Sandisfield Vacations from $388

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Your Sandisfield Vacation

When a city getaway is calling, answer it with a Sandisfield vacation package. The neighborhood of Canann Village Historic District, which is good for dining, culture and shopping, makes a fantastic base for your adventures. Want to start exploring your surroundings? Otis Reservoir, Otis Ridge and Tolland State Forest are three of the top places to visit during your trip to Sandisfield. A couple of quick clicks is all it takes to build a tailored Sandisfield vacation on Expedia.

The Latest Sandisfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Hotel & Suites West Coxsackie by IHG
Prospect Berkshires
The Equinox Golf Resort & Spa
Hasbrouck House
The Wiltwyck
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Sandisfield Hotel Deals

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Sandisfield
9.6/10 Exceptional! (40 reviews)
"The host was great and the property was wonderful. Extremely well kept house. The tennis court was such a unique touch to the home. It was such a peaceful home with lots of entertainment opportunities. The tree line made it feel so private. We really enjoyed having such easy access to Great Barrington ..."

Reviewed on Aug 8, 2025

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $120 total per night from Sep 7 to Sep 8
$120 total
Sep 7 - Sep 8
Total with taxes and fees
8.8/10 Excellent! (586 reviews)
"I stayed here for a work trip to a remote project site. This place was very impressive for the money. The rooms were large and had everything. The place was clean and staff very pleasant and accommodating. I didn’t expect a lot for what I paid but was pleasantly surprised."

Reviewed on Aug 23, 2025

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $179 total per night from Aug 25 to Aug 26
$179 total
Aug 25 - Aug 26
Total with taxes and fees
9/10 Wonderful! (693 reviews)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise"

Reviewed on Aug 21, 2025

Berkshires Untold
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 Sandisfield vacation package cost?
Offering excellent value package deals from $388 on Expedia, you'll be thrilled with how little a vacation to Sandisfield costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Sandisfield?
If you'd like to snag a cheap Sandisfield vacation package, consider traveling in October, November and December. You'll usually find better rates on flights and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Sandisfield?
With a well-organized itinerary, you can easily hit the most popular Sandisfield attractions in a few days. But if you prefer to discover lesser-known spots or take day trips, think about booking your Sandisfield vacation for longer.
How to find the best Sandisfield package deals?
Start your search for a Sandisfield package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Sandisfield package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Sandisfield adventure underway.
Is it cheaper to book a Sandisfield vacation as a package?
You can enjoy significant savings on your Sandisfield retreat by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to see the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Sandisfield?
If you're considering a spontaneous Sandisfield vacation, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land terrific deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Sandisfield vacation packages?
If you're like us, you love jet-setting around the world but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Sandisfield trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.