
Holiday rentals with a kayak in Dennis
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Top-rated Accommodation with a Kayak in Dennis
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

Directly on Pleasant Beach – 30 Steps to the 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.

SerenityViews | Waterfront | King Bed | Kayaks SUP
Enjoy our cottage's charm and comfort with panoramic views and abundant sunlight. Comfortably hosts 2 families. 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!

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 Watch the birds, relax out back in peace & privacy or go explore! 📍 Centrally located ❌ NO FEES ⛱️ Year Round Beach Vacation ➡️Bayside_Retreat_Capecod

★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

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!

Romantic Cottage w/ Bikes, Paddle Boards & Kayaks
This newly remodeled, nautically themed cottage includes countless amenities designed for a fun, romantic getaway with all the comforts of home. - Bikes, paddle boards, 2-person kayak, yard games, beach chairs/towels & cooler - Outdoor fire pit and gas grill - Stocked kitchen with quality cookware, organic coffee/tea, water filtration pitcher + more - Organic, vegan, unscented, allergen-free soaps & cleaning products - Extreme COVID sanitation protocols as well as quarterly deep cleanings

*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. In Sept and Oct, weeks are 20% discounted.

Cape Cod Life is Good Rentals
Mid-cape Home Relax in a spacious home that is central to many attractions 8 minutes to the beach, 2 minutes to local golf course and 5 min to Cape Cod Trail. If you are looking for a day trip only 13 min away to Hyannis ferry to Martha's Vineyard/Nantucket or head to visit "P-Town." Endless activities with 3 kayaks available, beach gears, and bikes for family & friends to explore the area. House is located in a quiet neighborhood where you can take a 5 min walk to the cranberry bogs.

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

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.

* Game Room, Linens, Quiet St, Central AC/Heat
Cape Cod - Harwich/Dennis Line - Entire Home, 7 Beds (4 Bd/2 Ba), 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. We would love to host you at CapeVaca.

One bedroom guest house on beautiful Cape Cod
Second level guest apartment with one bedroom, bathroom, kitchen, large walk-in closet and living room. Just about everything you need to feel at home. There is A/C in the bedroom and the living area is well vented and has a large ceiling fan. Two golf courses are within 3/4 of a mile, public access beach and boat ramp are within 1 mile. You will also find kayaking, bike trails, walking trails and many other Cape Cod amenities just a short drive away.
Popular amenities for Dennis kayak rentals
Holiday House Rentals with a Kayak

West Dennis Beach House - Steps to Beach

impeccable cottage STEPS to downtown OB & beach!

Sunburst Cottage on Long Pond

Plymouth's Lakeside Getaway

Private Lake Beach | Spectacular Views & Amenities

Large Mid-Cape 5 BR- 3 Bath Home A/C, 2mi to beach

Waterfront-Kayaks & SUPs-Firepit-Pet OK-Kingbed

Cozy Pet Friendly Falmouth Beach House
Cottages with a kayak

Spectacular Beach- front home, includes linen

The BeachBox

Little Boho Retreat by the Beach

Lakeside Waterfront House in Harwich: 4+beds, 3bth

WATERFRONT Cottage, Downtown w/ Beach

Ocean Front Cottage (July/Aug Sat-Sat only)

Cozy Cottage on a Private Pond

The Breeze Overlooking Minister's Pond
Cabin rentals with a kayak

The Flamingo House @ OBC Beach Resort and Habitat

Cozy Cape Cod Cabin | Pond, Pool & Pet-Friendly

Relaxing Retreat in Falmouth

Cozy Cabin at Peter’s Pond
When is the best time to visit Dennis?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $230 AUD | $246 AUD | $299 AUD | $299 AUD | $404 AUD | $500 AUD | $610 AUD | $621 AUD | $454 AUD | $345 AUD | $302 AUD | $282 AUD |
| 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 |
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 $86 AUD per night before taxes and fees

Verified guest reviews
Over 7,780 verified reviews to help you choose

Family-friendly holiday rentals
90 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
110 of Dennis holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Dennis rentals

4.9 Average rating
Dennis stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with a kayak Barnstable County
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Onset Beach
- Coast Guard Beach
- Pinehills Golf Club
- New Silver Beach
- Lighthouse Beach
- Sandy Neck Beach
- Nickerson State Park
- Cahoon Hollow Beach
- Cape Cod Inflatable Park
- Sea Gull Beach
- Popponesset Peninsula
- Scusset Beach State Reservation
- Race Point Beach
- Skaket Beach
- Saquish Beach
- Sandwich Glass Museum
- Bass River Beach
- Nauset Beach




