Sheffield Holidays

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    Save up to S$134 when you book a flight and hotel together*
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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.
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Top hotels in Sheffield

Race Brook Lodge
Race Brook Lodge
2 out of 5
864 S Undermountain Rd, Sheffield, MA
The price is S$256 per night from 29 Nov to 30 Nov
S$256
includes taxes & fees
29 Nov - 30 Nov
8.6/10 Excellent! (29 reviews)
"Amazing experience in every aspect!"

Reviewed on 28 Oct,2024

Race Brook Lodge
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$278 per night from 1 Dec to 2 Dec
S$278
includes taxes & fees
1 Dec - 2 Dec
8.8/10 Excellent! (1,001 reviews)
"Didn’t like that there are no trays in shower to hold any soaps or bottles while washing… nothing!!! Tub too high for elderly with slightest arthritis. No curtain on shower bathroom window. Took quite a while to get hot water to wash hands in sink. However, the inn is filled with amazing collectibles. ..."

Reviewed on 20 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$180 per night from 25 Nov to 26 Nov
S$180
includes taxes & fees
25 Nov - 26 Nov
9/10 Wonderful! (442 reviews)
"Staff were very friendly and the rooms were decorated adorably! We absolutely enjoyed our stay!"

Reviewed on 20 Nov,2024

Life House Berkshires
See all 1,167 properties in Sheffield
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 Sheffield holiday package cost?
Perhaps much less than you think — from just , actually! By combining flights, hotels and car rentals into your own custom-built holiday package, your trip to Sheffield is just a few clicks away.
How do I get a cheap travel package to Sheffield?
Find flights that suit your schedule, add a hotel to your booking and watch the savings rack up with a Sheffield holiday package. It’s that easy! From flights and hotels to tours and rental cars, Expedia is where your cheap holiday begins. And with more than 550 air carriers and 1,000,000 properties around the globe to select from, you’ll never be short of choice.
Where should I stay in Sheffield?
There’s so much to do in Sheffield, so stay close to its attractions and spend more time sightseeing. Magnolia Bluffs Casino is one spot to put on your must-see list.
What are the top hotels in Sheffield?
Book a room at Come Stay At The Sheffield Chalet. It’s one of this area’s most popular hotels. Another top-rated option in Sheffield is Little House In The Woods.
How far in advance should I book my Sheffield holiday?
To bag cheap prices, book as early as you can. Airlines usually begin selling tickets, along with some of the lowest fares, around a year in advance. Hotels, activities and car rental should also be booked well in advance to avoid disappointment. If you’ve decided on a last-minute getaway to Sheffield, there are always plenty of great deals to be had on Expedia. Check them out now!
What does an Expedia Sheffield travel package include?
Packages include rental cars, hotels and flights, but you can mix and match them to create your perfect Sheffield escape. You can also add on experiences and activities once you’ve made your booking. You’re in control! When you combine your bookings with Expedia, you’ll get access to discounts you won’t find anywhere else.
What should I know before booking a Sheffield travel package?
Tailor deals that fit your budget with an Expedia package. Airfares, hotels, rental cars — we have them all. You’ll save precious dollars just by bundling your bookings. Whether you’re taking off on an adventure in the snow or getting some sun on a warm beach, your perfect holiday is only clicks away.
Can I choose my airline with a Sheffield Expedia holiday package?
You can, and with more than 550 airlines to choose from across the globe, you have plenty of choice. Scroll through the available options and see which airline fits your needs and budget.
If I'm not able to travel, can I cancel my Sheffield holiday package?
Whether it’s your hotel, flight or rental car, you can cancel or alter it. Booked your Sheffield holiday package in the last 24 hours? You may be able to make changes for free. For bookings made more than 24 hours ago, you may incur a charge from your hotel, airline or car rental company. For more information, check out our Customer Service Portal. We’ll 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.