Book Holiday Homes in Monterey

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Monterey

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
The price is AU$1,107 per night from 18 Aug to 19 Aug
AU$1,107
18 Aug - 19 Aug
includes taxes & fees
With a stay at this vacation home in Lee, you'll be within a 10-minute drive of Tanglewood Music Center and Housatonic River.
Spacious 5-bedroom house in charming Lee with WiFi
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Egremont
Located in Egremont, this vacation home is in a rural location, within a 10-minute drive of W.E.B. Du Bois Boyhood Homesite and Mount Everett State ...
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Great Barrington
Located in Great Barrington, this vacation home is on the waterfront, within a 10-minute drive of Art et Industrie and Housatonic River.
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Save an average of 15% on thousands of hotels when you're signed in
Berkshire Ashmere Lake lodging. Quiet  room, Fantastic sunsets.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale
With a stay at this vacation home in Hinsdale, you'll be within a 15-minute drive of Bas Ridge Golf Course and Crane Museum of Papermaking.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires

Russell
The price is AU$568 per night from 6 Aug to 7 Aug
AU$568
6 Aug - 7 Aug
includes taxes & fees
Located in Russell, this vacation home is within a 10-minute drive of Westfield River and Strathmore Park.
Big farmhouse in the foothills of the Berkshires
Taconic Hideaway – Swimming, BBQ Pit, Hiking

Taconic Hideaway – Swimming, BBQ Pit, Hiking

2 out of 5
Copake
With a stay at this vacation home in Copake, you'll be within a 10-minute drive of Copake Town Hall and Callan Family Care.
Taconic Hideaway – Swimming, BBQ Pit, Hiking
Falls Reach In The Heart of Copake

Falls Reach In The Heart of Copake

Copake Falls
Located in Copake Falls, this vacation home is in a rural location, within a 5-minute drive of Taconic State Park and Callan Family Care.
Falls Reach In The Heart of Copake
Poolside Luxe at Long Pond

Poolside Luxe at Long Pond

Great Barrington
Located in Great Barrington, Poolside Luxe at Long Pond is in a rural location, within a 10-minute drive of Monument Mountain and Housatonic River.
Poolside Luxe at Long Pond
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Richmond
With a stay at this vacation home in Richmond, you'll be within a 10-minute drive of Tanglewood Music Center and Fairfield Brook WMA.
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Don't see what you're looking for?
See all available properties in Monterey
View all properties
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
AU$123
Highest Price
AU$1,107
Popular accommodation
Spacious 5-bedroom house in charming Lee with WiFi, Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT, Lakefront Berkshires Retreat w/ Deck, Dock & Boat!, Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. , Big farmhouse in the foothills of the Berkshires, Taconic Hideaway – Swimming, BBQ Pit, Hiking, Falls Reach In The Heart of Copake, Poolside Luxe at Long Pond, Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

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
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's ...
Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$123 per night from 18 Aug to 19 Aug
AU$123
18 Aug - 19 Aug
includes taxes & fees
Located in Pittsfield, FairBridge Inn Express is in the suburbs, a 4-minute drive from Crane Museum of Papermaking and 6 minutes from Berkshire Athenaeum.
FairBridge Inn Express
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$732 per night from 8 Aug to 9 Aug
AU$732
8 Aug - 9 Aug
includes taxes & fees
Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.
Berkshires Untold
Save an average of 15% on thousands of hotels when you're signed in
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
The price is AU$227 per night from 2 Sept to 3 Sept
AU$227
2 Sept - 3 Sept
includes taxes & fees
With a stay at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG in South Lee, you'll be near ski lifts, within a 15-minute drive of Tanglewood ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Don't see what you're looking for?
See all available properties in Monterey
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.