
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.

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 strong Wifi World Class Fishing, Ausable Rivers are close This is our family cabin. Enjoy it as we have.
4.95 out of 5 average rating, 286 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!
4.97 out of 5 average rating, 118 reviews
ADK Lux A-Frame Cabin w Hot Tub
Experience the ultimate retreat in the heart of the Adirondacks at our luxurious A-frame cabin with a hot tub! Accommodating up to ten guests, our cabin is just 20 minutes from Whiteface Ski & stunning Lake Placid. You will enjoy relaxing getaway w cozy comfort & breathtaking beauty throughout your stay. Unwind in the fully equipped kitchen, three inviting living areas & spacious outdoor deck featuring a hot tub—perfect for soaking in the tranquility of nature. Make unforgettable memories here!
4.94 out of 5 average rating, 165 reviews
Sauna, Cold Plunge, Hot Tub, Paddle Boards, Bikes
*New art! It hasn’t been photographed but it’s on the walls! Burlington’s 1st Spa + Stay. Recently renovated and upgraded! A sauna, cold plunge, 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!
4.98 out of 5 average rating, 279 reviews
Quiet 3 Bedroom Cottage on Lake Champlain
You'll have a relaxing visit at this cozy, comfortable family camp. Enjoy swimming, kayaking and hiking. Explore gorgeous Lake Champlain or enjoy the view from the porch. The sunrises are spectacular! Lake Champlain is known for great year-round fishing. Tip: Bring your water shoes for maximum swimming comfort. Hop on the Essex Ferry to Vermont to experience shopping, art, restaurants and museums. The Shelburne Museum and ECHO, Leahy Center for Lake Champlain are perfect for families.
4.95 out of 5 average rating, 122 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.
4.93 out of 5 average rating, 199 reviews
Secluded ADKcabin | family fun & Fall Foliage hike
Relax with the whole family or a group of like-minded friends at this peaceful and ultra secluded wooden cabin. On the property, you can use fire pit, play ping pong, and enjoy in any way you prefer. The house is adjacent to former cross-county skiing trails that are used as hiking trails. You can easily make a short drive to Lake Placid & Whiteface for skiing. Keene with many hiking trails is 20 minutes away; many hiking trails are within 3-5 minutes drive (Rocky Peak, Hurricane, Baxter).
4.82 out of 5 average rating, 297 reviews
Adirondack Cabin Retreat – Hot Tub + Lake
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. Lastly for security, we have a camera focused on driveway entrance.
4.93 out of 5 average rating, 161 reviews
Log Cabin • 10 Min to Whiteface • Hot Tub • Sauna
Perfect for couples & large groups! Cozy cabin + outbuildings. 10 minutes to the ski resort, on-site swimming hole & fishing access, cedar hot tub & sauna, foosball, hiking, walkable restaurants, level 2 EV charger, boutique furnishings. The Log Cabin at Warner’s Camp is a piece of art. This property consists of a bespoke 3 bed, 2 bath log cabin, a studio cabin with additional bed and bath, plus an extra sleeper cabin (a charming enclosed lean-to, overlooking a stream).
4.99 out of 5 average rating, 136 reviews
The Cabin @ The Birches
Nestled on the serene shores of Lake Champlain, this rustic log cabin offers the perfect escape from city life. Located at 41 Kibbe Farm Rd. in South Hero, VT, this idyllic retreat promises tranquility and natural beauty in abundance. Whether you seek a peaceful retreat or an adventure-filled getaway, this lakeside log cabin provides the perfect setting. Book your stay today and experience the beauty of Vermont from the comfort of your own cabin on Lake Champlain.
4.98 out of 5 average rating, 126 reviews
Secluded Chalet w/ Hottub & Stunning Mtn Views
Welcome to our cozy secluded Jay Peaks Chalet! Tucked away on 11 acres of natural beauty, this charming home is just a 15-minute drive from White Face Mountain, making it the ideal starting point for your mountain adventures or relaxation. Cozy bedrooms with forest views, a private hot tub, Firepit, screened in porch, and plenty of privacy. Book now for an unforgettable escape for the entire family. Your dogs will love it too!
4.88 out of 5 average rating, 135 reviews
The Paddle Inn
Our house is very open and spacious. It is designed to get around easily. There are multiple places to sit and eat or enjoy nature. The house has numerous windows and is well lit. There is a lot of deck space and a big back yard for games. We are always friendly and open, just down the road if anything is needed! We love meeting new people and do what we can to make your stay comfortable!
4.85 out of 5 average rating, 152 reviewsPopular amenities for Chesterfield pet-friendly home rentals
Pet-friendly house rentals

