Explore top 2025 4 Star Hotels in Ashuwillticook Rail Trail

Name: General Williams Estate House Lenox/Stockbridge
Address: Stockbridge

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Top Ashuwillticook Rail Trail 4 Star hotels

The Williams Inn

101 Spring Street, Williamstown, MA

$197 nightly

$220 total

Nov 17 - Nov 18

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! (532 reviews)

Didn’t have the breakfast. Only drawback was the beds. Mattresses made our backs hurt.

Reviewed on Oct 31, 2025

The Central Downtown Inn & Suites

20 W Housatonic St., Pittsfield, MA

$107 nightly

$120 total

Nov 6 - Nov 7

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! (338 reviews)

Very helpful staff, clean and spacious rooms. Has everything you need - well equipped.

Reviewed on Nov 3, 2025

Lakehouse Inn

615 Laurel St., Lee, MA

$170 nightly

$189 total

Nov 6 - Nov 7

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! (287 reviews)

A charming inn in the center of the Berkshires.

Reviewed on Oct 29, 2025

South Shire

124 Elm St, Bennington, VT

Fully refundableReserve now, pay when you stay

$164 nightly

$180 total

Dec 6 - Dec 7

Total with taxes and fees

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! (116 reviews)

The house is a beautiful New England structure with a variety of rooms to choose from. Our room, the Gold room was luxurious and spacious with great light during the day. The "private bath" is across the hall requiring proper dress to exit the room and enter the bathroom. It's a small point but different ...

Reviewed on Nov 2, 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 18 - Nov 19

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! (84 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

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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The Four Chimneys Inn

21 West Road, Bennington, VT

$249 nightly

$271 total

Dec 3 - Dec 4

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 ...

9.6/10 Exceptional! (222 reviews)

This is a beautiful, historic property and pretty consistent with the photos on the website. The room I had was just as pretty with some antique furnishings, but of course in person you notice that it is an old building. The room was a great size, and I loved the hardwood floors. The bathroom was ...

Reviewed on Sep 2, 2025

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

$369 nightly

$412 total

Nov 21 - Nov 22

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! (133 reviews)

Great place!!!

Reviewed on Oct 12, 2025

The Inn at Stockbridge

30 East Street, Lee, MA

$289 nightly

$322 total

Nov 9 - Nov 10

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

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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.