Holiday rentals in Bolton

A bright, open kitchen space is visible with modern appliances and a small breakfast bar featuring two stools. Natural light floods the area through large windows, with light wood beams adding a rustic touch. The dining area includes a simple wooden chair beside a neatly made bed.

4.92 out of 5 average rating, 158 reviews

The Loft at The High Meadows

Welcome to The Loft at The High Meadows – your stylish Vermont retreat! Perfect for solo adventurers or couples who need a basecamp for exploring Vermont. You're minutes away from downtown Burlington, shopping in Williston, skiing at Stowe/Bolton, kayaking on Waterbury Reservoir, blueberry picking at Owls Head Blueberry Farm, and savoring craft brews at Stone Corral. The Loft offers a well-appointed kitchen with dishwasher, laundry, luxurious queen bed, & more. Book your Vermont getaway today!

4.96 out of 5 average rating, 212 reviews

The living area features a comfortable sofa facing a TV stand, with a television present. Natural light enters from large windows adorned with simple treatments, casting a warm glow on wooden floors. Various art pieces decorate the walls, and a small coffee table is positioned centrally.

Cottage in Duxbury

Camel's Hump Remote Mountain Cottage

Escape to this peaceful getaway with beautiful mountain views. Our cottage is ideal for the adventure seeker, nature lover or remote worker. Located less than two miles from Camel’s Hump trail head and less than 30 miles from ski resorts, including Stowe, Sugarbush, Bolton, Cochran and Mad River. The area offers plenty of outdoor activities from hiking, cross country skiing, snow shoeing, mountain biking, fishing, swimming, kayaking and only 15 min from local restaurants, breweries and shops.

Apartment in Bolton Valley

A comfortable sectional sofa is positioned in the living area, accented by a light throw and decorative pillows. Nearby, a bright lamp provides soft illumination, while a coffee table complements the modern aesthetic. Large windows allow natural light to fill the space, offering views of the outside.

Slopeside Condo ~ Luxe & Cozy ~ Ski, Ride, XC/BC

It doesn’t get more slopeside than this! Impeccably clean & well-appointed. Four Winds condo is the perfect home base for fall & winter activities at Bolton Valley Resort. Located next to Wilderness Lift and the uphill route, ski down to the front door. Short walk to Vista Lift, Base Lodge (Rentals, Tix, Tavern), Sport Center (Pool, Sauna), and XC trails. 1 mile to The Ponds & Timberline Lodge. BTV Airport & downtown Burlington 35 mins; Waterbury & Richmond 18 mins; Sugarbush & Stowe 50 mins.

4.99 out of 5 average rating, 128 reviews

4.96 out of 5 average rating, 158 reviews

A spacious living area features a brown sectional sofa with decorative pillows. A wooden coffee table is centered in front of the sofa. Light fills the room from windows, and a doorway leads to a kitchen and dining area, visible in the background.

Home in Bolton

Modular - 3 bedroom house

Modular home has only ever been a short term rental and never fully lived in. 3 bedrooms and 2 bathrooms, including one master bathroom. Electric fireplace to gather around after a long day playing in the snow. Large movie collection for stay at home days. Keurig machine for fresh coffee in the morning or some hot chocolate. 30 minutes to Stowe, Burlington and Montpelier. Lots of places to eat and shop within 30 minutes. Bolton ski resort 5 minutes down the road. Great view of the mountains.

4.94 out of 5 average rating, 179 reviews

A modern kitchen features sleek white cabinetry and granite countertops with ample workspace. A stainless steel refrigerator and oven stand ready for use. A decorative wall showcases a playful pattern. A spiral staircase leads to the upper level, with natural light flowing through a nearby window.

Guest house in Richmond

Send It Inn: Newly Renovated Guest House

Our beautifully renovated guest house is thoughtfully set up for you and your friends to take advantage of the best Vermont and our amazing town has to offer. Located in the center of Richmond, Vermont you are literally footsteps or a short peddle away from restaurants, breweries, trails, swimming holes, and more. Richmond's mountain bike trail system can be accessed out your door. Five of Vermont's best ski resorts are within 45 minutes. Burlington is only a 15 minute drive. Send It!!!!

4.96 out of 5 average rating, 515 reviews

The exterior of the cabin is framed by lush greenery, featuring a welcoming pink door and multiple windows adorned with flower boxes. The structure is nestled among the trees, providing a sense of privacy and tranquility in a natural setting.

Tiny home in Bolton

Tiny House Cabin between Burlington and Stowe

The Four Seasons has all the comforts of home with the calm and quiet of the mountains. Enjoy the beautiful sunset views from the wooded deck or in front of the cozy wood stove. We are minutes from hiking the Long Trail, rock climbing the Bolton Dome, skiing Bolton Valley, Stowe Mountain Resort, or Smugglers Notch, swimming in Lake Champlain, or playing golf at the West Bolton Golf Course. We are also less than an hour drive to Burlington, Montpelier, Stowe and the Canadian border.

Apartment in Bolton Valley

A modest front deck is visible, featuring railings and a few steps leading to an entrance door. A potted plant hangs above, while vibrant flowers are located below, set against a backdrop of trees displaying autumn foliage.

Cozy Little Mountain Condo at BV Ski Resort

Relax on the mountain in our little condo. A cozy space to enjoy fresh mountain air. Enjoy easy access for ski in/out, hiking, mountain biking, leaf peeping…something to love here during every season! Bedroom with a queen bed. Pull out couch is best suited for children or one adult—two large adults may find it a tight fit. Located approximately half-way between Burlington and Stowe, about 30 minute drive to either/or. Or check out Waterbury (our favorite) about 15 minutes away!

