
Pet-friendly vacation 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.

"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!

Petite+Perfect Modern Pad: parking+laundry+yard
PRIVATE and CLEAN apartment with all new amenities- simple, modern uncluttered little landing pad in the Old North End. Pet Friendly with yard. NESPRESSO coffee provided free. DESIGNATED OFFSTREET parking and porch. Close to bike path and convenient to downtown Burlington. Super FAST WiFi and modern new furniture. People enjoy this place because it is: -Clean -Laundry -Modern KITCHEN -Private -Cute -Easy No Host interaction needed-although, available for any assistance - Hope you Enjoy!

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.

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.

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.

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.

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!

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.

Porcupine Farm Barn
A converted barn attached to my house, this newly remodeled space is beautiful and inviting. Everything is new and high-end, yet it retains it's barn-y charm. For a couple who are looking to get away in the Adirondacks, this is a unique and appealing option. The house is 3.5 miles from the town of Essex, NY in the Champlain Valley. Gorgeous view of the Green Mountains to the east and farm land all around. The location is convenient to many attractions!

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!

Luxe Zen-Den Ski Haus Brewers walk-shop-dine UVM
While waiting for check-in: pvt dog run and restaurants on site! Excellent drinks and dining on the first floor with many more restaurants a short walk away! 2.5 m to Church St, 1+ m to UVM, the Riverwalk, and Breweries. Whether you're here to hit the slopes, explore the beaches, or sample local brews at Four Quarters brewery, enjoy our fully accessible location for your lake Champlain adventures! Book now for the best of Vermont.

Autumn retreat w/ hot tub perfect for couples
Plan a peaceful stay for up to 5 people in this cozy, well-appointed cabin with lake access that marries rustic charm with modern amenities. This is a vintage Adirondack retreat with access to a quiet and private lake perfect for swimming, paddling and fishing. We have loons and a resident bald eagle. A local winery and brewery are so close by too! Ausable Chasm is fun family-friendly attraction just down the road.
Popular amenities for Chesterfield pet-friendly home rentals
Pet-friendly house rentals

Aunt Shy's Hide-Away

Running Brook

Cozy Mountain House- 50 acres/Trails/Whiteface mnt

Entire House. 2+ bed, 2 bath near Lake & bikeway

Sunny 2BR w/ Pond + Fireplace | Walk to Stowe

Wilmington Range Log Cabin on the AuSable River

Forest Hideaway

Enjoy every season in the Lake Champlain Region
Pet-friendly home rentals with a pool

Epic Views of the Green Mountains

Lower Yurt Stay on VT Homestead

Apartment, comfy and cozy with kitchen/gas fire

EPIC Stowe Getaway - Great For Families & Friends

Cute Cottage - Poolside - Minutes To Activities

Cozy Lodge with Hottub/Sauna/Games near Whiteface

InSmuggs 5* 6 Daycations daily inc Mtn. View!

3BR Stonybrook * Near Mountain Rd and Trapp Family
Private, pet-friendly home rentals

Hill Section Carriage House

A slice of Heaven

Cozy cottage in peaceful location

Cozy & Peaceful Cabin on 40 Acres - Pups Welcome

Rustic 5th wheel camper close to lake.

Historic 2BR Loft • Quiet • Work-Ready • Downtown

TheADKChalet w/ Hot Tub (Adirondacks)

Quiet & Peaceful 2bdrm walk to town pet friendly
Quick stats about vacation rentals that are pet-friendly in Chesterfield

Total vacation rentals
Explore 40 vacation rentals in Chesterfield

Nightly prices starting at
Chesterfield vacation rentals start at $113 CAD per night before taxes and fees

Verified guest reviews
Over 3,000 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
40 of Chesterfield vacation 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!
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- Sugarbush Resort
- Parc Safari
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Autumn Mountain Winery
- Country Club of Vermont
- Ethan Allen Homestead Museum
- Leahy Center for Lake Champlain
- Burlington Country Club
- Vermont National Country Club
- Lincoln Peak Vineyard
- Shelburne Vineyard
- Snow Farm Vineyard & Winery
- Boyden Valley Winery & Spirits
- Titus Mountain Family Ski Center
- North Branch Vineyards




