Monterey Holidays from £955

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Your Monterey Holiday

Say goodbye to planning hassles and hello to a Monterey holiday package. With your travel details organised 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, organising your ultimate tailored Monterey holiday is a cinch with Expedia.

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Vacation Village in the Berkshires

Things to do near Monterey

Monterey, Massachusetts, is an ideal destination for outdoor enthusiasts and couples seeking a romantic getaway amidst stunning scenery. Visitors can enjoy a variety of activities, including skiing at local resorts, embarking on boat trips, and indulging in wine tours. Additionally, the Monterey Bay adventure and guided tours offer unique experiences to explore the area's natural beauty and charm. It's a perfect spot for an adventurous and memorable holiday.

Shopping

For unique gifts, visit Hoffman's Pottery, located 20.9km away. If you're up for a drive, Lee Premium Outlets offers a variety of brands and entertainment, just 12.9km away. The Berkshire Mountain Country Store, 14.5km from Monterey, is perfect for local treats and souvenirs.

Recreation

At Lake Mansfield Park, enjoy tranquil walks and serene picnics surrounded by nature's beauty, ideal for relaxation. Experience the enchanting performances at Jacob's Pillow, where dance meets culture in a romantic atmosphere. The Mahaiwe Performing Arts Center offers captivating shows, perfect for families seeking entertainment and cultural enrichment.

Adventure

The Housatonic River Walk, located 12.9km from Monterey, offers a scenic hiking trail perfect for outdoor enthusiasts. For skiing, head to Ski Butternut or Otis Ridge, both situated 9.7km away, where you can enjoy thrilling sports in a picturesque winter landscape.

Nightlife

In Monterey, Massachusetts, the nightlife is quaint yet charming, with cosy bars and local eateries. Enjoy live music at the Monterey General Store or sip cocktails at nearby venues. The atmosphere is relaxed, perfect for unwinding after a day of exploring the beautiful surroundings.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Monterey

Monterey, Massachusetts, is perfect for a romantic getaway or scenic outdoor adventures. Visitors can explore historic houses, serene lakes, and nearby national and state parks. Don't miss the beautiful Monastery Beach, the picturesque Monterey Peninsula, and the charming Monterey Harbour and Bay. For a delightful experience, take a stroll along the famous Pebble Beach, making it an ideal destination for culture and adventure enthusiasts alike.

  • Norman Rockwell Museum: Situated 16.1km from Monterey, this museum is dedicated to the beloved American illustrator Norman Rockwell. Visitors can immerse themselves in his iconic artworks that capture the essence of everyday life, accompanied by engaging exhibitions that explore American culture and history.
  • Ventfort Hall Mansion and Gilded Age Museum: Located 20.9km away, this historic mansion offers a glimpse into the opulent lifestyle of the Gilded Age. The stunning architecture and lavish interiors reflect the grandeur of the era, while guided tours reveal fascinating stories of its past residents.
  • National Shrine of the Divine Mercy: Just 14.5km from Monterey, this serene shrine is a peaceful retreat for reflection and prayer. Its beautiful grounds and inspiring architecture create a tranquil atmosphere, inviting visitors to explore the spiritual heritage and experience a sense of calm.

Best time to go to Monterey

The best time to visit Monterey is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.2°F (-4.9°C)Light RainMostly CloudyAverageAverage
February24.8°F (-4.0°C)Light RainMostly CloudyAverageAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May55.9°F (13.3°C)Light RainMostly SunnyAverageAverage
June63.7°F (17.6°C)Light RainMostly SunnySlightly HighAverage
July69.8°F (21.0°C)Light RainMostly SunnySlightly HighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnySlightly HighSlightly High
September60.8°F (16.0°C)Light RainMostly SunnyAverageAverage
October49.8°F (9.9°C)Light RainMostly SunnySlightly LowSlightly High
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowSlightly Low
December29.7°F (-1.3°C)Light RainMostly CloudySlightly LowAverage

Tips to save on your trip to Monterey

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Monterey.
  • Consider traveling during the off-peak season (typically March to April and November) for more affordable package holidays to Monterey.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Monterey Essential Information

Language
English
Currency
U.S dollars
Population
950
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Norman Rockwell Museum, Ski Butternut and October Mountain State Forest

Top hotels in Monterey

Lakefront Retreat with Stunning Views | Forget-Me-Not by AvantStay

Lakefront Retreat with Stunning Views | Forget-Me-Not by AvantStay

Monterey MA
9.6/10 Exceptional! (12 reviews)
We had a wonderful time thank you

Reviewed on 20 Apr 2026

Lakefront Retreat with Stunning Views | Forget-Me-Not by AvantStay
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is £89 per night from 24 May to 25 May
£89
24 May - 25 May
includes taxes & fees
9/10 Wonderful! (923 reviews)
Room very spacious and clean. Full kitchen is a great bonus.

Reviewed on 4 May 2026

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is £79 per night from 7 May to 8 May
£79
7 May - 8 May
includes taxes & fees
9/10 Wonderful! (930 reviews)
This is a very nice, quasi-boutique hotel. The rooms are nicely furnished but small. It is not fancy but it is comfortable, clean, and perfectly fine…just not fancy. But I’m not a fancy person so I like this place and will stay again without hesitation. The only reason for a 4-star rating is that, ...

Reviewed on 4 May 2026

Berkshires Untold
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.

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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. Flight-inclusive packages are ATOL protected.