Holiday rentals with a kayak in Cohasset

4.93 out of 5 average rating, 398 reviews

Apartment in Medford

Garden Apartment for Vacation & Business Travelers

The perfect place to rest, relax or work. Visit universities, Salem or family and friends in the area. This English Basement apartment is located on the Mystic River, 10 minutes from Harvard University in Cambridge and 20 minutes from the City of Boston. Enjoy many local outdoor amenities including the Mystic Lakes, parks, playgrounds, tennis/pickleball/basketball courts and jogging paths, all behind our house. We warmly welcome people from all backgrounds as we value and respect diversity.

Outdoor spacesLocationComfort

5.0 out of 5 average rating, 107 reviews

The exterior of a contemporary two-story home is shown at dusk, featuring large glass windows and a wooden deck. Soft lighting emanates from the inside, highlighting the airy design. Leaf-strewn landscaping surrounds the house, enhancing its serene setting.

Home in Scituate

Stella Maris, 6 bedroom coastal home, water views

Stella Maris is an inter-coastal sanctuary, located on a private, tree lined street, with ever changing views of Cohasset Harbor & surrounding marsh & waterways. The airy floor plan of this contemporary home is perfect for entertaining family and friends. Gathering on the deck at sunset is a favorite. A short walk to Minot Beach and the lovely Minot neighborhood. Close to charming Scituate & Cohasset Harbors with their great restaurant scenes. 5 minutes to the Commuter rail into Boston.

Outdoor spacesLocationCheck-in

4.93 out of 5 average rating, 124 reviews

Cottage in Marshfield

Ocean View Humarock Beach Cottage

Quintessential Humarock Beach cottage just steps from the ocean. Wake up to sea breezes, enjoy sunset walks along the shoreline, and experience one of the South Shore’s most relaxing coastal escapes. Perfect for both relaxation and adventure, the cottage doubles as a sports haven with a beach volleyball court and includes use of kayaks and paddleboards for exploring the coastline and the river. Spend your days on the sand, in the water, or unwinding on the deck as the ocean breeze rolls in.

LocationOutdoor spacesCheckout

4.86 out of 5 average rating, 7 reviews

Cabin in Cohasset

Cohasset Woodland Cabin

Private cabin tucked on a beautiful 10-acre property just 5 minutes from downtown Cohasset. Surrounded by more than 100 additional acres of woods, fields, and walking trails, the cabin offers a rare blend of seclusion and convenience. The property also neighbors Holly Hill Farm, a charming organic farm open to the community. This is a perfect retreat for guests seeking comfort, simplicity, and connection to nature—while still being close to Cohasset’s shops, restaurants, beaches, and harbor.

LocationQuietBathroom

4.77 out of 5 average rating, 166 reviews

A serene waterfront view showcases a calm pond surrounded by trees in autumn colors. An inviting sandy beach area features bright blue adirondack chairs and a kayak resting on the shore, reflecting a peaceful outdoor setting.

Condo in Plymouth

Clear Pond Pet Friendly Retreat

Welcome to our beautifully renovated pondfront retreat —Private Residence on a Pondfront Estate. The perfect peaceful getaway experience near Plymouth that comfortably sleeps six! This pet-friendly escape offers the best of relaxation and outdoor adventure all in one place. Enjoy kayaking, boating, and fishing right from your private beachfront along the pond. Spend your mornings walking the scenic trails with your dogs, and your evenings gathered around the fire pit under the stars.

ValueLocationKitchen

4.98 out of 5 average rating, 58 reviews

An open floor plan showcases the modern kitchen, equipped with an island and bar seating. A cozy living area features a gray sofa, decorative pillows, and a coffee table. Large windows allow natural light to fill the space, complimenting the calming color palette.

