Deals on vacations and trips to Housatonic

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Housatonic flight + hotel vacation packages

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

Windham NY Escape

3 out of 5
Price was $890, price is now $797 per person
$797
per person
Oct 23 - Oct 26
found 20 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
Luggage storage is available at this cabin. Take advantage of the free self parking.
Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

3 out of 5
Save 100% on your flight
Price was $6,130, price is now $4,762 per person
$4,762
per person
Oct 23 - Oct 26
found 20 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

3 out of 5
Save 100% on your flight
Price was $6,142, price is now $4,775 per person
$4,775
per person
Oct 23 - Oct 26
found 20 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
An outdoor pool, free self parking, and barbecue grills are featured at this cottage. WiFi in public areas is free. A terrace is also provided.
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $1,378, price is now $1,214 per person
$1,214
per person
Oct 8 - Oct 11
found 18 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Hudson (HCC)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a lobby fireplace, and a communal living room are also on offer.
Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

3 out of 5
Price was $3,365, price is now $3,061 per person
$3,061
per person
Oct 8 - Oct 11
found 18 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Hudson (HCC)
This chalet features a hot tub and a sauna. Free self parking and a terrace are also offered on site.

Top Housatonic hotels deals

The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$153 nightly
The price is $171 total per night
$171 total
Sep 13 - Sep 14
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$125 nightly
The price is $139 total per night
$139 total
Aug 31 - Sep 1
Total with taxes and fees
This aparthotel 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.
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$142 nightly
The price is $159 total per night
$159 total
Sep 9 - Sep 10
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.
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
$61 nightly
The price is $68 total per night
$68 total
Aug 27 - Aug 28
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. The front desk is staffed around-the-clock and laundry facilities are on offer.
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Free Cancellation
$119 nightly
The price is $133 total per night
$133 total
Sep 24 - Sep 25
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
$208 nightly
The price is $232 total per night
$232 total
Sep 8 - Sep 9
Total with taxes and fees
This historic 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. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
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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 Housatonic?
Your travel dreams can become a reality in Housatonic from an impressive $797. Package deals include flights and hotels, and they'll make booking your trip nice and easy. All you'll have to worry about is what amazing attraction you'll head to first.
Where can I get the best vacation package deals for Housatonic?
Travelocity has everything you need to score an amazing Housatonic package deal. Take your pick of 400 air carriers and 1,000,000 properties around the globe and put together a vacation package that's suited to you. With so many options at hand, now's the time to book your next big adventure.
Why should I purchase my Housatonic vacation package with Travelocity?
By booking your flights, hotel, activities and car rental all in the one place, you'll save time and money. We have a professional customer service support team available round-the-clock, and you'll know that you'll always be getting the best deal in town with our Price Match Guarantee. So, what are you waiting for? Book the vacation of your dreams today and start packing!
Will I save money on my Housatonic car rental if I book it with hotels and flights?
With a Housatonic vacation package, you can combine your flight, car and hotel bookings and save tons. When you're ready to see the best of this impressive area, why not head to Times Square? This must-see attraction is 110 mi from Housatonic. With your own set of wheels, you'll be there soon enough.
Which airport is best for Housatonic?
Bradley Intl. Airport (BDL) is a main hub. You'll find it around 40 mi southeast of Housatonic. Other options worth checking out are Albany Intl. Airport (ALB) (40 mi away from central Housatonic) and Hartford, CT (HFD-Hartford - Brainard) (50 mi away from central Housatonic).
Where should I stay when visiting Housatonic?
If you're looking for somewhere to base yourself, check out the Sweet Cozy Victorian in Housatonic. Close to everything.. It's the top pick for many visitors.

Photos of local treasures

Browse Housatonic vacation photos for more inspiration

A river flanked by autumn-colored trees and residential areas.
A snow-covered landscape with a small gazebo by a river.
A red brick building with arched windows and a small attached structure.