Book Holiday Homes in Monterey
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Featured Holiday Homes in Monterey

Deluxe Queen Room with 2 Queen Beds

Beautiful retreat in a lake community to the enjoy the summer season.

4 Mi to Great Barrington: Berkshires Retreat!

Large Barn styled vacation home that fits groups with space to spare.

Stay Lakeside This Summer!

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Spectacular views and close to Great Barrington.

Rustic 3bd Lake Front Country Cottage

Garfield Townhouse in the Berkshires on Main St
Monterey 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 Monterey vacation homes are the perfect way for you to wing it.
Holiday houses in Monterey 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 Monterey 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 Monterey adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Monterey 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 Monterey 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.
Monterey Holiday Homes essential information
Accommodation | 419 Holiday Homes |
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Highest Price | |
Popular accommodation | Deluxe Queen Room with 2 Queen Beds, Beautiful retreat in a lake community to the enjoy the summer season. , 4 Mi to Great Barrington: Berkshires Retreat!, Large Barn styled vacation home that fits groups with space to spare. , Stay Lakeside This Summer!, Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Spectacular views and close to Great Barrington., Rustic 3bd Lake Front Country Cottage, Garfield Townhouse in the Berkshires on Main St |
Holiday Homes in Monterey
Top Locations for Holiday Homes in Monterey
More accommodations in Monterey
Top trending hotels in Monterey

Quality Inn

The Yankee, Trademark Collection by Wyndham

Best Western Plus Berkshire Hills Inn & Suites

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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Top picks
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^Subject to availability and chosen travel dates.