Cottage in Scituate

Humarock Beach Family-Friendly Cottage "Shore Bet"

"Shore Bet" cottage is located in Humarock Beach, a picturesque seaside village of Scituate, MA. Just a short walk to a private beach, it's perfect for a relaxing family getaway, featuring miles of beach, kayaking, paddle boarding, biking, water sports, fishing, and gorgeous marshland. Just a short walk to the village center with two restaurants, coffee shop, gift shop, fresh seafood store, rental/surf shop, post office, and ice cream! Offering long-term WINTER RENTALS: October - April.

LocationOutdoor spacesIndoor spaces

4.87 out of 5 average rating, 124 reviews

A serene view of the lake at sunset is framed by lush greenery and a manicured lawn. Three blue Adirondack chairs are positioned near the water's edge, offering a perfect spot to enjoy the fading light. The sky displays warm hues reflecting on the calm surface of the lake.

Guest suite in Braintree

Sunset LAKE VIEW studio. Recently upgraded!

Welcome to Sunset Lake! Enjoy beautiful sunsets year round! Cozy in the winter with plenty of extra blankets and a great heating system! Light a fire at night. We are walking distance to South Braintree Square. You will enjoy nature and still have close proximity to city. Walk to a super market, pharmacy, nail salon, bank, a tavern w/ live music. Other restaurants within walking distance include Mexican, Thai, Sushi, Italian, Vietnamese (pho), pizza and a great local coffee shop ☀️ 🌅

Outdoor spacesLocationComfort

4.78 out of 5 average rating, 45 reviews

An outdoor dining table is set for a meal, featuring plates of olives, cheese, and a bottle of wine. The table is positioned on a deck with a clear view of the ocean, where calm waves meet the horizon under a bright blue sky.

Home in Scituate

Scituate Oceanfront | Hot Tub & Steps to Beach

Welcome to The Turner Tide, a peaceful coastal escape in Scituate, MA. Perched along the scenic shoreline, this charming home offers sweeping ocean views, salty breezes, and the soothing sound of waves—perfect for couples, small families, or anyone seeking a classic New England beach getaway. Sand Hills beach- less than a minute walk Scituate Lighthouse - 5 min Scituate Harbor - 5 min Museum Beach - 5 min Peggotty Beach- 8 mins drive Explore Scituate magic with us & Learn More Below!

LocationOutdoor spacesBackyard

4.99 out of 5 average rating, 144 reviews

The exterior of a welcoming home is shown, featuring a porch with elegant front doors. Soft lighting illuminates the entryway, while lush greenery and colorful flowers enhance the landscape, providing a warm and inviting entrance.

Apartment in Pembroke

Beautiful Lakeside Apt between Boston and Cape Cod

Beautiful apartment, with extraordinary lake views, located on a quiet street and midway between Boston and Cape Cod. Access to the lake is just feet from your back door. Enjoy grilling, swimming and the use of kayaks, canoe and standup paddle boards. 1 bed, 1 bath, can sleep 5 with a pull out queen and twin couches. Full kitchen, laundry, internet, cable. Your own access with keypad and off street parking is an added bonus. NO SMOKING OF ANY KIND IN OR OUTSIDE-NO EXCEPTIONS.

LocationOutdoor spacesDecor

Guest suite in Marblehead

A light-filled living area features a pull-out sofa adorned with striped cushions and a coffee table with a decorative book and lamp. A sliding glass door opens to a sleeping area with a spacious bed, while bright curtains frame the window, offering a view of the exterior.

Ocean Park Retreat

Bright and cheery 1 bedroom ground floor apartment with two+ car parking on quiet street in Marblehead's Ocean Park neighborhood, just steps from the ocean. Full size bed and pull-out full-size sofa in living room, private bathroom with in-floor heating, kitchenette with microwave, dishwasher, sink, double induction cook-top, refrigerator, and toaster oven. Laundry access. Walk to the waterfront, watch the sailboats drift by. Fifteen- minute walk to Historic town center.

