Southampton Vacation Packages 2025/2026 from $496

Southampton flight + hotel vacation packages

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

the Alander

$496

per person

Oct 31 - Nov 2

found 15 hours ago

Roundtrip non-stop flight included

Omaha (OMA) to Pittsfield (PSF)

A restaurant and a bar/lounge are featured at this lodge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Take advantage of the free self parking.

Little Cat Lodge

$886

per person

Oct 31 - Nov 2

found 15 hours ago

Roundtrip non-stop flight included

Omaha (OMA) to Pittsfield (PSF)

This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Enjoy the sauna and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a garden are also on offer.

Top Southampton hotels deals

MGM Springfield

One MGM Way, Springfield, MA

$179 nightly

$203 total

Oct 1 - Oct 2

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.

DoubleTree by Hilton Hartford - Bradley Airport

16 Ella T. Grasso Turnpike, Windsor Locks, CT

Free Cancellation

Reserve now, pay when you stay

$140 nightly

$161 total

Sep 14 - Sep 15

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like free self parking.

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

185 Ella Grasso Turnpike, Windsor Locks, CT

Free Cancellation

Reserve now, pay when you stay

$67 nightly

$77 total

Sep 28 - Sep 29

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free self parking, and a free airport shuttle. Traveling on business? Take advantage of the business center and free WiFi in public areas. You'll appreciate the free area shuttle, free grocery shopping service, and express check-in.

La Quinta Inn & Suites by Wyndham Springfield MA

100 Congress Street, Springfield, MA

$121 nightly

$137 total

Sep 29 - Sep 30

Total with taxes and fees

This hotel features an indoor pool and a gym. Families will appreciate the arcade/game room and onsite laundry facilities. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking.

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

64 Ella Grasso Turnpike, Windsor Locks, CT

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$124 total

Sep 14 - Sep 15

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free self parking, and a free airport shuttle. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a gym on site, and a 24-hour front desk and dry cleaning are also provided.

Candlewood Suites Windsor Locks Bradley Arpt by IHG

149 Ella Grasso Turnpike, Windsor Locks, CT

$93 nightly

$107 total

Sep 14 - Sep 15

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Families will appreciate the bowling alley and onsite laundry facilities. There's no skimping on freebies - guests receive free WiFi, free self parking, and a free airport shuttle.

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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.

Popular places to visit

Conant Park

After visiting Conant Park, make a plan to see the other sights and activities in Southampton. Make some time to visit the shops while you're in the area.

Southampton Town Hall

After visiting Southampton Town Hall, make a plan to see the other sights and activities in Southampton. Make some time to visit the shops while you're in the area.

Southampton Center Historic District

Explore the great outdoors at Southampton Center Historic District, a lovely green space in Southampton. Make some time to visit the shops while you're in the area.

Frequently asked questions

How much are vacation packages to Southampton?

Prepare to be surprised — you can recharge your batteries in Southampton for as low as $496. Here at Travelocity, we save you money and time with our awesome vacation packages. With flights, hotels and experiences all ready to go at our one-stop shop, what's holding you back?

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

Travelocity is where to go to score an incredible Southampton package deal. Take your pick of 400 partner airlines and 1,000,000 properties all over the world and create a vacation package that suits your style. With so many options at hand, it's time to start booking your next big adventure.

Why should I purchase my Southampton vacation bundle with Travelocity?

Whether you're in search of the ultimate unplugged escape or you crave the fun and excitement of a towering metropolis, booking everything with Travelocity saves you time, money and hassle. No need to comb through hundreds of different websites looking for the best deal — our Price Match Guarantee ensures you'll always get the lowest possible price, and our team of customer service experts are available 24/7 should you need anything at all.

Can I save on my Southampton car rental if I combine it with a hotel or flight?

You certainly can — combine your car, flight and hotel into a Southampton vacation package and you can save a handsome sum. With so many things to do in the Southampton area, having your own wheels will make exploring a joy. Once you've settled into the driver's seat, turn up the stereo and head to Times Square, a top attraction roughly 120 mi from Southampton.

Which airport is best for Southampton?

One option is Bradley Intl. Airport (BDL). From here, you'll need to head north for 20 mi to reach the heart of Southampton. Another convenient choice is Hartford, CT (HFD-Hartford - Brainard), which is 35 mi away from central Southampton.

Where should I stay when visiting Southampton?

Many travelers check in to the Cute Home! Bike Trail Access. It's an excellent base for your Southampton getaway.