
Family-friendly holiday rentals in Brewster
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Brewster

Total holiday rentals
Explore 420 holiday rentals in Brewster

Nightly prices starting at
Brewster holiday rentals start at $168 NZD per night before taxes and fees

Verified guest reviews
Over 10,600 verified reviews to help you choose

Pet-friendly accommodation
Find 150 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
230 properties have a dedicated workspace

Wi-Fi availability
410 of Brewster holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Brewster rentals

4.9 Average rating
Brewster stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated family-friendly rentals in Brewster
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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.

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/2bedroom-2bath Condo
Recently renovated end unit townhouse located in the heart of The OE Villages. Beautiful views towards the golf course, and southern exposure with lots of natural light, A/C, W/D and private patio with Weber grill and outdoor furniture. Sports Membership so Guest passes are available for purchase at Linx for use of pools, hot tubs and gyms. Additional costs for use of courts may apply. Bike rail trail, Ice cream store, great restaurants, coffee, beaches and Kayak/Bike rentals are all close by.

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.

Cape Cod Oasis: pool, hot tub, firepit & grill!
Over 4500 sqft of living space in the heart of Cape Cod, with an inviting pool, a hot tub, magnificent garden and expansive outdoor living space big enough to fit your entire party. Welcome to your own private resort! This beautiful custom-built center entrance colonial has room to roam, both inside and out. 5 beds, 5 baths (3 full baths, 2 half baths), eco pool, The building is surrounded by lush landscape and tastefully decorated. Fully equipped chef's kitchen. Short drive to the 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 !

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.

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.

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!

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.

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.

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.
Popular amenities for Brewster family-friendly rentals
Family-friendly home rentals with a hot tub

Ocean Edge Resort-Pool Access-CentralAC-2 bdr/2bth

Local Beach+ Fireplace + Hot Tub Under the *Stars*

Bayside Oasis with Hot Tub & Game Room

Slate House - a modern waterfront getaway

Seacoast Shores Oasis-Steps From Private Beach Bay

Sun Sand & Sea House- Fenced Yard and Hot Tub!

Hideout at Water's Edge, 131 North Shore Blvd, #4

Waterfront•Hot Tub • Kayaks/SUP's • King Bed •Dock
Family- and pet-friendly home rentals

Shining Sea Condo

Spacious cottage beach Wychmere < 4 min Central AC

Fabulous Waterfront with Spectacular Sunset Views!

Abundant Blessings Cottage – Wellfleet

Pet Friendly - Walk to Downtown Dennis Port!

Bayside retreat - Brewster flats

Amazing Sunsets

Beautiful 4 bed/3 bath in Brewster, MA
Family-friendly home rentals with a pool

"Cape Escape" luxury home w/pool & beach access.

Seaview Summit | Ocean Views, Indoor Pool, Beach

Modern Cape, Private Heated Pool, Beach, Golf

Bright Cape Condo in Ocean Edge

Two Bedroom Condo in Ocean Edge Resort

Resort Pools & Golf Views · Walk to Bay Beaches

Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access

5-bedroom Cape with a pool and yard games.
When is the best time to visit Brewster?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $589 NZD | $589 NZD | $530 NZD | $530 NZD | $572 NZD | $686 NZD | $832 NZD | $832 NZD | $565 NZD | $521 NZD | $496 NZD | $496 NZD |
| Avg. temp | 0°C | 0°C | 3°C | 7°C | 12°C | 17°C | 21°C | 21°C | 18°C | 13°C | 8°C | 3°C |
Destinations to explore
- Rentals with pools Brewster
- Rentals with lake access Brewster
- Rentals with a hot tub Brewster
- Condo rentals Brewster
- Rentals with a kayak Brewster
- Apartment rentals Brewster
- Waterfront rentals Brewster
- Beachfront rentals Brewster
- House rentals Brewster
- Rentals with beach access Brewster
- Pet-friendly rentals Brewster
- Cottage rentals Brewster
- Family-friendly rentals Barnstable County
- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- Onset Beach
- East Sandwich Beach
- Duxbury Beach
- Saquish Beach
- Sandy Neck Beach
- Nauset Beach
- New Silver Beach
- Skaket Beach
- Falmouth Heights Beach
- Pinehills Golf Club
- Cape Cod Canal
- Popponesset Peninsula
- Race Point Beach
- Coast Guard Beach
- Inkwell Beach
- Cape Cod Inflatable Park
- Nickerson State Park
- Cahoon Hollow Beach
- Sea Gull Beach
- Marconi Beach





