Holiday rentals with a kayak in Berkshire County

Elegant Year-Round Lakeside Retreat with AC

The Haven, an elegant cottage surrounded by woods, located on a pristine lake with private dock. 4 bedrooms, 3 baths. This year-round vacation cottage with hot tub provides an experience in the Berkshires you won’t forget! Leaf-peep in fall, ski in winter, hike in spring, kayak & swim in summer, or browse the boutique shops in quaint towns like Great Barrington, Lenox and Stockbridge. Newly installed mini-splits provide AC in all bedrooms and LVR/DR/Kitchen common area. 1 house-trained dog ok.

Hilltop Retreat w Magic View! Lake Beach 1 mile

Please enjoy our little slice of paradise! Perched just up the hill from Lake Garfield, The Hupi House offers a truly magical view of the lake and mountains for miles beyond. Let breathtaking sunsets be your evening entertainment! Inside you will find a stocked kitchen, high-quality appliances and bedding, fast wifi, and wooded seclusion. Outside you will find swimming, kayaking, hiking, leaf-peeping, star-gazing, skiing...Minutes to Ski Butternut, Great Barrington, Jacob's Pillow, Tanglewood.

Cozy Cottage in the Berkshires

Come and enjoy our "happy place" year round! Our cozy, neat as a pin cottage is located in the beautiful Berkshires with gorgeous Ashmere lake views, spectacular flower beds and beach/lake access. Summer, fall, winter or spring, the cottage welcomes you, complete with a gift basket and fresh flowers. Enjoy the view of the lake off the spacious deck or play games in the grassy yard complete with fire pit for roasting marshmallows. Waterfront is only a minute or two walking distance away.

Waterfront oasis in heart of Berkshires

This house is a one-of-a-kind water front retreat that offers total privacy, spa-like serenity, and easy access to all the Berkshires has to offer. You'll find a fully stocked, professional-grade kitchen, a dining room perfect for family meals, and a living room with a wood-burning stove. There are two bedrooms downstairs and two upstairs. The house is close to skiing and tubing at Butternut, farm-to-table dining, shopping in Great Barrington and Lenox, Jacob's Pillow, and Tanglewood.

Lake front retreat - Stylish Berkshire home

Absolute privacy! Escape to this beautifully renovated mid-century home w/ 4 bedrooms on Long Bow Lake. Featuring stylish wood floors & modern design, the cozy dining room boasts a gas fireplace. This family-friendly retreat offers exclusive lake frontage complete w/ a dock & 4 kayaks for endless fun! Enjoy serene moments on the screened porch, fire up the Weber grill, or challenge each other to ping pong. Located just 20 mins from Downtown Lee, outlets, hikes, & Otis Ridge skiing

Wildlife Retreat in the Forest

Home in the Birkshires! 12 minutes away from Jacob's Pillow, 2.5 hours away from NYC. Our Beautiful Lindal Cedar Contemporary home has everything you'll need. It is tucked away on a private 9+ acre estate with 4 large bedrooms, 2.5 baths. The Master Bedroom can be your own private getaway with 2 balconies. One overlooks the large living room with floor to ceiling windows and stone fireplace. The other overlooks the expansive property. It's definitely a tranquil place to rest and relax.

Lakefront | Pvt Dock | Kayaks | Firepit | 1G | W/D

The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit (access via uneven steps) • Canoe & 2 kayaks • Smart TV & 4 Google smart speakers • 1 Gigabit Wi-Fi • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

Lovely Berkshire Home

"We are located in the heart of America's cultural epicenter known as the Berkshires. Known as the "Gatehouse" to upscale Erskine Park, this truly one of a kind Craftsmen inspired home is filled with unique features and materials seldom found including eucalyptus and Brazilian Cherry flooring, Jerusalem stone and porcelain plank tiles. Inviting color and intriguing design elements make this an extraordinarily pleasing home. Every detail has been thoughtfully considered within. Dreamy!"

Amazing Berkshire Mountains Cabin

Our incredible 4 bedroom home is situated on 2 beautiful secluded acres in picture perfect Monterey - the quintessential Berkshire County getaway, with modern kitchen, screened porch, 2 fireplaces a fabulous outdoor hot tub and a beautiful brook on the property. Enjoy hiking the Appalachian Trail in nearby Beartown State Forest or kayaking and swimming in the incomparable Lake Garfield. We are a quick ride to Ski Butternut, Catamount, Tanglewood, Lenox and Great Barrington.

Wildlife Lakeside Cottage; views/wildlife

Fully furnished and remodeled with new upgrades in Spring 2025 including a cathedral master bedroom suite with a full bath. Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. Incredible amount of wildlife, especially all types of birds. The home has sunny views everywhere. Seasonal weeds do grow in the adjacent lake which can impact water activities, especially in the summer months. Sleeps 6. Ther are two full and one 1/2 baths.

Lakeside Oasis w/ Kayaks & Charm

Escape to this charming lakeside oasis on Cheshire Lake in the heart of The Berkshires. This nicely appointed 2-bedroom, 1-bath home offers stunning water views, a warm indoor fireplace, and a spacious deck perfect for relaxing or dining outdoors. Enjoy kayaking right from the backyard, grilling al fresco, or cooking up some s'mores at the fire pit. Whether you seek tranquility or adventure, this spot is your perfect lakeside escape, book now before it's too late!

Beautiful Victorian. The heart of the Berkshires.

The whole group will enjoy easy access to everything from this centrally located place. The house has been completely renovated. The side patio has plenty of room for a large group with a brand new Weber grill and propane fire pit. Enjoy morning coffee on the front porch. Just steps from the Ashuwillicook Rail Trail. Greylock Glen is less than a half mile away with hiking trails. Mass MoCA is 5 miles away. This Victorian beauty is cozy, warm, and inviting.