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Holiday rentals with a kayak in Pioneer Valley

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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.

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Guest favourite
A charming two-story house is nestled by the water, featuring a wraparound deck adorned with seating. The landscaped yard includes rocky pathways and a small gathering area with Adirondack chairs, inviting moments of relaxation by the water's edge.
Home in Sturbridge

Lake Front Home Sleeps 6-8 on a private Peninsula!

Stunning year-round waterfront home on its own private peninsula—sleeps 6–8 with 3BR/2BA, a spacious living room with sliders to a wraparound deck, and a heated sun porch offering panoramic lake views. Nearly every window overlooks the water. Outside, enjoy a private dock, new stone patio & firepit, small beach area, kayaks, canoe, and rowboat. Perfect for families, couples, or a friends’ getaway. See walkthrough videos at on YouTube @CedarLakeCottage Summer: 4-night min | Holidays: 3-night min

4.94 out of 5 average rating, 324 reviews
Top Guest favourite
Cottage in Brimfield

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.

4.98 out of 5 average rating, 104 reviews
Top Guest favourite
A chalet-style home is surrounded by lush greenery, featuring a large three-sided wrap-around deck. Tall windows dominate the front, allowing ample natural light. To the side, a wooden garage complements the main structure, set against a backdrop of trees and an expansive lawn.
Chalet in Stamford

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).

4.94 out of 5 average rating, 132 reviews
Guest favourite
A serene lakefront home is nestled among tall trees, featuring a welcoming porch that overlooks the water. The exterior is painted in soft yellow, set against a backdrop of lush greenery. Nearby structures showcase a variety of architectural styles along the lakeshore.
Cottage in Shutesbury

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.

4.92 out of 5 average rating, 249 reviews
Guest favourite
A serene pond reflects the surrounding greenery, with kayaks resting on the shore. A cozy cabin is visible in the background, framed by trees. The tranquil setting invites outdoor activities such as swimming or fishing, creating a peaceful natural atmosphere.
Cabin in Colebrook

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! 🦉

4.95 out of 5 average rating, 129 reviews
Top Guest favourite
A hot tub with bubbling water is showcased under a covered patio, offering a view of the serene lake and surrounding trees. Soft lighting enhances the tranquil setting, while glimpses of the lake's shoreline and distant boats are visible in the background.
Cottage in Southwick

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

4.98 out of 5 average rating, 167 reviews
Guest favourite
A serene lake reflects a clear blue sky and lush green forests surrounding it. The water, calm and inviting, showcases the vibrant colors of autumn foliage along the banks, with tall grasses in the foreground adding to the natural landscape.
Cottage in Lanesborough

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.

4.85 out of 5 average rating, 300 reviews
Superhost
A contemporary cedar home is set on a spacious green lawn surrounded by trees. The two-story structure features a large front porch and a combination of wooden and glass elements, enhancing its integrated design with nature. A gravel pathway leads to the entrance.
Cabin in Becket

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.

4.84 out of 5 average rating, 141 reviews
Top Guest favourite
A quaint lakeside cottage features large windows for scenic views and a deck with outdoor seating. A grill is positioned nearby for easy outdoor cooking. The property is framed by lush greenery, enhancing the natural setting by the water's edge.
Home in Becket

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.

5.0 out of 5 average rating, 116 reviews
Guest favourite
The cabin is positioned near Lake Chaffee, featuring a deck area with seating for outdoor relaxation. Surrounding trees add a natural backdrop, while the sunset casts warm light over the landscape. The tranquil lake reflects the colors of the evening sky.
Cabin in Ashford

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

The Hidden Gem of Connecticut: Experience Lakefront bliss at our charming cabin boasting breathtaking water views of Lake Chaffee. ● 371 Mbps Wi-Fi | 50” 4K UHD Smart TV | Washer & Dryer | Indoor Fireplace ● 3x Kayaks | 2x Stand Up Paddle Boards | Private Dock | Outdoor Fireplace ● “Pink” Record Player w/ Vinyl Collection | Board Games ● Patio w/ Gas Grill | Full Kitchen | Coffee (Keurig) Drive to: ● UCONN (10 Mins) | Hartford (20 Mins) | Boston (1 Hour) | NYC (2 Hours)

4.85 out of 5 average rating, 149 reviews
Top Guest favourite
A charming Victorian home is showcased at dusk, with bright windows illuminating the exterior. The wraparound porch features decorative railings and flower planters, complementing the elegant architectural details. The two-story structure is framed by a darkening sky, enhancing its inviting presence in the neighborhood.
Home in Adams

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.

