
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!

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.

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.

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.

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

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

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!

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!

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.

The Trailhead
Our guest suite is located on our small horse farm in the foothills of the Adirondacks. The space has a cozy rustic charm, and has everything you’ll need for a quiet mountain getaway in any season. We are located right at the entrance of the Blueberry Hill Trails, a 1000-acre trail system designed for hiking, snowshoeing, skiing, mountain biking, and horseback riding. Head out the door and you're right on the trails.
Popular amenities for Chesterfield pet-friendly home rentals
Pet-friendly house rentals

Running Brook

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

Convenient Cape | Explore Burlington & Stowe

Cute and Cozy Burlington Bungalow-Pet Friendly

Wilmington Range Log Cabin on the AuSable River

Enjoy every season in the Lake Champlain Region

Forest Hideaway

Brthtkng New Premier Lake Champlain Wfrnt Escape!
Pet-friendly home rentals with a pool

Epic Views of the Green Mountains

Ski Patrol Cabin -Pets, Shared Hot Tub & Lap Pool

Mott House, South Hero Vermont

Dog-Friendly Secluded Cabin

Lakeside Bungalow ~ Pool | Hot Tub | Beach

Apartment, comfy and cozy with kitchen/gas fire

Large Cozy Lodge Near Whiteface w/ Hottub & Sauna

InSmuggs 5* 6 Daycations daily inc Mtn. View!
Private, pet-friendly home rentals

Hill Section Carriage House

Charming Private Apt in South End w/ Hot Tub

VT Hideaway studio: breweries,hiking, dogs welcome

Tiny on the Hill - Sauna + Burlington + Stowe

Organic Farm Hideaway Home and Pond

VanHoevenberg Ridge upper level apartment.

A-frame w/ sauna near Whiteface & Lake Placid, NY

Edin's Chalet Adirondacks-Whiteface 4 Beds-2 Baths
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 G$16,734 GYD 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 & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Chesterfield vacation rentals include wi-fi 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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- Rentals with lake access Chesterfield
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 - Pet-friendly rentals United States
 
- Sugarbush Resort
 - Parc Safari
 - Bolton Valley Resort
 - Whiteface Mountain Ski Resort
 - Fort Ticonderoga
 - Cochran's Ski Area
 - Autumn Mountain Winery
 - Cozy Cottages & Otter Valley Winery
 - Ethan Allen Homestead Museum
 - Leahy Center for Lake Champlain
 - Burlington Country Club
 - Country Club of Vermont
 - 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