Monterey Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Monterey
The Yankee Inn
461 Pittsfield Rd Lenox MA
S$236
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (1,023 reviews)
"The room was clean. Linens in good shape. Good access to lots of activities nearby. Breakfast can be crowded. Go early."
Reviewed on 11 Aug, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
S$164
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (1,060 reviews)
"Good location, nice room, easy access"
Reviewed on 10 Aug, 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
S$185
9 Sept - 10 Sept
includes taxes & fees
9/10 Wonderful! (1,025 reviews)
"Very clean-great beds!"
Reviewed on 11 Aug, 2026
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.
Stay near popular Monterey attractions
Lake Garfield
Commune with nature and explore the great outdoors at Lake Garfield during your travels in Monterey. While you're in the area, wander around the forests.
Bidwell House Museum
You can spend an afternoon exploring the galleries in Bidwell House Museum in Monterey. While you're in the area, stroll along the lakeside.
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?
- 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.
- 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.
- 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.
- 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.
