Holiday rentals with a kayak in Berkshire County

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.

Private Lakehouse in the heart of the Berkshires

Welcome to our lakehouse in the Berkshires! Chat GPT wants you to know this tranquil & picturesque getaway offers a perfect blend of relaxation & outdoor adventure, making it an ideal destination for nature lovers, families, & those seeking a peaceful retreat. The house is on the lake with water views from every room. Curl up on our window seats or the back deck to enjoy the sunshine. With direct access to the lake, you can swim, kayak, paddleboard, & lay on the dock (snowshoeing too!).

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

Cozy lakehouse

Relax with family or friends at this sweet cottage on Center Lake in the Berkshires. This lakeside cottage is charming and rustic. Enjoy a beautiful day on the lake swimming, fishing off the dock and kayaking. Grill dinner on your private deck and watch the stars come out in the evening Or enjoy all that the Berkshires have to offer, Jacob’s Pillow (15 min), Berkshire Theater (20 min), Tanglewood (30 min). There are plenty of nearby hiking trails and charming towns to explore.

Berkshires Lakefront Boho Modern Retreat

Welcome to Watson Pond Lodge in the Berkshires. This beautiful lakefront contemporary home, with architecture that intentionally focuses on the peaceful lake view, has been designed for your comfort and relaxation. Explore the Berkshires year round and see what the area has to offer: from skiing in the winter, to Tanglewood and Jacob’s Pillow in the summer and leaf peeping in the fall. Or just enjoy the tranquility of our lakefront lodge for a rejuvenating weekend away.

Amazing Berkshire Mountains Cabin

Our incredible 4 bedroom home is situated on 2 beautiful secluded acres in picture perfect Monterey - the ultimate 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.