
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.

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

MODERN 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

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!

“Cozy Cottage” on Great Bay
Our Cozy waterfront cottage is located 120ft from great bay. Our closest beach is 2.5 miles and we are 4 miles from the center of town. Equipped with gas heat and Central A/C. We also have a gas fired fireplace to keep you cozy. Outside shower for days at the beach. We have one single kayak, two double Kayaks, a rowboat and a canoe for a scenic view of Great Bay. Quiet spot.

Beachfront at Days' Cottages! Renovated, Kayaks!
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! Enjoy majestic views and romantic sunsets. This newly updated cottage is carefully decorated to ensure a comfortable, relaxing, and memorable stay.

Pebbles-romantic cottage for two!
Pebbles, our sun drenched romantic cottage, is on nearly an acre of complete privacy with convenient parking. One adorable king BR, queen pull-out sleeper sofa in the living room, gas fireplace heats entire cottage, cable TV, full internet. Full indoor bath and outside shower and tub--complete privacy. Full kitchen and eating area.
Popular amenities for kayak rentals in Chatham
House rentals with a kayak

impeccable cottage STEPS to downtown OB & beach!

The Cape Codder: Large Yard, Steps to Town & Beach

Lake charm

Cape Cod; John’s Pond beach w/2 kayaks -SuperHost!

Waterview, Private, Walk to Beach, Mile to Town

Vineyard Haven Walk to Ferry

Cozy Cape Stay! bike path, beaches, water view!

Nehemiahs Nest: Healing Cape Cod Pond View Cottage
Cottage rentals with a kayak

Spectacular Beach- front home, includes linen

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

The BeachBox

SerenityViews | Waterfront | King Bed | Kayaks SUP

Cape Escape-The Perfect Getaway

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

WATERFRONT Cottage, Downtown w/ Beach

Cozy Cottage on a Private 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
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 $116 SGD per night before taxes and fees

Verified guest reviews
Over 660 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 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

4.8 Average rating
Chatham stays are highly rated by guests – averaging 4.8 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
- Sandy Neck Beach
- Pinehills Golf Club
- New Silver Beach
- Cahoon Hollow Beach
- Nickerson State Park
- Popponesset Peninsula
- Lighthouse Beach
- Cape Cod Inflatable Park
- Saquish Beach
- Nauset Beach
- Race Point Beach
- Skaket Beach
- Sea Gull Beach
- Marconi Beach
- Falmouth Heights Beach
- Sandwich Glass Museum




