Pet-friendly holiday rentals in Chester

4.99 out of 5 average rating, 155 reviews

A spacious living area features a central stone fireplace, surrounded by cozy seating. Large windows frame scenic views of the trees outside, filling the space with natural light. The rustic wooden beams and walls add warmth, while the open layout connects to the kitchen and loft above.

Barn in Andover

Fat Cat Barn - Close Okemo & Magic, Vermont

Welcome to Fat Cat Barn! This is an incredibly unique, family oriented 1850's Mennonite built Post & Beam barn on 10+ acres in the pastoral hills of Andover, VT. We are wedged between the wonderful villages of Weston, Ludlow & Chester. Just 15 minutes from Okemo and Magic ski mountains with Stratton, Bromley & Killington all within 40 minutes. This is a wonderful four season property with plenty of options for fun right outside our door step. The Stratton mountain views and sunsets are stunning

4.95 out of 5 average rating, 270 reviews

The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.

Cabin in Londonderry

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba

Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

4.95 out of 5 average rating, 324 reviews

The exterior of a two-story contemporary home is depicted, featuring green-framed windows and a pathway lined with gravel. Adjacent grassy areas and trees create a natural setting. A blue flag flutters near the entrance, enhancing the welcoming feel of the property.

Home in Weston

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly

Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!

The exterior of the fully renovated home is surrounded by greenery, featuring a spacious yard and a fenced area. A large deck is visible on the back of the house, along with a detached garage and ample outdoor space for gatherings.

4.92 out of 5 average rating, 102 reviews

Updated 6BR Home 4 min to Okemo w fenced in yard!

Fully renovated! This single-family home is a perfect getaway for you and your friends or family to enjoy some of the best terrain in the Northeast at Okemo Mountain, located just 5 minutes away. After a day on the slopes come home, unwind and relax or head to downtown Ludlow area to enjoy restaurants, bars, shopping and more. Pet-friendly, large fenced in yard. Nearby attractions: - Camp Plymouth State Park & Echo Lake - Fox Run Golf - Buttermilk Falls hiking and swimming - Killington Skiing!

4.99 out of 5 average rating, 105 reviews

The exterior of a two-story house is depicted, featuring a welcoming entrance with wooden steps and a green door. Window boxes with plants are positioned below each window on the light gray facade, surrounded by a landscaped yard with a gravel pathway leading to the front door.

Flat in Londonderry

Bread and Butter Apartment

Our house is located just a few minutes from Magic Mountain and less than thirty minutes from Bromley, Stratton and Okemo. Chester and Londonderry are a short drive away, and there are many wonderful hikes nearby. The apartment occupies the entire second floor of our house and has a private entrance. It includes two cozy bedrooms, a 3/4 bath, a small kitchen and a comfy living room. The apartment still has that old Vermont charm and is perfect for a relaxed weekend in the Green Mountains.

4.91 out of 5 average rating, 253 reviews

The timber frame house is surrounded by dense trees, showcasing a natural setting. Large windows illuminate the exterior, providing glimpses of the interior. Sturdy wooden steps lead to the door, enhancing accessibility amid the forest environment.

Tiny home in Athens

Luxury “Tiny” House With Sauna (Timbery)

The Timbery: This is a new, fully handmade, timber frame "tiny" house featuring a custom Norwegian Sauna. The house is nestled in the forest, accessible by foot. With 17 vertical ft. of floor to ceiling windows, this property represents a unique experience to fully immerse yourself into nature. It is like lying down in a tent on the forest floor, except instead of wet sleeping bags and dirty hair, you enjoy a queen sized bed, in home theater, full kitchen, sauna and 71in soaking tub.

4.85 out of 5 average rating, 109 reviews

Home in Chester

Charming Chester Farmhouse Near VT Slopes

Unplug at our spacious 4-bed Chester farmhouse, a four-season retreat minutes from Okemo, Magic & Bromley. Highlights: *Chef’s kitchen & coffee bar *Fast Wi-Fi, dedicated workspace & Smart TV *Spacious backyard for dining & stargazing *Easy 10–20 min to skiing, hiking & local towns *Pet-friendly, family-ready Spend your days hiking, swimming, leaf peeping, or exploring nearby towns. In winter, hit the slopes, then gather for games and a movie. Book your Vermont getaway today!

4.99 out of 5 average rating, 155 reviews

An interior view showcases a modern staircase with wooden steps and a metal railing, leading to a second floor. Natural light floods the space through large glass windows, illuminating the wooden walls and a stone fireplace. A green plant adds a touch of nature.