Outdoor spacesLocationBathroom

4.91 out of 5 average rating, 319 reviews

4.84 out of 5 average rating, 19 reviews

A large dog stands on a porch, overlooking a serene waterfront view. The sky features soft clouds, transitioning from blue to pink as the sun sets. An American flag flutters nearby, while a well-maintained pathway leads to the water's edge.

Cottage in Hull

Relaxing Beachfront Cottage, 20min Ferry to Boston

Relax at this peaceful beachfront home. Just 30min to Gillete stadium! Ferry access to downtown Boston only a 5 minute walk and just a 20min ride to Boston. By far the best way to get in and out of the city. 3 story home with water on 3 sides, beautiful views and sunsets that will melt away all your stress. Kayaks and beach gear available, pet friendly. Weekly and Monthly Discounts

ValueOutdoor spacesCondition

4.81 out of 5 average rating, 21 reviews

Home in Weymouth

Bayfront Retreat with Private Ramp &Stunning Views

Make some memories at this unique and family-friendly place. This is a peaceful single family home with a private boat ramp that can also be used as beach access. Beautiful views of the bay and sunrise, the house has 3 bedrooms (sleeps up to 7, or utilize the couch on the sunroom to accommodate more), sunroom, garage, wood burning stove and outdoor seating. NON-smoking property.

LocationValueIndoor spaces

Popular amenities for Cohasset kayak rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

A wooden boardwalk extends towards the calm ocean, framed by a sandy beach and gentle blue waves. Smooth rocks accompany the path, and the sky is clear with wispy clouds, creating a serene coastal scene.

5.0 out of 5 average rating, 63 reviews

The Quarterdeck | Oceanfront Fun for All Ages

LocationOutdoor spacesAir conditioning

4.94 out of 5 average rating, 16 reviews

An aerial view showcases a coastal neighborhood adjacent to a sandy beach. The vibrant blue ocean stretches into the distance, while homes are positioned along the streets, creating a welcoming residential area. Green spaces and beach access are visible, enhancing the locale's appeal.

Home in Marshfield

Walk to Private Beach, Sleeps 11, Pool, Pets ok

LocationOutdoor spacesWalkability

4.6 out of 5 average rating, 10 reviews

Home in Duxbury

Powder Point Bay View Escape

LocationValueFamily

5.0 out of 5 average rating, 63 reviews

A stunning sunset paints the sky with vibrant colors reflected in the calm water of Woods Pond. The outdoor deck features seating arrangements, while two fishing poles stand ready for use by the private dock. Trees frame the serene view, adding a natural touch.

Home in Middleborough

Pelicans Bog on Woods Pond in Middleboro

Outdoor spacesLocationCheck-in

5.0 out of 5 average rating, 84 reviews

An outdoor deck is showcased, featuring a modern grill and a table surrounded by a set of black wicker chairs. Lush greenery provides privacy, while a door leads into the interior of the cottage. The space is designed for relaxation and gatherings.

Home in Marblehead

Dotey Cottage: Walk to the Beach w/ Fenced in Yard

LocationValueBarbecue

4.87 out of 5 average rating, 47 reviews

A welcoming entrance is displayed with a polished brick pathway leading to a well-maintained white house. The front features large black-framed windows and a pair of bold red doors flanked by pots of colorful flowers, complemented by lush green landscaping.

Home in Canton

Hidden Gem near Boston w/ Private lake access

Outdoor spacesLocationBeach

A landscaped yard features a white picket fence and a stone pathway leading to the house. Steps ascend from the yard to the deck above, surrounded by greenery and framed by trees. The calm waters of Fresh Pond are visible in the background under a clear sky.

4.98 out of 5 average rating, 58 reviews

Secluded Waterfront, Lake View, With Private Dock

ValueLocationBackyard

A wooden deck extends from the house, featuring a seated area with an Adirondack chair. Expansive views of the ocean and shoreline are visible, framed by low coastal vegetation and a wooden fence. A clear sky with scattered clouds creates a serene backdrop.

