Sandisfield Vacations from $425

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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.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $567, price is now $425 per person
$425
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
8.8/10 Excellent! (2,134 reviews)
Clean rooms, chimney did not work

Reviewed on Jan 4, 2026

Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $799, price is now $429 per person
$429
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Miami (MIA) to Albany (ALB)
9.4/10 Exceptional! (13 reviews)
Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession.

Reviewed on Nov 29, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Manchester Village Historic District
Save 100% on your flight
Price was $2,071, price is now $1,438 per person
$1,438
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Albany (ALB)
7.4/10 Good! (567 reviews)
Was surprised at the dirty floors in common area and in my room one of the curtain sheers was ripped, other curtains were hanging off hokks, caulking at sink looked old, cracked, carpets in staircase dirty. I fear this beautiful hotel is in a downward spiral. One front desk person directed me to closed restaurants...

Reviewed on Jan 9, 2026

The Manchester View

The Manchester View

2.5 out of 5
Price was $1,011, price is now $702 per person
$702
per person
Feb 13 - Feb 18
found 20 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
9.4/10 Exceptional! (772 reviews)
The place is great. Especially the wood burning stove in the room.

Reviewed on Jan 7, 2026

Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Price was $896, price is now $692 per person
$692
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Albany (ALB)
8.8/10 Excellent! (600 reviews)
Everything was good, The refrigerator was barely working, so we had to take the food outside.

Reviewed on Jan 7, 2026

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Sandisfield Hotel Deals

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $113 total per night from Jan 19 to Jan 20
$113 total
Jan 19 - Jan 20
Total with taxes and fees
9/10 Wonderful! (1,010 reviews)
All of the above!

Reviewed on Jan 3, 2026

The Yankee, Trademark Collection by Wyndham
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 Feb 8 to Feb 9
$120 total
Feb 8 - Feb 9
Total with taxes and fees
9/10 Wonderful! (807 reviews)
I've stayed here several times over the past two years. A real gem of a location, especially if you are staying several nights.

Reviewed on Jan 5, 2026

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $136 total per night from Jan 11 to Jan 12
$136 total
Jan 11 - Jan 12
Total with taxes and fees
9/10 Wonderful! (832 reviews)
This is a nice, upscale version of a motel with a club room at front. The front of the house is understaffed, with the front desk checking people in, acting as bartender, waiter and food runner. Fortunately (unfortunately), not many people to wait on. The kitchen suffers from a lack of customers ...

Reviewed on Jan 5, 2026

Berkshires Untold
See all 1,066 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.

Find the Best Sandisfield Vacation Packages

Sandisfield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
840
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Otis Ridge, Umpachene Falls Park and Les Trois Emme Winery

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Frequently asked questions

How much does a Sandisfield vacation package cost?
Offering excellent value package deals from $425 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.