Cherry Plain Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Cherry Plain Vacation Deals

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

Valley Craft Ales

2 out of 5
Price was CA $1,136, price is now CA $1,109 per person
CA $1,109
per person
Sep 18 - Sep 21
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
8.4/10 Very good! (225 reviews)
The staff was very helpful! Great restaurant with great pizza! Easy to get to and easy parking. I would definitely stay at Valley Craft Ales again!

Reviewed on Jun 29, 2026

The White House Inn

The White House Inn

3.5 out of 5
Price was CA $1,469, price is now CA $1,342 per person
CA $1,342
per person
Sep 18 - Sep 21
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
9.2/10 Wonderful! (328 reviews)
Beautiful historical inn with so much charm and friendly staff.

Reviewed on Jun 30, 2026

Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was CA $1,571, price is now CA $1,449 per person
CA $1,449
per person
Sep 18 - Sep 21
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
9.2/10 Wonderful! (16 reviews)
The cabin and grounds are well-maintained. The pool was crystal clear and the slide was a nice addition. Gorgeous views!

Reviewed on Jun 28, 2026

Knotty Pine

Knotty Pine

2.5 out of 5
Price was CA $1,257, price is now CA $1,213 per person
CA $1,213
per person
Sep 18 - Sep 21
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
8.6/10 Excellent! (108 reviews)
The property was a retro experience, which was okay. A few issues: 1. The electrical outlets didn't work well - we plugged a couple of devices overnight and they weren't charged at all by morning. The multi-plug extender provided connections that were too loose to work. 2. The sink was very small (about 8.5 x 11) with a cabinet overhang. It was difficult to impossible to position your mouth over the sink while brushing your teeth. 3. I wanted to lower the temperature in the shower and mistakenly moved the lever an inch in the wrong direction, which resulted in scalding hot water. Had to be very careful after that. That being said, the location was convenient and we slept well.

Reviewed on Jun 29, 2026

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
Price was CA $1,282, price is now CA $1,254 per person
CA $1,254
per person
Sep 18 - Sep 21
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
8.2/10 Very good! (1,000 reviews)
Friendly staff, pet friendly, breakfast is very basic and did not have fruits.

Reviewed on Jun 28, 2026

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Cherry Plain Hotel Deals

The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
The price is CA $203 per night from Jul 6 to Jul 7
CA $203
CA $227 total
Jul 6 - Jul 7
includes taxes & fees
9.2/10 Wonderful! (1,011 reviews)
"The friendly atmosphere coming from the staff."

Reviewed on Jun 30, 2026

The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
The price is CA $169 per night from Jul 14 to Jul 15
CA $169
CA $204 total
Jul 14 - Jul 15
includes taxes & fees
8.8/10 Excellent! (2,412 reviews)
"Staff was super friendly, splash pad was being renovated so that wasn’t available m.. we had fun but hate that check in is so late and check out so early!"

Reviewed on Jun 30, 2026

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from Jul 30 to Jul 31
CA $199
CA $254 total
Jul 30 - Jul 31
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"Rooms were clean, parking easy, staff very helpful"

Reviewed on Jul 1, 2026

Berkshire Mountain Lodge
See all 626 properties in Cherry Plain
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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Frequently asked questions

How much does a Cherry Plain vacation package cost?
Get your credit card ready, because a getaway to Cherry Plain starts from an affordable CA $1,109. When you bundle your flights, hotels and more into a package, you'll walk away with the biggest deals.
How do I get a cheap travel package to Cherry Plain?
Combine your flight and hotel bookings, add extras such as activities or a rental car, and save with a Cherry Plain vacation package. You won't just pick up big discounts on your getaway — you'll have plenty of choice too. When you book through Expedia, you can choose from more than 550 air carriers and 1,000,000 hotels around the world. Your next affordable adventure starts right here, right now!
How far in advance should I book my Cherry Plain vacation?
While not all air carriers release tickets early, customers are usually able to compare international flights on Expedia up to a year in advance. This is when you can score some fantastic bargains. If you're booking last minute, there's a chance you could get lucky. Low prices sometimes emerge just weeks before departure.
What does an Expedia Cherry Plain travel package include?
It all depends on what sort of escape you're planning. Cherry Plain vacation deals can include flights, car rentals and hotels. You can mix and match to find the bundle that suits your style and budget. You can also add on experiences and activities after you've booked to get even bigger discounts.
What should I know before booking a Cherry Plain travel package?
Our prices are always low. However, you'll enjoy even more savings when you book your hotels, flights and car rentals together. With an Expedia package, you'll get transparent pricing and loads of choice.
Can I choose my airline with a Cherry Plain Expedia vacation package?
Expedia offers access to more than 550 airline partners globally, so you definitely can. Just select the airline you want and create the perfect Cherry Plain getaway.
If I'm not able to travel, can I cancel my Cherry Plain vacation package?
If your vacation plans in Cherry Plain have been upended, it's comforting to know that you can cancel or amend your booking. If you booked within the last 24 hours, you may be eligible for a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose a cancellation fee. To learn more, visit our Customer Service Portal.

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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.