Sandisfield Vacations from $492

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Photo by Photo courtesy of Berkshire Visitors Bureau

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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.
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
Save 100% on your flight
Price was $829, price is now $492 per person
$492
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
18.4/10 Exceptional! (110 reviews)
It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!

Reviewed on Oct 27, 2025

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
Save 100% on your flight
Price was $734, price is now $530 per person
$530
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
19.6/10 Exceptional! (38 reviews)
Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you!

Reviewed on Nov 10, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Price was $819, price is now $605 per person
$605
per person
Jan 7 - Jan 10
found 3 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
14.8/10 Exceptional! (567 reviews)
We feel that the resort fee to access the pool and hot tub as well as the other services covered are over priced. We stay at resorts and hotels all over the US and you are the ONlY place that charges for this.

Reviewed on Nov 21, 2025

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Price was $693, price is now $520 per person
$520
per person
Dec 26 - Dec 28
found 23 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
17.6/10 Exceptional! (3 reviews)
The room was nice and clean, but the hotel itself was still under construction and it took 45 minutes for us to get in our room for check-in I was able to ask for extended check out and we got two complementary drinks from the bar but overall they should have waited to open

Reviewed on Nov 12, 2025

Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House

Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House

3 out of 5
Save 100% on your flight
Price was $1,012, price is now $791 per person
$791
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
12/10 Exceptional! (1 review)
The location of the house was very near for food and supplies,yet very private. The inside was very clean and well kept. We enjoyed the quietness and surrounding grounds with views of local wild life. The things that we did not like was the musty - moldy smell when we first got there. Every time you used the water it smelled. Red light on fridge for changing filter. Bought spring water to use for drinking, coffee, and cooking. All reported to host upon departure.

Reviewed on Aug 23, 2025

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Sandisfield Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $110 total per night from Dec 7 to Dec 8
$110 total
Dec 7 - Dec 8
Total with taxes and fees
9/10 Wonderful! (763 reviews)
The room was very clean, appreciated the friendly and helpful staff. Well stocked kitchen, super close to grocery stores and restaurants.

Reviewed on Nov 21, 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
$95 nightly
The price is $106 total per night from Nov 30 to Dec 1
$106 total
Nov 30 - Dec 1
Total with taxes and fees
9/10 Wonderful! (801 reviews)
Enjoyed the Clubhouse before retiring in for the evening. Cozy, comfortable, and relaxing atmosphere.

Reviewed on Nov 10, 2025

Berkshires Untold
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $206 total per night from Dec 21 to Dec 22
$206 total
Dec 21 - Dec 22
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Quaint Inn located in the Berkshire. Dinner in the tavern was delish. The main inn lobby has plenty of seating to lounge around and people watch. We enjoyed our stay.

Reviewed on Nov 20, 2025

The Red Lion Inn
See all 1,068 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 $492 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.