Vacation rentals in Chester Depot

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Top-rated vacation rentals in Chester Depot

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

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!

Oct 4 – 11

$91 per night
Guest favorite

Apartment in Springfield

4.9 out of 5 average rating, 221 reviews

Farm Barn apt. 3 bedr, 2 bath, fiberoptic internet

Getaway for families, couples or groups. Apt. in our Barn. High speed internet, so ideal for "work from home". Full kitchen with oven, microwave, dishwasher, big fridge , 3 bedrooms, 2 baths, Dining/Living room with TV ( Antenna, no cable, Roku: bring your passwords for Netflix..) Fields, forest, hill and river on our property. We allow one friendly dog at a time but it is not allowed to stay in the apt. by itself (daycare in Spgf avbl). Please add the dog to your booking for the one time 35 $.

Apr 16 – 23

$87 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.

Dec 31 – Jan 7

$80 per night

Popular amenities for Chester Depot vacation rentals

Stay near Chester Depot's top sights

Country Girl Diner29 locals recommend
MacLaomainn's Scottish Pub31 locals recommend
The Pizza Stone VT.27 locals recommend
Fullerton Inn12 locals recommend
Southern Pie Cafe18 locals recommend
the Free Range15 locals recommend

Other great vacation rentals in Chester Depot

Guest favorite

Apartment in Claremont

4.88 out of 5 average rating, 108 reviews

Beautiful 1 bedroom apartment with balcony

Oct 14 – 21

$77 per night
Guest favorite

Home in Putney

4.94 out of 5 average rating, 332 reviews

Vermont Botanical Studio Apartment

Nov 25 – Dec 2

$95 per night
Superhost

Condo in Ludlow

4.92 out of 5 average rating, 116 reviews

All Season Lovely and Zen Okemo Mt Lodge Condo

May 22 – 29

$88 per night
Superhost

Guest suite in Chester

4.84 out of 5 average rating, 43 reviews

Adorable, Cozy 2 bedroom apartment walk to village

Oct 13 – 20

$122 per night
Guest favorite

Home in Chester

4.92 out of 5 average rating, 26 reviews

Stunning farmhouse in historical village

Aug 20 – 27

$287 per night
Guest favorite

Farm stay in Chester

4.97 out of 5 average rating, 37 reviews

Rivers Edge Farm’s Cozy Cabin

Sep 16 – 21

$78 per night
Guest favorite

Home in Chester

4.95 out of 5 average rating, 19 reviews

Spring Skiing! Location! Minutes from Okemo!

Sep 20 – 27

$259 per night
Guest favorite

Tiny home in Chester

5.0 out of 5 average rating, 76 reviews

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Dec 24 – 31

$222 per night
Guest favorite

Guesthouse in Grafton

4.89 out of 5 average rating, 90 reviews

VT Sugar House-Guesthouse

Oct 22 – 29

$63 per night
Guest favorite

Home in Chester

4.92 out of 5 average rating, 26 reviews

Private Home in Chester, VT

Dec 7 – 14

$278 per night
Guest favorite

Farm stay in Baltimore

4.93 out of 5 average rating, 94 reviews

Hawk Mtn Farm's lovely one bedroom apartment!

Apr 10 – 17

$95 per night
Guest favorite

Home in Chester

5.0 out of 5 average rating, 81 reviews

Historic VT Grist Mill on the Williams River

Mar 15 – 22

$737 per night
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