Middlefield Vacation Packages 2026 from $442

Middlefield flight + hotel vacation packages

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

The Dewey

$442

per person

Mar 16 - Mar 19

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

Prospect Berkshires

$523

per person

Mar 16 - Mar 19

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a picnic area are also on offer.

The Landing Hotel at Rivers Casino & Resort

Nothside

$617

per person

Mar 6 - Mar 10

found 2 hours ago

Roundtrip non-stop flight included

Austin (AUS) to Albany (ALB)

A casino, 5 restaurants, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking is free for guests, and you can enjoy a meal in one of the 2 coffee shops/cafes.

Gedney Farm

$466

per person

Mar 16 - Mar 19

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace, a garden, and a communal living room are also on offer.

The Cornell Inn, Lenox & The Berkshires

$503

per person

Mar 16 - Mar 19

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden 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

$126 nightly

$141 total

Jan 12 - Jan 13

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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

Free Cancellation

$98 nightly

$109 total

Jan 23 - Jan 24

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Pet friendly

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$113 total

Jan 19 - Jan 20

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$120 total

Feb 9 - Feb 10

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

Berkshires Untold

194 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$136 total

Jan 13 - Jan 14

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

Hotel Northampton

36 King Street Northampton MA

Free Cancellation

Reserve now, pay when you stay

$165 nightly

$184 total

Jan 12 - Jan 13

Total with taxes and fees

This historic hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a coffee shop, and a terrace are also offered.

Parking included

Free WiFi

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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 $442, 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.