Middlefield Vacation Packages 2025/2026 from $380

Middlefield flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Valley Craft Ales

$380

per person

Dec 9 - Dec 16

found 2 hours ago

Roundtrip flight included

New York (JFK) to Albany (ALB)

This lodge doesn't skimp on freebies - guests receive free WiFi and free self parking. A fireplace in the lobby and a communal living room are also provided.

The White House Inn

Save 100% on your flight

$549

per person

Dec 9 - Dec 16

found 2 hours ago

Roundtrip flight included

New York (JFK) to Albany (ALB)

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace and a garden are also provided.

Vacation Village in the Berkshires

Save 100% on your flight

$450

per person

Dec 9 - Dec 16

found 2 hours ago

Roundtrip flight included

New York (JFK) to Albany (ALB)

This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

The Equinox Golf Resort & Spa

Save 100% on your flight

$803

per person

Dec 9 - Dec 16

found 2 hours ago

Roundtrip flight included

New York (JFK) to Albany (ALB)

This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.

Aspen At Manchester

Save 100% on your flight

$477

per person

Dec 9 - Dec 16

found 2 hours ago

Roundtrip flight included

New York (JFK) to Albany (ALB)

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and a lobby fireplace are also on offer.

Top Middlefield hotels deals

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Williamstown, MA

Free Cancellation

Reserve now, pay when you stay

$86 nightly

$96 total

Nov 2 - Nov 3

Total with taxes and fees

This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Pool

Parking included

Berkshire Mountain Lodge

8 Dan Fox Dr, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$113 nightly

$126 total

Nov 2 - Nov 3

Total with taxes and fees

This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.

Pool

Hot Tub

Quality Inn & Suites Northampton - Amherst

117 Conz St, Northampton, MA

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$141 total

Oct 7 - Oct 8

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Parking included

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

190 Meadow Street, South Lee, MA

Free Cancellation

Reserve now, pay when you stay

$129 nightly

$144 total

Nov 2 - Nov 3

Total with taxes and fees

This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.

Pool

Air conditioning

Berkshires Untold

194 Pittsfield Rd, Lenox, MA

Free Cancellation

Reserve now, pay when you stay

$88 nightly

$98 total

Nov 2 - Nov 3

Total with taxes and fees

A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and express check-in are also on offer.

Pet friendly

Parking included

The Red Lion Inn

30 Main Street, Stockbridge, MA

Free Cancellation

Reserve now, pay when you stay

$199 nightly

$223 total

Nov 4 - Nov 5

Total with taxes and fees

This smoke-free hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

Pool

Spa

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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.

Popular places to visit

Skyline Trail

You can take time to visit Skyline Trail during your travels to Middlefield. Stroll along the area's lakeside, or simply savor its charming coffeehouses.

Frequently asked questions

How much are vacation packages to Middlefield?

With vacation packages available from as low as $380, it's not necessary to wipe out your bank balance for your trip to Middlefield. Travelocity is here to help. Bundle up experiences, flights and hotels into a package and walk away with serious discounts. The more you book, the more you save.

Where can I get the best vacation package deals for Middlefield?

It's simple — head to Travelocity. With no less than 400 air carriers and 1,000,000 properties worldwide, it's easy to craft a Middlefield package deal that satisfies your wanderlust.

Why should I purchase my Middlefield vacation bundle via Travelocity?

Savings, support and a stress-free booking are just the beginning. Enjoy a fulfilling travel experience knowing you have access to 24/7 customer support. With the Travelocity Price Match Guarantee, you know you're getting the best deal available.

Will I save money on my Middlefield car rental if I bundle it with hotels and flights?

Absolutely — bundle your hotel, flight and car into a Middlefield vacation package and you can save plenty. With so many places to explore in the Middlefield area, having your own wheels will make exploring a breeze. Once you're behind the wheel, turn up the stereo and make your way to Times Square, a top attraction around 120 mi from Middlefield.

Which airport is best for Middlefield?

Bradley Intl. Airport (BDL) is a main hub. You'll find it around 35 mi southeast of Middlefield. Other options worth checking out are Albany Intl. Airport (ALB) (50 mi away from central Middlefield) and Hartford, CT (HFD-Hartford - Brainard) (45 mi away from central Middlefield).

What is there to do in Middlefield?

Skyline Trail should be at the top of your itinerary. Once you've crossed off this famous attraction, simply stroll the streets of Middlefield and learn what really makes this exciting city tick.

Where should I stay when visiting Middlefield?

The NEW! Sunday Farm - 1840's Whaling Captain's Estate is the number one choice of many visitors. Book soon before it's too late.