Best & Cheap Romantic Getaways in The Berkshires, MA

Compare romantic getaways, From $12/night

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Best & Cheap Romantic Getaways in The Berkshires, MA: Top Deals

Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna! Great Location!
Villa · 2 Guests · 2 Bedrooms
Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna! Great Location!
4.7 (47 reviews)
This Villa is located in a great location and provides numerous activities to enjoy, including access to pools, a hot tub, mini golf, and a sauna. It can accommodate up to 2 people and is not pet friendly. Nearby popular restaurants include The Remedy Bar & Bistro, The Lion's Den, and Chez Leon. Popular activities nearby include hiking at Bash Bish Falls State Park, boating on Lake Buel, and visiting the Hancock Shaker Village Museum.
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$245 /night*
Gedney Farm
Hotel
Gedney Farm
4.5 (54 reviews)
This Hotel is located in Gedney Farm, which is close to popular attractions such as the Taconic State Park, Bash Bish Falls, and the Appalachian Trail. The area also features a variety of restaurants, such as Red Rooster Cafe, The Old Mill Restaurant & Bar, and the Catamount Ski Area. Pets are not allowed at this hotel.
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$199 /night
Spacious Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna!
Villa · 2 Guests · 2 Bedrooms
Spacious Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna!
4.6 (5 reviews)
This Villa is a great choice for an escape to the countryside with access to Pools, a Hot Tub, Mini Golf and a Sauna! Located just outside of town, this villa is within close proximity to popular restaurants such as The Old Forge Restaurant and The Whistling Swan Inn. Additionally, there are plenty of outdoor activities and trails nearby like Bozenkill Park and Thompson's Lake State Park.
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$277 /night*
Chambery Inn
Bed And Breakfast
Chambery Inn
This Bed And Breakfast, Chambery Inn, is located in the city of Pittsfield, Massachusetts. It offers easy access to popular attractions such as Berkshire Theatre Group, The Colonial Theatre, and Mission Bar & Tapas. Nearby restaurants include Mazzeo's Ristorante, Bounti-Fare Restaurant & Catering, and Mezze Bistro + Bar. Outdoor enthusiasts can explore trails at Springside Park, Pontoosuc Lake Park, and Onota Lake Park. Animals are not allowed at this accommodation.
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$171 /night
Villa with Access to 2 Pools, a Hot Tub, an 18-Hole Mini Golf Course, and More
Villa · 2 Guests · 1 Bedroom
Villa with Access to 2 Pools, a Hot Tub, an 18-Hole Mini Golf Course, and More
4.7 (9 reviews)
This Villa is a great choice for those looking for a fun and relaxing vacation. It has access to two pools, a hot tub, an 18-hole mini golf course, and more. Nearby popular restaurants include The Stagecoach Tavern, The Spot Cafe, and Freight Yard Pub & Restaurant. Other nearby activities include the Berkshire East Mountain Resort for skiing and snowboarding, Zoar Outdoor for whitewater rafting, and the Robert Frost Trail for hiking.
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$200 /night*
Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires an IHG Hotel
Hotel
Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires an IHG Hotel
4.2 (214 reviews)
This Hotel is the Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires, an IHG hotel located in the beautiful Berkshire Mountains of Massachusetts. Popular nearby attractions include The Mount, a National Historic Landmark and former home to Edith Wharton; Jiminy Peak Mountain Resort, offering skiing, snowboarding, and summer activities such as mountain biking; and the Norman Rockwell Museum. For dining options, guests can enjoy the on-site restaurant, Ironwood Café, or visit local favorites like The Old Mill Pub & Restaurant and Mission Bar & Tapas.
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$119 /night
Holiday Inn Club Vacations Oak N' Spruce Resort
Hotel
Holiday Inn Club Vacations Oak N' Spruce Resort
The Holiday Inn Club Vacations Oak N' Spruce Resort offers guests a pet-friendly destination located in the beautiful Berkshire Mountains. The hotel is close to popular local attractions such as the Jiminy Peak Mountain Adventure Park, Bousquet Ski Area and Hancock Shaker Village. There are also plenty of restaurants nearby including Mezze Bistro & Bar, The Old Forge Restaurant and The Carriage House. Guests can also enjoy outdoor activities like hiking along the Taconic Crest Trail or biking on the Ashuwillticook Rail Trail.
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$119 /night
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How Does The Vacation Home Rental Price Look Like in The Berkshires, MA?
Vacation House & Cottage Rental Price Information in The Berkshires, MA
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The graph shows the percentages of vacation homes in each price bucket. The Berkshires has the largest percentage (17.14%) of homes in $500+ price range.
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How Many Rental Accommodations Are Pets Friendly in The Berkshires, MA?
Pets Allowed vs Not Allowed in The Berkshires, MA
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37.08% of vacation homes in The Berkshires are pet friendly. Either you bring your loved pets on vacation or you have pet allergies, make sure to select the homes by applying the right filters.
What are the best restaurants for a romantic honeymoon in The Berkshires, MA?
Romantic Restaurants in The Berkshires
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The Berkshires is an ideal destination for couples looking to enjoy a romantic getaway. There are many restaurants in this beautiful region that offer an intimate dining experience with delectable food and a cozy atmosphere. Whether it's a special occasion or just a night out with your significant other, these restaurants will make your experience memorable.

  • CaféADAM: This charming American-style restaurant serves up delicious dishes crafted from local ingredients. Enjoy a glass of wine from their extensive selection while you savor one of their signature dishes such as the Chateaubriand steak or the Berkshire pork chop.
  • Six Depot Roastery & Café: This rustic café has a relaxed vibe and serves up specialty coffee drinks, homemade pastries, sandwiches, and salads. With its cozy atmosphere, Six Depot Roastery & Café is the perfect place to spend some quality time with your significant other.
  • Ventfort Hall Mansion and Gilded Age Museum: Enjoy a gourmet dinner at Ventfort Hall Mansion and Gilded Age Museum, a restored mansion that was built in 1893. The museum offers both lunch and dinner options, including a three-course prix fixe menu with seasonal ingredients. A romantic evening awaits!
What are the most romantic activities for honeymooners in The Berkshires, MA?
Romantic Activities in The Berkshires
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The Berkshires is filled with many romantic activities for couples to enjoy. From outdoor adventures to cultural experiences, there's something here for every couple. So grab your significant other and explore all that this picturesque area has to offer.

  • Berkshire Botanical Garden: Take a stroll through the 15-acre garden and admire the beauty of nature. The gardens feature native and exotic plants, trees, shrubs, and flowers, making it the perfect spot for a romantic walk together.
  • Naumkeag: Explore the historic grounds of Naumkeag, which features terraced gardens, wooded trails, and a preserved 19th century cottage. Take a peaceful walk around the property and take in the stunning views of the surrounding mountains.
  • Bousquet Mountain: Spend the day skiing or snowboarding down the slopes of Bousquet Mountain. After a long day on the slopes, relax in the spa and enjoy a romantic dinner at the on-site restaurant. What better way to end a day of adventure than with a romantic evening with your loved one?
Best Tourist Attractions in The Berkshires, MA?
Top Rated Places to Visit in The Berkshires, MA
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