, 15 reviews

Private Campsite 37 Acres (Pet-Friendly!)

Destinations to explore