Deals on vacations and trips to Sheffield

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Sheffield flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $776, price is now $664 per person
$664
per person
Jul 16 - Jul 19
found 7 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Manchester Village Historic District
Save 100% on your flight
Price was $4,100, price is now $3,368 per person
$3,368
per person
Jul 15 - Jul 22
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.
Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Price was $1,331, price is now $1,139 per person
$1,139
per person
Jul 15 - Jul 22
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and a lobby fireplace are also on offer.
The Yankee Inn

The Yankee Inn

2.5 out of 5
Price was $887, price is now $763 per person
$763
per person
Jul 16 - Jul 19
found 7 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Wilburton Inn

Wilburton Inn

3.5 out of 5
Price was $1,759, price is now $1,519 per person
$1,519
per person
Jul 15 - Jul 22
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
This hotel features an outdoor tennis court and a seasonal outdoor pool. Families will appreciate the picnic area and in-room childcare. Guests will appreciate free perks like free self parking and WiFi in public areas.

Top Sheffield hotels deals

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street Sheffield MA
Free Cancellation
Reserve now, pay when you stay
$193 nightly
The price is $215 total per night
$215 total
Jun 22 - Jun 23
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
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 14 - Jun 15
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.
Pool
Hot Tub
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$111 nightly
The price is $124 total per night
$124 total
Jun 14 - Jun 15
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.
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $151 total per night
$151 total
Jun 16 - Jun 17
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.
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Free Cancellation
$94 nightly
The price is $105 total per night
$105 total
Jun 14 - Jun 15
Total with taxes and fees
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A picnic area and barbecue grills are also provided.
Breakfast included
Parking included
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
$191 nightly
The price is $214 total per night
$214 total
Jun 22 - Jun 23
Total with taxes and fees
This historic hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Spa
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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

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

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

Frequently asked questions

How much are vacation packages to Sheffield?
You'll be surprised — you can recharge your batteries in Sheffield for a paltry $664. 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