
Holiday rentals with a kayak in Pioneer Valley
Find and book unique kayak rentals on Airbnb
Top-rated Accommodation with a Kayak in Pioneer Valley
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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.

Peaceful VT Chalet w/ Mountain View’s
Our Peaceful chalet has everything you need. A fully equipped kitchen, 3 bedrooms, 2.5 baths, 2 living rooms, elec heat fireplace, outdoor fire pit, washer, dryer, Roku TV’s, great fiber optic internet. Accessible ATV/ snowmobile trails from property. 20 miles to Mt. Snow. Short driving distance to popular golf courses, shops, restaurants,breweries, kayaking, fishing, hiking, white water rafting ect An ideal base to explore the Green Moutain National Forests (VT) or the Berkshire Mountains (MA).

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.

Rustic Pond Cabin: Nature, Stars & Serenity
🦉Serene rustic cabin in Colebrook, Ct in beautiful Litchfield County! Cozy King bed under skylight, queen downstairs, woodstove and all the comforts of home. All natural pond- swim, fish, canoe n kayak! Sits far from main roads on quiet back road. Can walk, run or bike to local trails or stay n walk the trail around the pond, have campfires outside in firepit! Clean and no crazy rules. Surrounded by nature! Private Great WIFI! Close to ski resorts, dispensaries and amazing Berkshires! 🦉

Lake - King - Gym - Kayak - Fire Pit - Pets Allowed - WD
The Lake House, a two-story Designer's Dream, boasts scenic water and starry sky views. ● 397 Mbps Wi-Fi | 2x 55” Smart UHD TVs | Washer & Dryer | Indoor Fireplace ● Nintendo (NES) w/ 30 Games | Record Player w/ Vinyl Collection ● 3x Kayaks | 2x Stand Up Paddle Boards | 2x Cruiser Bikes | 2-Car Garage ● Gym (Bike, Yoga Mats, Weight Bands, Power Tower) ● Patio w/ Fire Pit & Grill| Full Kitchen | Coffee (Keurig) Drive to: ● UCONN (10 Mins) | Hartford (20 Mins) | Boston (1 Hour) | NYC (2 Hours)

Lake Views from Deck Fire Pit & Hot Tub 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

Vermont lake house near Mt. Snow-fab 360 views!
Welcome to our fabulous farmhouse on 3 green acres! Enjoy amazing views of Lake Sadawga and the surrounding Green Mountains as you kick back in our cozy stylishly furnished home. The house comfortably sleeps 8+ with 4 bedrooms, 2 full bathrooms, and a finished loft space. We are located off the beaten path on a paved road with multi-car parking. This wonderful year-round retreat is a short drive to skiing at Mt. Snow, boating in Harriman Reservoir, and easily accessible to local amenities.

Wildlife Lakeside Cottage; views/wildlife
Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. There is an incredible amount of wildlife, especially all types of birds. Sunny views abound. The house boasts a bright wood interior with a cozy feel. It has two and a half baths. There is a first floor queen bedroom with cathedral ceiling, and on the 2nd floor another queen room and a twin room-2 single beds.The adjacent lake teams with wildlife, seasonal weeds do grow. Contact us for conditions.

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.

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.

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!

Beautiful Victorian. The heart of the Berkshires.
The whole group will enjoy easy access to everything from this centrally located place. The house has been completely renovated. The side patio has plenty of room for a large group with a brand new Weber grill and propane fire pit. Enjoy morning coffee on the front porch. Just steps from the Ashuwillicook Rail Trail. Greylock Glen is less than a half mile away with hiking trails. Mass MoCA is 5 miles away. This Victorian beauty is cozy, warm, and inviting.
Popular amenities for Pioneer Valley kayak rentals
Holiday House Rentals with a Kayak

Berkshires Retreat w Magic View! Beach/Swim 1 mi!

Red Door River House

Peaceful Lake Escape w/ Porch, Fire Pit & Kayak

Lake front retreat - Stylish Berkshire home

Lovely Berkshire Home

Gorgeous Vermont Lakefront with epic sunsets!

Direct Lakefront Home on Otis Reservoir Giant Yard

D. Chief's Lodge Cheerful Cabin at the Camp
Cottages with a kayak

Cozy Cottage in the Berkshires

The Lake Cottage: A Sweetwater Stay

Cozy Lakefront Cottage

Lake House with view of mountain

Sunset and Sunrise views at this lake cottage.

Lake Escape: Lakefront Cottage in the Berkshires

Berkshire lakefront cabin with modern luxuries

Cozy Cottage with lake view and indoor fireplace
Cabin rentals with a kayak

Cozy Cabin ~16 Mi. to Slopes on 10 Acres of Woods!

Amazing Berkshire Mountains Cabin

The Hideaway Camp

Rustic cabin with A/C at historic orchard & cidery

Happy Valley Lake House Waterfront • Kayaks/Canoe

Berkshires Lakefront Boho Modern Retreat

Berkshires! Walk to LAKE, kayaks, dog friendly.

Enjoy 43 Acres on Two Ponds!
Destinations to explore
- New York Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Jersey City Holiday rentals
- Portland Holiday rentals
- Newark Holiday rentals
- Baltimore Holiday rentals
- Mont-Tremblant Holiday rentals
- Atlantic City Holiday rentals
- Newport Holiday rentals
- Providence Holiday rentals
- Pet-friendly rentals Pioneer Valley
- Condo rentals Pioneer Valley
- Waterfront rentals Pioneer Valley
- Bed and breakfasts Pioneer Valley
- Cabin rentals Pioneer Valley
- Apartment rentals Pioneer Valley
- Rentals with breakfast Pioneer Valley
- Rentals with pools Pioneer Valley
- Rentals with beach access Pioneer Valley
- House rentals Pioneer Valley
- Guesthouse rentals Pioneer Valley
- Family-friendly rentals Pioneer Valley
- Rentals with lake access Pioneer Valley
- Cottage rentals Pioneer Valley
- Private suite rentals Pioneer Valley
- Rentals with a hot tub Pioneer Valley
- Hotel rooms Pioneer Valley
- Rentals with a kayak Massachusetts
- Rentals with a kayak United States
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Taconic State Park
- University of Connecticut
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Ski Sundown
- Dcu Center
- Mount Monadnock
- Clark University
- Naumkeag
- University of Massachusetts Amherst
- Massachusetts Museum of Contemporary Art
- Norman Rockwell Museum
- Mount Greylock
- Hancock Shaker Village
- Mount Holyoke College
- Connecticut Convention Center
- Naismith Memorial Basketball Hall Of Fame





