Book Holiday Homes in Monterey

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Featured Holiday Homes in Monterey

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Jiminy Peak Mountain ...
Opens in a new windowBeautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Stockbridge Village in Summer

Stockbridge Village in Summer

Stockbridge
Stay at this vacation home in Stockbridge. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Tanglewood Music Center and Berkshire Theatre ...
Opens in a new windowStockbridge Village in Summer
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington
Stay at this vacation home in Great Barrington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions W.E.B. Du Bois Boyhood Homesite and Great ...
Opens in a new windowNEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
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Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
The price is NZ$1,422 per night from 21 Oct to 22 Oct
NZ$1,422
21 Oct - 22 Oct
includes taxes & fees
Stay at this vacation home in Lee. Enjoy laundry facilities and in-room fireplaces. Popular attractions Tanglewood Music Center and Berkshire Mountain Country ...
Opens in a new windowSpacious 5-bedroom house in charming Lee with WiFi
Amore Estate -  beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
Book a stay at this family-friendly vacation home in Lenox. Enjoy private pools, laundry facilities, and in-room jetted tubs. Popular attractions Tanglewood ...
Opens in a new windowAmore Estate - beautiful room with many places to explore and relax in.
General Williams Estate House Lenox/Stockbridge

General Williams Estate House Lenox/Stockbridge

4 out of 5
Stockbridge
Stay at this vacation home in Berkshire County. Enjoy private pools, a garden, and laundry facilities. Popular attractions Tanglewood Music Center and National ...
Opens in a new windowGeneral Williams Estate House Lenox/Stockbridge
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Sheffield
The price is NZ$879 per night from 13 Oct to 14 Oct
NZ$879
13 Oct - 14 Oct
includes taxes & fees
Stay at this vacation home in Sheffield. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Drury Preserve and Lime Kiln Farm Wildlife Sanctuary ...
Opens in a new windowCheerful 3-bedroom cottage with woodstove
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge
Book a stay at this family-friendly vacation home in Stockbridge. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Tanglewood Music Center ...
Opens in a new windowWalk into town, soak up sun on enclosed porch & steps away from nature trails!
Falls Reach In The Heart of Copake

Falls Reach In The Heart of Copake

Copake Falls
Stay at this vacation home in Copake Falls. Enjoy a garden, laundry facilities, and an in-room coffeemaker. Popular attractions Copake Town Park and Bash Bish ...
Opens in a new windowFalls Reach In The Heart of Copake
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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
439 Holiday Homes
Lowest Price
NZ$219
Highest Price
NZ$1,422
Popular accommodation
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, Stockbridge Village in Summer, NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE, Spacious 5-bedroom house in charming Lee with WiFi, Amore Estate - beautiful room with many places to explore and relax in., General Williams Estate House Lenox/Stockbridge, Cheerful 3-bedroom cottage with woodstove, Walk into town, soak up sun on enclosed porch & steps away from nature trails!, Falls Reach In The Heart of Copake

Top trending hotels in Monterey

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is NZ$219 per night from 29 Sept to 30 Sept
NZ$219
29 Sept - 30 Sept
includes taxes & fees
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowBerkshire Mountain Lodge
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
The price is NZ$275 per night from 2 Oct to 3 Oct
NZ$275
2 Oct - 3 Oct
includes taxes & fees
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
Opens in a new windowHoliday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$247 per night from 29 Sept to 30 Sept
NZ$247
29 Sept - 30 Sept
includes taxes & fees
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
Opens in a new windowBerkshires Untold
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The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is NZ$380 per night from 30 Sept to 1 Oct
NZ$380
30 Sept - 1 Oct
includes taxes & fees
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
Opens in a new windowThe Red Lion Inn
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.