Cherry Plain Vacations from $663

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The Latest Cherry Plain vacation packages

Price found within the past 48 hours. Click for updated prices.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
per person
Sep 21 - Sep 26
found 19 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
8.8/10 Excellent! (493 reviews)
The apartment was clean and in good condition. The lodge desk staff was helpful. The pool was really nice. The weight room had some broken equipment and needed an update and it would’ve been nice to have some hooks outside by the hot tub. I also noticed that the showerhead in our bathroom was hilariously low and barely tall enough to get my head under at 5 foot five. Overall, we had a good visit and it is good for families with really convenient parking by the front door.

Reviewed on Jun 22, 2025

Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Save 100% on your flight
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
9.2/10 Wonderful! (34 reviews)
Wonderful property. Exceptional staff. Will be back.

Reviewed on Jun 26, 2025

Gedney Farm

Gedney Farm

3.5 out of 5
per person
Sep 21 - Sep 26
found 19 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.2/10 Wonderful! (119 reviews)
Beautiful and rustic, less than 15 minutes to Butternut and Great Barrington.

Reviewed on Feb 25, 2025

The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
per person
Sep 21 - Sep 26
found 19 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
8.6/10 Excellent! (121 reviews)
A good place for vacation that you can enjoy and rest. Very nice and safe place.

Reviewed on May 14, 2025

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
per person
Sep 21 - Sep 26
found 19 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9/10 Wonderful! (1,000 reviews)
Very nice inn and a friendly staff. Breakfasts were quite good. The property is nicely landscaped.

Reviewed on Jun 26, 2025

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Cherry Plain Hotel Deals

Hotel Downstreet, Ascend Hotel Collection
Hotel Downstreet, Ascend Hotel Collection
3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $170 total per night from Jul 13 to Jul 14
$170 total
Jul 13 - Jul 14
Total includes taxes and fees
8.6/10 Excellent! (1,004 reviews)
"Very cute hotel. The room was huge and the staff were friendly."

Reviewed on Jun 29, 2025

Hotel Downstreet, Ascend Hotel Collection
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
8.6/10 Excellent! (1,836 reviews)
"The property was perfect for a getaway. 1 bedroom suite or more with balconies. Non heating Fireplace for aesthetics. The suite was a jack and Jill! Shower, but also a jet tub separate from shower. All dishes and cooking utensils that you needed. You can grill onsite or cook in your suite as take ..."

Reviewed on Jun 24, 2025

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Vacation Village in the Berkshires
The Williams Inn
The Williams Inn
4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
$237 nightly
The price is $265 total per night from Jul 9 to Jul 10
$265 total
Jul 9 - Jul 10
Total includes taxes and fees
9.6/10 Exceptional! (458 reviews)
"Wonderful stay. Helpful, professional staff."

Reviewed on Jun 27, 2025

The Williams Inn
See all 660 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.

Find the Best Cherry Plain Vacation Packages

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 $663 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.