Monterey Vacations from $471
Book a Hotel + Flight or Car together to unlock savings
Your Monterey Vacation
Say goodbye to planning hassles and hello to a Monterey vacation package. With your travel details organized before you leave, you can focus on discovering this city, starting with Canann Village Historic District, which is good for dining, culture and shopping. You'll want to do a little exploring during your trip to Monterey. Don't miss leading attractions such as Ski Butternut, Otis Ridge and Lake Buel. No matter your travel plans or budget, organizing your ultimate tailored Monterey vacation is a cinch with Expedia.
The Latest Monterey vacation packages
Price found within the past 48 hours. Click for updated prices.
The Cornell Inn, Lenox & The Berkshires
$945
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
9.2/10 Wonderful! (1,007 reviews)
Lovely people and place. Breakfast was great and so was the room. Highly recommend.
Reviewed on Aug 31, 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
$1,145
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
9.2/10 Wonderful! (116 reviews)
My stay at Diane’s bed and breakfast was absolutely wonderful. Diane herself is incredibly warm, welcoming, and genuinely informative — she made the entire experience feel personal and cared for. The room was quaint, cozy, and charming in that classic New England way, with comfortable beds, plenty of towels, and a generous selection of bath amenities that made settling in effortless.
Breakfast was a standout: a truly amazing cook‑to‑order meal that felt both homemade and high‑end. Every dish was fresh, delicious, and clearly prepared with pride. Parking was plentiful and convenient, making arrival and departure stress‑free.
Overall, this B&B is a gem — comfortable, inviting, and thoughtfully run. I’d happily return and recommend it to anyone looking for a relaxing stay.
Reviewed on Aug 21, 2026
Prospect Berkshires
$1,532
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
10/10 Exceptional! (42 reviews)
It was beautiful but quite expensive. There was no housekeeping included so trash was not picked up and the breakfasts were grossly overpriced!
Reviewed on Aug 19, 2026
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 browsing the exhibits at Bidwell House Museum during your trip to Monterey. While you're in the area, stroll along the lakeside.
Mount Wilcox
Commune with nature and explore the great outdoors at Mount Wilcox during your travels in Monterey. While you're in the area, wander around the forests.
Monterey Hotel Deals
Lakefront Retreat with Stunning Views | Forget-Me-Not by AvantStay
Monterey MA
9.4/10 Exceptional! (14 reviews)
"The house & location are wonderful. We were there for a week & we totally enjoyed ourselves. The difference between a good house & an excellent house is that everything works in an excellent house. There are a few items that do need attention. (1) The lock on the back door to the patio was broken ..."
Reviewed on Jun 15, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$113 nightly
$126 total
Oct 1 - Oct 2
Total with taxes and fees
9/10 Wonderful! (1,115 reviews)
"Clean rooms.."
Reviewed on Sep 2, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$100 nightly
$112 total
Sep 28 - Sep 29
Total with taxes and fees
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.
Find the Best Monterey Vacation Packages
Monterey Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 950 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Norman Rockwell Museum, Ski Butternut and October Mountain State Forest |
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Frequently asked questions
How much does a Monterey vacation package cost?
You'll find cheap prices from $471 on Expedia for your Monterey break. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Monterey costs.
What are the cheapest months to go to Monterey?
If you're looking to book a cheap Monterey vacation package, consider traveling in November, December and January. You're likely to find better rates on hotels and airfares during these quieter months — perfect for a budget-friendly break.
How many days is enough for Monterey?
With a well-organized itinerary, you can easily tick off the most popular Monterey attractions in a handful of days. But if you'd like to discover lesser-known spots or take day trips, think about booking your Monterey vacation for longer.
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 vacation package well in advance.
Is it cheaper to book a Monterey vacation as a package?
You can enjoy significant savings on your Monterey break by booking a personalized vacation 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 vacation package to Monterey?
If you've got your Monterey vacation 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.
Does Expedia offer Book Now, Pay Later Monterey vacation packages?
Your Monterey getaway is meant to be a relaxing escape from your daily routine, not a reason for money worries. So to give you more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
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- Berkshire Mountain Country Store
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- Visit The Berkshires
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- Otis Ridge
- Jacob's Pillow
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- Visit South Lee
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- Ashintully Gardens
- Visit Otis
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- Visit Lee
- Visit Monterey
- Bidwell House Museum
- Visit Great Barrington
- Pyramid Lake
- Questing
- Visit Stockbridge
- Housatonic River Walk
- Umpachene Falls Park
- Goose Pond Reservation
- Animagic Museum of Animation
- Magnolia Bluffs Casino
- Lee Premium Outlets
- National Shrine of the Divine Mercy
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.