Stockbridge Vacation Packages

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Your Stockbridge Vacation

With a Stockbridge vacation package, say goodbye to endless planning and hello to hassle-free adventure. Every detail of your escape has been taken care of before departing, so you can make the most of your time experiencing this lively city. Eager to venture out and explore? Tanglewood Music Center, National Shrine of the Divine Mercy and Lee Premium Outlets are three of the best places to visit during your trip to Stockbridge. Your perfect Stockbridge vacation is a couple of clicks away. Browse hotels, airfares and more on Expedia for a getaway that's tailored just for you.

Top Stockbridge Vacation Deals

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

The Yankee Inn

2.5 out of 5
Price was CA $1,202, price is now CA $1,005 per person
CA $1,005
per person
Jun 13 - Jun 20
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (1,003 reviews)
My partner and I just moved back to MA so we are local to the area. We have stayed there just to have an evening of respite together and solo and send our family there during holidaze! Very friendly staff, comfortable rooms, prime location, and breezy breakfast options.

Reviewed on May 8, 2026

Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was CA $4,161, price is now CA $3,295 per person
CA $3,295
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
9.4/10 Exceptional! (579 reviews)
Nice place, peaceful & quiet.

Reviewed on May 6, 2026

Hilton Garden Inn Saratoga Springs

Hilton Garden Inn Saratoga Springs

3 out of 5
Price was CA $2,072, price is now CA $1,787 per person
CA $1,787
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
8/10 Very Good! (1,003 reviews)
The room was bright, clean, and very comfortable. The staff checked in each morning to see if I needed fresh towels or housekeeping, which I appreciated. The hotel was conveniently located near several coffee shops and only about a five-minute drive to the town’s Main Street with plenty of restaurants and bars. Parking was easy and convenient, and the WiFi worked reliably for both my laptop and cellphone throughout my stay.

Reviewed on May 11, 2026

Sundowner on Lake George

Sundowner on Lake George

2.5 out of 5
Price was CA $2,102, price is now CA $1,845 per person
CA $1,845
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
7.6/10 Good! (248 reviews)
The place was nice and clean with plenty of room for 2 couples

Reviewed on Mar 1, 2026

The Lake George Inn

The Lake George Inn

2 out of 5
Price was CA $1,698, price is now CA $1,495 per person
CA $1,495
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
5.6/10 (8 reviews)
No soap, no shampoo.

Reviewed on Oct 12, 2025

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Stockbridge Hotel Deals

The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from May 18 to May 19
CA $197
CA $281 total
May 18 - May 19
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
Lovely and historic property. Friendly staff and very comfortable room. Dinner and breakfast were wonderful. We are repeat visitors.

Reviewed on May 11, 2026

The Red Lion Inn
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
The price is CA $423 per night from May 25 to May 26
CA $423
CA $512 total
May 25 - May 26
includes taxes & fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Spacious Living, Covered Porch & Forest Setting | Beaver Creek by AvantStay

Spacious Living, Covered Porch & Forest Setting | Beaver Creek by AvantStay

Stockbridge MA
9.6/10 Exceptional! (4 reviews)
The house is large with great space inside and out. The beds and pillows were comfortable and the kitchen is functional. The location in between Stockbridge and Lenox was great. Cons: ladybug infestation upstairs was pretty disgusting, the dishwasher is in an odd location, and 2 of the doors accessible ...

Reviewed on Apr 13, 2026

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Spacious Living, Covered Porch & Forest Setting | Beaver Creek by AvantStay
See all 1,378 properties in Stockbridge
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.
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Discover the most popular places to visit in Stockbridge

Norman Rockwell Museum

Norman Rockwell Museum

4.5/5(6 reviews)

You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.

Norman Rockwell Museum

National Shrine of the Divine Mercy

5/5(1 review)

Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.

National Shrine of the Divine Mercy

Naumkeag Museum

You can spend time browsing the exhibits at Naumkeag Museum during your travels in Stockbridge. While you're in the area, stroll along the lakeside.

Naumkeag Museum

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.