Monterey Vacations from $206

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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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Save 100% on your flight
Price was $291, price is now $206 per person
$206
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
9/10 Wonderful! (756 reviews)
The roomy and comfortable suite was a step above a typical hotel room. We took advantage of the full kitchen to prepare our own meals. We enjoyed the pool and hot tub. We will definitely consider staying here again at a future trip to the Berkshires.

Reviewed on Dec 7, 2025

Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Save 100% on your flight
Price was $372, price is now $236 per person
$236
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
9.2/10 Wonderful! (218 reviews)
The place was fantastic in every way, clean, great service, beautiful location and close to everything you want to do in and around Saratoga Springs. I will book this beautiful spot again!

Reviewed on Dec 1, 2025

The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Stockade Historic District
Price was $759, price is now $500 per person
$500
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
Everything about our stay was perfect! The lady at check-in was super friendly, the room was extremely clean and modern. Definitely recommend The Landing!

Reviewed on Nov 23, 2025

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Save 100% on your flight
Price was $716, price is now $474 per person
$474
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
8.8/10 Excellent! (3 reviews)
The room was nice and clean, but the hotel itself was still under construction and it took 45 minutes for us to get in our room for check-in I was able to ask for extended check out and we got two complementary drinks from the bar but overall they should have waited to open

Reviewed on Nov 12, 2025

The Clocktower Hotel at Century House, an Ascend Collection Hotel

The Clocktower Hotel at Century House, an Ascend Collection Hotel

2.5 out of 5
Price was $644, price is now $512 per person
$512
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
8.4/10 Very Good! (1,004 reviews)
Everything was great except we stayed 4 nights and never once was our room cleaned or towels refreshed.

Reviewed on Dec 7, 2025

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Discover the most popular places to visit in Monterey

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.

Bidwell House Museum

Monterey Hotel Deals

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
$92 nightly
The price is $103 total per night from Dec 12 to Dec 13
$103 total
Dec 12 - Dec 13
Total with taxes and fees
8/10 Very Good! (979 reviews)
Clean room, convenient and tasty restaurant

Reviewed on Dec 5, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $120 total per night from Jan 7 to Jan 8
$120 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
9/10 Wonderful! (781 reviews)
The roomy and comfortable suite was a step above a typical hotel room. We took advantage of the full kitchen to prepare our own meals. We enjoyed the pool and hot tub. We will definitely consider staying here again at a future trip to the Berkshires.

Reviewed on Dec 7, 2025

Berkshire Mountain Lodge
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
$89 nightly
The price is $100 total per night from Dec 16 to Dec 17
$100 total
Dec 16 - Dec 17
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
The room was spacious and clean, the jetted tub was a nice treat, and the breakfast was fresh.

Reviewed on Dec 3, 2025

The Yankee, Trademark Collection by Wyndham
See all 1,151 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.

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 $206 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.