Deals on vacations and trips to Sheffield

Save when you book Sheffield package deals

Choose two or more items and save on your trip:

Sheffield flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $941, price is now $743 per person
$743
per person
Nov 5 - Nov 10
found 20 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to Albany (ALB)
Free WiFi in public areas is available at this guesthouse. Take advantage of the free self parking.
The Old Catskill Game Farm Inn

The Old Catskill Game Farm Inn

3.5 out of 5
Save 100% on your flight
Price was $5,305, price is now $3,825 per person
$3,825
per person
Nov 5 - Nov 10
found 20 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to Albany (ALB)
A sauna, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. A communal living room, a picnic area, and free newspapers are also on offer.
The Perch Hotel

The Perch Hotel

2 out of 5
Save 100% on your flight
Price was $1,575, price is now $1,137 per person
$1,137
per person
Nov 5 - Nov 10
found 20 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Stockade District
Price was $1,209, price is now $948 per person
$948
per person
Nov 5 - Nov 10
found 20 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to Albany (ALB)
This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the sauna and free perks like continental breakfast and free self parking.
Farmhouse at Leeds by Avantstay Catskills Farmhouse + Barn Suite + Firepit Mins to Hudson + Kaaterskill Falls

Farmhouse at Leeds by Avantstay Catskills Farmhouse + Barn Suite + Firepit Mins to Hudson + Kaaterskill Falls

3 out of 5
Save 100% on your flight
Price was $1,987, price is now $1,582 per person
$1,582
per person
Nov 5 - Nov 10
found 20 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to Albany (ALB)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.

Top Sheffield hotels deals

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street Sheffield MA
$206 nightly
The price is $231 total per night
$231 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
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$158 nightly
The price is $176 total per night
$176 total
Sep 14 - Sep 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.
Pool
Hot Tub
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$125 nightly
The price is $139 total per night
$139 total
Aug 31 - Sep 1
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
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$145 nightly
The price is $162 total per night
$162 total
Sep 8 - Sep 9
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
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
$119 nightly
The price is $133 total per night
$133 total
Sep 14 - Sep 15
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.
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
$215 nightly
The price is $240 total per night
$240 total
Sep 9 - Sep 10
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
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.

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 $743. 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.