5.0 out of 5 average rating, 104 reviews

A spacious living area is designed with large windows allowing ample natural light and views of the surrounding greenery. A comfortable sectional sofa and armchair are arranged around a coffee table, while a flat-screen TV is mounted on the wall. A sliding door leads to an outdoor deck.

4.93 out of 5 average rating, 27 reviews

Cozy 2 br Apt in Bolton Valley w/ Wood Fire Sauna

Welcome to your perfect Vermont escape! Nestled in the serene mountain town of Bolton, our comfortable 2-bedroom apartment offers the ideal basecamp for year-round adventure and relaxation. Located a short walk from Bolton Valley Resort, you’ll have access to skiing/snowboarding, Nordic trails in the winter, and incredible mountain biking and hiking in the warmer months. Wake up to crisp mountain air and stunning forest views. Outdoor Vermont-made sauna coming summer 2025!

4.94 out of 5 average rating, 35 reviews

SlopeSide Escape: Ski In/Out

Welcome to Your Slopeside Sanctuary at Bolton Valley Resort! Mountain getaway with true ski, bike, hike in/out access. Nestled in the heart of Bolton Valley Resort. Steps from the lifts, trails, and all BV has to offer. - Ski-in/ski-out convenience - Relax in an inviting space perfect for unwinding after a day outdoors. - Prepare meals in the well-appointed kitchen with modern appliances and cookware. - Accommodates up to 4 guests.

4.93 out of 5 average rating, 136 reviews

Home in Huntington

Happy Hollow Barn

This one of a kind 4 bedroom home was built in 2018. We refinished an old barn frame from Waitsfield, VT and had it moved to our property. The hand-hewn frame of this early 1800's barn is a piece of art in itself. We have used as much of the original structure as we could to create a warm, rustic, and inviting space for you to get away from reality for a little while. Come enjoy a peaceful retreat in the mountains of Vermont.

A cozy living area features a green couch adorned with colorful throw pillows and a warm blanket. A round blue chair offers additional seating, complemented by a simple black coffee table placed on a striped rug. Natural light brightens the space from nearby windows.

4.95 out of 5 average rating, 294 reviews

Hideaway studio: breweries, skiing, dogs welcome

New construction, private entrance 600+ sq ft apartment close to skiing & all outdoor activities Vermont has to offer, with a unique piece of Phishtory. Steps from hiking & mountain biking trails, lots of ski areas & swimming holes close by. Our studio is a great basecamp or a relaxing getaway. Bright, large & sunny, located in between Burlington & Waterbury/Stowe. 1.5 miles from the charming Richmond village.

4.99 out of 5 average rating, 226 reviews

A modern treehouse is elevated on wooden stilts, surrounded by trees. A spacious outdoor deck, supported by slender posts, extends from the structure. Leafy forest floor is visible below, showcasing a natural setting with a path leading to the entrance.

Treehouse in Bolton

Secluded Vermont Treehouse - Escape and Unwind

Welcome to our Vermont Treehouse! Adventure awaits on our 500 acre maple syrup farm at the base of Robbins Mountain. There are endless outdoor opportunities. Hiking, biking, boating, swimming and skiing are right outside the door. The treehouse abuts Camels Hump State Forest, however it is very close to quaint small towns, dining, breweries and the interstate for easy travel.

Popular amenities for Bolton holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Bolton

5.0 out of 5 average rating, 29 reviews

A modern home is set against a backdrop of vibrant fall foliage. The structure features a mix of dark wood and stone accents, with large windows that provide ample natural light. A manicured lawn with yellowing leaves is visible in the foreground.

Home in Bolton

Home in Bolton, Vermont Unit #1

5.0 out of 5 average rating, 52 reviews

Apartment in Bolton

4-bedroom Condo at Bolton Valley

4.93 out of 5 average rating, 27 reviews

Sunset Mountain Retreat at Bolton Valley (2F)

Superhost

A spacious living area features timber ceiling beams and large sliding doors leading to a furnished deck. Comfortable seating includes a sectional sofa and two accent chairs, complemented by a decorative area rug and a coffee table. Natural light fills the room, highlighting mountain views.

4.93 out of 5 average rating, 82 reviews

Family condo w/ resort access & patio

The exterior of a charming mountain retreat is featured, with a green wooden façade and a copper metal roof. Natural stone steps lead to the welcoming front door, flanked by flourishing flower pots. Lush greenery surrounds the home, enhancing the serene mountain setting.

5.0 out of 5 average rating, 13 reviews

Home Base

4.99 out of 5 average rating, 99 reviews

A spacious living area features a large sectional sofa arranged around a stone fireplace. Floor-to-ceiling windows let in natural light, offering views of the surrounding trees. A dining table with wooden chairs is visible in the background, creating an inviting space for gatherings.

Loft in Bolton Valley

Modern loft - ping pong / ski in, ski out

5.0 out of 5 average rating, 14 reviews

A dark green house with wooden accents is nestled among greenery, showcasing a welcoming front entrance. A spacious gravel driveway leads to a detached garage on the left, with a vehicle parked nearby. Natural light filters through the trees, enhancing the serene outdoor setting.

Home in Richmond

Elegant Ski-in Ski-out House at Bolton Valley