
Vacation rentals with a kayak in Cape Cod Bay
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Top-rated kayak rentals in Cape Cod Bay
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2BR Directly on Pleasant Beach – 30 Steps to Ocean
You are not near the beach- You are on it! Only 30 steps from your door to the ocean! Fall asleep to waves. This is a true beachfront cottage located directly on Pleasant Beach. Drink your morning coffee watching the tide roll in. This adorable cottage is reflective of old Cape Cod and is part of a direct beachfront triplex property in the heart of Cape Cod with panoramic views of Pleasant Beach. You'll never feel like you need to leave the cottage but it is close to the quaint Harwich village.
Outdoor spacesLocationCheckout
4.82 out of 5 average rating, 129 reviews
Freshwater Cottage - 1 min walk to private beach
Welcome to Freshwater Cottage, our home is designed with comfort and relaxation in mind, offering a perfect blend of modern amenities and rustic charm. Whether you're looking to escape the hustle and bustle of daily life, enjoy quality time with your family and explore the beauty of the surrounding landscape. Our retreat is located in a quiet neighborhood 3 houses from Sandy Beach and Wall Pond and 4 minutes to fully recreational Big Sandy Pond with private association beaches and boat landing.
Outdoor spacesLocationCondition
4.95 out of 5 average rating, 113 reviews
Water Front Pond House - 3 acre Cape Cod Sanctuary
Extraordinary pondfront sanctuary on Cape Cod. 1300 sq.ft. home sleeps 8 in 3 bedrooms and 1 bath. Private dock and beach area. House is on the Pond and sited on 3 pristine acres - this property offers exceptional privacy with full water recreation opportunities while also being close to everything "Cape Cod". Centrally located in laid-back Brewster, 5 minutes to Bayside beaches, 10 mins to Chatham, Harwich Port, and Orleans. Local owners have 22 years of online vacation rental experience.
LocationValueAir conditioning
4.87 out of 5 average rating, 245 reviews
★Waterview ★Pet Friendly ★Kayaks ★Trails ★
Welcome to SEAGLASS COTTAGE! 🔸 200 MBPS WIFI 🔸 Steps to sandy beach on a crystal clear pond 🔸 Pet friendly 🔸 Linens & towels are included. Beds will be made 🔸 Swim, fish or use our 2 kayaks & 2 SUP’s 🔸 Bluestone private patio w/waterviews+charcoal BBQ 🔸 Outdoor shower 🔸 Sunroom w waterview 🔸 Washer+dryer 🔸 Fully equipped kitchen w/Carrera marble counter 🔸Gas firepit 🔸Ductless A/C & Heat 🔸Small library of books, didn't finish the book? Take it! 🔸Pet fee $25/day
LocationOutdoor spacesBathroom
4.98 out of 5 average rating, 250 reviews
Charming Pond-Front Boathouse
Charming antique boat house located directly on Long Pond. Quiet, peaceful accommodations with 180 views. Watch the American Bald Eagles and Osprey search for fish at dusk from your private deck that reaches out over the pond. Long Pond is full recreation, two kayaks and a canoe are available. Hiking, bicycling, golfing, fishing, swimming, boating, snorkeling, sunbathing, and napping are just a few of the activities that can be enjoyed in the quaint, semi-private, pond-front accommodation.
