Pet-friendly holiday rentals in Eastham

1940 Cottage Studio/Loft Style Stunner! Dogs ok!

Charming stand alone Cape Cod Cottage, part of the historic Cottage Grove cottages of Eastham. A perfect respite for the busy world! The open and airy cottage exudes character: exposed beams, vaulted ceilings, fireplace, and a vintage soapstone sink. The wall of windows leads out to the spacious private cedar deck with picnic table and chairs for outdoor dining or relaxing among the trees. Cottage is dog friendly and located near the celebrated Fort Hill hiking trails at the National Seashore.

10 min walk to Beach - Amazing View & Huge Deck

Enjoy an incredible view of Duck Meadow Tidal Marsh from this cozy cottage. Only a 10 minute walk to Boat Meadow Landing, a great bayside beach. Sip your morning coffee on our huge deck while enjoying the view. The deck includes a retractable roof if you would prefer to sit in the shade. Only minutes from incredible restaurants & shops in Orleans. This home includes AC, office space w/ monitors & a natural gas fireplace. Near the Cape Cod Rail Trail, hiking trails and numerous beach options!

Brook House on the Bay Side

Classic Cape Charm! Welcome to Herring Brook, a beautifully updated 2-bedroom, 1-bath cottage in the heart of Eastham. Sleeps 4. Enjoy new flooring, a spacious screened porch, wraparound deck, large yard, and classic Cape Cod outdoor shower. Features include an updated kitchen and bath, Wi-Fi, Smart TV, A/C, washer/dryer, linens, and beach chairs. Bay and ocean beaches, Cape Cod Rail Trail, restaurants, shops, and family attractions are just minutes away. Pets considered with prior approval.

Time and Tides on Cape Cod Bay

Relaxing TIME and spectacular TIDES is why so many come to outer Cape Cod Bay. That is exactly what you will find with our beautiful cottage. Just feet from the beach (40 second walk), you can stroll to the shore at any time. So many things to do and places to see just minutes away. Or do nothing but relax, take in the amazing sunsets and enjoy one of the most beautiful locations on Cape Cod. We welcome pets but there will be an additional $125.00 charge for cleaning. 2025 New AC added !!

Abundant Blessings Cottage-Wellfleet

Couple/family fun all year in a charming, private Cape Cod cottage w/ screened in porch, patio & outdoor shower (in Nov/Dec/Jan becomes a Gingerbread cottage). Inside: open living space w/ queen bed & sitting space. Ladder leads to a short height sleeping loft w/ 2 twin beds. Full bathroom w/ indoor shower. Kitchenette- see description below. We supply tea, local coffee, spices, condiments, gas grill, ice chests, beach towels & chairs. To sleep up to 8, also rent our Upper Room on Airbnb.

Spacious cottage beach Wychmere < 4 min Central AC

Entire spacious newly renovated modern cottage in Harwich Port. Open concept living room with a large kitchen island. Great space for families ! Bank street Beach and Wychmere Beach Club wedding venue are 4 min drive from us ! We’re very close to Harwich Port downtown with great restaurants. We’re centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy the bike trail nearby with rental location if needed.

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.

Dog friendly, close to bay beaches & bike path

Welcome to Bralla by the Bay, an Outer Cape 4 bedroom cottage that is only half a mile to the beautiful bay beaches and a 5 minute drive to both the National Seashore and kettle ponds. Our cottage is located in a quiet, wooded quintessential Cape Cod neighborhood which offers easy access to beach, nature, and dining activities. It is cozy, yet spacious enough to accommodate a larger group with its ample parking and yard.

Walk to Beach, Pet Friendly, New Fenced Backyard!

Welcome to The Library! This newly renovated Eastham home is just a short walk to Thumpertown Beach and a quick drive to the National Seashore. Enjoy a redesigned eat-in kitchen, a screened-in three-season room, and a fully fenced backyard with brand-new pavers, a fire pit, and space for kids and dogs to play. Pet friendly and perfect for relaxing—come unwind and enjoy the best of the Cape

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!

Game Room- Movie Projector Room- Fire Pit

Nestled in the heart of the Cape, our cozy and beautifully styled retreat becomes a magical group getaway, why we coined it "Gimlet Getaway". While many envision Cape Cod as a summer playground, it can become the best spring sanctuary for you and your large group! (Pool OPENING date is May 20th, pool closes early September depending on weather)

Wellfleet Cottage By The Sea

Small, rustic cottage on the beach for one or two couples. Back door opens onto a long driveway to a sand road, front door opens onto a stairs to the beach. It's like a movie or book come to life. If you love The Notebook or The Outermost House you'll likely fall in love with the place. Please note, this property has NO HEAT.