Explore top 2026 4 Star Hotels in Old Chatham

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Top Old Chatham 4 Star hotels

The Wick, Hudson, A Tribute Portfolio Hotel

The Wick, Hudson, A Tribute Portfolio Hotel

4 out of 5
41 Cross Street Hudson NY
Fully refundableReserve now, pay when you stay
$224 nightly
The price is $253 total per night from Sep 14 to Sep 15
$253 total
Sep 14 - Sep 15
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 and free WiFi in public areas. ...
Opens in a new windowThe Wick, Hudson, A Tribute Portfolio Hotel
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St. Pittsfield MA
$99 nightly
The price is $111 total per night from Aug 31 to Sep 1
$111 total
Aug 31 - Sep 1
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 ...
8.4/10 Very Good! (399 reviews)
"ok"

Reviewed on Aug 29, 2026

Opens in a new windowThe Central Downtown Inn & Suites
The Inn at Stockbridge

The Inn at Stockbridge

4 out of 5
30 East Street Stockbridge MA
$396 nightly
The price is $442 total per night from Sep 13 to Sep 14
$442 total
Sep 13 - Sep 14
Total with taxes and fees
This bed & breakfast features a 24-hour gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free ...
9.8/10 Exceptional! (104 reviews)
"The property and grounds are beautiful and perfectly appointed. The staff are friendly and accommodating. The room was very comfortable. The gym is small but was very functional for our purposes and we appreciated having it available. The pool is beautiful but sadly we were unable to use it as it ..."

Reviewed on Aug 25, 2026

Opens in a new windowThe 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

4.5 out of 5
26 Glendale Road, RR 183 Stockbridge MA
$358 nightly
The price is $399 total per night from Sep 28 to Sep 29
$399 total
Sep 28 - Sep 29
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! (116 reviews)
"My stay at Diane’s bed and breakfast was absolutely wonderful. Diane herself is incredibly warm, welcoming, and genuinely informative — she made the entire experience feel personal and cared for. The room was quaint, cozy, and charming in that classic New England way, with comfortable beds, plenty ..."

Reviewed on Aug 21, 2026

Opens in a new windowThe Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Seven Hills Inn

Seven Hills Inn

4 out of 5
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, ...
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Opens in a new windowSeven Hills Inn
33 Main

33 Main

4 out of 5
33 Main Street Lenox MA
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 ...
10/10 Exceptional! (76 reviews)
"This was our second stay at 33 Main. Wonderfully maintain, homey environment, with friendly, welcoming and helpful staff. Welcoming cookies, and beautiful water bottle. They even remembered that we asked for the beach and gave us excellent recommendation. Convenient parking in the back. My only suggestion ..."

Reviewed on Jul 27, 2026

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Opens in a new window33 Main
Hampton Terrace Inn

Hampton Terrace Inn

4 out of 5
91 Walker Street Lenox MA
$233 nightly
The price is $260 total per night from Sep 21 to Sep 22
$260 total
Sep 21 - Sep 22
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 ...
9/10 Wonderful! (44 reviews)
"Hot tub in the cottage was wonderful. The provided guide was very comprehensive and we appreciated all the amenities available in the main and carriage house."

Reviewed on Mar 3, 2026

Opens in a new windowHampton Terrace Inn
Lakehouse Inn

Lakehouse Inn

4 out of 5
615 Laurel St. Lee MA
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! (303 reviews)
"Our stay at the Lakehouse was fabulous--even though a cold and rainy weekend in May. I want to return to be able to take advantage of the kayaks on the beautiful Lake Laurel! Everything was perfect: lovely room, delicious breakfast, great location near Melville's house at Pittsfield and the Hancock ..."

Reviewed on Jun 22, 2026

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Opens in a new windowLakehouse Inn
Devonfield Inn B&B

Devonfield Inn B&B

4 out of 5
85 Stockbridge Rd. Lee MA
$389 nightly
The price is $435 total per night from Sep 3 to Sep 4
$435 total
Sep 3 - Sep 4
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 ...
10/10 Exceptional! (140 reviews)
"The owners are so nice!!! Tha property is beautiful and the people that play the piano and sing during the day is the most relaxing and incredible experience!!!!"

Reviewed on Aug 4, 2026

Opens in a new windowDevonfield Inn B&B
Family-friendly Hancock Home: Walk to Slopes!

Family-friendly Hancock Home: Walk to Slopes!

4 out of 5
Hancock MA
This apartment doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the arcade/game room and barbecue grills. ...
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Opens in a new windowFamily-friendly Hancock Home: Walk to Slopes!
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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.

Recent Old Chatham hotel reviews by fellow wanderers

Albany Plaza Hotel

Albany Plaza Hotel

4 out of 5
Posted less than an hour ago
Travelocity Verified Review
"I was satisfied with the room. Breakfast is very modest."
A verified traveler stayed at Albany Plaza Hotel
Albany Plaza Hotel

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