Hampshire County Vacation Packages 2025/2026 from $501

Search vacation packages deals in Hampshire County's top destinations

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Hampshire County flight + hotel vacation packages

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

Trainmasters Inn

$501

per person

Nov 22 - Nov 25

found 6 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Worcester (ORH)

This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free on-the-go breakfast each morning. A library is also provided.

Copper Lantern Motor Lodge

$514

per person

Nov 22 - Nov 25

found 6 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Worcester (ORH)

Free self parking is available and the motel's front desk is staffed around-the-clock. WiFi in public areas is free. A garden and a picnic area are also provided.

Top Hampshire County hotels deals

Comfort Inn & Suites

400 Russell St, Hadley, MA

Free Cancellation

Reserve now, pay when you stay

$148 nightly

$165 total

Oct 6 - Oct 7

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

Pool

Breakfast included

Hotel UMass

1 Campus Center Way, Amherst, MA

Free Cancellation

Reserve now, pay when you stay

$170 nightly

$190 total

Oct 8 - Oct 9

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a coffee shop, and a snack bar/deli are also offered.

Breakfast included

Free WiFi

The Ellery

259 Elm Street, Northampton, MA

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$122 total

Oct 27 - Oct 28

Total with taxes and fees

This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning. A garden, a lobby fireplace, and a picnic area are also on offer.

Breakfast included

Pet friendly

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Williamstown, MA

Free Cancellation

Reserve now, pay when you stay

$112 nightly

$125 total

Nov 2 - Nov 3

Total with taxes and fees

This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Pool

Parking included

MGM Springfield

One MGM Way, Springfield, MA

$179 nightly

$203 total

Oct 7 - Oct 8

Total with taxes and fees

This hotel features a casino and 8 restaurants. Relax with a drink at one of the 5 bars/lounges and enjoy perks like free self parking. There's a seasonal outdoor pool on site, and a 24-hour front desk and a coffee shop are also provided.

Pool

Pet friendly

Red Roof Inn PLUS+ West Springfield

1254 Riverdale Street, West Springfield, MA

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$112 total

Nov 2 - Nov 3

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Pet friendly

Parking included

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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.

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Frequently asked questions

How much are vacation packages to Hampshire County?

$501 is all you'll need for a fantastic break in Hampshire County. Bundle your flights and hotel into a vacation package with Travelocity and watch the savings start to add up. With such good prices, traveling has never been so accessible.

Where can I get the best vacation package deals for Hampshire County?

Travelocity can help you get an unbeatable Hampshire County package deal. With 400 airlines and 1,000,000 properties around the world, you're bound to find the perfect mix.

Why should I purchase my Hampshire County vacation bundle via Travelocity?

Nothing beats the feeling of knowing you've bagged the best price available — that's our Price Match Guarantee. Add to that our incredibly broad range of destinations and 24/7 team of customer service professionals and you've got the formula for a stress-free vacation.

Can I save money on my Hampshire County car rental if I book it with my hotel or flight?

You most certainly can — and booking one of our Hampshire County vacation packages is the ideal way to do this. Bundle any combination of a hotel, flight, car and tour and score serious discounts. The more you bundle, the more you'll save. There are plenty of exciting sights around Hampshire County to add to your itinerary, including Fenway Park (80 mi from Hampshire County). Nothing tops exploring amazing places like this with the freedom of your own wheels.

What is there to do in Hampshire County?

As you're ambling around Hampshire County, remember to check out Amherst College and Mount Holyoke College. Don't worry, you won't be bored here!