A winding road through a forest with autumn foliage.

Monterey Vacations from $1,241

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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.
  • Dec 21 - Dec 27

    Hotel Kinsley + Flight

    Stockade District
    6 nights
    3.5 star property
    9.0/10 - Wonderful (411 reviews)
    Roundtrip • Fort Myers (RSW) - Albany (ALB)
    RSW - ALB • 1 stop ALB - RSW • 2 stops
    $1,523
    $1,241
    per traveler
    found 1 day ago
    Hotel Kinsley
  • Dec 21 - Dec 27

    The Painted Lady by Avantstay Grand Victorian + Balcony Firepit + BBQ + Flight

    Catskill
    6 nights
    3.0 star property
    Roundtrip • Fort Myers (RSW) - Albany (ALB)
    RSW - ALB • 1 stop ALB - RSW • 2 stops
    $2,777
    $2,206
    per traveler
    found 1 day ago
    The Painted Lady by Avantstay Grand Victorian + Balcony Firepit + BBQ
  • Dec 21 - Dec 27

    Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views + Flight

    Stone Ridge
    6 nights
    3.0 star property
    10/10 - Exceptional (1 review)
    "Wonderful "
    Reviewed March 29, 2026
    Roundtrip • Fort Myers (RSW) - Albany (ALB)
    RSW - ALB • 1 stop ALB - RSW • 2 stops
    $2,206
    $1,777
    per traveler
    found 1 day ago
    Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views
  • Dec 21 - Dec 27

    Ohana Nature Escape by Avantstay Creekside + Firepit + Grill Waterfall + Beaver Pond Walks + Flight

    Catskill
    6 nights
    3.0 star property
    Roundtrip • Fort Myers (RSW) - Albany (ALB)
    RSW - ALB • 1 stop ALB - RSW • 2 stops
    $1,699
    $1,404
    per traveler
    found 1 day ago
    Ohana Nature Escape by Avantstay Creekside + Firepit + Grill Waterfall + Beaver Pond Walks
  • Dec 21 - Dec 27

    Luxury Private Estate w Pool Near Rhinebeck + Flight

    Red Hook
    6 nights
    2.0 star property
    Roundtrip • Fort Myers (RSW) - Albany (ALB)
    RSW - ALB • 1 stop ALB - RSW • 2 stops
    $10,916
    $9,046
    per traveler
    found 1 day ago
    Luxury Private Estate w Pool Near Rhinebeck

Where to stay near Monterey

Monterey offers a perfect blend of outdoor adventures, romantic scenery, and family-friendly activities. Visitors can enjoy a relaxing atmosphere while exploring nearby cities and neighborhoods that cater to sports, entertainment, and adventure, ensuring a memorable getaway for every type of traveler.

Great Barrington

For travelers seeking a memorable trip, Great Barrington offers a charming blend of family-friendly activities and outdoor adventures. Nestled near scenic destinations such as the National Shrine of the Divine Mercy and the tranquil Lake Buel, visitors can enjoy everything from hiking in the national state park to skiing at nearby resorts. Located about 8 miles away from Monterey, Great Barrington makes for an ideal base to explore the beauty of the Berkshires while enjoying a welcoming community atmosphere.

Lenox

Experience the charm of Lenox, an excellent hub for travelers seeking family-friendly activities, cultural experiences, and natural beauty. This vibrant city offers access to highlights like the National Shrine of the Divine Mercy, The Mount historic house, and the Norman Rockwell Museum. With a moderate seasonal visitor flow, Lenox provides a welcoming atmosphere year-round. Conveniently located about 14 miles by car from Monterey, it’s a smart choice for your next getaway, blending relaxation with enriching experiences.

Stockbridge

If you are a culture enthusiast or a family traveler, look no further than Stockbridge, known for its rich artistic heritage and beautiful natural surroundings. Just a short drive from Monterey, this charming town offers access to the Norman Rockwell Museum and the Naumkeag Museum, perfect for exploring art and history. With opportunities for outdoor activities and local concerts, Stockbridge provides a delightful retreat year-round, making it a smart choice for your vacation accommodations.

Lee

Lee stands out as a prime spot for travelers seeking family-friendly experiences while exploring the beauty of Massachusetts. With its rich cultural offerings, including the Norman Rockwell Museum and The Mount, as well as outdoor adventures near local lakes and mountains, Lee provides a perfect blend of relaxation and entertainment. Located about 10 miles by car from Monterey, this charming city is an ideal choice for a getaway, ensuring a memorable stay filled with diverse activities.

Otis

Travelers visiting the area often choose Otis, especially those seeking a weekend getaway or family adventure amidst nature. This charming town offers easy access to the stunning Otis Reservoir for boating and fishing, the serene Tolland State Forest for hiking, and the tranquil National Shrine of the Divine Mercy for reflection. Located about 6 miles by car from Monterey, Otis provides a perfect blend of outdoor activities and scenic beauty, making it a smart choice for your vacation stay.

Discover the most popular places to visit in Monterey

Monterey Hotel Deals

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

What's included in a Monterey vacation package?

A Monterey vacation package lets you combine round-trip flights, hotel stays, and a rental car. Many hotels in Monterey offer conveniences like free breakfast or airport shuttle services to and from airports such as Hartford, CT (BDL-Bradley Intl.), though these specific inclusions will vary by property.

How can I save money on a Monterey vacation package?

When you bundle, you can save up to 30%*. To save money on a Monterey package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What are the top things to do in Monterey?

Monterey, an outdoor and nature destination, offers a variety of activities for your Monterey vacation. You can explore its scenic beauty and cultural sites:


Browse and book things to do in Monterey on Expedia.

Do you need to rent a car in Monterey, or is public transport enough?

For a Monterey vacation package, a rental car is highly recommended to explore this outdoor and nature destination. Having a car provides the flexibility to visit attractions like Bidwell House Museum, about 1 mile from central Monterey, or Ski Butternut, about 12 miles away. This is especially useful for travelers booking Monterey vacation packages with flights, as it allows for easy access from airports serving the region, such as Bradley International Airport (BDL) in Hartford, CT, or Albany International Airport (ALB) in Albany, NY.

Can I change or cancel my Monterey vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Monterey vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Monterey vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Monterey vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Monterey?

To find last-minute vacation packages to Monterey, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Monterey vacation packages?

Free cancellation on a Monterey vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Monterey vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Monterey getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Monterey vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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