Holiday rentals with a kayak in Hampshire County

Lakefront Oasis at Lake Wyola

Come enjoy our fully appointed lakefront home on Lake Wyola. With your own waterfront access and 180 degree views from the living, kitchen, dining, and master bedrooms, this comfortable getaway will not disappoint. We are just 20 min from Amherst and 35 min to Northampton with easy access to all of the five colleges. Enjoy morning coffee with flawless views from our wraparound deck. Miles of hiking trails just steps away. Three bedrooms with fully equipped kitchen and open concept living/dining.

Lake Wyola House Shutesbury Massachusetts

Bright, airy recently remodeled three Bedroom lakefront home on Lake Wyola. Most rooms have a Lake View. Beds and bedding are new, each bedroom has a ceiling fan. A super place to make awesome memories. Perfect for a family vacation or romantic getaway. (6 people, two cars max) Close to local colleges, Amherst, Northampton and many attractions. Comfortable and relaxing. Big Screen TVs in the living room and master bedroom. Cable and Wifi. Full kitchen, washer & dryer. Sorry no pets.

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!

Charming Riverfront Cottage

Charming 2 bedroom, 1 bathroom 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 with a futon couch/bed. Two TV's (Roku). 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)!

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!).

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

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

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.

Happy Valley Lake House Waterfront • Kayaks/Canoe

Welcome to the Happy Valley Lake House — your lakefront escape in Western Mass! With private water access, a firepit, and a 2-minute walk to the beach, this stylish cabin is perfect for summer — and cozy in cooler months with a big wood stove and plenty of wood. Paddle a kayak or canoe, roast s’mores, or relax in the airy, light-filled living room. Just 5 minutes to the country store, 10 minutes to Montague, 20–25 minutes to Amherst, Greenfield, Turners Falls, and Northampton.

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.

Cozy Cottage with lake view and indoor fireplace

Lake view cottage on Lake Wyola, Shutesbury MA is the perfect relaxing getaway. Whether you are planning a summer, fall, winter or spring trip you are sure to love this cozy cottage. Plenty of hiking/ biking trails, boating, swimming and fishing. You will be located only 25 minutes from Amherst and the 5 colleges. This cottage is family friendly and ready for you to have a relaxing and enjoyable vacation. A short 4 minute walk to one of Wyola's association beaches.

Perfect Serene Waterfront All Season Retreat!

Enjoy everything the Berkshires has to offer from this beautiful, secluded, nicely renovated waterfront house set on two wooded acres of forested land. Explore the stream that runs through the property, or just sit on the large deck or down by the crystal clear lake and listen to the sounds of nature while feeling the warm sun on your face. Very private--just one near neighbor. The sunny house has 2 bedrooms, study with sofa bed, 2 full baths, full kitchen!