Deals on vacations and trips to Sheffield

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Sheffield flight + hotel vacation packages

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Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
Price was $569, price is now $470 per person
$470
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Albany (ALB)
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.
The Yankee Inn

The Yankee Inn

2.5 out of 5
Price was $657, price is now $522 per person
$522
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Albany (ALB)
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.
Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $994, price is now $801 per person
$801
per person
Jul 5 - Jul 9
just found
Roundtrip non-stop flight included
Houston (HOU) to Albany (ALB)
This smoke-free hotel features a casino, a nightclub, and a restaurant. Enjoy the indoor pool and perks like free self parking and a free area shuttle. You'll appreciate the 24-hour gym, bar/lounge, and snack bar/deli.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was $1,068, price is now $864 per person
$864
per person
Jul 22 - Jul 27
found 23 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $956, price is now $782 per person
$782
per person
Jul 22 - Jul 27
found 23 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Top Sheffield hotels deals

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street Sheffield MA
$180 nightly
The price is $201 total per night
$201 total
Jun 7 - Jun 8
Total with taxes and fees
This bed & breakfast features free self parking and a garden. Free cooked-to-order breakfast is served. A lobby fireplace, a communal living room, and a picnic area are also on offer.
Breakfast included
Parking included
Luxury Private Estate in the Berkshires | Whitney by AvantStay

Luxury Private Estate in the Berkshires | Whitney by AvantStay

Sheffield MA
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield MA
Get rates
This vacation home features a gym and a hot tub. There's fun for all ages with a playground and an arcade/game room, and childcare is an added bonus. Limo/town car service, a garden, and laundry facilities are also on offer.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$155 nightly
The price is $173 total per night
$173 total
Jun 4 - Jun 5
Total with taxes and fees
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
$119 nightly
The price is $133 total per night
$133 total
Jun 4 - Jun 5
Total with taxes and fees
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. A terrace, a lobby fireplace, and express check-in are also on offer.
Pet friendly
Parking included
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
$106 nightly
The price is $118 total per night
$118 total
Jun 4 - Jun 5
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
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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

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

Bartholomews Cobble

Explore the great outdoors at Bartholomews Cobble, a lovely green space in Sheffield. Make some time to visit the casinos while you're in the area.

Bartholomews Cobble

Bartholomew's Cobble

You can take time to visit Bartholomew's Cobble during your travels to Sheffield. Make some time to visit the casinos while you're in the area.

Bartholomew's Cobble

Frequently asked questions

How much are vacation packages to Sheffield?
You'll be surprised — you can recharge your batteries in Sheffield for a paltry $470. Here at Travelocity, we save you money and time with our excellent vacation packages. With experiences, hotels and flights all available at our one-stop shop, what are you waiting for?
How long should my Sheffield vacation be?
Around 2 nights is the average time frame visitors vacation in Sheffield. But how long is right for you depends on how many treasured memories you want to create. Why not stay a bit longer and explore some hidden gems?
Where can I get the best vacation package deals for Sheffield?
Snapping up the perfect package deal to Sheffield is a cinch with Travelocity. With 400 air carriers and 1,000,000 properties across the globe, the choice is yours when selecting your hotels and flights.
Why should I book my Sheffield vacation bundle via Travelocity?
We offer round-the-clock support, exceptional service and a Price Match Guarantee. Life is all about the journey — and we have exciting destinations for you to journey to all across the world. Roam with us and your bank balance will thank you for it.
Can I save on my Sheffield car rental if I book it with hotels and flights?
You certainly can — bundle your flight, hotel and car into a Sheffield vacation package and you'll save a ton. With so much to discover in Sheffield, having your own set of wheels will make it easy to explore. Once you've buckled yourself in, hit the wide open road and make tracks to Times Square, a famous sight approximately 100 mi from Sheffield.
Which airport is best for Sheffield?
Bradley Intl. Airport (BDL) is one of the best airports for Sheffield. You'll find it 35 mi east of the buzzing city center. Your other choices are Albany Intl. Airport (ALB) (50 mi away from central Sheffield) and Stewart Intl. Airport (SWF) (55 mi away from central Sheffield).
What is there to do in Sheffield?
While hopping off the tourist trail can be rewarding, you shouldn't ignore the well-known sights that make a destination famous. Magnolia Bluffs Casino and Ashley House are a couple of them in Sheffield.
Where should I stay when visiting Sheffield?
The Built in 1739, near Appalachian Trail & River, 7 Min. From Great Barrington is popular with many travelers. Book as soon as possible before it's too late.

Photos of local treasures

Browse Sheffield vacation photos for more inspiration

FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA
Sheffield