Southampton Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Southampton Vacation

Our Southampton vacation packages give you the power to customize your own adventure. Tailor your journey to your needs and interests and make every moment count in this lively city. A trip to Southampton is a terrific opportunity to go sightseeing. Be sure to look around big-name attractions such as Mount Tom, Little Tom Mountain and Wistariahurst Museum. Browse Expedia's extensive range of travel options and start planning your ultimate vacation to Southampton today.

Southampton Hotel Deals

MGM Springfield

MGM Springfield

4 out of 5
One MGM Way Springfield MA
$159 nightly
The price is $180 total per night from Jan 29 to Jan 30
$180 total
Jan 29 - Jan 30
Total with taxes and fees
8.8/10 Excellent! (1,470 reviews)
everything was perfect!

Reviewed on Jan 26, 2026

MGM Springfield
Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

2.5 out of 5
149 Ella Grasso Turnpike Windsor Locks CT
Fully refundable
$79 nightly
The price is $91 total per night from Feb 2 to Feb 3
$91 total
Feb 2 - Feb 3
Total with taxes and fees
8.2/10 Very Good! (1,008 reviews)
Yes, front dest very pleasent

Reviewed on Jan 25, 2026

Candlewood Suites Windsor Locks Bradley Arpt by IHG
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $136 total per night from Jan 30 to Jan 31
$136 total
Jan 30 - Jan 31
Total with taxes and fees
9.2/10 Wonderful! (2,245 reviews)
Friendly staff. Enjoy the homey feel, different from the cookie cutter box feel of chains.

Reviewed on Jan 24, 2026

D. Hotel Suites & Spa
See all 450 properties in Southampton
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.

Find the Best Southampton Vacation Packages

Southampton Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
5,500
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Eric Carle Museum of Picture Book Art, Historic Summit House and Hadley Farm Museum

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Southampton vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to Southampton costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Southampton?
January, October and December are the best times to look for cheap Southampton vacation packages. Choosing to travel in less busy months means you can typically find reduced prices on hotels and flights.
How many days is enough for Southampton?
The ideal duration of your Southampton vacation depends on what you'd like to see. Usually, a few days to a week will give you plenty of time to visit all the main attractions and explore some hidden treasures along the way.
How to find the best Southampton package deals?
Finding a cheap Southampton package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most economical Southampton package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are typically lower.
Is it cheaper to book a Southampton vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component individually. And you'll still get the flexibility to create a personalized Southampton vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Southampton?
If you're planning a spur-of-the-moment Southampton getaway, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land sensational deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Southampton vacation packages?
Secure your dream escape to Southampton with Expedia's Book Now, Pay Later vacations. No need to scrimp and save or hold off until your next payday — we've joined forces with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily budget for your trip and snap up bargains before they sell out.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.