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
Website: www.chesterhouseinn.com

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
Website: www.thefreerangevt.com 

Fullerton Inn

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
Website: www.fullertoninn.com

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
Website: www.henryfarminn.com

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
Website: www.huggingbear.com

Inn Victoria

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
Website: www.innvictoria.com


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
Website: www.maclaomainns.com

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
Website: www.motelinthemeadow.com

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
Website: www.stonehearthinnvermont.com

Other Properties

  • Karass Inn
    225 Pleasant St, Chester, VT 05143

Map: Where to Stay + Eat