
Holiday rentals with a kayak in Dennis
Find and book unique kayak rentals on Airbnb
Quick stats about holiday rentals with a kayak in Dennis

Total holiday rentals
Explore 110 holiday rentals in Dennis

Nightly prices starting at
Dennis holiday rentals start at €122 per night before taxes and fees

Verified guest reviews
Over 8,330 verified reviews to help you choose

Family-friendly holiday rentals
90 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
110 of Dennis holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Dennis rentals

4.9 Average rating
Dennis stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated rentals with kayak in Dennis
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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.
4.82 out of 5 average rating, 129 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.
4.87 out of 5 average rating, 245 reviews
Local Beach+ Fireplace + Hot Tub Under the *Stars*
Welcome to the Bayside Retreat! Enjoy the real Cape Cod in this Quintessential Beach Rental Featuring: Private hot tub, outdoor patio & sofa set in a peaceful backyard 🕊️ 2️⃣ Kayaks- Outdoor Shower- Gas Grill 🔥 Indoor Gas Fireplace ❄️ Mini Splits ✔️Games ✔️Washer/Dryer 📺 55” Sony TV w/ Apps & DirectTV 🛋️ Comfy Furnishings➕Stocked Kitchen 🛁New Bathroom 🕊️Relax out back in peace & privacy or go explore! 📍 Centrally located ❌NO FEES ⛱️ Year Round Beach Vacation ➡️Bayside_Retreat_Capecod
4.96 out of 5 average rating, 169 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
4.98 out of 5 average rating, 249 reviews
*Bass River Victorian Escape* Central A/C*WiFi
Get away from it all. This beautiful Victorian semi-detached home is part of a former sea captain’s house. Refurbished to a high standard, it is light and spacious with 2 bedrooms and 1.5 bathrooms, fully equipped kitchen, and a 3-season porch with its own entrance. The open floor plan, central A/C, W/D in basement, WiFi, smart TV, outdoor BBQ, and shelves filled with books and games for all ages will make your family vacation that much better. Ask about 20% off weeklong stays in Sept & Oct.
4.94 out of 5 average rating, 170 reviews
Cape Escape-The Perfect Getaway
Enjoy Nantucket Sound beaches, Cape Cod Rail Trail bike path, shops, restaurants and charter boat fishing. Take a scenic drive to Provincetown or stroll seaside festivals. You will love this quintessential Cape cottage for its charm, location, and outdoor space. Spring and fall are beautiful times with everything open without the crowds of the summer. Winter provides a combination of solitude and comfort. Explore the nuances of Cape Cod from this centrally located cottage All are welcome!
4.93 out of 5 average rating, 138 reviews
* Walk to the beach - Swiss Beach House! *
Walk to the beach! Less than a 1/2 mile (0.7 km)! Perfect spot for paddle boarding. Paddleboards and gas grill (available in summer). Private European - style house. Rustic charm. Laid-back atmosphere. 3 Bedroom, 2.5 bathroom. Comfortably sleeps 6-7, up to 8. Fire pit. Outdoor shower. Farm table for group dining. Fantastic central Cape Cod location. Natural environment. 15 min. to Hyannis for ferries to Nantucket or Martha's Vineyard. Enjoy something unique. Experience the real Cape Cod.
4.87 out of 5 average rating, 191 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
5.0 out of 5 average rating, 368 reviews
Lakefront House/Private Dock/Year Round Hot Tub/AC
Beautiful cottage nestled on a half-acre of waterfront property on Swan Pond. The dock offers direct water access. Available are two kayaks, a canoe and two paddleboards. The kitchen offers beautiful views of the water while you enjoy your morning coffee. Local beaches are just minutes away. Enjoy the hammock, swings, hot tub, grill, outdoor fire pits and cocktails on the deck. Wanderers' Rest is located close to bike trails, boat rentals, movie theaters, restaurants, and bars.
4.96 out of 5 average rating, 239 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
4.99 out of 5 average rating, 133 reviews
Waterfront•Hot Tub • Kayaks/SUP's • King Bed •Dock
✅All linens provided & beds made ✅ King bed / Queen / Twin over Full bunk ✔ Direct lake access = natural cold plunge ✔ Private waterfront hot tub (open year-round) ✔ 1 King bed + Queen + twin over bunk room ✔ Dock for swimming & fishing ✔ 2 kayaks + 2 SUPs ✔ Gas fireplace ✔ Large waterfront dining room ✔ Fully stocked kitchen w/ marble counters ✔ Patio + fire pit + deck dining ✔ Washer/Dryer ✔ Dog friendly ($30/day) ✔ All linens & towels provided Locally managed
4.94 out of 5 average rating, 271 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.
4.98 out of 5 average rating, 177 reviewsPopular amenities for kayak rentals in Dennis
House rentals with a kayak

