Cottage Getaway in The Berkshires
Food scene
This restaurant is located 1 minute from the cottage. It is great for casual and delicious take out or dine-in. They have wood-fired pizza, salads, and great entreés. In the summer, they have a very nice enclosed outdoor patio and offer live music on certain nights.
14 locals recommend
Roasted Garlic
483 W Housatonic StThis restaurant is located 1 minute from the cottage. It is great for casual and delicious take out or dine-in. They have wood-fired pizza, salads, and great entreés. In the summer, they have a very nice enclosed outdoor patio and offer live music on certain nights.
Great spot for wine, cheese, beer, great food and specialty groceries. You can shop or take away prepared meals.
248 locals recommend
Guido's Fresh Marketplace
760 S Main StGreat spot for wine, cheese, beer, great food and specialty groceries. You can shop or take away prepared meals.
A great eatery in downtown Pittsfield that always serves up delicious meals. Wonderful for everything from casual to special dining.
54 locals recommend
District Kitchen & Bar
40 West StA great eatery in downtown Pittsfield that always serves up delicious meals. Wonderful for everything from casual to special dining.
Great downtown cafe with an artsy vibe, delicious food and a variety of coffee drinks.
51 locals recommend
Dotties Coffee Lounge
444 North StGreat downtown cafe with an artsy vibe, delicious food and a variety of coffee drinks.
Patrick's Pub
26 Bank RowCasual Traditional Irish Pub. Great wings, large menu, full bar.
Amazing Italian eatery in quaint downtown Lenox. Great for a special evening out.
42 locals recommend
Frankie's
80 Main StAmazing Italian eatery in quaint downtown Lenox. Great for a special evening out.
Café with home roasted coffee in adorable downtown West Stockbridge.
82 locals recommend
No. Six Depot Roastery & Cafe
6 Depot StCafé with home roasted coffee in adorable downtown West Stockbridge.
Mazzeo's Ristorante
1015 South StGreat Italian food for dine-in or take-out.
New pizza spot with style, offering up delicious stone oven pizzas.
20 locals recommend
Pizzeria Boema
84 Main StNew pizza spot with style, offering up delicious stone oven pizzas.
Classic local tavern in downtown Lenox with great food and full bar. Outdoor patio in the summer.
20 locals recommend
The Olde Heritage Tavern
12 Housatonic StClassic local tavern in downtown Lenox with great food and full bar. Outdoor patio in the summer.
Vong's Thai Cuisine
157 Seymour StFavorite local Thai food for take out or dine-in.
CRUST
505 East StreetGreat new pizza spot in Pittsfield. Order online and pick-up, simple & delicious!
Great cafe in downtown Pittsfield with yummy breakfast and lunch options, awesome local coffee!
17 locals recommend
The Marketplace Cafe
53 North StGreat cafe in downtown Pittsfield with yummy breakfast and lunch options, awesome local coffee!
Sibaritas
Amazing non-traditional Italian food with a twist! Wonderful owners and friendly service.
Cozy Italian spot with huge menu and exceptional service. Fresh seafood, pasta, steak, amazing homemade breadsticks!
RJ'S RESTAURANT SEAFOOD/CHOPS/PASTA
Cozy Italian spot with huge menu and exceptional service. Fresh seafood, pasta, steak, amazing homemade breadsticks!
Traditional Italian fine dining, a family favorite in the Berkshires!
34 locals recommend
Mazzeo's Ristorante
1015 South StTraditional Italian fine dining, a family favorite in the Berkshires!
Chic bar and lounge with fireplace. Delicious sharing plates and cocktails. Awesome outdoor patio too! Great for couples, business, or friends to meet up for pre-dinner happy hour or a light fare meal.
Life House, Berkshires
Chic bar and lounge with fireplace. Delicious sharing plates and cocktails. Awesome outdoor patio too! Great for couples, business, or friends to meet up for pre-dinner happy hour or a light fare meal.
Moody and cozy lounge in The Apple Tree Inn in Lenox that’s lively and great for drinks and/or dinner. Adult hang-out spot with fine dining and live music (check site for events).
The Ostrich Room
Moody and cozy lounge in The Apple Tree Inn in Lenox that’s lively and great for drinks and/or dinner. Adult hang-out spot with fine dining and live music (check site for events).