4.91 out of 5 average rating, 149 reviews
Superhost
A uniquely designed raised container home features multiple levels and large windows that offer expansive views of the surrounding landscape. The structure includes a covered outdoor area below, and the combination of dark wood and metal creates a striking exterior appearance.
Shipping container in Whitingham

The House of Pi

WE now pay your 15.5% Guest Service fee!!! Welcome to The House of Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock and Kayaks. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views. Hot Tub and Custom Cedar Sauna!

4.88 out of 5 average rating, 121 reviews

Popular amenities for Pioneer Valley kayak rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Holiday House Rentals with a Kayak

Top Guest favourite
A serene path meanders through lush green grass, leading to a charming farmhouse surrounded by trees. The clear blue sky and gentle clouds create a peaceful backdrop, enhancing the natural setting of the property.
Home in Whitingham

Vermont lake house near Mt. Snow-fab 360 views!

4.92 out of 5 average rating, 119 reviews
Guest favourite
A light blue two-story house is positioned along a road, featuring a covered front porch with white railings and red doors. Lush greenery frames the property, while distant mountains create a scenic backdrop.
Home in Charlemont

Red Door River House

4.98 out of 5 average rating, 108 reviews
Top Guest favourite
The exterior of a Craftsman-inspired home is showcased against a colorful sunset sky. Natural materials create a warm facade, with a prominent stone chimney and large windows enhancing the inviting atmosphere. Lush landscaping surrounds the property, highlighting its connection to nature.
Home in Lee

Lovely Berkshire Home

4.98 out of 5 average rating, 138 reviews
Guest favourite
Home in Stafford

Serene Lakefront Retreat

4.93 out of 5 average rating, 107 reviews
Top Guest favourite
Home in Monterey

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

4.89 out of 5 average rating, 121 reviews
Top Guest favourite
A modern two-story house with large triangular windows is set against a twilight sky. The elevated structure features a spacious deck wrapped with a railing, providing outdoor seating options. The ground level showcases garages, and soft lighting highlights the exterior architecture.
Home in West Brookfield

Peaceful Lake Escape w/ Porch, Fire Pit & Kayak

4.91 out of 5 average rating, 110 reviews
Superhost
Home in Becket

Lake front retreat - Stylish Berkshire home

4.92 out of 5 average rating, 180 reviews
Top Guest favourite
The lakefront home features a rustic wooden exterior with multiple balconies overlooking the water. Surrounded by lush greenery, the property includes a sprawling lawn and vibrant shrubs, while the serene lake and gentle hills can be seen in the background.
Home in Whitingham

Gorgeous Vermont Lakefront with epic sunsets!

4.99 out of 5 average rating, 102 reviews

Cottages with a kayak

Top Guest favourite
A serene lake reflects the colors of twilight, with calm waters mirroring the darkening sky. A crescent moon is visible, while silhouettes of trees line the horizon. The scene captures the tranquil beauty of dusk over the peaceful landscape.
Cottage in Hinsdale

Cozy Cottage in the Berkshires

4.99 out of 5 average rating, 168 reviews
Guest favourite
The exterior of a modern, dark-colored cottage is shown amidst a foggy landscape. A wooden deck extends towards the lake, surrounded by trees. A pathway leads to the entrance, with gravel and a patch of grass in the foreground.
Cottage in Orange

The Lake Cottage: A Sweetwater Stay

4.9 out of 5 average rating, 227 reviews
Top Guest favourite
A private outdoor patio area features a round table surrounded by four chairs, positioned on a brick surface. A swing chair is visible nearby. The peaceful lake view extends beyond, framed by trees and rolling hills under a bright blue sky.
Cottage in Holland

Cozy Lakefront Cottage

4.96 out of 5 average rating, 101 reviews
Top Guest favourite
A charming cottage is set amidst colorful autumn foliage, with a gravel driveway leading up to the entrance. Large windows allow natural light to enter, while a wooden deck is visible at the side, showcasing a welcoming outdoor area with surrounding greenery.
Cottage in Wales

Sunset and Sunrise views at this lake cottage.

