Book Holiday Homes in Brewster
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Featured Holiday Homes in Brewster

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Historic Connecticut Home w/ Grill & Spacious Yard

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Pet-Friendly Beacon Area Vacation Rental: 6 Acres

Main Street Westport, walk to shops, dining, downtown

Contemporary Cozy Cottage
Brewster Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Brewster vacation homes are the perfect way for you to wing it.
Holiday houses in Brewster let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Brewster in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Brewster adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Brewster with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Brewster vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Brewster Holiday Homes essential information
Accommodation | 341 Holiday Homes |
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Lowest Price | AU$199 |
Highest Price | AU$664 |
Popular accommodation | Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo, Historic Connecticut Home w/ Grill & Spacious Yard, 1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views, Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake, Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger, Bright Stylish Chic 4BR 4BA Home Pet Friendly!, Pet-Friendly Beacon Area Vacation Rental: 6 Acres, Main Street Westport, walk to shops, dining, downtown, Contemporary Cozy Cottage |
Holiday Homes in Brewster
Top Locations for Holiday Homes in Brewster
More accommodations in Brewster
Top trending hotels in Brewster

Heidi's Inn

Comfort Inn

The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!.

EVEN Hotel Norwalk by IHG
More ways to explore Brewster
Top picks
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^Subject to availability and chosen travel dates.