Home in Londonderry

Modern 3-bedroom A-frame in Londonderry w/ Pond

This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min). STR License 26-23-185

4.89 out of 5 average rating, 125 reviews

The exterior of an 1840s stone house is displayed, featuring a warm red door and large windows under a sloping roof. A well-maintained garden surrounds the entrance, and a tall tree provides shade. A gravel path leads to the house, with a visible stone wall along the yard.

Cottage in Chester

Quaint stone house!

⭐️ 2022 Rockingham Old House Award ⭐️ Take it easy at this unique and tranquil getaway. The Cairn of Vermont is an 1840s stone house located in the sleepy remnants of Bartonsville Village, now part of Chester, VT. 20 minutes to skiing and hiking, biking and the great outdoors are all around you! Less than 5 minutes to Vermont Country Store and make your way home through the Bartonsville Covered Bridge!

4.96 out of 5 average rating, 189 reviews

Guest house in Cavendish

Charming Cavendish Guesthouse w/ Sauna!

Cavendish Cottage Guest House! Freshly renovated with designer touches, this charming guest house blends style, comfort, and Vermont charm. Enjoy free access to our traditional sauna — shared with two other units and your host. Robes robes provided so you can unwind after skiing or hiking, then cozy up by the pellet stove. 10 minutes to Okemo, 2 minutes to groceries, and super comfy vibe await!

4.97 out of 5 average rating, 481 reviews

A bright interior is featured, showcasing a mix of seating options including a blue sofa and an upholstered armchair. A small dining table is complemented by wooden chairs. The kitchen area is visible, equipped with diverse utensils, while large windows on two sides allow natural light to fill the space.

Flat in Andover

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

4.93 out of 5 average rating, 104 reviews

A inviting corner of the cabin showcases a light-colored armchair beside a wooden cabinet. Soft natural light filters through two windows adorned with simple treatments, illuminating the warm wooden walls. A wood-burning stove stands nearby, enhancing the rustic charm of the space.

Cabin in Cavendish

Copper Hill House - VT getaway near Ludlow & Okemo

Welcome to Copper Hill House: a three-bedroom cabin in Cavendish, VT. 10 minutes from downtown Ludlow and Okemo Mountain. Dogs welcome with an additional pet fee (2 dogs max). Fully fenced-in side yard for the kids and pups.

Popular amenities for Chester pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

The renovated Victorian house is showcased under falling snow, highlighting its red exterior and distinctive architectural details. A wrap-around porch with white railings surrounds the home, while freshly fallen snow blankets the ground, complementing the winter scenery.

4.9 out of 5 average rating, 103 reviews

Ludlow Village Victorian with prime location

4.94 out of 5 average rating, 136 reviews

A spacious kitchen and dining area features a wooden table surrounded by chairs, with a decorative table runner. Stainless steel appliances, including a refrigerator and microwave, create a modern look. Large windows allow natural light to fill the room, providing views of the outdoor scenery.

Home in Charlestown

Private & Cozy Farmhouse in New Hampshire

4.94 out of 5 average rating, 112 reviews

The exterior of the renovated schoolhouse is illuminated at dusk, showcasing large windows that reflect a warm glow from within. The distinctive architectural features are highlighted against a twilight sky, with trees positioned in the background.

Home in Cavendish

Renovated Vermont Schoolhouse – Close to Okemo

4.93 out of 5 average rating, 103 reviews

Home in Reading

Private, Large 4BR home | Pet friendly | 10 Acres

The exterior of a cozy house is presented, featuring a sloped metal roof and green siding. Large windows with white trim provide natural light. Lush greenery and trees surround the property, creating a serene atmosphere, while a pathway leads toward the entrance.

4.96 out of 5 average rating, 112 reviews

Ludlow Village/Okemo Shuttle - Oma K's Kottage

A newly renovated lakefront home is showcased, featuring a spacious deck with comfortable seating and a covered lower level area. Soft lighting illuminates the exterior, highlighting the modern finishes and architectural details against a twilight sky.

4.88 out of 5 average rating, 104 reviews

VT Lakefront House, Lake Fun, Fall Foliage and Ski

4.99 out of 5 average rating, 170 reviews

Home in Woodstock

Cape Cod Home in Woodstock, Pet-Friendly & Wooded

4.96 out of 5 average rating, 283 reviews

A fully stocked kitchen features light-colored cabinets and a wooden island with three black stools. Kitchen appliances, including a stove and dishwasher, are visible alongside a variety of dishes neatly arranged on shelves. A decorative rug adds warmth to the space.

Home in Weston

Weston Farmhouse-Clean, Fast WiFi, Generator!

