Pet-friendly holiday rentals in Chatham

Modern Beach & Pond Getaway | Heart of Cape Cod

Your perfect Cape Cod escape awaits! Coastal chic home base w/ king bed & AC near all Cape Cod has to offer. <8 min to pristine beaches, endless local shopping, entertainment & dining. Short walk to Wings Grove Beach to fish, kayak or swim in serene Long Pond - perfect for kids! Take in nature while biking the Cape Cod rail trail (4 min away) & ride all the way to the outer cape! BBQ, enjoy the firepit, fenced in yard, and outdoor shower. On cool nights, cozy up next to the indoor gas fireplace.

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.

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.

** Vineyard Vacation Retreat ** with HOT TUB

Gated 2br house with lots of different places to lounge and relax. Drive through the 10’ granite gate onto the shell driveway. The house is filled with art from local artist Alan Whiting, Colin Rule, Kara Taylor and Scott McDowell. There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home. Updated 7/25/2025 we do not have any more firewood on the property.

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.

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!

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.

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!

Cape Cod Cotuit Cottage, 3 Bed Near Beaches

5 star rental Cottage in the beautiful village of Cotuit! This quaint 3-bedroom cottage is perfect for a getaway for friends and family. It is just a short distance to nearby beaches, local market, walking trails, Cape Cod league baseball stadium, shopping and restaurants. Relax on the private patio area and enjoy the peaceful, natural setting. Bring along your dog too!

Violet’s Place- king bed- pet friendly- hot tub!

Fully renovated Cape Cod bungalow, less than a mile to West Dennis beach, bass river, restaurants and convenience store! The interior is chic with all new walk-in shower, soaking tub, boho butchers block kitchen and a warm living space with king bed and flat screen TV. Enjoy the pedicured yard with grill, fire pit, and private open roof hot tub! Pet friendly!

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.

Forbes, a South Chatham cottage

This cozy, two bedroom cottage is nestled in a wooded neighborhood and has a full kitchen, living room, 2 air conditioned bedrooms, a full bath, cable TV, Internet, a screened-in porch, shaded yard, outdoor shower, and a gas grill. Cockle Cove beach is a short walk (3/4 mile) . Weekly summer rentals only, Saturday until Saturday.