Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Southampton Vacations

Pack those stellar shades. We have Southampton vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Southampton – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Southampton vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Southampton

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Southampton vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Southampton well.

Southampton Flight + Hotel packages

Top Hotel Deals

See all 98 Hotels in Southampton
La Quinta Inn & Suites Springfield

La Quinta Inn & Suites Springfield

100 Congress Street, Springfield
3.5 out of 5.0

Located in the heart of Springfield, this hotel is within 1 mi (2 km) of Quadrangle and Springfield Armory. Naismith Memorial Basketball Hall of Fame is 1.4 ...

$85

$85
Tower Square Hotel Springfield

Tower Square Hotel Springfield

2 Boland Way And East Columbus Avenue, Springfield
4.0 out of 5.0

Located in the heart of Springfield, this hotel is within a 15-minute walk of MassMutual Center and Naismith Memorial Basketball Hall of Fame. Springfield Armory ...

$139

$139
Days Inn Windsor Locks-Bradley International Airport

Days Inn Windsor Locks-Bradley International Airport

185 Ella Grasso Turnpike, Windsor Locks
3.0 out of 5.0

Situated in Windsor Locks, this hotel is within 6 mi (10 km) of New England Air Museum, Northwest Park, and Broad Brook Brewing. Connecticut Fire Museum and ...

$67

$67
La Quinta Inn & Suites Hartford-Bradley Airport

La Quinta Inn & Suites Hartford-Bradley Airport

64 Ella Grasso Turnpike, Windsor Locks
3.0 out of 5.0

Situated near the airport, this hotel is within 6 mi (10 km) of Northwest Park, New England Air Museum, and Oliver Ellsworth Homestead. Vintage Radio and Communications ...

$70

$70
Hampton Inn Chicopee/Springfield

Hampton Inn Chicopee/Springfield

600 Memorial Dr, Chicopee
3.0 out of 5.0

Situated near the airport, this hotel is 1 mi (1.7 km) from Chicopee Falls Dam and within 6 mi (10 km) of Volleyball Hall of Fame and Holyoke Heritage State ...

$122

$122
Hotel UMass

Hotel UMass

1 Campus Center Way, Amherst
2.5 out of 5.0

Situated in Amherst, this hotel is 0.2 mi (0.3 km) from Mullins Center and 1.8 mi (2.8 km) from Amherst College. University of Massachusetts-Amherst and Emily ...

$139

$139
Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke

229 Whiting Farms Road, Holyoke
3.0 out of 5.0

Situated in Holyoke, this hotel is 0.6 mi (1 km) from Holyoke Mall and within 3 mi (5 km) of Wistariahurst Museum and Holyoke Heritage State Park. Volleyball ...

$107

$107
Howard Johnson Express

Howard Johnson Express

1356 Boston Rd, Springfield
1.5 out of 5.0

Situated in Springfield, this hotel is within 6 mi (10 km) of Blunt Park, Springfield Armory, and Indian Motorcycle Museum. Chicopee Falls Dam and Springfield ...

$59

$59
Hampton Inn & Suites Springfield / Downtown

Hampton Inn & Suites Springfield / Downtown

851 East Columbus Ave, Springfield
3.0 out of 5.0

Located in the heart of Springfield, this hotel is within 1 mi (2 km) of Titanic Museum and Naismith Memorial Basketball Hall of Fame. Springfield Armory is ...

$118

$118
Regency Inn & Suites

Regency Inn & Suites

21 Baldwin Street, West Springfield
2.5 out of 5.0

Situated in the entertainment district, this hotel is 0.1 mi (0.2 km) from Eastern States Exposition and within 3 mi (5 km) of Springfield Armory and Naismith ...

$89

$89

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.