4.97 out of 5 average rating, 76 reviews
Top Guest favourite
A charming light blue house is positioned near the water, surrounded by tall trees. A small deck with steps leads to the water's edge, which features a private dock. The grassy area in front adds to the serene outdoor setting.
Cottage in Orange

Lake House with view of mountain

4.99 out of 5 average rating, 95 reviews
Top Guest favourite
Cottage in Otis

Lake Escape: Lakefront Cottage in the Berkshires

5.0 out of 5 average rating, 33 reviews
Top Guest favourite
A bright, open living area features large glass sliding doors that overlook the lake. A dining table surrounds by chairs is set in the foreground, with a comfortable seating area visible to the right. Bookshelves and a decorative rug add warmth to the space.
Cottage in Otis

Berkshire lakefront cabin with modern luxuries

4.98 out of 5 average rating, 93 reviews
Top Guest favourite
The exterior of a cozy cottage is shown, featuring a dark front door and multiple windows adorned with window boxes filled with flowers. A welcoming deck area holds two chairs and a small table, surrounded by lush greenery.
Cottage in Shutesbury

Cozy Cottage with lake view and indoor fireplace

4.99 out of 5 average rating, 82 reviews

Cabin rentals with a kayak

Top Guest favourite
A warm living area features high wooden ceilings and exposed beams. A cozy seating arrangement is set near a stone fireplace, adorned with holiday decorations. A television is mounted above the fireplace. Natural light filters through large windows, creating a welcoming atmosphere.
Cabin in Whitingham

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

4.99 out of 5 average rating, 134 reviews
Top Guest favourite
A spacious log cabin with a metal roof is surrounded by trees. The front porch is lined with a railing, and large windows invite natural light. A gravel driveway leads up to the cabin, with a small shed visible to the side.
Cabin in Monterey

Amazing Berkshire Mountains Cabin

4.95 out of 5 average rating, 311 reviews
Top Guest favourite
The cabin is situated among lush greenery, featuring a light green exterior that complements the natural surroundings. Large windows allow for ample light, while ferns frame the building at the front. The wooded area provides a sense of privacy and tranquility.
Cabin in Whitingham

The Hideaway Camp

4.96 out of 5 average rating, 130 reviews
Guest favourite
Cabin in New Salem

Rustic cabin with A/C at historic orchard & cidery

4.96 out of 5 average rating, 28 reviews
Guest favourite
A cozy fire pit area is surrounded by multiple wooden chairs, inviting relaxation. The serene lake reflects the surrounding trees and colorful autumn foliage, adding to the peaceful setting. The lush green grass blends effortlessly with the natural landscape.
Cabin in Otis

Berkshires Lakefront Boho Modern Retreat

4.96 out of 5 average rating, 25 reviews
Top Guest favourite
The main living area features a spacious layout with natural light flooding in from large windows. A comfortable sofa and armchairs surround a wooden coffee table, while a dining area includes a bright table set for meals. A wood stove stands ready to provide warmth.
Cabin in Shutesbury

Happy Valley Lake House Waterfront • Kayaks/Canoe

4.95 out of 5 average rating, 78 reviews
Guest favourite
Cabin in Becket

Berkshires! Walk to LAKE, kayaks, dog friendly.

4.92 out of 5 average rating, 53 reviews
Guest favourite
The open living space showcases a vaulted ceiling with exposed beams and a stone fireplace. Light wooden cabinets and countertops create a warm ambiance. Two seating areas include a cozy couch, a reclining chair, and a patterned rug, inviting relaxation and conversation.
Cabin in Otis

Enjoy 43 Acres on Two Ponds!

4.89 out of 5 average rating, 70 reviews

Destinations to explore