Sandisfield Vacation Packages 2026 from $442

Sandisfield flight + hotel vacation packages

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

The Dewey

$442

per person

Mar 16 - Mar 19

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

Prospect Berkshires

$523

per person

Mar 16 - Mar 19

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a picnic area are also on offer.

Gedney Farm

$466

per person

Mar 16 - Mar 19

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace, a garden, and a communal living room are also on offer.

The Cornell Inn, Lenox & The Berkshires

$503

per person

Mar 16 - Mar 19

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.

Wilder House Berkshires

$479

per person

Mar 16 - Mar 19

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This bed & breakfast features free self parking and a garden. Free cooked-to-order breakfast is served. A lobby fireplace, a communal living room, and a picnic area are also on offer.

Top Sandisfield hotels deals

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$113 total

Jan 19 - Jan 20

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$120 total

Feb 9 - Feb 10

Total with taxes and fees

This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.

Pool

Hot Tub

Berkshires Untold

194 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$136 total

Jan 14 - Jan 15

Total with taxes and fees

A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and express check-in are also on offer.

Pet friendly

Parking included

Simsbury 1820 House

731 Hopmeadow St Simsbury CT

Free Cancellation

Reserve now, pay when you stay

$174 nightly

$200 total

Jan 12 - Jan 13

Total with taxes and fees

The bed & breakfast's indoor pool, gym, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy a meal from the restaurant and perks like free continental breakfast and free self parking.

Pool

Breakfast included

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

190 Meadow Street South Lee MA

Free Cancellation

$130 nightly

$145 total

Jan 14 - Jan 15

Total with taxes and fees

This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.

Pool

Air conditioning

The Red Lion Inn

30 Main Street Stockbridge MA

Free Cancellation

Reserve now, pay when you stay

$182 nightly

$204 total

Jan 20 - Jan 21

Total with taxes and fees

This smoke-free hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

Pool

Spa

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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.

Frequently asked questions

How much are vacation packages to Sandisfield?

Travelocity provides flight and hotel packages starting from just $442. With such great deals, you'll be exploring all of Sandisfield in a flash.

Where can I get the best vacation package deals for Sandisfield?

Travelocity will be able to help you find a terrific Sandisfield package deal. With no less than 400 airlines and 1,000,000 properties around the world, we know you'll be able to put together the perfect itinerary.

Why should I purchase my Sandisfield vacation package via Travelocity?

Nothing tops the feeling of knowing you've bagged the best price around — that's our Price Match Guarantee. Add to that our impressively broad range of magical destinations and 24/7 team of customer service professionals and you've got the formula for an unforgettable vacation.

Can I save money on my Sandisfield car rental if I bundle it with hotels and flights?

With a Sandisfield vacation package, you can bundle your flight, hotel and car bookings and save loads. When you're ready to uncover the best of this fabulous location, why not start with Times Square? This popular attraction is 100 mi from Sandisfield. With your own wheels, you'll be there in a flash.

Which airport is best for Sandisfield?

For plenty of visitors, a stay in Sandisfield means going through Bradley Intl. Airport (BDL). This buzzing airport is 25 mi southeast of the city center. You could also choose to fly into Albany Intl. Airport (ALB) (55 mi away from central Sandisfield) or Tweed - New Haven Regional Airport (HVN) (60 mi away from central Sandisfield).

Where should I stay when visiting Sandisfield?

The Cozy Cabin in the Berkshires is the top choice of many visitors. Book soon before it's too late.