
Pet-friendly holiday rentals in Chatham
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Chatham
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

★TINY HOUSE★4/10mi Beach & Village★Pet OK★2 Bikes
Welcome to SAND PEBBLE COTTAGE! We are PET FRIENDLY! ($25/nt) This 300sq.ft "TINY HOUSE" is 0.4 mi from the ocean beach & 1/2 mi from Dennisport village At the end of a cul-de-sac, this tiny cottage has everything you need ✅ 4/10mi to beach & village ✅ Kitchen w/marble counters ✅ 2 Bike ✅ Deck w/furniture & charcoal BBQ ✅ Parking-2 cars ✅ Separate bedroom ✅ Full A/C ✅ Bring your sheets/towels-we do not provide linens ✅ Pet friendly-only 1 pet as the cottage is tiny $25/nt

Slate House - a modern waterfront getaway
Water front on Frost Fish Creek! This recently renovated 3 bedroom (sleeps 9) 2 bath home is tucked off the road in a private oasis with panoramic water front views from almost every room. The bright open floor plan with fireplace, blue slate floors, high open ceilings to second floor, three pairs of sliders that boast nature, water views, fire pit, and screened in lounge and abundant sunlight. Walking distance to a small private dog friendly beach. Driving distance to many great beaches.

Ocean Side, Amazing View, close to town/beach, Spa
PRICING IS FOR 2 GUESTS, 1 BEDROOM, 1 BATH ONLY, can add additional bed/bath for a fee, YOU WILL HAVE THE HOUSE TO YOURSELF. We only use this listing to fill gaps when the larger listing isn't rented & will decline ALL WEEKENDS, HOLIDAYS, PEAK times and will only accept mid-week, non summer/holidays. Please read additional info. OCEAN FRONT, HISTORIC SUMMER COTTAGE, AMAZING VIEWS, GREAT LOCATION, less than 1 mile walk to town and beach. Hot tub, fireplace, stocked kitchen, fresh linens.

Upper Cape Cozy Cottage
Simple but cozy cottage on an acre property next to the main house. Moderate sized bedroom and living room. Small kitchen and bathroom. The kitchen is fully equipped for cooking. Air conditioning is a portable unit and only in the bedroom. Games, books, and puzzles provided. There is no cable but a smart TV is included with access to Netflix etc. if you have an account. Outdoor area includes charcoal grill and seating . Large back yard with yard games, basketball hoop and fire pit.

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
Cape Cod Classic Cottage Near Forest Beach
See Cape Cod at its most traditional in this cozy, fully renovated cottage. Get a good night's sleep in the cozy bedrooms with central a/c and blackout shades. Prepare for the day in the clean and bright interior. Pack up your beach chairs and cooler and take a short walk down to Forest Beach. Grab your bike and hop on the Cape Cod Rail trail nearby or take a short drive into charming downtown Chatham. After a day in the sun, unwind in the hammock or enjoy a BBQ on the deck.

The Driftwood Home, 5 min from Mashpee Commons, AC
- NOW PET FRIENDLY! - 15 min to Old Silver, South Cape, and Falmouth Heights beaches - 5 min to Mashpee Commons - 15 min to Falmouth Main St - 1600 square feet, built in 2014, w/ central AC - Large kitchen w/ all cookware and utensils - Outdoor deck with seating, fire pit, and grill - 55” Smart TV - 10 min to Shining Sea Bike Trail - Less than 10 min to Falmouth, Cape Cod, and Quashnet Valley Country Clubs - Centrally located to all of the Upper Cape - No parties or events!

Your dog will love it here and you will too.
If you love to travel with your dog (dogs), like I do, then this is the perfect place for you and your dog. We have a large fenced in yard for your dog to play in and for you to relax in with your dog. We have a one bedroom apartment with a full kitchen, bath, living room and dining area When you book would you PLEASE let me know whether or not you will be traveling with a dog and if you are what breed of dog will you be bringing. Thanks!

Unique Waterfront Artist Cottage
Once a horse stable, Lil Rose now sleeps up to five just a short walk from a private beach. PLEASE READ BEFORE BOOKING: Rentals in season (April-October) are only offered by the week (Saturday-Saturday). November rentals are offered with a 4-night minimum. Rentals December-March are offered with a 3-night minimum. Pets are accepted (max 2) but you MUST let us know in your booking request about your pet so that we can prepare the property.

Cape Hideaway
Private suite on the first floor guests have exclusive use of the entire place. The second floor is my residence. The suite has a bedroom with queen temperpedic mattress, living room with queen sleep sofa, small kitchenette and bath. The kitchen is equipped with a small refrigerator, microwave, coffee maker, kettle, single burner cooktop and crockpot. Guests have access to the upper deck (shared space) which has a patio set and gas grill.

