House holiday rentals in Brewster

The exterior of The Drake Cottage is surrounded by lush greenery and a well-landscaped yard. The charming two-story structure features a mix of wood and stone siding, complemented by a gravel driveway leading to the entrance. Natural stones and native plants are arranged in the gardens.

4.83 out of 5 average rating, 204 reviews

The Drake Cottage - Brewster Beach Getaway

Experience quintessential Cape Cod in The Drake Cottage located right on 6A in Brewster, Ma. The Drake Cottage is conveniently situated within a mile of Drummer Boy Park, The Cape Museum of Natural History, Paines Creek Beach and a 9 min drive from Oceans Edge. The 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.

A wooden dock extends into a serene freshwater pond, surrounded by lush green foliage. The calm water reflects the clear blue sky and distant tree line, creating a tranquil setting for relaxation and outdoor activities.

4.87 out of 5 average rating, 242 reviews

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.

4.98 out of 5 average rating, 50 reviews

Beautiful 4 bed/3 bath in Brewster, MA

Plan a Fall Getaway! Beautiful 4 bedroom 3 bath spacious fully renovated cape house in Brewster MA. The private full acre lot backs directly up to Nickerson State park. Easy access to bay beaches and ponds. Master with king bed and en-suite bath, 2 additional upstairs bedrooms. One with 2 twin beds and one with a queen plus twin. 1st floor bedroom with queen and the third full bath. Rear deck and outdoor shower. NOTE: Pets considered on an individual basis. Additional pet cleaning fee applies

The exterior of the single-floor home is showcased, featuring a gabled roof and large floor-to-ceiling windows. A private deck extends from the house, with outdoor seating visible. Lush greenery surrounds the home, creating a serene, park-like atmosphere.

4.87 out of 5 average rating, 138 reviews

Sun filled single level retreat, outdoor shower

Wonderful 3 Bed, 2 full bath single floor home. Bedrooms on two separate wings. Fully stocked kitchen with center island and breakfast bar. Large living room, vaulted ceiling exposed beams, floor to ceiling windows overlooking private backyard. Central A/C, wifi, smart TVs, washer/dryer, outdoor seating/eating, fire-pit, outdoor shower. Very close to Cape Cod Rail bike path, restaurants, Beaches, Nickerson State Park, golfing, shopping. Dog allowed by request; $30 per night or $150 per week.

A modern kitchen features sleek white cabinets and stainless steel appliances, including a double door refrigerator. A spacious island with seating for four is highlighted, while a wooden dining table accommodates additional guests. Natural light filters through multiple windows, illuminating the light wood flooring.

5.0 out of 5 average rating, 69 reviews

Renovated Beach House, Central AC, Private Ponds

Renovated Cape Cod vacation home, centrally located in Brewster near beaches, abutting conservation land in a quiet private neighborhood. Steps from scenic Greenland Pond, Long Pond, and close to Cape Cod Rail Trail, downtown Brewster, and mid-Cape attractions. Enjoy stunning sunsets and swimming at nearby ponds and visit local beaches. Enjoy newer furnishings, fast WiFi, stocked kitchen, 2 smart TVs, comfy beds, workspace, finished basement, patio with fire pit and outdoor furniture.

The exterior of the Brewster Farmhouse is showcased, featuring a charming stone facade with green trim. A well-maintained yard surrounds the house, adorned with autumn foliage. The entryway includes two large windows framed by shrubs, with a welcoming double door at the center.

4.98 out of 5 average rating, 105 reviews

Cape Cod Farmhouse: Walk to the Beach in Brewster!

Defined by understated furnishings throughout, The Brewster Farmhouse is a serene beach retreat, right across the street from Ocean Edge Resort and a 10 minute walk to Ellis Landing Beach. Total of 3 bedrooms and 4 full bathrooms, with central AC and heating. All bedrooms have queen-sized beds, and their own private, en-suite bathrooms. Right next door to cute antique shops, art galleries, and boutique farms. Close walk or drive to all of the best restaurants and cafes in Brewster!

