Deals on vacations and trips to Sheffield

Save when you book Sheffield package deals

Choose two or more items and save on your trip:

Top Sheffield hotels deals

Race Brook Lodge

Race Brook Lodge

2 out of 5
864 S Undermountain Rd, Sheffield, MA
The price is $145 per night
$145
per night
Jun 25 - Jun 26
This hotel features a restaurant and 2 bars/lounges. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A garden and a virtual front desk are also provided.
Pool
Parking included
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
The price is $119 per night
$119
per night
Jun 25 - Jun 26
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. Express check-in is provided and the front desk is staffed around-the-clock.
Pet friendly
Parking included
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
The price is $125 per night
$125
per night
Jun 26 - Jun 27
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Free Cancellation
Reserve now, pay when you stay
The price is $165 per night
$165
per night
Jun 26 - Jun 27
A full-service spa, 3 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the gym, bar/lounge, and concierge services.
Pool
Spa
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

3 out of 5
435 Laurel St, Lee, MA
Free Cancellation
Reserve now, pay when you stay
The price is $134 per night
$134
per night
Jun 24 - Jun 25
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A 24-hour business center, a snack bar/deli, and a picnic area are also on offer.
Breakfast included
Pet friendly
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
The price is $89 per night
$89
per night
Jun 24 - Jun 25
An outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A garden and express check-out are also provided.
Don't see what you're looking for?
See all available properties in Sheffield
View all properties
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.

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

Photos of local treasures

Browse Sheffield vacation photos for more inspiration

Sheffield

Frequently asked questions

How much are vacation packages to Sheffield?
is all you’ll need for an exhilarating vacation in Sheffield. Bundle your flights and hotel into a vacation package with Travelocity and see the savings add up. With prices this good, it’s never been easier to travel!
Where can I get the best vacation package deals for Sheffield?
You can lock in terrific Sheffield package deals with Travelocity. Pick from as many as 400 air carriers and 1,000,000 worldwide properties and turn those vacation daydreams into a reality.
Why should I book my Sheffield vacation bundle with Travelocity?
The three S’s — savings, support and a stress-free booking — are just the tip of the iceberg. Enjoy a fulfilling travel experience knowing you can rely on our team of customer support experts around-the-clock. With the Travelocity Price Match Guarantee, you can rest easy knowing you’ll always get the best deal available.
Can I save money on my Sheffield car rental if I bundle it with my hotel or flight?
Combining your car, flight and hotel into a Sheffield vacation package is a great way to score better prices. Plus, having your own rental car gives you total freedom to find your way to all those amazing sights you want to explore. Situated 100 mi from Sheffield, Times Square is one place that should feature on your itinerary. Fasten your seat belt and make a day trip of it.
What is the best time of year to go to Sheffield?
If you love to wander wisely, is the perfect time to do it. That’s when you’ll find room rates are at their cheapest. In contrast, prices reach their highest around . February, March and May are the most popular months to stay in Sheffield, so expect long lines for major tourist sites. Rather avoid high season? You’ll find more manageable crowds during October, November and December.
Which airport is best for Sheffield?
Bradley Intl. Airport (BDL) (35 mi away from downtown), Albany Intl. Airport (ALB) (50 mi away from central Sheffield) and Stewart Intl. Airport (SWF) (55 mi away from central Sheffield) are the main hubs in Sheffield.
What is there to do in Sheffield?
Sheffield is teeming with places to discover, like Magnolia Bluffs Casino and Ashley House. These well-known attractions are at the top of most tourists’ to-do lists.
Where should I stay when visiting Sheffield?
Many visitors opt to spend their nights at the Whitney by AvantStay | Private Berkshires Estate. It’s the perfect base for your Sheffield escape.