Hip spot at the base of Bousquet Ski Mountain. Top floor of their lodge with huge bar, dining room and outdoor roof deck. Floor to ceiling windows and a front row seat view of the mountain. Food is elevated casual and very good.
Drifters Bar & Restaurant
Hip spot at the base of Bousquet Ski Mountain. Top floor of their lodge with huge bar, dining room and outdoor roof deck. Floor to ceiling windows and a front row seat view of the mountain. Food is elevated casual and very good.
City/town information
Adorable quintessential New England town. Great for shopping at unique boutique stores. Many wonderful restaurants. Home to many famous local attractions such as, Tanglewood, Kripalu, & The Mount.
86 locals recommend
Lenox
Adorable quintessential New England town. Great for shopping at unique boutique stores. Many wonderful restaurants. Home to many famous local attractions such as, Tanglewood, Kripalu, & The Mount.
Northampton
Sweet, artsy, fun shopping and great food scene. A great day trip!
Great Barrington
A lovely downtown scene with shops, dining, and theatre.
Home to modern art museum, Mass MOCA and some great restaurants. You'll be surrounded by beautiful mountain views.
33 locals recommend
North Adams
Home to modern art museum, Mass MOCA and some great restaurants. You'll be surrounded by beautiful mountain views.
Home to Williams College and The Clark Art Museum. A beautiful drive up to northern Berkshire County. Great food & comfortable cafés, right on the border of Vermont.
41 locals recommend
Williamstown
Home to Williams College and The Clark Art Museum. A beautiful drive up to northern Berkshire County. Great food & comfortable cafés, right on the border of Vermont.
Activity
Apple picking, the best hot apple cider donuts, and they make their own wine! The perfect autumn adventure spot.
41 locals recommend
Hilltop Orchards Home of Furnace Brook Winery
508 Canaan RdApple picking, the best hot apple cider donuts, and they make their own wine! The perfect autumn adventure spot.
Local winery with outdoor music, food trucks and fun. Dogs and kids welcome!
29 locals recommend
Balderdash Cellars
81 State RdLocal winery with outdoor music, food trucks and fun. Dogs and kids welcome!
Local ski area that is perfect for families, first-timers, or a relaxing casual ski day.
115 locals recommend
Bousquet Ski Area
101 Dan Fox DrLocal ski area that is perfect for families, first-timers, or a relaxing casual ski day.
Famous summertime outdoor music venue with many notable performers. Favorite annual events include 4th of July, James Taylor, & Movie Night. Bring a blanket and some chairs, pack a picnic and some wine and enjoy music on the lawn underneath the stars!
398 locals recommend
Tanglewood
Famous summertime outdoor music venue with many notable performers. Favorite annual events include 4th of July, James Taylor, & Movie Night. Bring a blanket and some chairs, pack a picnic and some wine and enjoy music on the lawn underneath the stars!
Family owned dairy farm and Berkshires staple. Seasonal activities, great for kids and families. Cafe that serves breakfast certain days and sandwiches during hours. Maple syrup shack where they make their own for purchase!
31 locals recommend
Ioka Valley Farm
3475 Hancock RoadFamily owned dairy farm and Berkshires staple. Seasonal activities, great for kids and families. Cafe that serves breakfast certain days and sandwiches during hours. Maple syrup shack where they make their own for purchase!
Beautifully preserved Berkshires Cottage. Check The Trustees website for events. Popular for fall: The Naumkeag Pumpkin Show, winter: The Winterlights Show, summer: date nights and outdoor concerts. Tickets to events sell fast, rec purchasing early.
109 locals recommend
Naumkeag
5 Prospect Hill RdBeautifully preserved Berkshires Cottage. Check The Trustees website for events. Popular for fall: The Naumkeag Pumpkin Show, winter: The Winterlights Show, summer: date nights and outdoor concerts. Tickets to events sell fast, rec purchasing early.
The National Shrine of The Divine Mercy
2 Prospect Hill RdFamous Catholic Shrine and home to the Marian Fathers.
Great farm with local groceries, sandwich shop, greenhouse, playground, petting zoo, ice cream, pumpkins, hayrides, corn maze.
