Boston Vacations from $500

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The Latest Boston vacation packages

Price found within the past 48 hours. Click for updated prices.
Hahira Inn By OYO near Valdosta

Hahira Inn By OYO near Valdosta

2.5 out of 5
Price was $549, price is now $500 per person
$500
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Dayton (DAY) to Valdosta (VLD)
4.6/10 (123 reviews)
Did not meet my expectations.

Reviewed on May 25, 2025

The McKey

The McKey

2 out of 5
Price was $885, price is now $769 per person
$769
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Dayton (DAY) to Valdosta (VLD)
9.4/10 Exceptional! (80 reviews)
Quaint and quiet. Really enjoyed my stay.

Reviewed on Jul 31, 2025

OYO Hotel Valdosta GA I-75

OYO Hotel Valdosta GA I-75

2 out of 5
Price was $625, price is now $564 per person
$564
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Dayton (DAY) to Valdosta (VLD)
6.6/10 (691 reviews)
It was a great stay will be back

Reviewed on Aug 14, 2025

Candlewood Suites Valdosta Mall by IHG

Candlewood Suites Valdosta Mall by IHG

2.5 out of 5
Price was $752, price is now $714 per person
$714
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Valdosta (VLD)
8.8/10 Excellent! (378 reviews)
Clean and comfortable bed/pillows

Reviewed on Sep 7, 2025

Holiday Inn Conference Center - Valdosta by IHG

Holiday Inn Conference Center - Valdosta by IHG

3 out of 5
Price was $701, price is now $665 per person
$665
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Valdosta (VLD)
8.8/10 Excellent! (1,000 reviews)
The room was nice and spacious

Reviewed on Aug 17, 2025

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Boston Hotel Deals

Red Roof Inn & Suites Thomasville

Red Roof Inn & Suites Thomasville

2 out of 5
14866 US Hwy 19 South, Thomasville, GA
Fully refundableReserve now, pay when you stay
$57 nightly
The price is $71 total per night from Sep 15 to Sep 16
$71 total
Sep 15 - Sep 16
Total with taxes and fees
Red Roof Inn & Suites Thomasville
Best Western Plus Rose City Conference Center Inn

Best Western Plus Rose City Conference Center Inn

2.5 out of 5
133 Liberty Street, Thomasville, GA
$88 nightly
The price is $108 total per night from Sep 21 to Sep 22
$108 total
Sep 21 - Sep 22
Total with taxes and fees
Best Western Plus Rose City Conference Center Inn
Baymont by Wyndham Thomasville

Baymont by Wyndham Thomasville

2.5 out of 5
1470 Remington Ave, Thomasville, GA
Fully refundableReserve now, pay when you stay
$64 nightly
The price is $79 total per night from Sep 16 to Sep 17
$79 total
Sep 16 - Sep 17
Total with taxes and fees
Baymont by Wyndham Thomasville
See all 120 properties in Boston
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 Boston vacation package cost?
You can snap up a vacation package to this top destination from $500 on Expedia. But how much your vacation to Boston costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Boston?
If you're looking to score a cheap Boston vacation package, consider planning a trip in April, June and December. You'll typically find lower rates on accommodations and flights during these quieter months — ideal for a budget-friendly break.
How many days is enough for Boston?
With a well-organized travel plan, you can easily hit the most popular Boston attractions in a few days. But if you prefer to discover lesser-known spots or go on day trips, consider booking your Boston vacation for longer.
How to find the best Boston package deals?
Landing a cheap Boston package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can customize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most economical Boston package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Boston vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight 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 have the flexibility to create a personalized Boston vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Boston?
If you're planning a spur-of-the-moment Boston vacation, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Boston vacation packages?
If you're like us, you love jet-setting around the world but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Boston vacation across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.

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.