Vacation rentals with a kayak in Hampshire County

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Top-rated kayak rentals in Hampshire County

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Guest favorite

Home in Williamsburg

4.85 out of 5 average rating, 41 reviews

Cute and Cozy Lake Cottage

Small cottage with lake view & access. No motorboats, pristine and quiet lake (SUPs & kayaks provided). Rare, but true, aurora borealis sitings on this lake (see pic)!. Cottage abuts the DAR State Forest, which has 15 miles of hiking (for all levels), birdwatching, and XC skiing. 25 min drive to Northampton, known as an academic, artistic, musical, and countercultural hub and home to Smith College. 30 min drive to Berkshire East Ski Resort and Stumps XC Skiing Center, others about 50 mins away.

Guest favorite

Cottage in Becket

4.94 out of 5 average rating, 210 reviews

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 • Canoe & 2 kayaks • 50" smart TV and 4 Google Smart Speakers • 1 Gigabit Wi-Fi 'gorgeous with amazing views' • 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

Guest favorite

Guest suite in South Hadley

4.85 out of 5 average rating, 93 reviews

River front guest suite

Unique 2 bedroom guest house on the Connecticut River in South Hadley, Sleeps 8 1 bathroom Covered parking Dock available Kayaking Boat rental available Paddle bikes and boards Views Fire pit Tour boat next door at Brunelle’s Marina. Patio Ice machine 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

Guest favorite

Home in Otis

4.93 out of 5 average rating, 15 reviews

Spacious Lake Front Home

The 330 acre lake is calm and surrounded by forest. You can enjoy the lake from your personal sandy beach front yard and wrap around deck. The house has 5 bedrooms, comfortably sleeps 11 with 2.5 baths The first floor is modern and comfortable. The family room has a pellet stove, record player, superior sound system, and TV. The master bedroom comes with a private full bathroom, closet, and lake views. The second floor has fully equipped kitchen and family room close to local skiing

Guest favorite

Cottage in Becket

4.81 out of 5 average rating, 53 reviews

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.

Top guest favorite

Home in Belchertown

4.99 out of 5 average rating, 71 reviews

Moonstone Lake House – romantic, serene, fun!

Hey! We just had a 3 week July-Aug cancellation so dates have opened up! Incredible swimming in our 10 acre lake Lots of swim toys. Float with friends, fish for small bass and sunfish Fire pit/grill two feet from the lake Your own private swimming cove Huge deck 3 kayaks, (1 ) 3-person canoe Cozy propane wood stove in the living room. Hiking, museums... Note: Our home is right next door separated by an 8 ft tall screen fence. *Dog lovers? Please scroll to "Other Details to Note"

Guest favorite

Home in Becket

5 out of 5 average rating, 14 reviews

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!).

Guest favorite

Home in Becket

4.94 out of 5 average rating, 31 reviews

Lakefront Cottage on Private Beach

House is right on the lake! Step into the water or the dock from the private flat yard! Enjoy the amazing lake view from the patio or the glass sunroom! Located in the heart of the Berkshires - 10 mins from Jacob's Ladder, 20 mins from Lee Outlets, and 30 mins from the Norman Rockwell Museum or Tanglewood. Enjoy farm-to-table restaurants in the area, or make home-cooked meals using the well-equipped kitchen. House is surrounded with trees and perfect for a quiet and relaxing getaway!

Top guest favorite

Cabin in Athol

4.97 out of 5 average rating, 75 reviews

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

Top guest favorite

Home in Becket

5 out of 5 average rating, 61 reviews

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.

Superhost

Cabin in Otis

5 out of 5 average rating, 4 reviews

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.

Guest favorite

Cottage in Shutesbury

4.98 out of 5 average rating, 54 reviews

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.