20 locals recommend
Whitney's Farm Market & Garden Center
1775 S State RdGreat farm with local groceries, sandwich shop, greenhouse, playground, petting zoo, ice cream, pumpkins, hayrides, corn maze.
Local dairy farm with amazing homemade ice cream straight from their cows!
32 locals recommend
High Lawn Farm
535 Summer StLocal dairy farm with amazing homemade ice cream straight from their cows!
Historic preserved shaker village and museum. Open year round with various events offered including sheep sheering, baby animals (spring), haunted tours (fall), goat yoga (summer), hiking trails, and workshops - to name a few.
161 locals recommend
Hancock Shaker Village
1843 W Housatonic StHistoric preserved shaker village and museum. Open year round with various events offered including sheep sheering, baby animals (spring), haunted tours (fall), goat yoga (summer), hiking trails, and workshops - to name a few.
Celebrated museum & performing arts center highlighting the work of contemporary artists since 1999.
382 locals recommend
MASS MoCA
1040 Mass MoCA WayCelebrated museum & performing arts center highlighting the work of contemporary artists since 1999.
Amazing art museum and research center on a beautiful campus in Williamstown. Permanent collection galleries and special exhibitions offered. Hiking trails on campus great for summer exercise or fall leaf peeping. Cafe and museum store. Everything you need for an inspiring day trip in the Berkshires.
329 locals recommend
The Clark Art Institute
225 South StAmazing art museum and research center on a beautiful campus in Williamstown. Permanent collection galleries and special exhibitions offered. Hiking trails on campus great for summer exercise or fall leaf peeping. Cafe and museum store. Everything you need for an inspiring day trip in the Berkshires.
Local famous artist Norman Rockwell’s collection of art in his hometown in The Berkshires. Lectures, programs, workshops and other activities offered (check website for details). Terrace cafe during museum hours offers sandwiches, salads, sweets, snacks and beverages.
344 locals recommend
Norman Rockwell Museum
9 Glendale RdLocal famous artist Norman Rockwell’s collection of art in his hometown in The Berkshires. Lectures, programs, workshops and other activities offered (check website for details). Terrace cafe during museum hours offers sandwiches, salads, sweets, snacks and beverages.
An upstate NY Farm Brewery offering high quality beer made with locally grown ingredients using ethical and sustainable agricultural methods. Owned and run by the Sanford family since the 1800s, the farm has evolved from multi-faceted production, to dairy, and now farm brewery. In addition to brewing beer, they produce hay and raise cattle. Offers live music and events - check calendar online for details.
18 locals recommend
S&S Farm Brewery
174 Middle RdAn upstate NY Farm Brewery offering high quality beer made with locally grown ingredients using ethical and sustainable agricultural methods. Owned and run by the Sanford family since the 1800s, the farm has evolved from multi-faceted production, to dairy, and now farm brewery. In addition to brewing beer, they produce hay and raise cattle. Offers live music and events - check calendar online for details.
Small local craft brewery turning out unique beers using locally grown ingredients. Set in a cozy atmosphere inside a revived industrial mill, The Stationery Factory, the breu haus also offers food, trivia nights and live music. Check online for events.
11 locals recommend
Shire Breu-Hous
63 Flansburg AveSmall local craft brewery turning out unique beers using locally grown ingredients. Set in a cozy atmosphere inside a revived industrial mill, The Stationery Factory, the breu haus also offers food, trivia nights and live music. Check online for events.
Sightseeing
The highest point in Massachusetts with beautiful views of the Berkshire Hills. The Appalachian trail passes through the summit amongst many other hiking trails. In a JK Rowling short story, it is the site of the New England wizarding school “Ilvermorny”. You can drive to the summit during specific seasons. There is a tower at the top, viewing areas, bathrooms and some snacks/beverages available.
213 locals recommend
Mount Greylock
The highest point in Massachusetts with beautiful views of the Berkshire Hills. The Appalachian trail passes through the summit amongst many other hiking trails. In a JK Rowling short story, it is the site of the New England wizarding school “Ilvermorny”. You can drive to the summit during specific seasons. There is a tower at the top, viewing areas, bathrooms and some snacks/beverages available.