Cape Cod Life is Good Rentals
4.96 out of 5 average rating, 223 reviews
Cape Fever - 161 Berry Ave
4.82 out of 5 average rating, 101 reviews
"Cape Escape" luxury home w/pool & beach access.
4.99 out of 5 average rating, 103 reviews
Oceanfront | Firepit | Gameroom | Pets | Kayaks
4.98 out of 5 average rating, 122 reviews
Sunburst Cottage on Long Pond
4.99 out of 5 average rating, 92 reviews
Stunning Waterfront Home w/ Hot Tub, Deck & Office
4.97 out of 5 average rating, 39 reviews
Pet-Friendly Home, Easy Access to Bay, Sound & Rt6
5.0 out of 5 average rating, 8 reviews
Waterfront 3 BR Cottage with Dock
5.0 out of 5 average rating, 25 reviewsCottage rentals with a kayak

MODERN COTTAGE W/ BIKES, PADDLE BOARDS & KAYAKS
4.93 out of 5 average rating, 542 reviews
“Cozy Cottage” on Great Bay
4.94 out of 5 average rating, 232 reviews
Cozy Cottage on a Private Pond
4.85 out of 5 average rating, 285 reviews
The Breeze Overlooking Minister's Pond
4.96 out of 5 average rating, 278 reviews
Spectacular Beach- front home, includes linen
4.87 out of 5 average rating, 115 reviews
Serenity Point Waterfront (Now Booking for Fall)
4.99 out of 5 average rating, 68 reviews
Sand Pond Perfection
4.98 out of 5 average rating, 40 reviews
Across from Glendon Beach-Ocean View and Fire Pit!
5.0 out of 5 average rating, 22 reviewsOther holiday rentals with a kayak

Sheep Pond Get-Away
4.97 out of 5 average rating, 423 reviews
West Dennis Beach House - Steps to Beach
4.91 out of 5 average rating, 64 reviews
The Cape Codder: Large Yard, Steps to Town & Beach
4.95 out of 5 average rating, 19 reviews
Bass River with First Floor Master and Game room
4.89 out of 5 average rating, 85 reviews
Gorgeous Renovation - Boat Dock, Hot Tub, 5 Beds!
4.94 out of 5 average rating, 33 reviews
Updated, Cozy Cape Home, 5 min Walk to Long Pond
4.98 out of 5 average rating, 90 reviews
Pinewater Grand Waterfront w/kayaks & dog-friendly
5.0 out of 5 average rating, 14 reviews
Cape Cod Classic
4.97 out of 5 average rating, 30 reviewsWhen is the best time to visit Dennis?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €206 | €207 | €192 | €200 | €272 | €327 | €370 | €376 | €275 | €225 | €217 | €218 |
| Avg. temp | 0°C | 0°C | 3°C | 7°C | 12°C | 17°C | 21°C | 21°C | 18°C | 13°C | 8°C | 3°C |
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- Rentals with a kayak Barnstable County
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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
- Skaket Beach
- Popponesset Peninsula
- Cape Cod Canal
- Falmouth Heights Beach
- Pinehills Golf Club
- Race Point Beach
- Inkwell Beach
- Coast Guard Beach
- Cape Cod Inflatable Park
- Cahoon Hollow Beach
- Horseneck Beach
- Nickerson State Park
- Sea Gull Beach





