Pet-friendly vacation rentals in Chesterfield

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Chesterfield

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Shelburne

4.89 out of 5 average rating, 292 reviews

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!

Oct 22 – 29

G$26,876 GYD per night

Guest favorite

Cabin in Keene Valley

4.98 out of 5 average rating, 250 reviews

Unique Rustic Adirondack Cabin

This is a unique rustic cabin on a private dirt road nestled on a mountain brook in the forest adjoining the Giant Mountain Wilderness Area. This small (200 sq ft + 80 sq ft sleeping loft), Adirondack style cabin was completely refurbished this past year using locally sourced woods and built by hand. Located two miles from downtown Keene Valley, and at 1800 feet, this is an ideal place for those who prefer the quiet forest, the peaceful sound of a mountain brook, and possibily seeing animals.

Mar 3 – 10

G$21,776 GYD per night

Guest favorite

Guest suite in Colchester

4.96 out of 5 average rating, 198 reviews

Large & Cozy, Scenic Walks, Private Entry, Jacuzzi

Named Vermont's top new Airbnb in 2022. Spacious, quiet, cozy, private. An easy walk to wooded trails, dog-friendly park, bikepath, snowshoe, xc, skating, and breathtaking beach sunsets. Less than 15 minutes from downtown and UVM. This large, well-designed above-ground suite has "the world's most comfy" king bed, a breakfast nook, fast wifi, desk and even a jacuzzi tub. Electric bike rental and river access right around the corner. Store your bike or sports gear in onsite garage. We love pets!

Jan 4 – 11

G$28,899 GYD per night

Guest favorite

Chalet in Jay

4.95 out of 5 average rating, 147 reviews

Adirondack Base Camp 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

Feb 22 – Mar 1

G$31,286 GYD per night

Guest favorite

Tiny home in Jay

4.95 out of 5 average rating, 407 reviews

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!

Jan 14 – 21

G$14,324 GYD per night

Guest favorite

Apartment in Essex

4.97 out of 5 average rating, 107 reviews

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.

Dec 14 – 21

G$32,336 GYD per night

Guest favorite

Cabin in Lewis

4.98 out of 5 average rating, 137 reviews

Adirondack Cabin Sanctuary

This charming cabin hides in thirteen private wooded acres. Gorgeous views include a babbling brook, small pond, and delightful woodland paths. The cabin boasts hardwood floors, a stunning fireplace, functional kitchen and bathroom spaces, safe drinking water, electricity, an outside deck and a screened porch with firepit. Short drives will bring you to Whiteface Mountain, Lake Placid, and Lake Champlain.

Sep 5 – 12

G$31,139 GYD per night

Guest favorite

Tiny home in Jay

4.96 out of 5 average rating, 172 reviews

Cozy tiny house with endless Adirondack adventures

Center of: trout fishing in the AuSable river, hunting,skiing and hiking. 20 minutes from Whiteface Mt. ski center ,1/2 hour from Lake Placid and all Olympic venues, 20 minutes from High Falls Gorge. 5 minutes from grocery, gas,and deli. Enjoy an outdoor firepit ,barbecue and picnic area while relaxing in a country side setting with beautiful views of the AuSable River and Adirondack hillsides.

Feb 14 – 21

G$23,222 GYD per night

Guest favorite

Home in Keeseville

4.84 out of 5 average rating, 123 reviews

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!

Mar 23 – 30

G$30,209 GYD per night

Guest favorite

Guesthouse in South Hero

4.9 out of 5 average rating, 120 reviews

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.

Sep 12 – 19

G$23,421 GYD per night

Guest favorite

Cabin in Jay

4.96 out of 5 average rating, 659 reviews

Adirondack Mountainside A-Frame

A cozy pet friendly A-frame nestled in the Jay Range with view of Whiteface Mountain. The home features a living room, fireplace, loft bedroom and fully equipped kitchen. With endless activities to choose from, we are located just 10 minutes from Whiteface Mountain and 20 minutes from Lake Placid.

Feb 28 – Mar 7

G$39,456 GYD per night

Guest favorite

Guesthouse in Hinesburg

4.97 out of 5 average rating, 108 reviews

Cozy cottage in peaceful location

Adorable cottage in quiet location. Close to Burlington, hiking, skiing, and Lake Champlain. Cottage is completely separate from the main house with its own parking. Private, yet close enough to owners if anything is needed.

Jan 15 – 22

G$29,081 GYD per night