
Pet-friendly holiday rentals in Chesterfield
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Top-rated pet-friendly home rentals in Chesterfield
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"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!

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.

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

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.

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.

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.

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
Pet-friendly house rentals

Cozy Mountain House- 50 acres/Trails/Whiteface mnt

Running Brook

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

Wilmington Range Log Cabin on the AuSable River

The Guest House at Sky Hollow

Forest Hideaway

Enjoy every season in the Lake Champlain Region

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

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

Lodge At Spruce Peak Lux Studio | 1125

Large Cozy Lodge Near Whiteface w/ Hottub & Sauna
Private, pet-friendly home rentals

Rustic Creek Cabin in ADK/Whiteface w Hot Tub

Relax & Recharge in 40 Acres - Pups Welcome

Rustic 5th wheel camper close to lake.

VT Hideaway studio: breweries,hiking, dogs welcome

TheADKChalet w/ Hot Tub (Adirondacks)

Large & Cozy, Scenic Walks, Private Entry, Jacuzzi

The Barn in Shelburne

Camp Red Fox - Cozy cabin with AC
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £131 | £132 | £123 | £121 | £137 | £134 | £145 | £162 | £133 | £133 | £132 | £133 |
| Avg. temp | -6°C | -5°C | 0°C | 8°C | 15°C | 20°C | 22°C | 21°C | 17°C | 10°C | 4°C | -2°C |
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!
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- 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
- Leahy Center for Lake Champlain
- Ethan Allen Homestead Museum
- Burlington Country Club
- Country Club of Vermont
- Vermont National Country Club
- Lincoln Peak Vineyard
- Shelburne Vineyard
- Snow Farm Vineyard & Winery
- Titus Mountain Family Ski Center
- Boyden Valley Winery & Spirits
- North Branch Vineyards