4.97 out of 5 average rating, 173 reviews

A bright living area features large windows overlooking a scenic marshland and ocean view. A cozy cream-colored couch and an armchair are positioned near a glass coffee table, inviting relaxation. Natural light fills the space, enhancing the tranquil ambiance.

Home in Chatham

The Osprey Nest - Beach house with stunning views

The Osprey Nest is a classic Cape Cod beach house just steps to the ocean with panoramic views across the protected marsh. A cozy and timeless retreat, with modern amenities and spacious and light-filled rooms. This home has been in my family since the 1960’s and you will feel the warmth and charm the minute you step in the door. The location is perfect for nature lovers but within 10 minutes of stores, restaurants, and charming towns. A perfect base for Cape Cod sightseeing.

The living area features wooden cathedral ceilings and a cozy seating arrangement with two grey sofas, adorned with colorful pillows. A wooden coffee table is centered on a patterned rug, with a fully equipped kitchen visible in the background.

4.93 out of 5 average rating, 150 reviews

Shop, Swim, Hike, Bike in Historic Brewster

Sunny, air-conditioned, single-floor cottage on 3/4 private wooded acre — a rare combination of seclusion and location on Cape Cod. Breakwater Beach and Sheeps Pond are each 1.3 miles away: ocean one day, calm freshwater the next. The Cape Cod Rail Trail is a one-minute bike ride; Brewster Store and the Scoop are a half-mile stroll. Gather around the fire pit, rinse at the outdoor shower, and sleep well on newer mattresses. Beach chairs and toys included. Ample parking.

A charming exterior of a Cape Cod house is framed by verdant trees and a gravel driveway. The structure features a pitched roof, large windows, and a welcoming front porch with seating arrangements. Lush greenery surrounds the property, enhancing its serene rural setting.

4.94 out of 5 average rating, 62 reviews

Bayside retreat - Brewster flats

Cape Cod Beach House with Private Bay Access + Pet-Friendly! Enjoy a classic Cape escape just a 5 to 7-minute walk to a private Brewster Flats beach, one of the few where you can leave your chairs and umbrellas out all week. This 3-bedroom, pet-friendly home features a private outdoor shower, gas grill, fire pit, and all essentials included (linens, paper goods, soaps, shampoo). Once you arrive, park your car and walk or bike to shops, restaurants, and scenic spots.

A cozy sleeping area showcases a patterned bedspread with floral designs, complemented by matching pillows and a neatly arranged stack of towels. A bedside table holds a lamp and a small bouquet, while a striking floral wallpaper adds warmth to the room.

4.96 out of 5 average rating, 84 reviews

Luxury Beach House! Firepit&PetoK&2Kingbeds

⚓️THE CAPTAIN’S HOUSE ⚓️ *sleeps 8 (max 6 adults) * sq ft *2 king beds *1 queen *1 twin *1 tiny twin (38”W x 62”L) *3 full bathrooms *Laundry room *Gas fireplace *4 Smart TV’s/1 frame TV *Fullequipped kitchen *outdoor fire pit/seating (propane) *Dining for 8 *Cotton linens/towels provided *Dedicated Workspaces (2) *High Speed WiFi * Under 5 mins away=Paines Creek Beach, Drummer Boy Park, Cape Museum Natural History, and more! *1 dog allowed $30/per night pet fee

4.93 out of 5 average rating, 163 reviews

4BR/3B | Walk2Pond | Screened Porch | FireTbl | AC

Relax at this spacious mid-Cape retreat on a quiet private road, just a 5-minute walk to a private swimming beach and pond. Canoe included! Sleeps 8 with 4 bedrooms (2 on the main level, 2 upstairs) and 3 full baths with bidets. Enjoy central A/C, hardwood floors, a screened porch, 65" OLED TV, gas stove, gas fire table and grill, ping pong, and wooded yard. Convenient main-level washer/dryer. Near the Cape Cod Rail Trail, beaches, golf, tennis, boating.

An inviting living area features a comfortable seating arrangement with a grey sofa and an accent chair. A dining table is visible, accompanied by floral arrangements. Warm light filters through large windows, illuminating the space, while a fireplace and decorative elements enhance the cozy atmosphere.