4.97 out of 5 average rating, 39 reviews

Oceanfront Home on Cape Cod Bay with Beach Access

Outdoor spacesValueSleep quality

Cottages with a kayak

4.91 out of 5 average rating, 100 reviews

A wooden staircase leads down through lush greenery to a sandy beach, where the gentle waves meet the shore. The clear blue water stretches into the horizon under a bright sky, inviting visitors to enjoy the coastal atmosphere.

Cottage in Plymouth

Cozy Private Beach Getaway

ValueLocationWi-Fi

4.89 out of 5 average rating, 53 reviews

A private bedroom is viewed through large glass windows, offering a serene lake vista surrounded by trees. A small table with two stools is positioned near the window, while a bedside with a decorative plant enhances the space.

Cottage in Carver

Adorable Lake Front Cottage

LocationOutdoor spacesGetting around

Cottage in Plymouth

Lake View | Water Access | Deck | Firepit-AC-Kayak

Outdoor spacesLocationCheckout

4.69 out of 5 average rating, 13 reviews

4.89 out of 5 average rating, 47 reviews

A cozy outdoor seating area is positioned near the water's edge, featuring a small table and four chairs on a gravel surface. A large tree provides shade, and the serene view of the lake is framed by lush greenery and distant wooded shores.

Cottage in Plymouth

Quiet Plymouth Cottage on Great South Pond!

LocationOutdoor spacesHiking

5.0 out of 5 average rating, 39 reviews

Cottage in Scituate

Expansive coastal views, 3/2 newly renovated

LocationOutdoor spacesGetting around

Other holiday rentals with a kayak

4.92 out of 5 average rating, 66 reviews

Apartment in Marblehead

Mugford Manor

Outdoor spacesLocationSleep quality

4.93 out of 5 average rating, 27 reviews

Condo in Cambridge

“Luxury 2BR Cambridge | Pool + Parking”

ValueLocationGetting around

4.72 out of 5 average rating, 137 reviews

Guest suite in Canton

Newly renovated, close to Foxboro and Boston

ValueOutdoor spacesIndoor spaces

5.0 out of 5 average rating, 4 reviews

A modern kitchen with white cabinetry and a glossy countertop features a spacious eat-in island with three stools. A brick accent wall adds character, while a cozy seating area with a neutral sofa and decorative pillows offers relaxation. Natural light fills the space, complementing the artwork on the wall.

Condo in Marblehead

Amazing Location! New2 Bed downtown w AC sleeps 4

LocationWalkabilityAccuracy

4.85 out of 5 average rating, 48 reviews

The living area features a comfortable sectional sofa adorned with decorative pillows, a marble coffee table, and a vintage armchair. Light enters through the windows, illuminating the room. Two closed doors are visible, suggesting storage spaces, while a wall-mounted television is positioned on the opposite wall.

Apartment in Marblehead

Sailor’s Retreat – Old Town Stay Near Salem & Harb

LocationAccuracyAir conditioning

4.99 out of 5 average rating, 73 reviews

A cozy seating area is presented with two elegant chairs featuring floral upholstery, positioned around a small round table. Natural light floods the space through large bay windows, revealing a view of the outdoor deck and an umbrella. A white dresser adds functionality to the room.

Condo in Marblehead

Little Harbor House 1st Floor

Outdoor spacesValueCleanliness

A cozy living area features comfortable seating, including a dark armchair and a sectional couch draped with a blanket. A wooden coffee table is centrally positioned on a wood floor, while a glass side table adds functionality. Bright natural light filters through partially closed blinds.

Apartment in Medford

Home away from home!

LocationValueWi-Fi

4.86 out of 5 average rating, 112 reviews

The beach house features a light blue exterior with multiple windows, including a spacious sunroom. A front patio with Adirondack chairs overlooks a manicured lawn. A vehicle is parked in the driveway, while the upper deck is furnished for outdoor relaxation.