Pet-friendly holiday rentals in Chesterfield

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Chesterfield

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

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Top guest favourite
A cottage is seen perched on a grassy bank, overlooking a river. Tall trees frame the scene, providing a natural backdrop. The water's surface reflects the surroundings, while a hint of light is visible from the cottage window, suggesting warmth inside.
Home in Willsboro
4.97 out of 5 average rating, 115 reviews

"Beau Overlook" Enjoy 2 states from 1 great spot!

Come enjoy LOGISTICS to the Green Mountains of VT & the heart of the DACKS in one sweet spot. "Beau Overlook Cottage" perched high on the banks of the BOQUET RIVER, with sweet sounds of water tumbling over river rocks below. This home is situated 2 miles north of the Lake Champlain ~ Boquet River Delta. The beautiful LAKE scene at the sandbar of the delta must be seen to be appreciated. This relaxing sanctuary will provide an upscale and sophisticated home, whose logistics cannot be beat!

Top guest favourite
Aerial view of the vibrant Vermont landscape, showcasing rolling hills adorned with a diverse palette of fall foliage. The rustic barn sits among expansive fields, framed by trees displaying bright autumn colors, with distant mountains in the background under a partly cloudy sky.
Barn in Morristown
4.97 out of 5 average rating, 183 reviews

200 acre Stowe area Bunkhouse.

Hello and welcome to our Red Road Farm 'Bunkhouse' -- We're so happy to host you! Sitting on our 200 acre estate this authentic barn offers our guests a chance to relax in the beautiful rolling hills of Vermont. Access the vast majority of our historic Stowe area land -- from our apple orchards to our extensive walking paths in fields and woodland. We hope that you can experience such fun and quiet time in our cozy, western-style bunk room. Located only a 10 minute drive from downtown Stowe.

Top guest favourite
A rustic cabin is framed by lush greenery, surrounded by a manicured garden. An outdoor picnic table is situated on the grass, complemented by a patio umbrella and flower pots. The entrance features a welcoming door, adding charm to the serene woodland setting.
Place to stay in Peru
4.92 out of 5 average rating, 173 reviews

The Brookside Cabin

Our Cabin is nestled in the woods of the Adirondack Mountains. The Cabin is behind our family home. We are on a country road close to two towns. Our area offers many amenities such as fishing, hiking, boating, golf, hunting , wine tasting, leaf peeping. The cabin is heated by a wood stove and is the only heat source. “Wood Stove will injure a small child. Fast moving water in brook. Children 7 and up is ok with pre approval. The outside shower is heated, hot water available mid April -Nov.

Top guest favourite
A queen-sized bed is positioned against a wooden wall with slanted ceilings. Large triangular windows provide views of the surrounding forest and mountains, allowing natural light to fill the space.
Home in Keene
4.97 out of 5 average rating, 189 reviews

Ascent House | Keene

A unique retreat meticulously crafted for resting and recharging after exploring in our beautiful Adirondack Wilderness. Flooded with natural light, every room offers calming frames of nature. Watch the sun peak through the forest and rise over the mountains through expansive windows. Ascend the levels of the house, each revealing more landscape. Experience a designer woodfired traditional Finnish sauna & totally recharge while embracing our harsh Adirondack weather. We hope you love it here.

Top guest favourite
Two white Adirondack chairs are positioned on a grassy area overlooking the Ausable River. The river flows gently under a cloudy sky, surrounded by trees displaying vibrant autumn foliage in shades of orange and green.
Flat in Clintonville
4.87 out of 5 average rating, 258 reviews

Cozy Rustic Two Story Apartment

Located on the famous Ausable River. 20 minutes to Whifeface Mountiain or Plattsburgh and the Plattsburgh Airport. 10 minutes from the AuSable Chasm. This can be your resting point after spending a fun filled day in the Adirondacks. At this location you have the opportunity to walk down to the river to fish, paint or just sit and relax in the beautiful surroundings. You’re welcome to have an evening fire in our outdoors fire pit that can be set up for beautiful scenic views of the river.

Top guest favourite
An aerial view of a charming chalet surrounded by lush greenery. A spacious wrap-around deck features outdoor seating and a red umbrella, offering a cozy area for relaxation. Sunlight filters through the trees, enhancing the natural setting.
Chalet in Jay
4.95 out of 5 average rating, 242 reviews

Adirondack Timberwolf Cabin

Cozy Mountain Chalet in Jay, NY on beautiful Glen Road. Only .7 miles to the Jay Covered Bridge, 3 miles to the Jay Mountain summit trail head, 7 miles to Whiteface Mountain, and 16 miles to Lake Placid. Keene and Keene Valley trail heads are only minutes away. The cabin has 3 acres of wooded property with a front driveway as well as a back access drivweway which is nice to walk. There is Satellite TV and wifi. There is good cell coverage. World Class Fishing, Ausable Rivers are close

Top guest favourite
Two red Adirondack chairs are positioned on a wooden terrace, overlooking a vast landscape of green trees and rolling mountains in the distance. A rustic wood table stands between the chairs, providing a natural focal point amidst the serene outdoor setting.
Guest suite in Elizabethtown
4.96 out of 5 average rating, 363 reviews

