Monterey Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Monterey

Quality Inn
Quality Inn
2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is S$157 per night from 23 Jun to 24 Jun
S$157
23 Jun - 24 Jun
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Clean, quiet hotel in Great Barrington. Staff members were kind and attentive. Easy parking and check in / check out."

Reviewed on 17 Jun, 2025

Quality Inn
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 S$171 per night from 30 Jun to 1 Jul
S$171
30 Jun - 1 Jul
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Quiet, clean, great proximity to places and destinations."

Reviewed on 18 Jun, 2025

The Yankee, Trademark Collection by Wyndham
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is S$145 per night from 1 Jul to 2 Jul
S$145
1 Jul - 2 Jul
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"good stay, clean friendly and it was nice to be able to open the window in the room for fresh clean air. only drawback was it is close to the road and road noise was a little annoying. our room was facing the road and we had the window open so it was a trade off"

Reviewed on 14 Jun, 2025

Best Western Plus Berkshire Hills Inn & Suites
See all 1,130 properties in Monterey
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.

Frequently asked questions

How much does a Monterey holiday package cost?
You'll find cheap prices on Expedia for your Monterey break. However, factors like the length of stay, hotel choice and season will influence how much your holiday to Monterey costs.
What are the cheapest months to go to Monterey?
The off-season is the best time to head to Monterey if you're trying to save. Another tip for scoring cheap Monterey holiday packages? Try to avoid public holidays and any major festivals or events.
How many days is enough for Monterey?
The ideal duration of your Monterey holiday depends on what you'd like to do. Generally, a handful of days to a week will give you enough time to go to all the major attractions and explore some hidden gems along the way.
How to find the best Monterey package deals?
Use Expedia's filter tool to help you find some great Monterey package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Monterey package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your holiday package well in advance.
Is it cheaper to book a Monterey holiday as a package?
You can enjoy significant savings on your Monterey break by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to view the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Monterey?
If you've got your Monterey holiday dates confirmed, book as soon as you can to grab some unbeatable deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Monterey?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Monterey.
  2. Figure out your budget: Make sure you have enough money to pay for everything from dining out and transportation to flights and activities. Your hotel will probably be the biggest expense during your trip to Monterey.
  3. Decide how long to go for: Now that you're up to speed on Monterey, you can figure out the ideal length of your break. Put together a draft itinerary and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Monterey holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.