Vacation rentals in Bolton

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Top-rated vacation rentals in Bolton

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Guest favourite

Apartment in Waterbury

4.98 out of 5 average rating, 318 reviews

Village Suite

Modern + charming apartment with private entrance + deck located in Historic Waterbury Village within walking distance to popular shopping, coffee shops, pubs, and restaurants. The building is also home to the Stowe Street Cafe and Bridgeside Bookstore with plenty more shops and eateries just a short walk away. Bolton Valley, Sugarbush, and Stowe Mountain Resorts are just a 20-30 minute drive, and the Ben & Jerry's Factory and Waterbury Reservoir are less than 10 miles north. A perfect location!

May 6 – 13

$249 CAD per night

Superhost

Cabin in Richmond

4.9 out of 5 average rating, 110 reviews

Cozy Richmond Cabin

This tiny house nestled in the woods of Richmond is the perfect getaway for a small group. Inside you will find an open kitchen/living space, 2 bedrooms, and a full bath. The Guest Cabin has a futon, a space heater, and a wood stove (does not have plumbing). Outdoor features - backyard, fenced in yard space, a small porch, grill, and fire pit. **STEEP DRIVEWAY: snow tires, AWD/4WD necessary in Winter. Property can accommodate 6 guests if Guest Cabin is in use (most ideal for warmer weather)**

Oct. 15 – 22

$341 CAD per night

Guest favourite

Guest suite in Middlesex

5.0 out of 5 average rating, 275 reviews

Morningstar Meadow - your home in Vermont

You have a home in Vermont! 5-star one-bedroom apartment has country charm and contemporary panache. A perfect retreat to enjoy rural serenity, stunning views, woods and fields. Everything you need: well-appointed with attractive, high quality furnishings, separate entrance, full kitchen, open living/dining area, cozy bedroom with queen bed. Cable TV, WiFi, and cell service. Plentiful free parking. Centrally located 3 miles from Montpelier. Snow tires or all-wheel drive recommended Nov-March.

Sep. 6 – 13

$192 CAD per night

Guest favourite

Apartment in Waterbury

4.97 out of 5 average rating, 377 reviews

Village Oasis 2 -the crossroads of VT

A friend once referred to our town as Mayberry. It's definitely a small town where people look out for each other. In the heart of the village, walking distance from local restaurants, brewery's, and shops as well as mountain bike trails. 5 mi from a beach where you can rent canoes/kayaks/paddle boards. Enjoy the slopes, hiking, Ben and Jerry's, local brewery's, or the Vt. landscape, settle in with a warm jacuzzi tub. At the end of the day cozy up on a king sized bed watching Netflix's.

Jan. 8 – 15

$150 CAD per night

Guest favourite

Cabin in Worcester

4.97 out of 5 average rating, 169 reviews

the little house

Come rejuvenate in our sweet little cabin tucked into the Vermont mountains. It has such wonderful healing energy! ✨ Cozy up to read a book next to the fireplace or book a private kambal yoga session for you and your companion. ☺️ Kambal sessions include sound healing, yoga nidra, energy work & weighted blankets for deep relaxation. -On site Minister Brook access--5 min. walk -Lots of skiing, hiking, water to explore -18 min to Montpelier- funky downtown, eccentric shops & restaurants

Aug. 26 – Sep. 2

$239 CAD per night

Guest favourite

Condo in Richmond

4.95 out of 5 average rating, 184 reviews

Chic Mountainside Studio at Bolton Valley

After ski season, comes Vermont's gorgeous spring, summer and fall. From this chic mountainside retreat you'll enjoy beautiful vistas and the calming sounds of the babbling brook from the balcony. Step outside and there's so much to do: hiking & mountain bike trails, disc golf, swimming at Bolton Potholes and leaf peeping in the fall. This studio allows you to escape the hustle and bustle - but is still centrally located between Burlington and Waterbury/Stowe.

May 23 – 30

$220 CAD per night

Guest favourite

Treehouse in Bolton

4.99 out of 5 average rating, 142 reviews

Modern treehouse on working maple syrup farm

Welcome to Quinn’s treehouse. We are located on a 500 acre working 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 is close to local shops, dining and the interstate for easy travel. We also have a backcountry glamping site available. See https://www.airbnb.com/h/mapleglamping for details

Jun. 14 – 21

$522 CAD per night

Guest favourite

Barn in Starksboro

4.97 out of 5 average rating, 107 reviews

The Black Barn in a Mountain Hollow

The Ell at Prison Hollow Homestead is a lovingly renovated 1800's barn at the intersection of forest, field, and mountain. This quiet getaway offers sweeping easterly views and easy access to outdoor adventures including hiking, skiing, and fishing. Enjoy your morning coffee as the sun rises over the Green Mountains and relax in front of the fireplace at day's end. Conveniently located 35 minutes from Burlington and 30 minutes from Middlebury.

Oct. 19 – 26

$213 CAD per night

Guest favourite

Guest suite in Waterbury Center

4.94 out of 5 average rating, 415 reviews

Waterbury Center Guest Bedroom - 244 Howard

The guestroom room is very cozy with radiant heat in the floor during the winter. The separate entrance is off a covered porch. The porch has chairs and a table and is very pleasant in the warmer months The little kitchen alcove is convenient for coffee or tea or a light meal. We live in a historic building and our neighborhood is located very close to Rte 100. Waterbury village and Stowe as well as skiing, hiking and biking are all nearby.

Apr. 16 – 23

$81 CAD per night

Guest favourite

Apartment in Richmond

4.95 out of 5 average rating, 171 reviews

Hideaway studio: breweries, hiking, dogs welcome

Brand new 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.

Sep. 19 – 26

$209 CAD per night

Guest favourite

Apartment in Richmond

4.95 out of 5 average rating, 150 reviews

Vibrant Village Studio

Welcome to this sunny Richmond village studio! This newly renovated studio apartment features a dedicated bedroom space. The kitchen is fully equipped for your cooking needs, and conveniently located above a restaurant and bar. Enjoy village living where everything is in walking distance (market, coffee shop, restaurants, park, river)! Photography: Shem Roose

Jul. 19 – 26

$216 CAD per night

Guest favourite

Guest suite in Hinesburg

4.96 out of 5 average rating, 1115 reviews

Boston Magazine Pick! Barn Loft

*** Chosen by Boston Magazine as one of five New England barns to rent! *** Beautiful barn loft close to Burlington, the Green Mountains and Lake Champlain. Air conditioning, cathedral ceilings, plenty of natural light, rustic charm and lovely views. The space has its own entrance and is completely separate and private from the main house.

Oct. 23 – 30

$252 CAD per night