Book Exclusive Hinsdale Vacation Packages

Choose one or more items to build your trip:

Hinsdale flight + hotel packages

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

Pilgrim Inn

2.5 out of 5
per person
May 31 - Jun. 2
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Albany (ALB)
Book a stay at this golf hotel in Lee. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Tanglewood Music Center and Lee Library are located nearby.
Wilder House Berkshires

Wilder House Berkshires

2 out of 5
per person
May 31 - Jun. 2
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Albany (ALB)
Stay at this B&B in Sheffield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary are located nearby.
The Brooks Motel

The Brooks Motel

2 out of 5
per person
May 31 - Jun. 2
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Albany (ALB)
Stay at this motel in Hillsdale. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Catamount Aerial Adventure Park and Community Library are located nearby.
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
per person
May 31 - Jun. 2
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Albany (ALB)
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood are located nearby.

Top Hinsdale hotels deals

Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $138 per night
CA $138
CA $154 total
includes taxes & fees
Apr 21 - Apr 22
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.
Pet-friendly
Parking included
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $126 per night
CA $126
CA $141 total
includes taxes & fees
Apr 15 - Apr 16
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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

3.5 out of 5
190 Meadow Street, South Lee, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $153 per night
CA $153
CA $190 total
includes taxes & fees
Apr 9 - Apr 10
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
Pool
Air conditioning
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
The price is CA $347 per night
CA $347
CA $388 total
includes taxes & fees
Apr 20 - Apr 21
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Williams College Schow Science Library and Denison Park are located nearby.
Pet-friendly
Parking included
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $96 per night
CA $96
CA $107 total
includes taxes & fees
Apr 22 - Apr 23
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mahaiwe Performing Arts Center and Housatonic River Walk are located nearby.
Breakfast included
Parking included
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $180 per night
CA $180
CA $201 total
includes taxes & fees
Apr 27 - Apr 28
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions MCLA Gallery 51 and North Adams Center are located nearby.
Pool
Hot tub
Don't see what you're looking for?
See all available properties in Hinsdale
View all properties
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.

Popular places to visit

Bas Ridge Golf Course

Play a round of golf in Hinsdale at Bas Ridge Golf Course, and enjoy other activities such as skiing. Wander the lakeside in this quaint area.

Bas Ridge Golf Course

Hinsdale Vacations

It's a good idea to know a thing or two about your destination before you jet off on your trip. Draw a circle around Hinsdale on a map now and start planning for an incredible adventure!

From the center of The Berkshires, you'll need to venture northeast for 8 miles (13 kilometers) to reach this neighborhood.

Places to visit in Hinsdale

Getting all your travel tips off the internet is a piece of cake, but don't be too surprised if that "secret waterhole" isn't as serene as they say it is. For the foremost attractions in Hinsdale, nothing beats speaking to the locals.

Where do you fly into for Hinsdale?

Grab your bags and your passport and get ready for a memorable adventure. The moment you arrive at Bradley International Airport (BDL), you'll be just 40 miles (64 kilometers) southeast of Hinsdale.

Frequently asked questions

How much are vacation packages to Hinsdale?
With Travelocity vacation packages, you could paint the town red in Hinsdale for as low as CA $535. Flights, hotels and experiences — we’ve got it all. You’ll make great savings just for combining your bookings. With all of that taken care of before you even set off, you don’t have to worry about a thing.
How long should my Hinsdale vacation be?
Most travelers opt to spend about 2 nights in Hinsdale, but it’s your call. If you intend to venture out and explore all the amazing things this location offers, why not hang around for a little bit longer?
Where can I get the best vacation package deals for Hinsdale?
No matter how you travel, Travelocity can help you find a great Hinsdale package deal. The only thing you have to do is pick and choose between our 400 air carriers and 1,000,000 properties worldwide.
Why should I book my Hinsdale vacation bundle via Travelocity?
With our Price Match Guarantee, we’ll match any cheaper price you’re able to find. Add to that our 24/7 customer support and top-shelf service and the vacation you’ve been dreaming of is closer than ever before.
Can I save money on my Hinsdale car rental if I book it with my hotel or flight?
With a Hinsdale vacation package, you can combine your car, hotel and flight bookings and save a whole lot. If you’re eager to see the best of this awesome part of the world, why not check out Fenway Park? This top sight is 161 kilometers from Hinsdale. With a rental car, you’ll be there in a flash.
Which airport is best for Hinsdale?
Bradley Intl. Airport (BDL), around 64 kilometers southeast of central Hinsdale, is likely to be where you’ll step off the plane. Your other options are Albany Intl. Airport (ALB) (64 kilometers away from central Hinsdale) and Hartford, CT (HFD-Hartford - Brainard) (88 kilometers away from central Hinsdale).
What is there to do in Hinsdale?
Bas Ridge Golf Course is just one of the awesome sights that make Hinsdale such a popular tourist destination. But give yourself enough time to explore the city’s lesser-known attractions too. This is sometimes where the best vacation memories are made.
Where should I stay when visiting Hinsdale?
If you’re looking for a place to base yourself, consider the Berkshire Cabin by Lake Ashmere. It’s the top pick for many visitors.

Photos of local treasures

Browse Hinsdale vacation photos for more inspiration