Restaurants near Chesterwood

Price

$$
$$$
$$$$

Cuisine

AmericanItalianSteakhouseSeafoodFrenchMexican

Top Rated

CharmingFancyGood for business mealsGood for groupsGood for special occasionsGreat for brunch

Dining Options

All dining options

Delivery only

Takeout only

Seating Options

BarCounterStandardHigh TopOutdoor

Accessibility

Gender-neutral restroomWheelchair access

149 restaurants available nearby

How are Featured results ranked

The default order for search results reflects a number of factors, including table availability, restaurant location, search criteria, and restaurant reviews and ratings. In addition, payment made by a restaurant to OpenTable is also a factor for the relative ordering of restaurants.

1. The Red Lion Inn

4.6

Exceptional(3042)

$$$$Price: Expensive

• Contemporary American • Stockbridge

Booked 16 times today

Since welcoming its first guests in 1773, The Red Lion Inn has earned a reputation for outstanding food and genuine country hospitality. Those traditions are continued today by Executive Chef Jon Sterrett, whose kitchen features contemporary cuisine that is rooted in the region's history and harvests. Emphasizing the use of fresh, local ingredients and a huge proponent of buying locally and sustaining the region, Chef Sterrett regularly updates the Inn's menus to reflect the bounty of each season. Guests choose from the elegant Main Dining Room and the cozy Widow Bingham's Tavern. The wine list offers 500 plus selections, and has received the Wine Spectator best of Award of Excellence for ten consecutive years; Sommelier Tim Eustis helps pair wines with meals. If you would like to dine in the Tavern, please choose Bar when making your reservation.

A photo of The Old Inn On The Green restaurant

2. The Old Inn On The Green

5.0

Exceptional(974)

$$$$Price: Very Expensive

• Contemporary American • New Marlborough

Booked 3 times today

Dining at The Old Inn on the Green is an extraordinary experience: fine wine, great food, attentive, knowledgeable service and the dining rooms illuminated only by candle light. Chef and Owner Peter Platt, along with his team, work to create innovative and memorable meals that are an event unto themselves. Currently, we are offering a $85 prix fixe menu with 5-6 choices per course every night we are open. The hours for dinner are Wednesday through Sunday 5:30 pm to 9:00 pm for both indoors and in an all new screened outdoor room. The wine list is graced with an array of thoughtfully selected estate bottled wines from France, California, Italy and around the world. In addition to candlelight, in the colder months there are wood burning fireplaces in each room. A copy of our current menu can be found on the home page of our website www.oldinn.com.

A photo of Gateways Dine & Drink restaurant

3. Gateways Dine & Drink

4.4

Awesome(403)

$$$$Price: Moderate

• Farm-to-table • Lenox

Welcome to Gateways Dine & Drink, located in the historic Gateways Inn!Our menu has something for everyone to enjoy. Fresh dishes created by our chef and amazing staff for our locals and visiting guests alike. Our tasty grass-fed beef burger and salmon dishes are guest favorites! But don't forget to leave room for dessert...Please inquire about private events, up to and including wedding receptions.

4. Pillow Cafe

3.9

Excellent(207)

$$$$Price: Very Expensive

• American • Becket

The Pillow Cafe is the perfect dining option before or after a show at Jacob's Pillow! Dine al-fresco under our tent on the beautiful and historic grounds, which rest on the ancestral homelands of the Muh-he-con-ne-ok or Mohican people. Reservations start in May and are strongly encouraged.Executive Chef Stephen Will uses the finest, locally sourced ingredients to cultivate a delicious menu of appetizers, entrees and desserts. Enjoy the audience-favorite chilled lobster roll, or the cooked-to-order filet mignon, or a hearty Charcuterie spread! Take delight in choosing a libation, be it wine, beer, cocktails or mocktails! A 2023 OpenTable Diners Choice Award Winning Restaurant, we hope you will join us for a memorable dining experience which features the finest from The Berkshires.

5. Josie's Table

4.8

Exceptional(1105)

$$$$Price: Moderate

• American • Albany

Booked 51 times today

Josie's Table offers amazing local farm to table cuisine accompanied by our signature craft cocktails.Something new and unique to the Albany area.

A photo of American Bounty at The Culinary Institute of America restaurant

6. American Bounty at The Culinary Institute of America

4.8

Exceptional(4256)

$$$$Price: Expensive

• American • Hyde Park

Booked 44 times today

With a focus on the seasons and products of the Hudson Valley, contemporary and traditional regional dishes are brought to life in an honest and flavorful way by CIA students under the instruction of world-class faculty at the American Bounty Restaurant. Rounded out with a top-tier American wine list and comfortable warm service, this casually elegant restaurant sets the stage for an unparalleled dining experience in New York’s Hudson Valley.