Outdoor spacesLocationIndoor spaces
4.94 out of 5 average rating, 150 reviews
gorgeous waterfront cottage w/4kayaks and 2 SUPs
Small 500 sq ft gem . Quintessential Cape Cod cottage WATERFRONT on big Sandy Pond. Step back in time and enjoy being on Cape Cod in your own Camp. Come enjoy this charming cottage with 2 bedrooms and views of the pond throughout. Kayak, fish and swim from your front door. *1 Paddle Bd *4 kayaks- 4 adult/4 child life vests *Gas Fire-pit *Gas Grill *XL outdoor shower *Quiet lakeside hood *Gorgeous marble counters in the new kitchen *Remote control heating & cooling system *WiFi
LocationValueQuiet
5.0 out of 5 average rating, 368 reviews
Cozy Cottage on a Private Pond
This cozy cottage is located on a private 42 acre, spring fed, crystal clear private pond. Enjoy kayaking, swimming or fishing from the dock or just relax on the deck overlooking the pond. Sleeps 5 in 2 bedrooms and trundle bed in the 4 season room. There is good fishing and canal cruises, cafes and restaurants close by and a summer concert series in park. Many of our guests with children have visited Edaville Railroad and "Thomasville" It is about 15 miles from the cottage
ValueOutdoor spacesHeating
4.85 out of 5 average rating, 286 reviews
Sauna · Fireplace · Waterfront · 2 Kings · DogsYes
☆ Waterfront, located on private saltwater beach (with central location) ☆ Sauna (year-round) ☆ Cozy fireplace (electric) ☆ 3-season patio ☆ 1% donated to Cape nonprofits ☆ 2 Kayaks & 2 Paddle boards ☆ Outdoor fire pit & charcoal grill ☆ Ample workspace ☆ Dog Friendly ☆ Washer/dryer ☆ 2 King Beds with 50" TVs in bedrooms ☆ Outdoor shower (open May through fall) ☆ Beach chairs provided ☆ Linens, all towels provided ☆ 10min from bay or ocean beach ☆ 15min MV & Nantucket ferries
LocationValueAccuracy
4.99 out of 5 average rating, 133 reviews
SerenityViews | Waterfront | Kayaks SUP | King Bed
Enjoy our cottage's charm and comfort with panoramic views and abundant sunlight. Wake up to incredible sunrises. Lounge on the hammock or swim/fish/kayak in our beautiful backyard waterfront Long Pond. Explore the Cape in each direction: beautiful beaches and endless fun activities/interests. At the end of the day, enjoy dining on the deck as you grill. Sit back on the patio with a cocktail and gaze at the star filled sky and ambiance from the fire table. Welcome!
LocationValueGrill
4.99 out of 5 average rating, 260 reviews
* Game Room, Linens, Quiet St, Central AC/Heat
Cape Cod - Harwich/Dennis Line - Entire Home, 6 Beds + Futon (4 Bd/2 Ba), Includes 2 King Beds, Seasonal Outdoor Shower, Linens Included! Central A/C, Game Room, Cable, Wifi, Pet-Friendly, Near Beaches, Golf, Shopping & Attractions. Great Central Location at CapeVaca. Nearby Beaches: Mayflower, Earle, Pleasant Road, Corporation, West Dennis, Crowe's Pasture, Paines Creek, Harwich, Dennis, Brewster. Message us for early check-in options during the off-seasons.
LocationOutdoor spacesLayout
4.98 out of 5 average rating, 178 reviews
Private Beachfront, AC, EV, Kayaks, Renovated!
10% off Weeklong Off-Season bookings! Welcome to Larkspur Cottage, part of the "Days' Cottages," one of the 22 white and teal cottages located right before Provincetown, complete with its own private beach, portable AC unit and convenient located next door to an EV charging station! Enjoy majestic views and romantic sunsets. This newly updated cottage is carefully decorated to ensure a comfortable, relaxing, and memorable stay.
Outdoor spacesLocationWalkability
4.98 out of 5 average rating, 118 reviews
Sunset Cove Beach
This ocean view cottage is perfect for you and your family to relax, unwind and adore the wonderful scenery it has to offer. This charming cottage is on a quiet dead-end street, suitable for a small family or a couple, seeking to appreciate the neighborhood and beaches without the hassle of cape traffic. Come and enjoy the warm water, beautiful sunrises, breathtaking sunsets, and much more.
