Sheffield Holidays

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Your Sheffield Holiday

Our holiday packages to Sheffield allow you to customise your own adventure. Tailor your getaway to your style and interests and make the most of your time in this interesting city. If taking in sights is part of the programme during your trip to Sheffield, stop by leading attractions like Ski Butternut, Housatonic River Walk and Mahaiwe Performing Arts Centre. Stop dreaming and start travelling. Check out the many options on Expedia today and put your Sheffield holiday plans in motion!

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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Sheffield Holiday

Sheffield Essential Information

Language
English
Currency
U.S dollars
Population
3,400
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Ski Butternut, Norman Rockwell Museum and Bash Bish Falls State Park

Our pick of the best Sheffield Hotel Deals

Race Brook Lodge
Race Brook Lodge
2 out of 5
864 S Undermountain Rd, Sheffield, MA
The price is AU$292 per night from 24 Nov to 25 Nov
AU$292
includes taxes & fees
24 Nov - 25 Nov
8.6/10 Excellent! (29 reviews)
"Amazing experience in every aspect!"

Reviewed on 28 Oct. 2024

Race Brook Lodge
Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstove
Sheffield
The price is AU$784 per night from 4 Dec to 5 Dec
AU$784
includes taxes & fees
4 Dec - 5 Dec
9.8/10 Exceptional! (30 reviews)
"Delightful home in very quiet neighborhood near hiking trails. House had every amenity you might need (except tissues). Less than 20 minutes drive from Sheffield. Great restaurants in town. We very much enjoyed our stay in this house in the country and would highly recommend it to anyone wanting ..."

Reviewed on 16 Nov. 2024

Cheerful 3-bedroom cottage with woodstove
Antique Farmhouse Totally Restored
Antique Farmhouse Totally Restored
Sheffield
9.8/10 Exceptional! (50 reviews)
Lovely, spacious, comfortable House...
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily ..."

Reviewed on 23 Sep. 2024

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Antique Farmhouse Totally Restored
See all 1,170 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.
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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.