Book Holiday Homes in Monterey

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Featured Holiday Homes in Monterey

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is NZ$399 per night from 4 Apr to 5 Apr
NZ$399
includes taxes & fees
4 Apr - 5 Apr
Stay at this vacation home in Lanesborough. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Jiminy Peak Mountain Resort and Crane ...
Berkshire Village Carriage House - Super Private!!
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

East Otis
Book a stay at this family-friendly vacation home in Otis. Enjoy free WiFi, a garden, and a pool table. Popular attractions Otis Reservoir and Larkum Pond are ...
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Spectacular views and close to Great Barrington.

Spectacular views and close to Great Barrington.

Great Barrington
Stay at this vacation home in Great Barrington. Enjoy in-room jetted tubs, an in-room coffeemaker, and in-room fireplaces. Popular attractions Lake Mansfield ...
Spectacular views and close to Great Barrington.
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Peace and quiet on the lake

Peace and quiet on the lake

Becket
Stay at this vacation home in Becket. Enjoy free WiFi, a garden, and patios. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry are located ...
Peace and quiet on the lake
Lakeside Retreat Just You, The Lake & The View!

Lakeside Retreat Just You, The Lake & The View!

Great Barrington
Stay at this vacation home in Great Barrington. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Art et Industrie and Lake Mansfield Park ...
Lakeside Retreat Just You, The Lake & The View!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Craryville
The price is NZ$602 per night from 17 Apr to 18 Apr
NZ$602
includes taxes & fees
17 Apr - 18 Apr
Stay at this vacation home in Copake Lake. Enjoy air conditioning. Popular attractions Copake Lake and Mosquito Island are located nearby.
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Heart of Lenox Walk to Town Cozy Cottage!

Heart of Lenox Walk to Town Cozy Cottage!

Lenox
Stay at this vacation home in Lenox. Enjoy free WiFi, a garden, and in-room washers/dryers. Popular attractions Tanglewood Music Center and The Bookstore are ...
Heart of Lenox Walk to Town Cozy Cottage!
The Race Mountain House

The Race Mountain House

2 out of 5
Sheffield
Stay at this vacation home in Sheffield. Enjoy patios, in-room fireplaces, and air conditioning. Popular attractions Mount Everett State Reservation and Drury ...
The Race Mountain House
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Sheffield
The price is NZ$885 per night from 17 Apr to 18 Apr
NZ$885
includes taxes & fees
17 Apr - 18 Apr
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 ...
Cheerful 3-bedroom cottage with woodstove
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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
418 Holiday Homes
Lowest Price
NZ$173
Highest Price
NZ$885
Popular accommodation
Berkshire Village Carriage House - Super Private!!, 4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi, Spectacular views and close to Great Barrington., Peace and quiet on the lake, Lakeside Retreat Just You, The Lake & The View!, COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!, Heart of Lenox Walk to Town Cozy Cottage!, The Race Mountain House, Cheerful 3-bedroom cottage with woodstove

Top trending hotels in Monterey

Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$189 per night from 16 Apr to 17 Apr
NZ$189
includes taxes & fees
16 Apr - 17 Apr
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 ...
Life House Berkshires
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$173 per night from 16 Apr to 17 Apr
NZ$173
includes taxes & fees
16 Apr - 17 Apr
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
The Yankee, Trademark Collection by Wyndham
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 refundable
The price is NZ$257 per night from 6 Apr to 7 Apr
NZ$257
includes taxes & fees
6 Apr - 7 Apr
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 ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

3 out of 5
435 Laurel St, Lee, MA
Fully refundableReserve now, pay when you stay
The price is NZ$181 per night from 16 Apr to 17 Apr
NZ$181
includes taxes & fees
16 Apr - 17 Apr
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
The Black Swan Lee - Lenox, Ascend Hotel Collection
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See all available properties in Monterey
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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.