A lakeside town with autumn foliage, a bridge, and a rocky shoreline.

Find 5 Star Hotels in Sheffield, MA from $350

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Check availability on Sheffield 5 Star Hotels

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Sheffield 5-star hotels

A stone building with a wooden staircase and a garden with white flowers.
A wooden deck with a railing, a cushioned chair, and a small table with a bottle and glass.
A room with a hanging rattan chair, a wooden sofa, a small round table, and a ceiling fan. Large windows provide views of greenery outside.
A spacious hotel room with a large bed, a sitting area with a sofa and chairs, a dining table, and a kitchen area with cabinets and a coffee machine.

1. Troutbeck

Troutbeck
Amenia
United States
Charles
$710 nightly
$804 total
Oct 21 - Oct 22
Total with taxes and fees
Troutbeck
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Sheffield.
The White Hart

The White Hart

15 Under Mountain Rd Salisbury CT
$305 nightly
$350 total
Nov 15 - Nov 16
Total with taxes and fees
9.8/10 Exceptional! (155 reviews)
The White Hart
The Inn at Stockbridge

The Inn at Stockbridge

30 East Street Stockbridge MA
$383 nightly
$428 total
Nov 1 - Nov 2
Total with taxes and fees
9.6/10 Exceptional! (107 reviews)
The Inn at Stockbridge
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

26 Glendale Road, RR 183 Stockbridge MA
$393 nightly
$439 total
Nov 1 - Nov 2
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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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.

Learn more about Sheffield

Tucked in the Berkshires, this charming town offers scenic hikes at Bartholomew's Cobble and local art at the Sheffield Historical Society. Catch live performances at the Berkshire Theatre Festival in nearby Stockbridge or sample farm-fresh produce at the weekend farmers' market on the town green.

See all hotels in Sheffield
A lakeside town with autumn foliage, a bridge, and a rocky shoreline.

Top Sheffield Hotel Reviews

Find out more about Sheffield

You enjoy the finer things in life, both at home and on vacation. Treat your every whim on your next break. There's no reason to delay a getaway to Sheffield any longer. You'll join the multitudes of vacationers who have made Sheffield so fashionable recently. Besides that, you'll find that these hotels are kept in excellent condition and provide a fine place to lay your head at night. You deserve an outstanding getaway. Book one of Expedia's luxurious 5-star hotels in Sheffield and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Sheffield

Don't be afraid to live the high life while you're on vacation, along with the best conditions. High-end restaurants, concierges, and pillow-fluffing are all at the ready. You're sure to find exactly the accommodation you need. Not only that, the hotels in this area receive noteworthy marks for customer satisfaction, so you know you'll be looked after during your getaway. How do you want to relax? 24-hour room service, so you can order that chocolate soufflé© in the wee hours of the morning? A reflexology treatment that will leave you feeling refreshed and alive? Butler services? Whatever it is your heart desires, you're bound to find it here. Don't want to take our word for it? Plenty of visitors recommend this location.

You won't sleep and order room service the entire time, though. You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what you end up doing, the 5-star hotels in Sheffield are waiting for you to rest up after an exciting day.

Make Your Escape

The results are in, and Sheffield 5-star hotels are the place to be when you book your next vacation. These beautiful hotels are highly rated by the guests who stay in them, and you're about to join their ranks. Expedia can help you land a great deal on accommodation. Don't put off your dream vacation any longer. Select one of Expedia's Sheffield 5-star hotels today and relax in total tranquility tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Sheffield?
There are many different pricing options for 5-star hotels in Sheffield on Expedia. The amount you pay will depend on when you plan to travel, length of stay and other factors. Compare all of the available properties for your preferred dates and use our pricing and other filters to lock in the perfect upscale stay.
  • Search for the lowest price per night from $350
What makes a hotel 5 stars in Sheffield?
In Sheffield, a hotel must provide a certain level of upscale amenities to earn a 5-star rating. These may include on-site gyms, spas and saunas, gourmet restaurants, luxury bathroom products, premium bedding and more. What also sets 5-star hotels apart is their outstanding standard of service. You can expect things like in-room massages, concierge services and nightly turn-down services. Some may also offer special touches like welcome gifts.
Are there any 5-star all-inclusive resorts in Sheffield?
Expedia's filter tool is the quickest way to search for exactly what you're looking for. Select "5-star" and "All inclusive" to show the most luxurious hotels in Sheffield where your meals, lodging, entertainment and activities are included in the upfront price. At these escapes, your vacation is pure relaxation and indulgence from the moment you put down your suitcase.

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