Explore top 2025 4 Star Hotels in Old Chatham

Name: Hampton Terrace Inn
Price range: $331 total

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Top Old Chatham 4 Star hotels

The Wick, Hudson, A Tribute Portfolio Hotel

41 Cross Street, Hudson, NY

Fully refundableReserve now, pay when you stay

$203 nightly

$229 total

Nov 2 - Nov 3

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and ...

8.6/10 Excellent! (538 reviews)

Pretty good - nice location

It’s decent - a marriot - cool vibe, nice room, however the hallway seemed a bit rundown, carpet slightly musty, doesn’t look as new and fresh as in the pictures but still a decent stay for the cost

Reviewed on Sep 15, 2025

The Central Downtown Inn & Suites

20 W Housatonic St., Pittsfield, MA

$102 nightly

$114 total

Nov 2 - Nov 3

Total with taxes and fees

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, express check-in, and express check-out are also on ...

8.6/10 Excellent! (330 reviews)

Building is old but in good condition. Very clean. Maybe under new owners because our door combination etc was written on a sticky note but once we found someone to check us in they were friendly and helpful

Reviewed on Oct 21, 2025

Lakehouse Inn

615 Laurel St., Lee, MA

$191 nightly

$213 total

Nov 13 - Nov 14

Total with taxes and fees

This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free full breakfast each morning. A terrace, a snack bar/deli, and a ...

9.6/10 Exceptional! (285 reviews)

Lovely setting on a lake. Friendly staff. Nice breakfast. Peaceful

Reviewed on Oct 6, 2025

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

26 Glendale Road, RR 183, Stockbridge, MA

$335 nightly

$374 total

Nov 9 - Nov 10

Total with taxes and fees

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast ...

9.2/10 Wonderful! (83 reviews)

My husband and I thoroughly enjoyed our stay at the Stockbridge Inn. Diane, the owner, greeted us warmly and escorted us to our room. Our accommodations were comfortable, warm and spacious and quiet enough for us to have a good night sleep. Diane was very helpful in recommending other accommodations ...

Reviewed on Oct 12, 2025

Seven Hills Inn

40 Plunkett Street, Lenox, MA

This hotel features free WiFi in public areas, concierge services, and free self parking. Enjoy the free on-the-go breakfast each morning. A terrace, a garden, ...

Great breakfast, amazing property, comfortable beds! Water in shower wasn’t hot, had to take a “warm-cold” fast shower but it didn’t matter. The view, the quiet, nature and siting areas made the stay perfect. Will come again!!

Reviewed on Oct 30, 2023

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General Williams Estate House Lenox/Stockbridge

Stockbridge

This vacation home features a garden, laundry facilities, and barbecue grills.

Great Place!

This was a great place to house our family of 12 during the weekend of our daughter’s wedding. There was plenty of space for everyone to gather. The beds were comfortable and all the bedrooms upstairs had their own bathroom - so nice! The house made our weekend extra special. Definitely ...

Reviewed on Nov 19, 2022

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Devonfield Inn B&B

85 Stockbridge Rd., Lee, MA

$379 nightly

$423 total

Nov 4 - Nov 5

Total with taxes and fees

An outdoor pool, free self parking, and concierge services are featured at this bed & breakfast. Guests will appreciate free perks like full breakfast and WiFi ...

9.8/10 Exceptional! (132 reviews)

Great place!!!

Reviewed on Oct 12, 2025

The Inn at Stockbridge

30 East Street, Lee, MA

$364 nightly

$407 total

Nov 2 - Nov 3

Total with taxes and fees

This bed & breakfast features an outdoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, ...

9.6/10 Exceptional! (98 reviews)

We we were in the Out of Africa room, set apart in a complex of 4 suites in a unit apart from the Inn itself. The room was uniquely created to feel like an escape to Africa, and heated by a lovely gas fireplace. The breakfast both mornings, delicious. A perfect getaway!

Reviewed on Feb 18, 2025

Hampton Terrace Inn

91 Walker Street, Lenox, MA

$296 nightly

$331 total

Nov 7 - Nov 8

Total with taxes and fees

This hotel features an outdoor tennis court and a seasonal outdoor pool. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free ...

Beautiful historic house in a great location. Responsive owner. Great visit!

Reviewed on May 21, 2022

33 Main

33 Main Street, Lenox, MA

$445 nightly

$498 total

Nov 23 - Nov 24

Total with taxes and fees

This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free full breakfast each morning. A lobby fireplace, a communal living ...

9.8/10 Exceptional! (73 reviews)

Beautiful place. Wonderful owner and staff. Our stay there was a total delight.

Reviewed on Oct 15, 2025

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4 Star Hotels Old Chatham

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Old Chatham 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Old Chatham will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Old Chatham, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.