Middlefield Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in Middlefield

The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is S$319 per night from 2 Dec to 3 Dec
S$319
includes taxes & fees
2 Dec - 3 Dec
8.8/10 Excellent! (1,003 reviews)
"We liked the last century charm and excellent staff. We will definitely return"

Reviewed on 22 Nov,2024

The Red Lion Inn
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is S$205 per night from 29 Nov to 30 Nov
S$205
includes taxes & fees
29 Nov - 30 Nov
9/10 Wonderful! (447 reviews)
"Location. Service."

Reviewed on 24 Nov,2024

Life House Berkshires
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is S$134 per night from 1 Dec to 2 Dec
S$134
includes taxes & fees
1 Dec - 2 Dec
9/10 Wonderful! (1,001 reviews)
"Staff was very nice, friendly and accommodating. The room was nice, clean, comfortable and spacious."

Reviewed on 18 Nov,2024

The Yankee, Trademark Collection by Wyndham
See all 992 properties in Middlefield
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

How much does a Middlefield holiday package cost?
Much less than you might think — from just , in fact! By combining flights, hotels and car rentals into a tailor-made package, your trip to Middlefield is just a few clicks away.
How do I get a cheap travel package to Middlefield?
Bundle, bundle, bundle. Flights, hotels and rental cars — combine whatever you need into a Middlefield holiday package and save. Score even more bargains when you include extras such as experiences or tours to your booking. But that’s not the only good part. You have the freedom to tailor your holiday your own way. We offer over 550 airlines and 1,000,000 hotel options globally, so that everyone has an opportunity to travel and live out those holiday fantasies.
Where should I stay in Middlefield?
There’s so much to do in Middlefield, so stay close to its attractions and maximize your time sightseeing. Glendale Falls is one place to put on your must-see list.
How far in advance should I book my Middlefield holiday?
It all depends on the airline, but it’s usually possible to look up international fares on Expedia up to a year in advance. While it’s a good idea to book ahead of time, lucky customers occasionally nab a cheaper seat only weeks before departure dates.
What does an Expedia Middlefield travel package include?
Flights, hotels and a shiny set of wheels for your road trip adventures. Simply pick and choose your preferred bundle and get access to incredible deals. Once you’ve made your booking, add on a few experiences and tours and watch your savings grow. When it comes to organising your Middlefield getaway, you’re in charge!
What should I know before booking a Middlefield travel package?
So many places to visit, so many things to see and do. With a package, you can cross more of them off your list. Bundle your flights, hotels and rental cars and see how much you save.
Can I choose my airline with a Middlefield Expedia holiday package?
Yes — that’s one of the best things about an Expedia package. You can mix and match your flights, hotels and more. We have access to more than 550 partner airlines throughout the world, so you have lots of choice when arranging your Middlefield escape.
If I'm not able to travel, can I cancel my Middlefield holiday package?
Whether it’s your hotel, flight or rental car, you can cancel or change it. Booked your Middlefield holiday package in the last 24 hours? You may be able to make any changes for free. For older bookings, you may incur a charge from your hotel, airline or car rental company. For more information, visit our Customer Service Portal. We’re here to help you every step of the way.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.