Pet-friendly home rentals with a pool

4.91 out of 5 average rating, 1027 reviews

The exterior of the chalet is shown in twilight, with soft light emanating from a window. The rustic wooden structure features a sloped roof and is surrounded by snow-covered ground and trees in the background.

Guest house in Granville

Moon Valley Country Retreat no clean fee pets yes

4.79 out of 5 average rating, 279 reviews

A rustic log cabin features a porch with seating arrangements, including Adirondack chairs. The front yard is partially landscaped with small plants. Stacked firewood is visible next to the cabin, and the structure is surrounded by trees and greenery, providing a natural, secluded setting.

Cabin in Wardsboro

Log Cabin Near Stratton/Mt Snow

4.93 out of 5 average rating, 251 reviews

A Colonial home is positioned on a green lawn, showcasing a charming brick façade and a classic porch. Large trees provide shade, while an American flag is displayed proudly by the door. Nearby, a design studio is visible, highlighting the spacious front yard.

Home in Keene

The Brick House on Washington Street

4.9 out of 5 average rating, 184 reviews

A spacious ski home is surrounded by snow-covered trees, featuring a modern design with a sloped metal roof. Large windows allow natural light to enter, while a gravel driveway leads to the entrance. This bustling wooded area provides a serene backdrop during winter.

Home in Peru

Beautiful Bromley/Manchester VT Retreat w/hot tub

4.95 out of 5 average rating, 182 reviews

Apartment in Killington

Ski-In/Out, Pools, Hot Tub, Pet-Friendly

5.0 out of 5 average rating, 131 reviews

Chalet in Wilmington

Mt Snow Chalet: Peaceful Escape w/Hot Tub

4.89 out of 5 average rating, 183 reviews

A large outdoor pool is surrounded by a wooden deck with lounge chairs and umbrellas. The background features a multi-story building with expansive windows. Vibrant autumn trees with colorful foliage frame the scene, providing a serene and inviting atmosphere.

Home in Wilmington

Family-friendly 4BR | Pools Hot Tub | Near Mt Snow

4.93 out of 5 average rating, 115 reviews

A vibrant autumn landscape is visible, featuring a two-story green townhome bordered by a well-maintained lawn. Colorful foliage on nearby trees and surrounding hills creates a warm ambiance, highlighting the natural beauty of the area in this scenic outdoor view.

Townhouse in Killington

Topridge 3BR w Foliage Views & Private Hot Tub!

Private, pet-friendly home rentals

Guest house in Springfield

An aerial view captures a cozy cottage situated along the Connecticut River. Lush greenery borders the water, and a small pathway leads to the cottage. A boat glides along the river, highlighting the serene setting surrounded by forests and rolling hills.

Connecticut River-Cozy Cottage

4.84 out of 5 average rating, 413 reviews

4.83 out of 5 average rating, 229 reviews

A bedroom features green walls, with large windows dressed in light curtains allowing natural light to filter through. A wooden bed with white bedding is positioned near a yellow dresser. Two comfortable armchairs are provided, complemented by a floor lamp for additional lighting.

Flat in Rockingham

Apartment on Main Street

4.96 out of 5 average rating, 113 reviews

The modern timber frame cabin features a covered porch with wooden beams, providing a welcoming entry. Large windows offer views of the surrounding forest, while a landscaped path leads to the entrance, framed by lush greenery and natural stone steps.

Cabin in Ludlow

Modern Okemo Smart Cabin - As Seen On DIY Channel

4.98 out of 5 average rating, 256 reviews

Icicles hang from a ledge, glistening in the sunlight. The backdrop features rolling mountains with patches of snow and a clear blue sky, creating a serene winter landscape visible through the ice formations.

Guest suite in Weston

Spacious King Spa Suite Weston Hills

4.95 out of 5 average rating, 908 reviews

The spacious living area features warm wood paneling and a polished floor. A dining area with a wooden table is elevated, while a cozy seating arrangement with colorful cushions is nestled on the ground. Soft lighting from overhead fixtures creates a welcoming ambiance.

Loft in Ludlow

Spacious Renovated Barn Apt on 100 acres!

4.94 out of 5 average rating, 1384 reviews

The tiny house exterior features a charming porch with colorful railings and vibrant green doors. Tall trees surround the cottage, and a light dusting of snow covers the ground, adding to the serene atmosphere of the setting.

Tiny home in Jamaica

Apple Blossom Cottage: A Tiny House

4.96 out of 5 average rating, 123 reviews

The log cabin is viewed from the front, showcasing a welcoming porch with several chairs and warm light emanating from windows. The architectural details reflect a traditional style, surrounded by lush greenery, creating a serene evening ambiance.

Cabin in Ludlow

Cozy Log Cabin with Hot Tub | 1/2 mile to Okemo