Southampton Vacations from $638

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

The Latest Southampton vacation packages

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

the Alander

2.5 out of 5
Price was $643, price is now $638 per person
$638
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Pittsfield (PSF)
9/10 Wonderful! (157 reviews)
Good location, clean and nice touches in the rooms (french press coffee pot and freshly ground coffee, Harney teas, Saratoga Spring water, and other nice amenities). The fire pits are a nice plus!

Reviewed on Sep 12, 2025

Little Cat Lodge

Little Cat Lodge

2 out of 5
Price was $1,057, price is now $987 per person
$987
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Pittsfield (PSF)
9.4/10 Exceptional! (58 reviews)
Loved staying here. It was a beautiful room, clean and modern. Loved having a balcony to sit on at night. The breakfast was excellent and the service with a smile was great. Would love to come back again.

Reviewed on Aug 10, 2025

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Southampton Hotel Deals

MGM Springfield

MGM Springfield

4 out of 5
One MGM Way, Springfield, MA
$179 nightly
The price is $203 total per night from Oct 1 to Oct 2
$203 total
Oct 1 - Oct 2
Total with taxes and fees
8.8/10 Excellent! (1,410 reviews)
"The staff was absolutely amazing. I can't say enough about them."

Reviewed on Sep 9, 2025

MGM Springfield
DoubleTree by Hilton Hartford - Bradley Airport

DoubleTree by Hilton Hartford - Bradley Airport

4 out of 5
16 Ella T. Grasso Turnpike, Windsor Locks, CT
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $165 total per night from Sep 21 to Sep 22
$165 total
Sep 21 - Sep 22
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"hotel is fine for an overnight near the airport."

Reviewed on Sep 11, 2025

DoubleTree by Hilton Hartford - Bradley Airport
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

2 out of 5
185 Ella Grasso Turnpike, Windsor Locks, CT
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $77 total per night from Sep 28 to Sep 29
$77 total
Sep 28 - Sep 29
Total with taxes and fees
6.6/10 (1,552 reviews)
"Front desk people are rude and the hallway to the elevator smells like cat pee."

Reviewed on Sep 8, 2025

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport
See all 430 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.

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Frequently asked questions

How much does a Southampton vacation package cost?
Offering great value package deals from $638 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

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.