Holiday houses 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.

Family · Value · Checkout

Rare Ocean Edge House - Sleeps 8

Brand new listing at Ocean Edge in The Villages! Recently purchased and renovated, this standalone home is located at the end of a lovely cul-de-sac with backyard patio, resort amenities and direct access to the Cape Cod Rail Trail. Home includes fully equipped kitchen, two bedrooms, two full baths, living room, dining area, and large loft that sleeps four. Homeowners are golf-members at Ocean Edge, so renters may get sponsored guest passes to access the resort amenities for a small add-on fee.

Location · Family · Kitchen

“Rooster Cottage and Gardens” Entire Private Home

Rooster Cottage and Gardens is located on a quiet street in Brewster. The home has many new features including updated kitchen and new furniture. Distance to Cape Cod Bay, 4 mi.; Atlantic Ocean, 7 mi.; Ptown, 23 mi. For travel nurses, we are 13 miles from Cape Cod Hospital. There are nearby stores, bakeries, restaurants, and the excellent Brewster Ladies Public Library. The porch overlooks the private gardens. We love gardening and try for interesting views & foraging for birds even in winter.

Family · Location · Amenities

Claw Foot Tub & King Bed at Club Tanuki Cottage

Glorious gardens and bay breezes! King-sized Casper bed in romantic antique Cape Cod studio cottage with private entrance & patio, in-room double-slipper claw foot tub, luxe bath amenities, Brooklinen sheets. Just renovated soup-to-nuts! Marble & antique wooden floors, decorated with rotating collection of antiques, original local art & great light. Nestled along historic route 6A (Main Street) near other galleries, museums, walking trails, ponds and beaches; 90 seconds to closest beach.

Location · Long stay · Getting around

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!

Location · Family · Beach

Sheep Pond Get-Away

The AirbNB Studio Space is Private w/ its own separate entrance & exit. Our home is set in the 'Sheep Pond' area. We are walking distance to Sheep Pond to kayak & swim. We have kayaks, paddleboards, beachchairs, & towels for your use. A backyard w/ your own picnic table, seating area, & hammock. An outdoor shower ! Minutes away from bay & oceanside beaches, biking, hiking & Nickerson State Park. 40 mins from Provincetown; & surrounded by quaint Route 6a, restaurants & shopping !

Value · Location · Kitchen

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.

Location · Value · Decor

Brand new, on a secret pond

Welcome to our chic guest house. This brand-new retreat includes a bedroom with king bed, a living room with a sofa bed, smart TV, sleek breakfast bar, and a contemporary bathroom with rainshower and a heated towel rail. Steps away the beach invites you to relax by the water of a semi-private pond next to the rail trail. Welcome to a retreat that strikes the perfect balance between contemporary luxury and the tranquility of nature – for those who appreciate the finer things in life.

Value · Location · Laundry

Nehemiahs Nest: Healing Cape Cod Pond View Cottage

18+ Lovely waterfront tranquil getaway. All nearby houses hidden! This gem of a spot has been curated to soothe the soul! The cottage is sitting on Bakers Pond with an unobstructed view surrounded by conservation land *The driveway abuts a road* Wildlife can be observed. Swim or fish in this very clean kettle pond! The edges of the pond require water shoes for comfort as this is a natural body of water with no man-made beach/interference of nature. Kayaks, and life jackets available

Location · Family · Pets

The Book Nook

A book lover’s dream! Situated atop the historic Brewster Book Store, this charming, newly renovated one bedroom apartment comes with well-stocked bookshelves and a cozy reading room. Located in the heart of Brewster, the apartment gives you easy access to Cape Cod Bay, ocean beaches, Cape Cod Rail Trail, Nickerson State Park, Cape Rep Theater, Cape Cod Natural History History Museum, Cape Cod Baseball League games, walking trails, art galleries, antique stores and much more.

Family · Value · Beach

Shining Sea Condo

Ocean Edge Condo with cathedral ceilings! Beautiful private deck located on the 5th hole of the Ocean Edge golf course! Located within Eaton village. TWO KING beds, along with pullout couch allows 6 to sleep comfortably. Linens are included!! Large kitchen with washer/ dryer, AC units and heat throughout the entire unit. Wifi and THREE smart TVs with ROKU devices. Flexible dates allows guests to stay whatever length they would like instead of a mandatory week. Come enjoy!

Location · Family · Outdoor spaces

Oceanfront condo on Brewster Flats

Escape to this rare beachfront retreat where the ocean is your front yard. Unlike inland rentals, this studio condo offers direct beach access and the calming sound of waves to lull you to sleep. No driving, no packing—just step outside and you're there. Enjoy coffee on the deck, spend the day swimming or sunbathing just steps away, and watch the sunset over the water—all without leaving home. It’s the kind of coastal escape inland properties simply can’t match.

Family · Value · Hospitality