Holiday rentals with a kayak in Hampden County

Hillside Hideaway

Prepare for the perfect New England getaway when you book this Massachusetts lake retreat in West Brookfield! Bring friends & family and relax in this beautiful 3-bedroom, 2-bathroom vacation rental house boasting 1,700 square feet of open concept space and a wraparound porch. Your group of 8 will have walking access to the lake and outdoor fire pit for evenings under the stars. *New for Fall 2024* We have partnered w/ Chef Perkins to offer in-home private cooking! See menu for booking details!

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!

Peaceful Snowy Lake Views from Private Hot Tub

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

River front guest suite

Unique 2 bedroom guest house on the Connecticut River in South Hadley, Sleeps 4 adults and two children. Bunk bed top for children or pull out of 4 adults. 1 bathroom Kayaking Paddle bikes and boards Fire pit Tour boat next door at Brunelle’s Patio Boathouse restaurant Village commons 1 mile away McCrays farm 1 mile away Ledges golf course 2 miles away Malls etc. 15 min MGM casino 15 min Basketball hall of fame 15 min Airport 45 min Amtrak 10 min Mt sugarloaf 20min. Hiking trails l

Lakefront Jewel By: Evergreen Home

Evergreen Home Vacation Rentals invites you to this breathtaking lakefront jewel, offering unparalleled views and central AC. This stunning 3BR/2BA retreat is the ultimate spot for tranquility. Swim, paddleboard, or kayak right from your private deck. Ideally located just 9 minutes from Jacob’s Pillow and 30 minutes to Butternut Ski Mountain, you are close to the region's best theater and dining. Experience the perfect balance of adventure and relaxation. Book your lakefront escape today!

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.

Cabin with Hot Tub and Lake Access

Although we are new to Airbnb we have hosted 71 bookings, 259 nights rating 4.6 on Evolve and Booking websites. Escape to the Berkshires for serene stay at this 2 bed-2 bath, Tolland vacation rental. Perfect for relaxing with the whole family getaway or weekend with friends! The peaceful cabin boasts a lush yard, a private hot tub, access to Cranberry pond (four beaches) and kayaks. Explore the area world-class attractions , hikes, ski, or farm to table food and wine scene.

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)!

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.