Stylish modern lakehouse w/ Hot tub, Firepit & Gym
5.0 out of 5 average rating, 101 reviews
NEW! Cozy Family Home in Downtown Burlington
4.95 out of 5 average rating, 187 reviews
Ascent House | Keene
4.98 out of 5 average rating, 250 reviews
Lakefront w/ dock and sauna in the Adirondacks
4.93 out of 5 average rating, 123 reviews
Aunt Shy's Hide-Away
4.99 out of 5 average rating, 120 reviews
Enjoy every season in the Lake Champlain Region
4.93 out of 5 average rating, 144 reviews
The Jay House - 1840 Farmhouse
4.94 out of 5 average rating, 162 reviews
Stunning Views, Luxury, Near Whiteface,Lake Placid
4.98 out of 5 average rating, 332 reviewsPet-friendly home rentals with a pool

EPIC Stowe Getaway - Great For Families & Friends
4.98 out of 5 average rating, 313 reviews
Private Beach, Bikepath Lake Cabin Hot Tub ~ UVM
4.89 out of 5 average rating, 776 reviews
Château Chavis
4.98 out of 5 average rating, 188 reviews
Lower Yurt Stay on VT Homestead
4.94 out of 5 average rating, 484 reviews
Champlain Valley Alpacas
4.93 out of 5 average rating, 168 reviews
Cute Cottage - Poolside - Minutes To Activities
4.78 out of 5 average rating, 280 reviews
Ski Patrol Cabin -Pets, Shared Hot Tub
4.88 out of 5 average rating, 308 reviews
Cozy Little Mountain Condo at BV Ski Resort
5.0 out of 5 average rating, 104 reviewsPrivate, pet-friendly home rentals

Peaceful Adirondack Cabin right on John's Brook
4.97 out of 5 average rating, 211 reviews
Lodge with AC & Hot Tub
4.96 out of 5 average rating, 171 reviews
Lewis Brook Lodge
4.99 out of 5 average rating, 172 reviews
Secluded Village Gem: Cozy Studio Overlooks River!
4.92 out of 5 average rating, 520 reviews
A-frame w/ sauna near Whiteface & Lake Placid, NY
4.98 out of 5 average rating, 142 reviews
The Barn in Shelburne
4.91 out of 5 average rating, 139 reviews
Cozy Rustic Two Story Apartment
4.88 out of 5 average rating, 275 reviews
Downtown Burlington, Renovated, 1 bedroom+
4.96 out of 5 average rating, 234 reviewsDestinations to explore
- Sugarbush Resort
- Bolton Valley Resort
- Stowe Mountain Resort
- Fort Ticonderoga
- University of Vermont
- Middlebury College
- Lake Flower
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- Snow Farm Vineyard & Winery
- Warren Falls
- Shelburne Vineyard
- Shelburne Museum
- Cold Hollow Cider Mill
- Elmore State Park
- Waterfront Park
- Boyden Valley Winery & Spirits
- Lake Champlain Chocolates
- Branbury State Park
- Green River Reservoir State Park
- Alburg Dunes State Park
- Little River State Park
- Titus Mountain Family Ski Center
- Ethan Allen Homestead Museum
- Parc Safari





