
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.

Walk to the Lake. Quiet neighborhood. Comfy beds.
This completely remodeled apartment in a quiet neighborhood is walking distance to the Burlington Bikeway and Lake Champlain. Enjoy the well appointed kitchen with granite counters, full-sized, new appliances, dining table and countertop seating. The beds are very comfortable and we provide extra pillows and blankets. Filled with original artwork & designerly style. Included: high-speed internet & streaming TV, a printer, & whole-house HEPPA certified air purifier for your safety and comfort

"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!

Secluded Village Gem: Cozy Studio Overlooks River!
Unwind in a charming studio retreat ideally located in Shelburne Village. Peace and privacy on the edge of the nature preserve overlooking the LaPlatte River. Perfect for travelers visiting the Burlington area. 9 miles to downtown BTV. Gorgeous space with lovely furnishings. Super comfortable bed and leather seating. Private entrance. Compact kitchenette. Dedicated workspace and high-speed internet. Dog friendly. A/C for the occasional hot summer day. Miles of trails steps from your front door!

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.

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

Lovely Treehouse Loft in Burlington South End
Treat yourself to a unique stay in this open and airy South End loft apartment, featuring all the space, amenities and luxuries you need for a restful and refreshing getaway. Fantastic location in the heart of Burlington, VT - steps from City Market, breweries & parks. High ceilings, comfy nooks, beautiful light, a cozy day bed and epic year-round birdwatching from the large back deck are a few of the many highlights at The Treehouse. 5m to Downtown, 89, Rte 7, beaches & more!

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.

Winter Wonderland 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

Cozy Mountain House- 50 acres/Trails/Whiteface mnt

Running Brook

White Spruce Cottage ~ Wilmington/Whiteface Mtn NY

Enjoy every season in the Lake Champlain Region

Forest Hideaway

Brthtkng New Premier Lake Champlain Wfrnt Escape!

The Sanctuary: 3 Bedrooms, Easy Walking, +Parking!

Charming 2 Bedroom Modern 1880’s Farmhouse
Pet-friendly home rentals with a pool

Upper Yurt Stay on VT Homestead

Epic Views of the Green Mountains

3rd Floor Studio @ The Lodge at Spruce Peak

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

EPIC Stowe Getaway - Great For Families & Friends

Cute Cottage - Poolside - Minutes To Activities

Cozy Lodge with Hottub/Sauna/Games near Whiteface

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

Rustic Creek Cabin in ADK/Whiteface w Hot Tub

Hill Section Carriage House

Secluded ADK cabin | family fun & winter adventure

Cozy cottage in peaceful location

200 acre Stowe area Bunkhouse.

Historic River House • Sauna • Warner's Camp

VanHoevenberg Ridge upper level apartment.

Edin's Chalet Adirondacks-Whiteface 4 Beds-2 Baths
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
- Country Club of Vermont
- Ethan Allen Homestead Museum
- Burlington Country Club
- ECHO, Leahy Center for Lake Champlain
- Vermont National Country Club
- Lincoln Peak Vineyard
- Titus Mountain Family Ski Center
- Shelburne Vineyard
- Snow Farm Vineyard & Winery
- Boyden Valley Winery & Spirits
- North Branch Vineyards




