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.
The Whitlock

The Whitlock

2 out of 5
Price was $750, price is now $596 per person
$596
per person
Nov 5 - Nov 9
found 10 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A business center, a terrace, and a garden are also on offer.
Hutton Brickyards Riverfront Hotel + Venue

Hutton Brickyards Riverfront Hotel + Venue

3.5 out of 5
Price was $1,155, price is now $882 per person
$882
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A garden, a picnic area, and luggage storage are also on offer.
Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay

Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay

3 out of 5
Save 100% on your flight
Price was $6,200, price is now $4,875 per person
$4,875
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and barbecue grills are also provided.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,435, price is now $1,142 per person
$1,142
per person
Dec 23 - Dec 27
found 1 hour ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A garden, a lobby fireplace, and a communal living room are also on offer.
The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Nothside
Price was $1,002, price is now $810 per person
$810
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
A casino, 5 restaurants, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking is free for guests, and you can enjoy a meal in one of the 2 coffee shops/cafes.

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
$206 nightly
The price is $231 total per night
$231 total
Nov 1 - Nov 2
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
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.
Hot Tub
Kitchen
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$111 nightly
The price is $124 total per night
$124 total
Nov 2 - Nov 3
Total with taxes and fees
This aparthotel 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
$108 nightly
The price is $121 total per night
$121 total
Oct 27 - Oct 28
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
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Free Cancellation
$76 nightly
The price is $85 total per night
$85 total
Nov 1 - Nov 2
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
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5
190 Meadow Street South Lee MA
$129 nightly
The price is $144 total per night
$144 total
Oct 6 - Oct 7
Total with taxes and fees
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.
Pool
Air conditioning
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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.

Stay near popular Sheffield attractions

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.
See properties

Frequently asked questions

How much are vacation packages to Sheffield?
You'll be surprised — you can recharge your batteries in Sheffield for a paltry $596. 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

A covered wooden structure with a sloped roof, surrounded by greenery and trees.
A wooden covered bridge with a gabled roof, surrounded by trees and a body of water.