
Pet-friendly holiday rentals in Chesterfield
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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

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.

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!

Hydrangea House on the Hill
The loft is surrounded by woods in a quaint, picturesque, rural part of Northwestern Vermont close to Burlington and Mad River Glen. We are 25 mins to Mad River Glen, Bolton Valley and Burlington (Lake Champlain beaches) and 10 mins to Sleepy Hollow Ski and Bike Center, Camel's Hump Nordic Ski Area, Frost Brewery and Stone Corral. Enjoy complete privacy and peaceful surroundings of nature with the full amenities of a home.

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

Captain Tom's Cabin - Secluded Vermont Getaway

Running Brook

Cozy Mountain House- 50 acres/Trails/Whiteface mnt

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

Wilmington Range Log Cabin on the AuSable River

The Guest House at Sky Hollow

Enjoy every season in the Lake Champlain Region

Forest Hideaway
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

Cute Cottage - Poolside - Minutes To Activities

Large Cozy Lodge Near Whiteface w/ Hottub & Sauna

Hill Top Apartment With Amazing View Near Stowe

Château Chavís

Lodge At Spruce Peak | Mountain | Studio | 1117
Private, pet-friendly home rentals

Rustic Creek Cabin in ADK/Whiteface w Hot Tub

Hill Section Carriage House

Cozy cottage in peaceful location

A slice of Heaven

Cady’s Falls Cabin

VanHoevenberg Ridge upper level apartment.

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

The Log Cabin • Hot Tub • Sauna • Near Whiteface
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 $142 NZD 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 and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Chesterfield holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Chesterfield rentals

4.9 Average rating
Chesterfield stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
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- House rentals Chesterfield
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- Pet-friendly rentals Essex County
- Pet-friendly rentals New York
- 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
- Ethan Allen Homestead Museum
- Country Club of Vermont
- Cozy Cottages & Otter Valley Winery
- Burlington Country Club
- Leahy Center for Lake Champlain
- Vermont National Country Club
- Lincoln Peak Vineyard
- Shelburne Vineyard
- Snow Farm Vineyard & Winery
- Titus Mountain Family Ski Center
- Boyden Valley Winery & Spirits
- Smugglers' Notch Resort
- Spruce Peak
- North Branch Vineyards




