Vacation rentals with a kayak in Hampshire County

Fall foliage surrounded by 10,000 acres forest

Secluded Berkshire house surrounded by 10,000 acres forest is with marked trails & pond that sleeps up to 10 people comfortably. Central air & heat, fireplace, propane BBQ & charcoal BBQ & smoker BBQ, Fibre high-speed WiFi gigabit internet (new in January 2020), Roku streaming device with Netflix & Amazon Prime & hundreds more channels, gazebo, private pond, comfy mattresses/beds, 2 bathrooms, new laundry dryer, 16 foot C shaped couches, indoor garage parking, vegetable gardens, kayaks & more.

Berkshires Lakefront Stylish Retreat w/Gameroom

Welcome to Excalibur Lake Lodge in the Berkshires. This beautiful lakefront contemporary Lindal Cedar custom 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.

Cozy Cottage on the Lake

Relax in our rustic lake-front cottage for your next getaway in the Berkshires! Our small lake is perfect for kayaking, fishing, or just enjoying in any season. Come by in the Fall to soak in the stunning color reflecting off the lake. In the Winter, light up the fireplace after skiing the nearby hills or sledding the Knox Trail. Whether you want cook s'mores by the water, hike the Appalachian Trail, visit Berkshire towns, or just get away, we welcome you. Please Note-Animals not allowed.

Big Pond Hideaway

Tucked deep in the woods at the end of a winding dirt road, Big Pond Hideaway is a peaceful retreat steps from Big Pond, a 300-acre lake for fishing, swimming, and kayaking. Updated throughout, the home is bright and airy with lake views. A fully equipped kitchen makes cooking easy. As the sun sets, grill on the deck, gather around the fire pit under the stars, or sip a cocktail on the dock. Whether paddling or soaking in the quiet, memories await. Escape the noise. Find your hideaway.

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!).

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

Panoramic Sunroom | Soaking Tub | Modern Cabin

Located on a large serene pond, The Retreat at Eagleville is perfect for fishing enthusiasts, nature lovers, family fun, and anyone looking for an escape from the hustle of the city. Enjoy glamping amenities including a soaking tub, fully-equipped kitchen, outdoor BBQ & griddle, and a covered pavilion with picnic table. Relax by the firepit, unwind in the hammock, or lounge in Adirondack chairs. ☞ Complimentary wood for 1st fire ☞ No checkout rules ☞ Linens provided ☞ Self Check-in

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.

Charming Riverfront Cottage

We are a 2 bdrm, 1 bath cottage on a peaceful cove of the Connecticut River. Enjoy bird life, water views and magical sunsets in this nature lovers’ paradise. Bright and airy throughout. Fully equipped kitchen. Two bedrooms on the first floor, with a loft space for reading, enjoying the view or doing work. We've provided 2 touring kayaks (longer/heavier than other kayaks) in the shed. We recommend at least one strong person and bring water shoes (the bottom is yucky)!