7. La Bella Valatie

4.9

Exceptional(124)

$$$$Price: Expensive

• Italian • Hudson

Booked 1 time today

La Bella Restaurant & Pizzeria in Valatie, NY is an Italian restaurant where the true taste of the old country reigns supreme. The old family recipes used at La Bella remain true to the mouthwatering homemade dishes prepared in Mama's Cucina Italiana. In Italy, using only the finest and freshest ingredients in the preparation of the meal, is of the utmost importance. At La Bella we believe that is one tradition to revere and to follow every day.We hope you will join us soon for lunch, dinner, a pizza, or a slice to go.Buon Appetito!

A photo of Max Downtown - Hartford restaurant

8. Max Downtown - Hartford

4.6

Exceptional(230)

$$$$Price: Very Expensive

• American • Hartford

Booked 49 times today

Located right in downtown Hartford since 1996, Max Downtown continues to add to all that the city has to offer with its legendary service, food and drink selection. Max Downtown has won a number of awards including Connecticut Magazine's Best for Overall Excellence, Hartford Magazine's Best Power Lunch Spot, Best for Business Entertaining and Best Wine List; has been featured in the Hartford Courant's Great Steaks: The State's Sizzling Best and was rated "Don't Miss" by the New York Times.With a significant list of vintage and non-vintage wines stored in-house, Max Downtown is excited to additionally offer its stunning wine mezzanine as a focal point. Our selection is bound to have the perfect accompaniment for your occasion whether it’s by the glass or by the bottle.If spirits are more your style, Max Downtown's whiskey bar features a broad selection of international bourbons, ryes, scotches and whiskeys crafted across the globe, from Kentucky to Japan.

A photo of The Bocuse Restaurant at The Culinary Institute of America restaurant

9. The Bocuse Restaurant at The Culinary Institute of America

4.8

Exceptional(4464)

$$$$Price: Expensive

• French • Hyde Park

Booked 48 times today

Sleek and strikingly contemporary, The Bocuse Restaurant is named for the most famous chef in France, Paul Bocuse. Here, CIA students re-imagine the execution of classic French cuisine through the lens of ultra-modern cooking techniques under the instruction of world-class faculty. Enjoy casual yet sophisticated service alongside an exceptional French wine list and innovative cocktail program during your unique and exciting dining experience.

10. The Stewart House

4.8

Exceptional(120)

$$$$Price: Moderate

• American • Catskill

Booked 5 times today

Please note reservations are for the 1883 Tavern Only. For large parties please call to reserve the private dining room. 518-444-83171883 Tavern features an Art Deco bar and dining room. Farm-sourced dishes comprise an ever-evolving menu. Enjoy dinner in a historical setting on the banks of the Hudson River with weekly specials, an inventive cocktail, fine wine or local craft beer. Happy first hour each day we’re open (half price drinks), live music on Thursday nights and a burger & beer special, Friday martini & mussels special (every martini comes with a side of mussels), Sunday Bloody Mary menu and special Sunday Roast dinner with all the fixings.

See what locals rave about

From verified diners like you

J
John
New York City •1 review
4.0
Dined today
Great food with kind and responsive staff. Love this place.
More info
Josie's TablePrice: Moderate• American• Albany
•
4.8
V
VirginiaVIP
New York City •11 reviews
5.0
Dined on Mar 1, 2025
Always a great experience here; charming, quaint, and wonderful food/service.
More info
The Old Inn On The GreenPrice: Very Expensive• Contemporary American• New Marlborough
•
5
D
Diane
Central and Western MA •1 review
5.0
Dined on Feb 27, 2025
Delicious meals!! I had the Fillet Mignon which was cooked rare to perfection just the way I enjoy it!! Always enjoy coming to the Red Lion Inn!!
More info
The Red Lion InnPrice: Expensive• Contemporary American• Stockbridge
•
4.6
D
Darren
New York City •31 reviews
5.0
Dined on Nov 1, 2024
The service and food were great. The live piano music was amazing as well. The only thing was that there was a large gathering in the bar area that was really loud and disruptive to the diners in the restaurant area. Otherwise, it was a great time.
More info
Gateways Dine & DrinkPrice: Moderate• Farm-to-table• Lenox
•
4.4
D
Daniel
New York City •6 reviews
5.0
Dined on Aug 22, 2024
Fantastic amenity for patrons! Made for. Great evening.
More info
Pillow CafePrice: Very Expensive• American• Becket
•
3.9

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