Holiday rentals with a kayak in Hampden County

Sunset and Sunrise views at this lake cottage.

Ready to relax and have fun! Just bring your clothes, everything else is here at this cottage named Tramonto Sul-Lago – Sunset over lake. You and up to 5 guests will enjoy all amenities! You won’t want to miss sunrise either, it creates reflections of nature on the water. Grab a kayak and go for a paddle, set up a yard game, head to the dock with a fishing pole, pull up some chairs to the fire pit (firewood provided). The back yard is a private oasis. Winter offers skating and ice fishing!

Charming Riverfront Cottage

Amazing 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 upstairs for reading, enjoying the view or doing work. Roku TV. 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)!

Lake Views from Hot Tub Fire Pit & 4 Kayaks

Congamond House is the perfect lake home getaway. Kayak the calm North Pond. Get your breathtaking pics of the surrounding wildlife. Cuddle up on the deck and enjoy the stars or relax in the hot tub under the deck while gazing upon the lake. This 1500 sq ft cottage is the perfect size for a week long getaway with 2 work spaces. 25 minutes from Six Flags Amusement Park, the Big E and the Basketball Hall of Fame 4 Kayaks that seat 6. Paddles and life vests provided 20 min. from Bradley Airport

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

Berkshires! Walk to LAKE, kayaks, dog friendly.

A-Frame Cabin: Dog-Friendly! Walk to lake. -5 min walk to nearest lake; 8 neighborhood lake beaches -Stone fire pit w/swing -Picnic area -Back deck off master slider with grill & fridge -1/2 acre pine lot -Appalachian Trail -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 20-30 min! -30 min Berkshires Scenic Railway -Outlets/Small Shops -Wine/Dine/Breweries -Master w/Queen -Loft w/2 twin beds -Stocked Kitchenette -Whole House Mini Split for heating/AC

Serene Lakefront Retreat

This idyllic 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake accommodates up to 6 guests (4 beds), offering an unforgettable experience for your family. Enjoy breathtaking views from the cozy living area or the private deck. Kayak (2 included), swim off the floating dock, stargaze, grill out and enjoy your coffee on the deck! Separate workspace and free Wi-Fi for those working from home. Perfect for Brimfield Antique attendees. Book now for a relaxing getaway!

Relaxing Home nestled in Rural Hilltown

Beautiful Modern Home with large yard nestled next door to The Berkshires. Enjoy a coffee in the sunroom or deck. There is a large yard, fire pit and kayak access. Alexa enabled in most rooms. A three minute walk to the Blandford Country Store, Breakfast Bistro, and Watson Park. Within 15- 30 minutes of dining, shopping, hiking trails and ski trails. Otis Ridge Ski Area is 15 mins, Tanglewood is 40 mins, Jacobs Pillow 22 mins, Lee Premium Outlets 30 mins, MGM Casino 35 mins.

Charming water front cabin with boat dock

Escape to our charming lakefront cabin! This cozy retreat offers a peaceful getaway with direct access to the sparkling waters and a private dock for swimming, fishing, and kayaking. Unwind on the inviting covered porch sipping your morning coffee while mesmerizing a spectacle sunrise or gather for a barbecue while relishing the panoramic lake views. Whether you're seeking a romantic weekend or an outdoor adventure, this lakeside haven promises an unforgettable experiences!

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.

D. Chief's Lodge Cheerful Cabin at the Camp

Year round house: you'll have a great time at this comfortable place to stay. Camp Mishnoah, a former Girl's Club Camp, is undergoing restoration into a wellness retreat. This rental is a stand alone house. A very comfortable queen size bed and a single bed in a separate bedroom, lodge style living room with a vaulted ceiling, full kitchen, bathroom with shower and a half bath. Access to the pond and hiking trails. Nearby Sturbridge Village and Tree House Brewery.

Lake Escape: Lakefront Cottage in the Berkshires

5 North Lake is a seasonal cottage situated yards from the shore. The property has panoramic views of the largest recreational body of water in Massachusetts: Otis Reservoir. Great for kayaking, fishing, swimming, boating or just relaxing and watching the sunset from the dock or deck. **Our calendar leaves a day open after each rental for cleaning. If your ideal check-in/out date isn’t available, message us and we’ll do our best to see if we can accommodate you.