Cherry Plain Vacation Packages

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Top Cherry Plain Vacation Deals

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

The Wiltwyck

3.5 out of 5
Price was CA $1,441, price is now CA $1,107 per person
CA $1,107
per person
Sep 26 - Oct 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
9.4/10 Exceptional! (153 reviews)
Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was CA $2,197, price is now CA $1,276 per person
CA $1,276
per person
Sep 26 - Oct 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
9/10 Wonderful! (2 reviews)
Prospect was a wonderful stay with very friendly staff. The property is very well maintained. We had a great time with the all the lake activities. Would definitely recommend for a quick getaway

Reviewed on Jun. 23, 2025

Hasbrouck House

Hasbrouck House

4 out of 5
Price was CA $2,679, price is now CA $1,938 per person
CA $1,938
per person
Sep 26 - Oct 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
9.2/10 Wonderful! (47 reviews)
Great getaway property. We checked in for two nights, and stayed in a building with kitchen/2 bedrooms, which was great for our needs. We spent time in the property relaxing at the beautiful pool, sauna, and had a fabulous dinner at Butterfield. Played some shuffleboard, pool and video games in their clubhouse - very laid back vibe and perfect for a couples weekend. Great food options off property in the area, and my partner was able to get in a quick nine-hole game of golf at a nearby course.

Reviewed on Aug. 6, 2025

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

3 out of 5
Price was CA $1,877, price is now CA $1,490 per person
CA $1,490
per person
Sep 26 - Oct 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
No reviews
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3 out of 5
Price was CA $3,561, price is now CA $2,995 per person
CA $2,995
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
No reviews

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Cherry Plain Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Sep 11 to Sep 12
CA $147
CA $180 total
Sep 11 - Sep 12
includes taxes & fees
8.6/10 Excellent! (1,961 reviews)
"The property was nice and had activities like a volley ball net and basketball court however no balls were provided. All together the property was very nice but had potential to be nicer. Also daytime front desk staff were not very helpful and actually cranky sounding. Not so pleasant to deal ..."

Reviewed on Aug. 20, 2025

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 $106 per night from Sep 7 to Sep 8
CA $106
CA $149 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (583 reviews)
Satisfied customer
"as good as the last time we stayed there."

Reviewed on Aug. 21, 2025

Berkshire Mountain Lodge
Best Western Plus Franklin Square Inn Troy/Albany

Best Western Plus Franklin Square Inn Troy/Albany

2.5 out of 5
One Fourth Street, Troy, NY
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Aug 31 to Sep 1
CA $193
CA $215 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"It was clean, staff was friendly and accommodating. Breakfast was versatile."

Reviewed on Aug. 23, 2025

Best Western Plus Franklin Square Inn Troy/Albany
See all 652 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 $1,107. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.