Adirondack Mountain View Retreat

30 minutes from Lake Placid, this unique mountain-view space features a comfortable, secluded 3-room guest suite opening out to a private covered terrace showcasing unmatched views of the Adirondack Peaks. A pet-friendly space ideal for outdoor enthusiasts, a couple's getaway, those working from home, or those just looking to have a peaceful retreat in the countryside - come enjoy our 25 acres of fields, forests, ponds and private riverbank. Also available: airbnb.com/h/adkretreat

Top guest favourite
Two guests are seen enjoying drinks while seated in Adirondack chairs around a fire pit. The modern A-Frame cabin is highlighted in the background, with large windows and an inviting outdoor atmosphere enhanced by warm, ambient lighting.
Cabin in Jay
4.99 out of 5 average rating, 142 reviews

Modern Hot Tub Sauna A-Frame near Whiteface

Welcome to the Black Pine Lodge! Nestled in the heart of the Adirondacks, this modern A-Frame 3 bed/3 bath cabin can accommodate up to 8 guests. Amenities: Hot Tub Panoramic Barrel Sauna Pool Table Helix mattresses Fire Pit Kayaks Surrounded by beautiful trees this place feels tranquil and has lots of hiking trails outside the front door. Explore other hikes, rivers & dining in neighboring Wilmington, Keene and Lake Placid. End the day relaxing at this lodge that caters to all.

Superhost
The living area features a comfortable gray sofa adorned with patterned cushions, accompanied by a light-colored armchair and a wooden coffee table. Natural light enters through two windows, enhancing the cozy ambiance. Soft curtains frame the windows, and artwork is displayed on the walls.
Flat in Shelburne
4.85 out of 5 average rating, 110 reviews

Cozy 1BD in Historic Shelburne

Tucked in the heart of historic downtown Shelburne, The Pink House is the perfect place to soak in Vermont’s small-town charm while staying just steps away from coffee shops, boutiques, wine bars, and some of the best local eats. Whether you’re here to explore Shelburne Farms, sip your way through vineyards and breweries, or take a short drive to Burlington, this bright and effortlessly cozy one-bedroom apartment is designed for a relaxing stay with all the essentials you need.

Guest favourite
A scenic view of rolling hills and mountains is captured at sunset, with soft hues of orange and pink in the sky. In the foreground, sheep graze peacefully on vibrant green grass, framed by a rustic structure and a hint of electrified fence.
Tiny home in Jay
4.94 out of 5 average rating, 504 reviews

The Shepherd's Crook at Blue Pepper Farm

Tucked in the woods on our working sheep farm, our off-grid tiny house is the perfect escape and stepping stone into the Adirondack mountains for hiking, skiing, and snowshoeing. Enjoy the coziness of the Crook between forays into our north country wilderness! What you will find: adventure, peace, quiet, woodstove, candles, down blanket, fire pit, privacy, composting outhouse, firewood for sale. **Please note there is NO electricity and NO running water. Akin to glamping!

Top guest favourite
The exterior of the hand-crafted log cabin is showcased, highlighting the rustic wooden structure with a metal roof. A porch extends from the front, accompanied by outdoor seating and a cooler. Lush grass surrounds the cabin, bordered by trees, enhancing the serene setting.
Cabin in Jay
4.96 out of 5 average rating, 399 reviews

Adirondack Cozy Log Cabin

We are a pet friendly cozy cabin set in the Jay Range. This hand-crafted log cabin was built from the trees right on the property. Featuring authentic rustic charm along with all the modern conveniences, a new cook’s kitchen, dishwasher, gas range and a wood burning stove. Relax in the deep soaking tub, perfect for after a long hike in the high peaks district. If privacy, comfort and tranquility are what you are after, the Cabin is the right place for you.

Top guest favourite
An outdoor courtyard features a salt-water hot tub and natural wooden seating. Lush greenery envelops the space, creating an intimate feel. A rustic barrel-shaped structure adds a unique element to the design. The ground is covered in smooth gravel, enhancing the serene atmosphere.
Guest suite in New North End
4.98 out of 5 average rating, 227 reviews

Sauna, Cold Plunge, Hot Tub, Paddle Boards, Bikes

*Burlington’s 1st Spa + Stay. Recently renovated and upgraded! We added a sauna, a cold plunge, upgraded bicycles, enlarged the courtyard, added an exercise/yoga room, robes and sandals, an espresso machine… the list goes on! New photos were just added! We still have a king bed, a queen bed, and the two twins that make up the Dream Sofa in the living room. Pets are still welcome! We have new stuff for kids too! We’re right near the beach and bike path!

Popular amenities for Chesterfield pet-friendly home rentals

When is the best time to visit Chesterfield?

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

  • Total holiday rentals

    Explore 40 holiday rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield holiday rentals start at £60 per night before taxes and fees

  • Verified guest reviews

    Over 3,000 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    40 of Chesterfield holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chesterfield rentals

  • 4.9 Average rating

    Chesterfield stays are highly rated by guests – averaging 4.9 out of 5!