Cherry Plain Vacations from $577

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The Latest Cherry Plain vacation packages

Price found within the past 48 hours. Click for updated prices.
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Price was $835, price is now $577 per person
$577
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
No reviews
Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,148, price is now $722 per person
$722
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.6/10 Exceptional! (4 reviews)
I had an absolutely amazing time here, it is even more beautiful than the pictures. Where do I begin! Right from the start we were greeted by welcoming staff who gave us a tour of the property on a golf cart as we reached our cabin. Golf carts are offered and easily available for a lift to anywhere within the property that you’d like. The shower pressure was perfect and hot as well. Our cabin was curated to feel cozy and came equipped with beach chairs, umbrellas and beach towels. The saunas and locker rooms were beautifully made. We enjoyed spending timing at the lake going kayaking as well and then sitting at the fire pit to star gaze. We also enjoyed playing pickleball/tennis at the court. My only quip would be that the pool water is still quite cool despite being heated. The whole property is an experience in itself. You can tell it was produced with a lot of meticulous attention to detail. I am already dreaming of when I can come back here!

Reviewed on Sep 27, 2025

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $965, price is now $619 per person
$619
per person
Nov 20 - Nov 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9/10 Wonderful! (1,003 reviews)
Very friendly staff.

Reviewed on Oct 6, 2025

Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

3 out of 5
Save 100% on your flight
Price was $3,245, price is now $2,335 per person
$2,335
per person
Nov 20 - Nov 26
found 1 day ago
Roundtrip flight included
New York (NYC) 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
Save 100% on your flight
Price was $1,422, price is now $1,079 per person
$1,079
per person
Nov 20 - Nov 26
found 1 day ago
Roundtrip flight included
New York (NYC) 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
$112 nightly
The price is $125 total per night from Oct 30 to Oct 31
$125 total
Oct 30 - Oct 31
Total with taxes and fees
8.6/10 Excellent! (2,049 reviews)
Check-in Needs Improvement
"Why have an on-line pre-check process if you have to wait in a long line when you arrive. Need to have separate line(s) for those who pre-check."

Reviewed on Oct 11, 2025

Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $146 total per night from Nov 13 to Nov 14
$146 total
Nov 13 - Nov 14
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
"Super friendly staff, a free coffee bar in the lobby, loads of food and shopping options within walking distance, free on-site parking - what’s not to love! And the room was spotlessly clean and very very comfortable. We love this place!!!"

Reviewed on Oct 9, 2025

Hotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
$113 nightly
The price is $126 total per night from Nov 2 to Nov 3
$126 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (695 reviews)
"We stayed twice in the same week. The first room was great - no issues. The second stay (different room/different floor) seemed dated. Shower head was bad - so strong the tub filled. Moisture issues on the walls - walls peeling in bathroom, cracks in the sink around the bathroom sink drain. Crumbs ..."

Reviewed on Oct 12, 2025

Berkshire Mountain Lodge
See all 676 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.

Cherry Plain Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Albany Intl. Airport (ALB)

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Frequently asked questions

How much does a Cherry Plain vacation package cost?
You can grab a vacation package to this destination from $577 on Expedia. But how much your vacation to Cherry Plain costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Cherry Plain?
November, December and January are great times to look for cheap Cherry Plain vacation packages. Choosing to travel in less busy months means you can generally find reduced prices on hotels and flights.
How many days is enough for Cherry Plain?
The ideal length of your Cherry Plain vacation depends on what you'd like to see and do. Generally, a few days to a week will give you time to tick off all the leading sights and discover some hidden treasures along the way.
How to find the best Cherry Plain package deals?
Start your search for a Cherry Plain package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Cherry Plain package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Cherry Plain getaway off to a flying start.
Is it cheaper to book a Cherry Plain vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Cherry Plain vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Cherry Plain?
If you've got your Cherry Plain travel dates locked in, book as soon as you can to grab some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Cherry Plain?

  1. Pick your travel dates: The things you want to do in Cherry Plain and your preferred season will help you decide when to get away.
  2. Set your budget: Consider costs such as flights, food and transportation when calculating how much to save for your trip to Cherry Plain. Then, choose a property that works with your budget, whether that's a low-cost option or a swankier retreat.
  3. Use Expedia's trip planning tool to discover Cherry Plain: Research every part of your trip to Cherry Plain with this handy planner. Invite your family and friends to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Decide your trip length: Think about how much time you want to spend discovering Cherry Plain. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  5. Combine your airfare and accommodations: Once you've nailed down your trip dates and duration, lock in the ideal Cherry Plain vacation package for you.
  6. Book experiences or activities in advance: Whether it's entrance to a major attraction or a walking tour, you won't have to worry about missing out on the highlights of Cherry Plain. Find all the fun things to do in Cherry Plain with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Cherry Plain vacation packages?
Set off on your ideal getaway to Cherry Plain with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or hold off until payday — we've partnered with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stay on budget and snap up cheap deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.