Sandisfield Vacations from $439

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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.
Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Price was $597, price is now $439 per person
$439
per person
Oct 11 - Oct 14
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9/10 Wonderful! (72 reviews)
Very zen, peaceful ambiance. Lovely stay!

Reviewed on Aug 18, 2025

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Save 100% on your flight
Price was $1,112, price is now $764 per person
$764
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
No reviews
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $1,461, price is now $1,026 per person
$1,026
per person
Sep 24 - Sep 29
found 23 hours ago
Roundtrip non-stop flight included
Trenton (TTN) to Albany (ALB)
9/10 Wonderful! (1,000 reviews)
We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect.

Reviewed on Aug 19, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Save 100% on your flight
Price was $1,540, price is now $1,097 per person
$1,097
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Albany (ALB)
7.4/10 Good! (504 reviews)
I needed to be close to Rutland for a biz meeting and this was a very worthy extra drive and wonderful property.... Will be back !

Reviewed on Aug 9, 2025

Lakefront Terrace Resort

Lakefront Terrace Resort

3 out of 5
Save 100% on your flight
Price was $709, price is now $525 per person
$525
per person
Oct 11 - Oct 14
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
8.2/10 Very Good! (938 reviews)
The view is beautiful! The rooms just need to be cleaned better and the balcony needs a really good cleaning. The property has a lot of potential.

Reviewed on Aug 19, 2025

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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

Get rates
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 includes taxes and fees
8.8/10 Excellent! (571 reviews)
"Shower/tub side in accessible room was extremely high fyi."

Reviewed on Aug 17, 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 26 to Aug 27
$179 total
Aug 26 - Aug 27
Total includes taxes and fees
9/10 Wonderful! (680 reviews)
Upscale Motel
"Lovely reception area and comfortable room. I would describe the place as an upscale motel. Do not count on dining here. Choices are limited and neither my husband nor I enjoyed what we ordered. ."

Reviewed on Aug 16, 2025

Berkshires Untold
See all 1,057 properties in Sandisfield
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 $439 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.