
Holiday rentals with a kayak in Chatham
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Chatham
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.

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.

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

Little Boho Retreat by the Beach
Kick back and relax in the most calming, low charm country, coastal cottage the town of Marion has to offer. You’ll experience spectacular view of the beach right from the deck to watching the boats from the harbor. Don’t just limit yourself to life at the beach in just the summer months, come and make memories in this beautiful year-round cozy cottage. It's a perfect retreat to go swimming, kayaking, fishing, bird/seal/crabs watching and more right here in a private community on Dexter Beach.

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

* 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.

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.

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

Lakefront Spa Retreat • Hot Tub • 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

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!

Cozy Waterfront Apartment, Private Beach Access
Charming living space with nautical decor invites you to unwind off the grid for a few days. There is a window seat for reading, small high top for morning coffee, and all the accessories for a relaxing day at the beach. A five minute drive into town for local shopping and dining. Many scenic trails for walking and biking. Make us your base as you explore Cape Cod’s beautiful shores!
Popular amenities for kayak rentals in Chatham
House rentals with a kayak

1850 Orleans Antique Home with Path to Arey’s Pond

The Wellfleet Beach House. Sleeps 6

impeccable cottage STEPS to downtown OB & beach!

Swan nest escape

Waterview, Private, Walk to Beach, Mile to Town

Cozy ranch with private neighborhood beach

CapeSearenity-Large Pool-Beach Passes-Family Fun!

Waterfront | Modern | Pond for Boats and Swimming
Cottage rentals with a kayak

Spectacular Beach- front home, includes linen

Compass Rose Cottage ★ Steps to Flax Pond & Trails

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

The BeachBox

“Cozy Cottage” on Great Bay

Cape Escape-The Perfect Getaway

Walk to Beach, Private Deck, BBQ, Smart TV, Kayak

Cozy Cottage on a Private Pond
Cabin rentals with a kayak

The Flamingo House @ OBC Beach Resort and Habitat

Cape Cod Resort|Cabin w/Pool & Private Beach

Relaxing Retreat in Falmouth

Cape Cod Resort|Cabin w/Pool & Private Beach
Quick stats about holiday rentals with a kayak in Chatham

Total holiday rentals
Explore 30 holiday rentals in Chatham

Nightly prices starting at
Chatham holiday rentals start at £66 per night before taxes and fees

Verified guest reviews
Over 610 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Chatham holiday rentals include wifi access

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

4.9 Average rating
Chatham stays are highly rated by guests – averaging 4.9 out of 5!
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- East Sandwich Beach
- Duxbury Beach
- Onset Beach
- Coast Guard Beach
- Pinehills Golf Club
- Sandy Neck Beach
- New Silver Beach
- Nickerson State Park
- Popponesset Peninsula
- Cahoon Hollow Beach
- Nauset Beach
- Saquish Beach
- Lighthouse Beach
- Cape Cod Inflatable Park
- Race Point Beach
- Skaket Beach
- Sea Gull Beach
- Falmouth Heights Beach
- Marconi Beach
- Inkwell Beach





