Family-friendly holiday rentals in Brewster

Water Front Pond House - 3 acre Cape Cod Sanctuary

Extraordinary pondfront sanctuary on Cape Cod. 1300 sq.ft. home sleeps 8 in 3 bedrooms and 1 bath. Private dock and beach area. House is on the Pond and sited on 3 pristine acres - this property offers exceptional privacy with full water recreation opportunities while also being close to everything "Cape Cod". Centrally located in laid-back Brewster, 5 minutes to Bayside beaches, 10 mins to Chatham, Harwich Port, and Orleans. Local owners have 22 years of online vacation rental experience.

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

2nd floor Ocean Edge end unit condo located in the heart of Brewster with access to OE resort amenities: pools, gyms, tennis courts, as well as access to resort activities (fees apply). Easy access to Cape Cod Rail Trail for bicycles. Scenic route 6A offers arts & crafts galleries and local shops. A 10 minute car ride to a 36 hole Captains Golf course. Short ride to 10 Brewster bay beaches famous for tidal flats. A 30 minute ride to Cape Cod National Sea Shore. Welcome to your Happy Place!

Perfect Cape Cod vacation home

SUPER LOCATION for biking & hiking! Quiet neighborhood with direct access to 31 mile Cape Cod Rail Trail, 1900 acre Nickerson State Park and local clam shack / ice cream shop. Easy walking / biking access to Linnell & Crosby Landing Cape Cod Bay beaches and Flax & Cliff Pond fresh water beaches. Easy drive to towns of Orleans, Chatham, Harwich & Dennis. Whether it's a quiet walk, an exhilarating bike ride, salt or fresh water beaches, or a comfortable place to relax, this house has it all!

Songbird Studio- Secluded but close to everything!

Bright, sunny, secluded, green 600 sqft studio apartment at rear of Antique home in the heart of Brewster, Northside of Rt 6A. Private entrance. Private backyard with lawn & gardens. Small private deck, gas grill. Bird and small animal life abounds outside. Tons of stars at night.. salt air on the wind. Walking distance to coffee shop, convenience store, multiple restaurants, Bike Trail. Short car ride to bay beaches, easy drive to Ocean beaches. Gas "woodstove" for heat, AC for cooling.

The Drake Cottage - Brewster Beach Getaway

Come and experience quintessential Cape Cod in The Drake Cottage located right on 6A in Brewster, Ma. The Drake Cottage is conveniently situated within about a mile of Drummer Boy Park, The Cape Cod Museum of Natural History and Paines Creek Beach. The Drake Cottage offers an expansive private back yard with an acre of land. Enjoy a newly extended patio complete with fire pit, 10 person picnic table and BBQ grill. Our newly updated interior provides our guests with many modern amenities.

Antique Cape Home With Modern Conveniences

The Elisha Howland Saltbox provides your opportunity to experience the unmatched essence of a true 'Olde Cape Cod' home. We offer a restored antique Saltbox with 2 bedrooms and 2 bathrooms. For an additional charge, there is a detached cottage which can accommodate two more guests. PLEASE NOTE: we accept ONLY FULL WEEK RENTALS from mid-June to mid-September, but we welcome shorter or much longer stays during the rest of the year. Our home is a lovely place to spend a winter on Cape Cod.

Waterfront Cottage on White Pond(Graham Cracker)

Our cottage (Graham Cracker House) sits steps from crystal clear White Pond. The cottage offers private access to the pond for swimming, fishing and boating. The large outdoor space is great for dining and relaxing by the pond. It is 1.5 miles to the Cape Cod rail trail (bike trail), close to many dining options and 3 miles to some of the best beaches Cape Cod has to offer. There is another cottage on the property for rent that sleep 4 guests. No sharks here!

Privacy with Cape Cod charm

This lovely, private one bedroom apartment is located above the unused garage on the grounds of our classic half cape house, just a 3 minute walk to our private beach on the bay. It sleeps 2 with a double bed and has a full kitchen and bathroom, along with an outdoor shower, grill, fire pit and picnic table located in private yard. Linens will be provided. Coffee maker and coffee will be waiting for you...

Waterfront Romantic get away Nest

Prepare to be swept away by breathtaking panoramic views and bountiful wildlife. This is a secluded romantic getaway that is tucked back in the corner on our historic 9 acre cranberry bog and adjacent pond. Enjoy private pond access. Boats and fishing gear available for your enjoyment. The Nest tiny home is built Eco-Friendly and compliments the natural environment to give you and immersive feel.