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!

Cheerful cottage by Little Alum Lake & Sturbridge

Little Alum is a gorgeous spring-fed lake in the quintessential New England town of Brimfield, MA. Brimfield is known as home to the largest flea market in the country. Little Alum is regarded as one of the cleanest lakes in Massachusetts due to its pristine water quality. The charming cottage is a one level home within close proximity to highways & downtown Sturbridge and off route 20 just a few minutes to downtown Brimfield and Antique show/flea market. Partial water views, steps to the water.

Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB

The Wilde BNB is your modern rustic lake getaway near the Berkshires. This cozy cabin in the Wildwood community of Tolland, MA is steps from Cranberry Pond with 5 beaches, tennis, pickleball, basketball, fishing, and hiking. Enjoy swimming or paddling the lake with included kayaks and paddleboard, dinner under the stars, unwinding in the hot tub or warming up by the fireplace. With hiking, skiing, and wineries nearby, it’s perfect for summer escapes, fall foliage retreats, or a winter recharge.

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 2 families. (4 adults w/4 kids or 6 adults) 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

Berkshires winter in an A-Frame! Dog-Friendly!

A-Frame Cabin: Dog-Friendly! Walk to lake. -Stone fire pit w/swing -Picnic area -1/2 acre pine lot -Appalachian Trail -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 20-30 min! -Naumkeag Lights -Ski Otis Ridge 15 min or Butternut 30 min -30 min Monument Mt. & Berkshires Scenic Railway -Outlets/Small Shops l -Wine/Dine/Breweries -Master w/Queen, slider to deck -Loft w/2 twin beds -Stocked Kitchenette -Generator on site -Whole House Mini Split for heating/AC

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

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!

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)!

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.

Moonstone Lake House – Bring in the New Year!

Be our last guests at Moonstone before we relocate to Taos, NM : ) Book 3 nights, but stay two more nights FREE! Have a 5 day vacation for the price of 3! Share New Year's Eve w/ your friends! - DOG FRIENDLY - Nightlife in Northampton and Amherst - a fire pit/grill feet from lake - huge lakeside deck - cozy propane wood stove in the living room - fully equipped kitchen - Quabbin reservoir nearby - amazing hiking and trails - exceptional bakeries.... YUM! - museums

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.