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.

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Top guest favourite
A single-story house is framed by lush greenery and a serene pond. The structure features a large porch that extends along the front, with a chimney visible on the roof. The soft hues of sunset provide a warm ambiance to the setting.
Home in Westport
4.99 out of 5 average rating, 109 reviews

Aunt Shy's Hide-Away

Aunt Shy's hide-away is nestled on a dead end road in the Spruce Mill Brook Valley bounded by Saddle Hill and Hood Mountain (both on the 250-acre property). Situated in the Adirondack Park midway between the High Peaks and Lake Champlain (Exit 32 on I-87), this property is in an ideal base for enjoying the Adirondack Mountains and Lake Champlain Valley. Looking to get away from the daily grind, hike, bike, fish, ski, or just relax by the fire. Five minutes to the Meadowmount School of Music.

Top guest favourite
A cottage is seen perched on a grassy bank, overlooking a river. Tall trees frame the scene, providing a natural backdrop. The water's surface reflects the surroundings, while a hint of light is visible from the cottage window, suggesting warmth inside.
Home in Willsboro
4.97 out of 5 average rating, 116 reviews

"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!

Top guest favourite
A rustic cabin is framed by lush greenery, surrounded by a manicured garden. An outdoor picnic table is situated on the grass, complemented by a patio umbrella and flower pots. The entrance features a welcoming door, adding charm to the serene woodland setting.
Place to stay in Peru
4.93 out of 5 average rating, 174 reviews

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.

Top guest favourite
Sunlight filters through tall trees, casting elongated shadows on a grassy area by the lake. The serene water reflects the sky, creating a peaceful atmosphere. A few chairs are positioned on the grass, inviting relaxation and enjoyment of the picturesque surroundings.
Home in Willsboro
4.95 out of 5 average rating, 113 reviews

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.

Guest favourite
A charming wooden cabin is set amidst lush greenery, featuring a triangular roof and large front porch. Surrounding grassy areas are dotted with trees, providing a natural backdrop. The pathway leading to the entrance is bordered by low shrubs and plants.
Cabin in Elizabethtown
4.84 out of 5 average rating, 257 reviews

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).

Top guest favourite
Two white Adirondack chairs are positioned on a grassy area overlooking the Ausable River. The river flows gently under a cloudy sky, surrounded by trees displaying vibrant autumn foliage in shades of orange and green.
Flat in Clintonville
4.87 out of 5 average rating, 261 reviews

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.

Guest favourite
A panoramic view of lush green pastures and rolling hills under a dramatic sky. Clouds in various shades of grey and blue create a striking contrast with the vibrant landscape, highlighting the natural beauty of the surrounding mountain range.
Yurt in Jay
4.9 out of 5 average rating, 494 reviews

Adirondack Mountain Yurt at Blue Pepper Farm

Escape to our 30’ yurt atop a 25-acre pasture with breathtaking views of Whiteface mountain. Accommodating 2 to 6 guests, it’s perfect for family outings or adventures with friends. A winter camping experience: the yurt features basic insulation and is heated by a wood stove, with firewood for purchase on-site. Bring sleeping bags and slippers for warmth in colder temps. Embrace nature’s beauty—plan accordingly, read our reviews, and feel free to ask any questions. Your adventure awaits!

Top guest favourite
An aerial view of a charming chalet surrounded by lush greenery. A spacious wrap-around deck features outdoor seating and a red umbrella, offering a cozy area for relaxation. Sunlight filters through the trees, enhancing the natural setting.
Chalet in Jay
4.96 out of 5 average rating, 249 reviews

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

Top guest favourite
Two red Adirondack chairs are positioned on a wooden terrace, overlooking a vast landscape of green trees and rolling mountains in the distance. A rustic wood table stands between the chairs, providing a natural focal point amidst the serene outdoor setting.
Guest suite in Elizabethtown
4.96 out of 5 average rating, 371 reviews

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

Guest favourite
A cozy living area features reclaimed wood walls and large windows allowing natural light to fill the space. A comfortable sofa with striped fabric is complemented by an armchair, a wooden TV stand, and tasteful decor elements, all set on a rustic wooden floor.
Flat in Essex
4.94 out of 5 average rating, 145 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. The location is convenient to many attractions!

Top guest favourite
An outdoor courtyard features a salt-water hot tub and natural wooden seating. Lush greenery envelops the space, creating an intimate feel. A rustic barrel-shaped structure adds a unique element to the design. The ground is covered in smooth gravel, enhancing the serene atmosphere.
Guest suite in New North End
4.98 out of 5 average rating, 241 reviews

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!

Top guest favourite
The exterior of a cozy loft is framed by trees, featuring a wooden deck adorned with string lights that provide a gentle glow. The entrance is highlighted by large glass doors, leading into the inviting interior space.
Guest house in Hinesburg
4.99 out of 5 average rating, 383 reviews

Hydrangea House on the Hill

The loft is surrounded by woods in a quaint, picturesque, rural part of Northwestern Vermont close to Burlington and Mad River Glen. We are 25 mins to Mad River Glen, Bolton Valley and Burlington (Lake Champlain beaches) and 10 mins to Sleepy Hollow Ski and Bike Center, Camel's Hump Nordic Ski Area, Frost Brewery and Stone Corral. Enjoy complete privacy and peaceful surroundings of nature with the full amenities of a home.

Popular amenities for Chesterfield pet-friendly home rentals

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 $103 SGD 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!