Name: Hotel Downstreet, an Ascend Collection Hotel
Price range: $120 total
Rating: 8.6

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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.

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

Save 100% on your flight

$492

per person

Jan 16 - Jan 19

found 1 day ago

Roundtrip flight included

Tampa (TPA) to Albany (ALB)

18.4/10 Exceptional! (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

Wilder House Berkshires

Save 100% on your flight

$530

per person

Jan 16 - Jan 19

found 1 day ago

Roundtrip flight included

Tampa (TPA) to Albany (ALB)

19.6/10 Exceptional! (38 reviews)

Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you!

Reviewed on Nov 10, 2025

The Equinox Golf Resort & Spa

$605

per person

Jan 7 - Jan 10

found 3 hours ago

Roundtrip non-stop flight included

New York (JFK) to Albany (ALB)

14.8/10 Exceptional! (567 reviews)

We feel that the resort fee to access the pool and hot tub as well as the other services covered are over priced. We stay at resorts and hotels all over the US and you are the ONlY place that charges for this.

Reviewed on Nov 21, 2025

Pocketbook Hotel and Bath

$520

per person

Dec 26 - Dec 28

found 23 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

17.6/10 Exceptional! (3 reviews)

The room was nice and clean, but the hotel itself was still under construction and it took 45 minutes for us to get in our room for check-in I was able to ask for extended check out and we got two complementary drinks from the bar but overall they should have waited to open

Reviewed on Nov 12, 2025

Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House

Save 100% on your flight

$791

per person

Jan 16 - Jan 19

found 1 day ago

Roundtrip flight included

Tampa (TPA) to Albany (ALB)

12/10 Exceptional! (1 review)

The location of the house was very near for food and supplies,yet very private. The inside was very clean and well kept. We enjoyed the quietness and surrounding grounds with views of local wild life. The things that we did not like was the musty - moldy smell when we first got there. Every time you used the water it smelled. Red light on fridge for changing filter. Bought spring water to use for drinking, coffee, and cooking. All reported to host upon departure.

Reviewed on Aug 23, 2025

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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

Springfield showing heritage architecture

Metro Center

2 out of top 10 points of interest in this area

3.5/5(242 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.

Discover the most popular places to visit in Western Massachusetts

Hancock which includes signage and autumn leaves

Jiminy Peak Mountain Resort

4.5/5(98 reviews)

Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this family-friendly area.

Great bar and restaurant in a great area in Venice. Bar in front, restaurant tables al fresco in back; very cool. Good food, and hand crafted cocktails by a talented and enthusiastic staff.

University of Massachusetts Amherst

4.5/5(255 reviews)

Enjoy the collegiate vibe when you visit University of Massachusetts Amherst, during your travels in Amherst. Experience the area's live music or attend a sporting event.

A road near Tanglewood. Driving through the Berkshires is never a disappointing #roadtrip

Tanglewood Music Center

5/5(150 reviews)

You can get tickets for a performance at Tanglewood Music Center during your trip to Lenox. While you're in the area, stroll along the lakeside.

Western Massachusetts Hotel Deals

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Fully refundableReserve now, pay when you stay

$94 nightly

$105 total

Nov 25 - Nov 26

Total with taxes and fees

8.6/10 Excellent! (2,145 reviews)

Nice place to stay, off season. Price was very reasonable. Room was comfortable, (1st floor, Building 5), entire building was very quiet, hardly anyone on the property. Nice amenities, but we only walked through, did not use (pool, locker rooms, hot tub, fire pit). Room was nicely appointed and comfortable. ...

Reviewed on Nov 22, 2025

MGM Springfield

One MGM Way Springfield MA

$155 nightly

$176 total

Nov 25 - Nov 26

Total with taxes and fees

8.8/10 Excellent! (1,440 reviews)

Room is very clean just need to be safe if you decide to trace outside the hotel. Not the best area

Reviewed on Nov 18, 2025

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Fully refundable

$107 nightly

$120 total

Dec 20 - Dec 21

Total with taxes and fees

8.6/10 Excellent! (1,003 reviews)

Very clean and inviting Hotel located in downtown area. Very walkable area. Parking was free. Front desk very friendly and helpful. Would stay again.

Reviewed on Nov 3, 2025

See all 1,478 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.