The Sea-Cret Garden, Guest Apartment
Kick back and relax in this calm, stylish space! This comfortable and peaceful guest apartment is situated in an ideal location in a quiet, beautiful neighborhood that is close to beaches and a short drive to downtown. Take a quick stroll to the West Falmouth Market or the Shining Sea Bike Path. With easy access to Chapoquoit & Old Silver Beach, this perfectly situated apartment is in an ideal spot for your next Falmouth getaway!

Charming Cottage near Beach and Ferry.
2022 renovation (floors, bathroom, cabinets) The cottage is only 150 yards from a sandy residential beach. Good for couples, families (with kids), and furry friends (pets). Enjoy a great outdoor shower, grill and deck, wifi, central AC/heat, cable TV, linens, washer/dryer. Additional Beach gear. No host interaction required. Great place to work remotely. Private yard and picnic table with lots of takeout options nearby.
Popular amenities for Chatham pet-friendly home rentals
Pet-friendly house rentals

Coastal Retreat Near Saltwater Beaches & Boating

Shop, Swim, Hike, Bike in Historic Brewster

Your beach home away from home!

Lake charm

Cottage Oasis by Lake-Kayaks, Fire Pit & Huge Yard

Oceanfront Home on Cape Cod Bay with Beach Access

Sunny Cape Home, Bike to Beach, Central AC

A Cape Escape with Water Views from Every Room
Pet-friendly home rentals with a pool

Harwich Haven: Pool & Fire Pit

Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK

Sleeps 12 near beach. Hot tub game room

5-bedroom Cape with a pool and yard games.

Waterside Guest House

West Yarmouth beach house

Seaview Summit | Ocean Views, Indoor Pool, Beach

Winslow Acres [heated] Pool Escape; pool May 15
Private, pet-friendly home rentals

Spacious Cape Escape Near Rail Trail & Downtown

Cape Cod Cottage: Walk to the Beach in Brewster!

BlueSky Cottage! Tiny Luxury! Firepit/patio/petOK

Chatham, MA - 258 Orleans Rd 4BR + loft - Beauty!

Wellfleet Cottage By The Sea

New 2 Bedroom Modernist Oasis in Truro

Sunset Sabbatical Cape Cod

Marshfront Retreat | EV Charger | Private Deck
When is the best time to visit Chatham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | 
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $389 SGD | $442 SGD | $383 SGD | $468 SGD | $502 SGD | $611 SGD | $811 SGD | $819 SGD | $543 SGD | $485 SGD | $520 SGD | $494 SGD | 
| 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 that are pet-friendly in Chatham
 - Total holiday rentals- Explore 180 holiday rentals in Chatham 
 - Nightly prices starting at- Chatham holiday rentals start at $156 SGD per night before taxes and fees 
 - Verified guest reviews- Over 6,010 verified reviews to help you choose 
 - Family-friendly holiday rentals- 170 properties offer extra space & child-friendly amenities 
 - Rentals with dedicated workspaces- 100 properties have a dedicated workspace 
 - Wifi availability- 170 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! 
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Rentals with a patio Chatham
- Rentals with a hot tub Chatham
- Luxury rentals Chatham
- Rentals with a firepit Chatham
- Rentals with lake access Chatham
- Cottage rentals Chatham
- Rentals with beach access Chatham
- Waterfront rentals Chatham
- Rentals with pools Chatham
- Beach house rentals Chatham
- Beachfront rentals Chatham
- Rentals with a fireplace Chatham
- Rentals with outdoor seating Chatham
- Flat rentals Chatham
- House rentals Chatham
- Rentals with a kayak Chatham
- Fitness-friendly rentals Chatham
- Rentals with breakfast Chatham
- Rentals with a washing machine and dryer Chatham
- Family-friendly rentals Chatham
- Pet-friendly rentals Barnstable County
- Pet-friendly rentals Massachusetts
- Pet-friendly rentals United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Onset Beach
- White Horse Beach
- Coast Guard Beach
- Chapin Memorial Beach
- Pinehills Golf Club
- Nauset Beach
- Lighthouse Beach
- Inman Road Beach
- Town Neck Beach
- Ellis Landing Beach
- Nickerson State Park
- New Silver Beach
- Falmouth Beach
- Cape Cod Inflatable Park
- Scusset Beach
- Cahoon Hollow Beach
- Corn Hill Beach
- Priscilla Beach
