Middlefield, MA

Travel Guide

A snow-covered forest with a stone bridge in the background.
A cascading waterfall over rocky terrain surrounded by dense forest.
A stone bridge over a river with greenery on the sides.
A rocky stream with cascading water surrounded by trees.
A tall, deteriorating concrete structure with multiple square openings and scattered debris.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$128 nightly
The price is $143 total per night from Nov 1 to Nov 2
$143 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,713 reviews)
"Very spacious and clean room , at an affordable price vast of amenities surrounded by nature"

Reviewed on Oct 6, 2026

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$115 nightly
The price is $128 total per night from Nov 8 to Nov 9
$128 total
Nov 8 - Nov 9
Total with taxes and fees
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,187 reviews)
"The property was very nice. Needed some bathroom updating but was clean. Didn’t learn there was not a hot tub until the day before traveling via an email"

Reviewed on Oct 8, 2026

Berkshire Mountain Lodge
Hotel Northampton

Hotel Northampton

3.5 out of 5
36 King Street Northampton MA
$165 nightly
The price is $184 total per night from Oct 26 to Oct 27
$184 total
Oct 26 - Oct 27
Total with taxes and fees
Book a stay at this historic hotel in Northampton. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
Hotel Northampton
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.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,713 reviews)
"Very spacious and clean room , at an affordable price vast of amenities surrounded by nature"

Reviewed on Oct 6, 2026

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,187 reviews)
"The property was very nice. Needed some bathroom updating but was clean. Didn’t learn there was not a hot tub until the day before traveling via an email"

Reviewed on Oct 8, 2026

Berkshire Mountain Lodge
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7 Lenox MA
Stay at this aparthotel in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located ...
8.6/10 Excellent! (152 reviews)
"Air quality in the units is poor. HVAC systems are at least 30 years old. Beware."

Reviewed on Oct 4, 2026

The Ponds at Foxhollow
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 Middlefield attractions

Frequently asked questions

Is Middlefield worth visiting?
Middlefield is worth visiting for its outdoor experiences, including exploring the scenic Skyline Trail. Travelers can also enjoy a diverse food scene, with options ranging from classic North American dishes like burgers and comfort food, to delicious Italian pasta and pizza.
When is the best time to visit Middlefield?
The best time to visit Middlefield is from May through September, when the weather is generally pleasant. For fewer crowds and better value, the quieter months of November through February are a good option, offering a cooler experience during your trip.
What is Middlefield known for?
Middlefield is known for the Skyline Trail, a prominent natural landmark that draws travelers seeking outdoor experiences. Beyond its scenic routes, the destination also offers a taste of North American food culture, providing a variety of dining choices for travelers.
What is a good itinerary length for Middlefield?
A good itinerary length for Middlefield is one to two days to explore the Skyline Trail. For a slightly longer trip of three days, travelers can enjoy more time on the trail and sample the local dining scene, which offers North American, Italian, and Asian cuisine.
What are the top things to do in and around Middlefield?
In Middlefield, travelers can explore the Skyline Trail, a scenic landmark and point of interest.
What cuisines can you find in Middlefield?
In Middlefield, you can find New American cuisine, offering dishes like gourmet burgers, artisanal pizzas, and creative seasonal entrees. Travelers also have options for North American, Italian, Asian, European, and Latin American flavors. The area also features a selection of coffee shops.
Can I book a refundable hotel in Middlefield?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Middlefield by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Middlefield with Expedia?
Expedia makes it easier to plan your Middlefield trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Middlefield?
The best choice depends on your travel style. Hotels in Middlefield can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Middlefield trip on Expedia?
Once you've booked your Middlefield trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Middlefield trip?
Expedia offers customer support before, during, and after your Middlefield trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Middlefield?
If it's your first trip to Middlefield, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Middlefield hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Middlefield hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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