Where to STay & Eat: INNS and Restaurants in Chester
While there's certainly no lack of things to do in Chester, VT, it is not surprising that many visitors choose Chester as their base for exploring the rest of Southern Vermont. Centrally located to many of the region's top attractions, Chester is an ideal place to anchor a stay—whether you plan on keeping close to town or venturing further afield for all that the Green Mountains and the Okemo Valley have to offer. Returning from your day trips, you'll find a variety of dining options to satisfy everyone's tastes, from intimate fine dining experiences to cheery taverns, at the restaurants in Chester, VT.
Chester House Inn
Dating back to 1780, the Inn is located on the town green. The beautifully restored building reflects its rich history. The inn is handicap accessible, offering seven rooms to suit each guest’s needs. We offer excellent accommodations and warm hospitality to all guests.
Address: 266 Main St. | Google Maps
Phone: (802) 875-2205
The Free Range
Serving fresh creative comfort fare in a warm relaxed environment. Full bar, extensive wine list, locally sourced provisions, espresso & cappuccino, house made desserts, daily specials. Open Tues. – Sun. for dinner, Saturday lunch. Exquisite Sunday Brunch from 10 am – 2 pm.
Address: 90 Common St., Chester, VT | Google Maps
Phone: (802) 875-3346
On the Green – Chester. 20 guest rooms. Lunch & Dinner comfortable casual dining. Exceptional menu. Wines, 10 Vermont beers on tap and full bar. Large fireplace in lobby and also in our tavern. Front porch dining in season. Fine/Casual Dining Monday-Saturday 5 pm – 9 pm. Lunch Wed. – Sat 11:30 am – 3:00 pm. 40 Common St. (802) 875-2444
Address: 40 Common St., Chester, VT | Google Maps
Phone: (802) 875-2444
Henry Farm Inn
Yankee Magazine Top 10 Historic Inn! Nine spacious, sunny guest rooms, two with kitchen suites, all with private baths. Bountiful country breakfasts and WiFi included. Pond, river and beautiful meadow on site. Reasonable rates. Families very welcome. Okemo Stay & Ski Packages! Quilting and Yoga Retreats our specialty.
Address: 2206 Green Mountain Turnpike, Chester, VT | Google Maps
Phone: (800) 875-8213
Heritage Deli & Bakery
- Delicious breads, rolls and pastries
- Custom order sandwich selections
- Breakfast & lunch specials
- Catering your special events
- Wedding and Celebration Cakes
- Open everyday 7am-6pm
Address: 642 VT-103 , Chester, VT | Google Maps
Phone: (802) 875-3550
Hugging Bear Inn & Shoppe
Vermont Victorian family bed and breakfast inn and shopping destination welcomes all ages since 1982! Private baths, full breakfast, relaxed setting, with a pleasure to serve. Shop boasts 10,000 teddy bears. You get friends for life here! Across from the Village Green. See "Shopping".
Address: 244 Main St., Chester, VT | Google Maps
Phone: (802) 875-2412
Acclaimed by Yankee Magazine and Trip Advisor as providing the most “Romantic & Exceptional Experience” in South Central Vermont, this circa 1850 Victorian style B&B is admired and loved by many. Owners & purveyors, Penny & Dan Cote, welcome you to tour this village treasure while visiting Chester and the Okemo Valley Region.
Address: 351 Main St., Chester, VT | Google Maps
Phone: (802) 875-4288
Happily providing a SMILE to our customers since 1985. Jiffy Mart is your Home Town Convenience Store plus more. We now offer Subway and Ramunto's Pizza. Stop in for a Fresh Made Sub or a Fresh Made Pizza. Slice or Whole Pie. Also local made Syrup and Honey. STOP BY FOR A SMILE.
Address: 89 VT-103, Chester, VT | Google Maps
Phone: (802) 374-0040
Maclaomainn's Scottish Pub
Step through our door and you’ll be transported across the Atlantic and into an authentic Scottish pub where you will instantly sense centuries of Scottish hospitality. Join us at MacLaomainn’s Sunday thru Thursday 11:30AM-11:00PM, Friday-Saturday 11:30AM- Midnight.
Address: 52 South Main St., Chester, VT | Google Maps
Phone: (802) 875-6227
Moon dog cafE
Moon Dog is an eclectic organic café serving breakfast and lunch that features amazing soups, salads, sandwiches, a juice bar, cappuccino, smoothies, a full bakery and fresh produce. Also, find unique gifts from Europe and South America. Open seven days – cool place & cool people. Find Us on Facebook.
Address: 295 Main St., Chester, VT | Google Maps
Phone: (802) 875-4966
Motel in the Meadow & Gift Shop
Motel in the Meadow & Gift Shoppe is a small, well-kept motel offering a variety of accommodations including kitchenettes. Also, home of Music in the Meadow, a benefit concert for Susan G. Komen New England, For the Cure (concert dates June 24 & 25, 2017).
Address: 936 VT-11, Chester, VT | Google Maps
Phone: (802) 875-2626
Stone Hearth Inn & Tavern
Our classic Vermont country Inn features eight guest accommodations all with private bathrooms. Our kitchen offers a rotating menu of local and regional ingredients. We offer a full service bar including 13 microbrews on tap. We are designated as a green hotel and are members of the Vermont Fresh Network.
Address: 698 VT-11, Chester, VT | Google Maps
Phone: (802) 875-2525
- Karass Inn
225 Pleasant St, Chester, VT 05143