Name: The Yankee Inn
Price range: $169 total
Rating: 9.2

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Your Western Massachusetts Vacation

With a Western Massachusetts vacation package, you can forget about the stress of planning and simply focus on experiencing everything this exciting destination has to offer. Start your trip to Western Massachusetts with a couple of days in Springfield visiting popular sights like Six Flags New England and MGM Springfield. Lenox is another top city that lures crowds from far and wide. National Shrine of the Divine Mercy and Norman Rockwell Museum are two of the top places to see in this destination. Whether you're planning to travel for a week or a month, Expedia are here to help you customize your next dream Western Massachusetts vacation.

The Latest Western Massachusetts vacation packages

Price found within the past 48 hours. Click for updated prices.

Hideaway Inn Lenox

Save 100% on your flight

$546

per person

Sep 24 - Sep 27

found 24 hours ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Albany (ALB)

8/10 Very Good! (11 reviews)

Very pet friendly. Beautiful rooms. Great staff yard activities and common rooms have music and games coffee and fresh water. Close to town stores. Very friendly and welcoming community we enjoyed the sumner festival and food. Our car broke down and the Lennox police department was excellent in helping us. I recommend this quaint .cozy Beautiful hideaway and town i feel refreshed and relaxed.

Reviewed on Jul 10, 2026

The Cornell Inn, Lenox & The Berkshires

Save 100% on your flight

$586

per person

Sep 24 - Sep 27

found 24 hours ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Albany (ALB)

9.2/10 Wonderful! (1,002 reviews)

We felt warmly welcomed by the staff. Our room was lovely with the exception of being located at the front of the house. We could hear the traffic. The breakfast was delicious and freshly prepared. The woman serving us was very nice and efficient. We enjoyed our stay.

Reviewed on Jul 6, 2026

Lodges At Cresthaven

Save 100% on your flight

$2,177

per person

Aug 20 - Aug 25

just found

Roundtrip flight included

Denver (DEN) to Albany (ALB)

9.4/10 Exceptional! (616 reviews)

what a beautiful and special place! Theres a fantastic pool for kids/family overlooking the beautiful lake. I wish we were able to stay longer. It was really one of the most beautiful places I have stayed. The Cabin lodging, the rooms, the bathrooms, everything was just great! Check out is at 10am, I wish it was maybe till noon for what you pay for but I understand because the cabins need to be cleaned. It was great!

Reviewed on Jul 9, 2026

Prospect Berkshires

Save 100% on your flight

$1,003

per person

Sep 24 - Sep 27

found 24 hours ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Albany (ALB)

9.8/10 Exceptional! (31 reviews)

My husband and in laws each rented a cabin for a weekend. The property is beautiful, amenities are impressive, and the food is excellent! We enjoyed spending time by the pool reading (excellent book selection in the lobby,) relaxing in the dry saunas, kayaking on the lake, Sunday yoga and the peace of the guided evening float. Prospect Berkshires is incredibly curated from the moment you get out of your car. This was my second stay and will not be my last!

Reviewed on Jul 1, 2026

The Perch Hotel

Save 100% on your flight

$916

per person

Aug 13 - Aug 17

found 9 hours ago

Roundtrip flight included

Atlanta (ATL) to Albany (ALB)

9.6/10 Exceptional! (32 reviews)

Check in information was provided via email the day of check in. I was able to enter the hotel and my room without a problem. The hotel staff was responsive and helpful via text messages. The inside of our room was very comfortable, the staff left a few complementary drinks and snack in the room for us which was very much appreciated. The room had a home feeling to it which made for a comfortable stay. The location was safe, quiet and had lovely mountain side views. This location was close to many popular hiking spots in the area we had a lot of fun.

Reviewed on Jun 3, 2026

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Where to stay in Western Massachusetts

Find the best Western Massachusetts areas and neighborhoods for the activities you enjoy most. Learn more about Western Massachusetts

A river with a bridge, a large dome-shaped building, and a cityscape with various buildings and roads.

Metro Center

2 out of top 10 points of interest in this area

3.5/5(246 area reviews)

Explore Springfield Armory National Park, Quadrangle museums, and enjoy over 70 clubs, bars, and restaurants in the Club Quarter. Exceptionally walkable, with easy access to I-91, I-291, and Union Station.

Stay near popular Western Massachusetts attractions

A roller coaster at an amusement park with a clear sky.

Six Flags New England

8.4/10 (599 reviews)

New England's largest amusement park thrills with 11 roller coasters, including the top-rated Superman The Ride. Experience heart-pounding drops on Wicked Cyclone, or cool off at Hurricane Harbor water park.

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Western Massachusetts Hotel Deals

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Fully refundableReserve now, pay when you stay

$143 nightly

$159 total

Jul 12 - Jul 13

Total with taxes and fees

8.8/10 Excellent! (2,430 reviews)

"Very nice room and facility"

Reviewed on Jul 9, 2026

MGM Springfield

One MGM Way Springfield MA

$195 nightly

$221 total

Aug 3 - Aug 4

Total with taxes and fees

9/10 Wonderful! (1,557 reviews)

"Excellent casino and good place"

Reviewed on Jul 9, 2026

The Yankee Inn

461 Pittsfield Rd Lenox MA

Fully refundableReserve now, pay when you stay

$151 nightly

$169 total

Jul 12 - Jul 13

Total with taxes and fees

9.2/10 Wonderful! (1,012 reviews)

"Front desk staff was very accommodating. She was kind to let us check in as soon as rooms were cleaned. We traveled from California and were very sleepy and that made our stay more enjoyable."

Reviewed on Jul 10, 2026

See all 1,518 properties in Western Massachusetts

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.