Vacation rentals in Chester Depot

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chester Depot

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond in S Londonderry, VT. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery and hiking right outside your front door. The Cabin has an open floor plan with a galley kitchen, dining/living area with pullout futon couch & 1 full bathroom. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Aug 21 – 28

$91 per night

Guest favorite

Guesthouse in Springfield

4.86 out of 5 average rating, 321 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

Aug 18 – 25

$80 per night

Guest favorite

Tiny home in Athens

4.95 out of 5 average rating, 147 reviews

Luxury “Tiny” House, Immersed In Nature (Timbery)

The Timbery: This is a brand new, fully handmade, timber frame "tiny" house. 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 on the forest floor and looking out the front of your tent. Except instead of wet sleeping bags and dirty hair, you enjoy a queen sized bed, in home theater, full kitchen and 71in soaking tub. NO SMOKING

Sep 1 – 8

$219 per night

Guest favorite

Cabin in Grafton

4.98 out of 5 average rating, 171 reviews

Peaceful log cabin retreat...

Peaceful, restful and serene cabin...romantic getaway...writers retreat...artist's refuge set in 80 acres of forest. Cozy and comfortable place with radiant floor heat, long views across the meadow to the forest. Hawks, deer and moose sometimes visit the meadow to browse. A walk down the driveway to the beaver pond and you may see the beavers. Solar backup will provide Phone, Heat, Hot water, Wifi, lights and outlets in main room. Back 2 rooms & bathroom will not have power without grid.

Dec 8 – 15

$183 per night

Guest favorite

Barn in Chester

4.99 out of 5 average rating, 492 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

Sep 22 – 29

$89 per night

Guest favorite

Guest suite in Chester

4.91 out of 5 average rating, 155 reviews

Chester Carriage House-Cozy-Quintessential Vermont

Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and pubs, antique shops, art galleries, yoga studio and a country market. Explore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers + breweries. Close proximity to the best of Vermont's ski resorts! (Magic Mountain, Bromley, Stratton, Okemo and Killington) Come experience why Chester has been voted one of the top 10 most beautiful towns in Vermont!

Jul 20 – 27

$125 per night

Guest favorite

Home in Chester

4.91 out of 5 average rating, 11 reviews

Charming Chester Farmhouse

Welcome to this charming farmhouse on a peaceful residential street close to the heart of Chester. This home has comfortable living spaces, sizable bedrooms, and a fantastic kitchen to cook in––all combined with a thoughtful Vermont and mid-century aesthetic. The property is very close to several ski hills: Okemo, Magic, Bromley are 15-20 minutes from the house, Stratton is 40 minutes away. The house is spacious and is also conveniently located near all amenities in town.

Jun 13 – 20

$225 per night

Superhost

Guest suite in Chester

4.84 out of 5 average rating, 44 reviews

Adorable, Cozy 2 bedroom apartment walk to village

Welcome to this cute and cozy self-contained unit with all the amenities you could need! Walk to Chester VT Village green, just 14.2 miles from Okemo! Recently renovated, you have the apartment to yourself - 2 bedrooms with queen sized beds, a cozy living room and a kitchenette that provides everything you need for your stay! Washer/dryer, parking our front and even a deck off the back to enjoy in the warmer months! This is a great place for a getaway OR a longer stay!

Nov 5 – 12

$122 per night

Guest favorite

Guest suite in Chester

4.93 out of 5 average rating, 14 reviews

Stone Village Private Studio

Located in the Stone Village of Chester, VT. Our studio apartment is in one of the oldest homes built in 1835. Located 20 minutes to Okemo and Magic Mountain. Stratton is about 45 minutes away for our downhill/outdoor enthusiasts and we are centrally located for antiques and yummy food! Our cozy studio features a comfy queen size bed, fully stocked kitchen and bathroom with shower. Our living space features 2 arm chairs, an electric fireplace and a large screen TV.

Dec 5 – 12

$134 per night

Guest favorite

Cottage in Windsor

4.97 out of 5 average rating, 316 reviews

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins.

Nov 20 – 27

$118 per night

Guest favorite

Condo in Ludlow

4.92 out of 5 average rating, 122 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

Jul 27 – Aug 3

$87 per night

Guest favorite

Home in Chester

5.0 out of 5 average rating, 16 reviews

Cozy 1850 farmhouse in Stone Village of Chester

This is our very cozy 1850 home in the Stone Village of Chester. The house has many of the original features and charm including wide plank pine flooring, plaster walls and original molding. Some of the door hardware is very unique and original to pre-civil war. The Town of Chester has unique shopping and restaurants, and is one of the safest places in the US. The neighborhood is on the National Register of Historic Places.

Jan 27 – Feb 3

$109 per night