Outdoor spacesLocationHeating
4.99 out of 5 average rating, 120 reviewsPopular amenities for Cape Cod Bay kayak rentals
House rentals with a kayak

The Luxury Vineyard Yurt
ValueLocationHospitality
4.93 out of 5 average rating, 326 reviews
Waterfront•Hot Tub • Kayaks/SUP's • King Bed •Dock
ValueLocationWifi
4.94 out of 5 average rating, 271 reviews
Pebbles-romantic cottage for two!
LocationOutdoor spacesQuiet
4.97 out of 5 average rating, 122 reviews
Lakefront House/Private Dock/Year Round Hot Tub/AC
ValueLocationComfort
4.96 out of 5 average rating, 240 reviews
Oceanfront Home on Cape Cod Bay with Beach Access
ValueLocationCheck-in
4.98 out of 5 average rating, 40 reviews
The Quarterdeck | Oceanfront Fun for All Ages
Outdoor spacesLocationHospitality
5.0 out of 5 average rating, 63 reviews
Sunburst Cottage on Long Pond
ValueOutdoor spacesBathroom
4.99 out of 5 average rating, 93 reviews
Nehemiahs Nest: Healing Cape Cod Pond View Cottage
Outdoor spacesLocationParks
4.96 out of 5 average rating, 73 reviewsCottage rentals with a kayak

Local Beach+ Fireplace + Hot Tub Under the *Stars*
ValueLocationHiking
4.96 out of 5 average rating, 169 reviews
“Cozy Cottage” on Great Bay
LocationValueSleep quality
4.94 out of 5 average rating, 232 reviews
Little Boho Retreat by the Beach
ValueLocationCheckout
5.0 out of 5 average rating, 250 reviews
Waterfront Oasis minutes from Newport w/ hot tub!
ValueOutdoor spacesPets
4.98 out of 5 average rating, 178 reviews
Compass Rose Cottage ★ Steps to Flax Pond & Trails
LocationValueWalkability
4.95 out of 5 average rating, 136 reviews
Cottage 29 - Waterfront Cottage - Close to Newport
ValueOutdoor spacesRiver
4.99 out of 5 average rating, 145 reviews
Ocean View Humarock Beach Cottage
LocationValueGrill
4.93 out of 5 average rating, 124 reviews
MODERN COTTAGE W/ BIKES, PADDLE BOARDS & KAYAKS
ValueLocationShared spaces
4.92 out of 5 average rating, 544 reviewsOther vacation rentals with a kayak

Sheep Pond Get-Away
Outdoor spacesValueCleanliness
4.97 out of 5 average rating, 423 reviews
Frenchie Studio Apt @ The Dune Shack Awesome spot!
LocationOutdoor spacesSleep quality
4.92 out of 5 average rating, 173 reviews
Cozy Waterfront Apartment, Private Beach Access
Outdoor spacesValueFamily
4.95 out of 5 average rating, 340 reviews
Modern cottage on Long Pond at Cornish Point
Outdoor spacesLocationKitchen
5.0 out of 5 average rating, 14 reviews
Cozy 2-bedroom Cottage by the Pond
LocationValueCheck-in
4.95 out of 5 average rating, 74 reviews
Beachfront Condo, Superb Location!
Outdoor spacesLocationQuiet
4.92 out of 5 average rating, 36 reviews
Serenity Point Waterfront (Now Booking for Fall)
Outdoor spacesLocationBackyard
4.99 out of 5 average rating, 71 reviews
Lake Shore Cottage - Waterfront with Beach Access
LocationOutdoor spacesNearby
5.0 out of 5 average rating, 36 reviewsDestinations to explore
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- Onset Beach
- East Sandwich Beach
- Duxbury Beach
- Sandy Neck Beach
- Saquish Beach
- Nauset Beach
- New Silver Beach
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- Falmouth Heights Beach
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- Cahoon Hollow Beach
- Horseneck Beach
- Nickerson State Park
- Sea Gull Beach





