
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!

Panton / Near Vergennes , Middlebury Private Home
Begin your Vermont experience at our serenely secluded, wooded hide–a-way. This inviting private home features all the best amenities including luxury linens, fully equipped kitchen, bath with custom over sized shower, a beautiful deck with gas grill, teak and glass dining table, and lounge seating for 4. It is the perfect space for 2 adults and children, or up to 4 adults, providing easy access to the best Vermont has to offer from Lake Champlain, Vergennes, Middlebury, and all points beyond.

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

Sunny Historical Burlington Home (Pet Friendly)
This 'organic-modern' 1883 home is located in the South End of Burlington, a hub of art, food, boutiques, yoga, craft beer, and coffee. It offers free on-site parking and is sun-filled. And we love hosting well-behaved dogs! The house earns top marks for cleanliness from our guests. Strong Wifi, separate rooms perfect for virtual work meetings and a private backyard to escape to after your work day! Friday night food trucks + Saturday Farmers' Market in summer only two blocks away!

Peaceful Adirondack Cabin right on John's Brook
This cabin is set in a gorgeous, tree-rimmed meadow directly on John's Brook, just 1/2 mile from the village of Keene Valley. Miles of trails are outside your door for your summer or winter enjoyment. Fly fish in the brook just steps from the house or climb Marcy and the range from the front door! The cabin is cozy in the winter with wifi, a fully equipped kitchen and modern amenities. You will enjoy the entire property to yourself in a truly serene setting.

Sunrise over South Mountain
This is a spacious guesthouse/retreat where you can relax and unwind. There are great views and walking down the road is serene, with open fields bordered by woods and teaming with wildlife. In the winter you can Nordic ski or snowshoe right outside your door, through fields and woodland paths down by an active sugar-bush. We currently have chickens as well as my friendly dog Annie who loves to play. We also have a young kitty named LB who is a pip.

Cascade Brook Cabin
Four season log cabin in the heart of the Adirondack High Peaks region. The cabin is located on 7 private acres next to a beautiful stream that flows down from Cascade Lake. Both Porter and Cascade Mountain trailheads are 4 miles away and are on the 46 High Peaks register. Close proximity to hiking adventures for all abilities- biking trails, fishing, swimming, canoeing and during the winter months: downhill and cross-country ski activities.

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 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!

Rustic 5th wheel camper close to lake.
You'll always remember your time at this unique place to stay. Camper living in Vermont winters. Owners on-site. Camper is winter ready and offers an affordable place to stay close to the lake views. Plenty of on-site parking for boats/trailer. We are close to the NY ferry but you don’t need to take a ferry to get to our place.
Popular amenities for Chesterfield pet-friendly home rentals
Pet-friendly house rentals

Cozy Mountain House- 50 acres/Trails/Whiteface mnt

Birchwood Lodge - Our Home in the Woods

Beautiful timber frame just minutes to Middlebury!

3 BR House near Burlington

Forest Hideaway

Enjoy every season in the Lake Champlain Region

Brthtkng New Premier Lake Champlain Wfrnt Escape!

The Sanctuary: 3 Bedrooms, Easy Walking, +Parking!
Pet-friendly home rentals with a pool

3rd Floor Studio @ The Lodge at Spruce Peak

Mott House, South Hero Vermont

Lakeside Bungalow ~ Pool | Hot Tub | Beach

Cute Cottage - Poolside - Minutes To Activities

Cozy Lodge with Hottub/Sauna/Games near Whiteface

In Smuggs 5* 6 Daycations daily inc. Mtn. View!

Mountain View Luxury Studio Lodge At Spruce Peak

3BR Stonybrook * Near Trapp Family & Bike Path!
Private, pet-friendly home rentals

Woodpecker Cottage on the Lake

The Beech Retreat w/ Infrared Sauna

Treehut - Secluded Treehouse in the Forest

Charming Private Apt in South End w/ Hot Tub

The Trailhead

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

Edin's Chalet Adirondacks-Whiteface 4 Beds-2 Baths

The Barn in Shelburne
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island 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 outdoor seating Chesterfield
- Rentals with beach access Chesterfield
- Rentals with a fireplace Chesterfield
- Rentals with a kayak Chesterfield
- Rentals with lake access Chesterfield
- Rentals with a firepit Chesterfield
- Waterfront rentals Chesterfield
- House rentals Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Rentals with a patio Chesterfield
- Family-friendly 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
- Fort Ticonderoga
- Lake Flower
- Stowe Mountain Resort
- ECHO, Leahy Center for Lake Champlain
- University of Vermont
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- Adirondak Loj
- Shelburne Museum
- Middlebury College
- Boyden Valley Winery & Spirits
- Shelburne Vineyard
- Warren Falls
- Lake Champlain Chocolates
- Waterfront Park
- Snow Farm Vineyard & Winery
- Elmore State Park




