Sheffield Trips (flight + hotel)

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Top hotels in Sheffield

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 P5,595 per night from 28 Apr to 29 Apr
P5,595
per night
28 Apr - 29 Apr
8.8/10 Excellent! (867 reviews)
"What a pleasure to have the opportunity to stay in an historic inn such as the Red Lion."

Reviewed on Apr 13, 2024

The Red Lion Inn
Race Brook Lodge
Race Brook Lodge
2 out of 5
864 S Undermountain Rd, Sheffield, MA
The price is P10,070 per night from 26 Apr to 27 Apr
P10,070
per night
26 Apr - 27 Apr
10/10 Exceptional! (6 reviews)
"Beautiful property. Tavern is amazing. Staff is lovely."

Reviewed on Jan 27, 2024

Race Brook Lodge
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 P5,697 per night from 24 Apr to 25 Apr
P5,697
per night
24 Apr - 25 Apr
9/10 Wonderful! (222 reviews)
"Really nice place. Very nicely renovated, and a real bargain in the off season. My only issue was no shops/restaurants near to walk to and the highway it’s on is fast and busy making left turns out of the place a real challenge."

Reviewed on Apr 15, 2024

Life House Berkshires
See all 1,149 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 vacation package cost?
Perhaps much less than you think — from just , actually! By combining flights, hotels and car rentals into your own custom-built vacation 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 vacation package. It’s that easy! From flights and hotels to tours and rental cars, Expedia is where your cheap vacation 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 vacation?
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 vacation is only clicks away.
Can I choose my airline with a Sheffield Expedia vacation 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 vacation package?
Whether it’s your hotel, flight or rental car, you can cancel or alter it. Booked your Sheffield vacation 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.

Popular places to visit

Image for Magnolia Bluffs Casino

Magnolia Bluffs Casino

Why not roll the dice with a visit to Magnolia Bluffs Casino during your travels in Sheffield? Discover the area's breweries or seek out the hiking trails.

Magnolia Bluffs Casino
Image for Ashley House

Ashley House

You can learn about the history of Sheffield with a trip to Ashley House. Discover the area's breweries or seek out the hiking trails.

Ashley House
Image for Thom Reed UFO Monument Park

Thom Reed UFO Monument Park

Explore the great outdoors at Thom Reed UFO Monument Park, a lovely green space in Sheffield. Make some time to visit the casinos while you're in the area.

Thom Reed UFO Monument Park

More trip options

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.