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 $1,055, price is now $815 per person
$815
per person
Oct 28 - Nov 2
found 23 hours ago
Roundtrip flight included
Denver (DEN) 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.
The Manchester View

The Manchester View

2.5 out of 5
Price was $1,240, price is now $1,046 per person
$1,046
per person
Oct 10 - Oct 14
found 3 hours ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,024, price is now $901 per person
$901
per person
Oct 11 - Oct 15
found 9 hours ago
Roundtrip flight included
Denver (DEN) 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.
Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Price was $948, price is now $836 per person
$836
per person
Oct 11 - Oct 15
found 9 hours ago
Roundtrip flight included
Denver (DEN) 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 Wilmington Inn

The Wilmington Inn

3.5 out of 5
Price was $1,314, price is now $1,174 per person
$1,174
per person
Oct 11 - Oct 15
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
A bar/lounge and a terrace are featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like full breakfast and WiFi in public areas. A lobby fireplace, a library, and a picnic area are also on offer.

Top Sheffield hotels deals

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street Sheffield MA
$229 nightly
The price is $256 total per night
$256 total
Sep 13 - Sep 14
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
$108 nightly
The price is $120 total per night
$120 total
Oct 1 - Oct 2
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.
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $99 total per night
$99 total
Sep 17 - Sep 18
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
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$153 nightly
The price is $171 total per night
$171 total
Sep 7 - Sep 8
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.
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Free Cancellation
$118 nightly
The price is $132 total per night
$132 total
Sep 8 - Sep 9
Total with taxes and fees
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 hot tub and free perks like buffet breakfast and free self parking.
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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 $815. 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.