
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!

Entire House. 2+ bed, 2 bath near Lake & bikeway
Kick back and relax in this stylish space located less than 3 miles to downtown and under a mile walk to lake vistas & beaches. Access to the bike path is at the end of the street. Perfect for cyclists, runners, bikers, dog walkers & beach goers. Completely remodeled house with new appliances, fully equipped kitchen, laundry & high speed internet. Two bedroom suites each with their own bathroom; the King suite upstairs has additional TV & sitting area. Plus there is a bonus room with futon.

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.

Secluded ADK cabin | family fun & winter adventure
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).

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

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.

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!
Popular amenities for Chesterfield pet-friendly home rentals
Pet-friendly house rentals

Running Brook

2-Bedroom Home in Desirable Orchard Neighborhood

White Spruce Cottage ~ Wilmington/Whiteface Mtn NY

Forest Hideaway

Enjoy every season in the Lake Champlain Region

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

Whiteface Cottage~Level 2 EV Charger~Hot Tub~AC

Lovely Lil’ House- fenced yard!/Hot Tub
Pet-friendly home rentals with a pool

Luxury Alpine Studio Ski in Ski out mountainside

3rd Floor Studio @ The Lodge at Spruce Peak

Mott House, South Hero Vermont

Dog-Friendly Secluded Cabin

Lakeside Bungalow ~ Pool | Hot Tub | Beach

Concrete Ski House Near Sugarbush

Sweet Updated 1B Condo on Access Road- Powderhound

Cozy Lodge with Hottub/Sauna/Games near Whiteface
Private, pet-friendly home rentals

Cozy cottage in peaceful location

Rustic 5th wheel camper close to lake.

Tiny on the Hill - Sauna + Burlington + Stowe

Cozy Burlington Getaway w/ Private Deck & Yard

TheADKChalet w/ Hot Tub (Adirondacks)

Lewis Brook Lodge

Barn in Shelburne, Private Cross Country Ski Area

Panton / Near Vergennes , Middlebury Private Home
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Pocono Mountains Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Rentals with a patio Chesterfield
- Family-friendly rentals Chesterfield
- Rentals with lake access Chesterfield
- Rentals with outdoor seating Chesterfield
- Rentals with a firepit Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Waterfront rentals Chesterfield
- Rentals with beach access Chesterfield
- Rentals with a fireplace Chesterfield
- Rentals with a kayak Chesterfield
- House rentals Chesterfield
- Pet-friendly rentals Essex County
- Pet-friendly rentals New York
- Pet-friendly rentals United States
- Sugarbush Resort
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Lake Flower
- Fort Ticonderoga
- ECHO, Leahy Center for Lake Champlain
- Stowe Mountain Resort
- Adirondak Loj
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- University of Vermont
- Shelburne Museum
- Middlebury College
- Waterfront Park
- Shelburne Vineyard
- Boyden Valley Winery & Spirits
- Lake Champlain Chocolates
- Snow Farm Vineyard & Winery
- Warren Falls
- Elmore State Park
- Cold Hollow Cider Mill




