Sheffield Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Sheffield Vacation

The stress-free way to experience this unique city is with a custom-made Sheffield vacation package. Stay in the neighborhood of Canann Village Historic District, which is great for dining, culture and shopping or go someplace else — our package deals are all about you. Fill your free time with visits to Ski Butternut, Housatonic River Walk and Lake Buel, some of the things you really should see during a trip to Sheffield. Don't delay exploring this city any longer. Your ultimate Sheffield vacation is only a few clicks away with Expedia.

Sheffield Hotel Deals

Race Brook Lodge
Race Brook Lodge
2 out of 5
864 S Undermountain Rd, Sheffield, MA
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from May 29 to May 30
CA $199
CA $222 total
includes taxes & fees
May 29 - May 30
9.2/10 Wonderful! (8 reviews)
"It was quiet setting by the rooms are run down"

Reviewed on Apr. 25, 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 CA $136 per night from May 28 to May 29
CA $136
CA $152 total
includes taxes & fees
May 28 - May 29
9/10 Wonderful! (243 reviews)
"Love the lobby (even smells great!) Love the decor and the outdoor patio. Happy with entire stay."

Reviewed on May 16, 2024

Life House Berkshires
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 CA $218 per night from May 27 to May 28
CA $218
CA $274 total
includes taxes & fees
May 27 - May 28
8.8/10 Excellent! (886 reviews)
"Very comfortable beds. Quiet with very friendly staff. Wasn’t too thrilled with the antique bathtub, too high to step into safely for seniors."

Reviewed on May 18, 2024

The Red Lion Inn
See all 1,142 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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.

Discover the most popular places to visit in Sheffield

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

Other vacations you might like

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