Explore top 2026 4 Star Hotels in Ashuwillticook Rail Trail

Name: General Williams Estate House Lenox/Stockbridge
Rating: 9.8

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Top Ashuwillticook Rail Trail 4 Star hotels

The Williams Inn

101 Spring Street Williamstown MA

Fully refundableReserve now, pay when you stay

$186 nightly

$208 total

Mar 5 - Mar 6

Total with taxes and fees

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

9.6/10 Exceptional! (582 reviews)

nice aesthetics

Reviewed on Feb 24, 2026

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$102 nightly

$114 total

Mar 1 - Mar 2

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! (358 reviews)

Did not send check-in info via text, when I called they said they sent but never and resent, then gave me the wrong room. I booked double bed but got 1 king bed said double bed booking is not guaranteed and the rooms are sold out. However the worse part is the room is full of smoke smell so badly ...

Reviewed on Feb 21, 2026

South Shire

124 Elm St Bennington VT

A restaurant and a bar/lounge are featured at this inn. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, ...

9/10 Wonderful! (124 reviews)

Charming B&B style hotel in beautiful Bennington, VT.

Reviewed on Feb 27, 2026

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Lakehouse Inn

615 Laurel St. Lee MA

$139 nightly

$155 total

Mar 13 - Mar 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! (293 reviews)

It was perfect from the moment we walked in. Clean, hospitable and warm. Highly recommend

Reviewed on Feb 21, 2026

Devonfield Inn B&B

85 Stockbridge Rd. Lee MA

$329 nightly

$367 total

Mar 1 - Mar 2

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! (136 reviews)

Room was great, staff was awesome, amenities were cool

Reviewed on Feb 16, 2026

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, ...

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

26 Glendale Road, RR 183 Stockbridge MA

$335 nightly

$374 total

Mar 13 - Mar 14

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! (110 reviews)

It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!

Reviewed on Oct 27, 2025

The Four Chimneys Inn

21 West Road Bennington VT

$247 nightly

$270 total

Mar 15 - Mar 16

Total with taxes and fees

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 ...

9.4/10 Exceptional! (281 reviews)

This is a quintessential Vermont inn in beautiful historic Bennington. The inn was lovingly cared for by the owner who was very attentive to his guests. We will stay again.

Reviewed on Jan 12, 2026

33 Main

33 Main Street Lenox MA

$469 nightly

$524 total

Mar 5 - Mar 6

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 ...

10/10 Exceptional! (74 reviews)

Every point of contact I had at 33 Main was friendly, efficient, and accommodating. It’s evident Donna and her team run the inn with love. It’s clean and gorgeously furnished on the inside. You’ll recognize it from the outside, because it’s the most charmingly decorated on the block. I stayed in ...

Reviewed on Oct 24, 2025

General Williams Estate House Lenox/Stockbridge

Stockbridge MA

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

9.8/10 Exceptional! (115 reviews)

Very good location. Home was quite nice.

Reviewed on Jan 19, 2026

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4 Star Hotels Ashuwillticook Rail Trail

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 Ashuwillticook Rail Trail 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 Ashuwillticook Rail Trail 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 Ashuwillticook Rail Trail, 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.