Upton Vacations from $265

Book a Hotel + Flight or Car together to unlock savings

Your Upton Vacation

When you book a vacation package to Upton, you can relax and enjoy your getaway knowing that all your travel plans are under control. Uncover the many charms of this amazing city while based in a neighborhood like Blackstone, which is great for history. A trip to Upton is a wonderful opportunity to sightsee. Be sure to stop by well-known attractions like Hopkinton State Park, The Willard House & Clock Museum and Shining Rock Golf Club. Stop dreaming and start doing. Check out the wide range of options on Expedia today and finally put your Upton vacation plans in motion!

The Latest Upton vacation packages

Price found within the past 48 hours. Click for updated prices.
InnSeason Resorts Captain's Quarters

InnSeason Resorts Captain's Quarters

3.5 out of 5
Falmouth Heights
Save 100% on your flight
Price was $395, price is now $265 per person
$265
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (176 reviews)
We really enjoyed the warm hospitality, the spacious rooms, great location right by the beach and great size pool. It’s close to downtown and walkable to a few restaurants.

Reviewed on Aug 13, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $902, price is now $423 per person
$423
per person
Nov 11 - Nov 14
found 4 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $608, price is now $340 per person
$340
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (2,220 reviews)
Very nice hotel with great rooms for affordable price

Reviewed on Sep 3, 2025

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
Price was $1,250, price is now $812 per person
$812
per person
Nov 6 - Nov 9
found 23 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
10/10 Exceptional! (8 reviews)
thanks u for very nice place and clean i really loved i will cominng back soon

Reviewed on May 8, 2025

Wayfinder Newport

Wayfinder Newport

4 out of 5
Save 100% on your flight
Price was $940, price is now $612 per person
$612
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Providence (PVD)
8/10 Very Good! (968 reviews)
Like that it was pet friendly stay but would love to take my 8 lbs dog to the pool area…

Reviewed on Sep 3, 2025

Don't see what you're looking for?
See all available trips from Columbus to Upton
View all trips

Upton Hotel Deals

Courtyard by Marriott Boston Natick

Courtyard by Marriott Boston Natick

3 out of 5
342 Speen St, Natick, MA
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $124 total per night from Sep 11 to Sep 12
$124 total
Sep 11 - Sep 12
Total with taxes and fees
Courtyard by Marriott Boston Natick
Courtyard by Marriott Boston Marlborough

Courtyard by Marriott Boston Marlborough

3 out of 5
75 Felton St, Marlborough, MA
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $151 total per night from Sep 11 to Sep 12
$151 total
Sep 11 - Sep 12
Total with taxes and fees
Courtyard by Marriott Boston Marlborough
AVIA Residences on Research - Extended Stay

AVIA Residences on Research - Extended Stay

3 out of 5
25 Connector Road, Westborough, MA
$75 nightly
The price is $84 total per night from Oct 1 to Oct 2
$84 total
Oct 1 - Oct 2
Total with taxes and fees
AVIA Residences on Research - Extended Stay
See all 490 properties in Upton
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.

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 an Upton vacation package cost?
Offering great value package deals from $265 on Expedia, you'll be surprised at how little a vacation to Upton costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Upton?
November, December and January are great times to look for cheap Upton vacation packages. Traveling in quieter months means you can generally find reduced prices on flights and hotels.
How many days is enough for Upton?
Usually, a handful of days is enough to see the major sights during your Upton vacation. But if you prefer to have time to chill out or go on day tours, think about extending your trip.
How to find the best Upton package deals?
Use Expedia's handy filters to help you find some unbeatable Upton package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Upton package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book an Upton vacation as a package?
You can enjoy significant savings on your next Upton escape by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Upton?
Secure incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Upton adventure.
Does Expedia offer Book Now, Pay Later Upton vacation packages?
If you're anything like us, you love traveling but don't love the big 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 break down the cost of your Upton vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.