Pet-friendly holiday rentals in Chatham

Panoramic ocean views 100 ft above Cape Cod Bay

Our 5-bdrm Nantucket style beach house has a new kitchen & open living space, with a new deck, all overlooking the entire shoreline of Cape Cod Bay from a commanding perch atop a 100-foot bluff. Whales and seals can be seen from your deck. Located in a private community with its own rocky beach access about 5 min walk from the house where you can hunt for shells & observe the ocean wildlife. This beach is ideal for kayaking. Plymouth also boasts 4 of top 10 rated public golf courses in MA.

Outdoor spaces · Walkability · Barbecue

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.

Outdoor spaces · Walkability · Indoor spaces

Close to Beach Renovated Dog Friendly Cape Cottage

Welcome to our enchanting Cape Cottage in the heart of Chatham, where timeless charm meets modern comfort. 4 minutes from the beach and nestled on a spacious half acre, this newly revitalized and renovated home provides an authentic Cape Cod vacation experience. As you step into our home, you'll immediately sense the true heart and soul of a Cape Cod getaway. Our cottage boasts a warm and inviting atmosphere, perfect for families, couples, or friends seeking a luxurious escape to Chatham.

Outdoor spaces · Walkability · Decor

No Pet Fee, Waterfront, Fenced Yard, Close to Town

Soak up the ☀️ while enjoying the lush outdoor space at our waterfront home, Queen’s Quarters. Bring or rent a kayak or paddleboard as you have direct water access or unwind on the deck looking out for swans or our friend, the Great Blue Heron. From your morning coffee to evening cocktails, the alfresco dining space is suited for anyone at any time of day. Queen’s Quarters is multi-level with a finished basement providing ample space. Since dogs are part of the family, we consider pets.

Pets · Walkability · View

Meadow + Main

🍃🌊 Welcome to Meadow + Main, nestled between the serene 7-acre Twine Field Meadows and the charm of South Chatham's Main Street. A short walk to: • The Cape Cod Rail Trail • Chatham Farmers Market • Public Transportation • Local Dining A short drive to: • Forest Beach • Harwich Port • Ridgevale Beach • Wychmere Beach Club • Chatham Village • Wequassett Resort & Golf Club • Chatham Bars Inn Ideal for groups, the home comfortably sleeps up to 8, with table seating for up to 18.

Sleep quality · Beach · Laundry

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.

Pets · Outdoor spaces · TV

Delightful Chatham Cottage, Cheerful and Clean

AirBnB Superhost, local owner has 25 years of online vacation rental experience with this property. Refreshed and updated , our 1 bedroom cottage is an ideal getaway spot for a couple or young family. The cottage is located on a 1/2 acre lot in the geographical center of Chatham, on a private road in a quiet, tree-filled neighborhood. Guests all agree that we have a fantastic location at an affordable price. Enjoy a relaxing stay while being close to everything in town.

Outdoor spaces · Pets · Beach

Spacious Pet Friendly Cape, Large Yard

Our home is located in a quiet neighborhood close to beaches, golf courses and bike trails. It is a short drive to Chatham town center and is the perfect location to be close to all attractions but secluded enough to unwind. Take advantage of the outdoors on a new deck and large backyard. Large, mature plants and trees surround the property on three sides. Blackberry, raspberry and blueberry bushes in the backyard provide ripe fruit in the summer months.

Pets · Outdoor spaces · Air conditioning

The Sea Captain's Carriage House

The 1840s Carriage House has been beautifully remodeled. The first floor has a living room, dining area, kitchen, and powder room with washer/dryer. The backyard deck has seating for four and a Weber gas grill. Upstairs, the large, elegant bedroom features a king-sized bed, sitting area, reading nook/twin bed, writing desk, and ensuite bathroom with shower. The half acre property offers beautiful gardens for you to enjoy and a delicious outdoor shower.

Outdoor spaces · Pets · Layout

The Hideaway - Harwich Port Getaway

Your family will be close to everything Harwich Port & Cape Cod has to offer when you stay at this centrally-locally oasis! - Central Air! - Roku TV in everyroom! - Fully fenced in backyard for summer cookouts & fires! - Large outdoor shower with Hot & Cold water Come stay in our newly renovated home that has everything you will need. Only minutes from major beaches, shopping, restaurants and all of the beautiful things Cape Cod has to offer.

Outdoor spaces · Walkability · Getting around

The Chatham Bars White Foam House Steps From Beach

Settle back in one of the rocking chairs on the front patio and take in the views of the harbor. Charm and warmth abound in this Cape Cod cottage with Chatham Seaside Links located across the street. Leave the car and walk to local restaurants and shops. Watch band concerts at the park and bask in the views from the Chatham Lighthouse. Go for a long stroll along Claflin Landing Beach all the way to the Fish Pier and buy the day's fresh catch.

Outdoor spaces · Walkability · Indoor spaces

Chatham Cottage | Pond Views & Fire Pit

Amazing getaway with a delightful blend of comfort and convenience. Imagine the tranquil beauty of a nearby pond unfolding right before your eyes. The land in front of the house offers not only a captivating view but also a constant connection to the natural wonders that make Cape Cod so special. This property is a bird watcher's dream come true. You're also just a short distance from the inviting sands of the beach and downtown Chatham.

Walkability · Outdoor spaces · Parking