Upton Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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!
Top Upton Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
Dorchester
CA $665
per person
Sep 7 - Sep 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
Iris Hotel Boston
Coolidge Corner
CA $1,585
per person
Oct 17 - Oct 24
found 14 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
9.4/10 Exceptional! (612 reviews)
Staff was amazing to deal with. Room was beautiful. Comfortable bed. Great location. I would recommend.
Reviewed on Aug 6, 2026
Pier 7 Condominiums
Bass River
CA $854
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
8.6/10 Excellent! (13 reviews)
I loved this place so much! The place was extremely clean and I felt very comfortable during my stay. The air conditioning ran super cold, the kitchen provided most things needed to make a quick meal, and the pool was very comfortable. They also have games and ping pong available.
Reviewed on Aug 6, 2026
By the Sea Guests Bed & Breakfast & Suites
CA $700
per person
Oct 26 - Oct 29
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (203 reviews)
Gorgeous location, room and common areas with lots of historic charm mixed with thoughtful touches throughout. Lovely to have the well-kept private beach all set up and ready to enjoy. Room was bright and cheerful and breakfast was delicious as well. If you’re looking for peaceful and quiet, this is a great choice.
Reviewed on Aug 7, 2026
Ready to book your vacation to Upton?
Upton Hotel Deals
Sonesta Select Boston Foxborough Mansfield
35 Foxborough Boulevard Foxborough MA
Fully refundableReserve now, pay when you stay
CA $136
CA $152 total
Aug 18 - Aug 19
includes taxes & fees
8.6/10 Excellent! (1,039 reviews)
"Staff members were friendly. Room a little dusty."
Reviewed on Aug 7, 2026
Holiday Inn Express & Suites Norwood-Boston Area by IHG
225 Norwood Park S Norwood MA
Fully refundable
CA $165
CA $185 total
Aug 20 - Aug 21
includes taxes & fees
8.4/10 Very good! (1,007 reviews)
"Clean spacious room, good selection for breakfast"
Reviewed on Aug 6, 2026
Sonesta Select Boston Milford
10 Fortune Blvd Milford MA
Fully refundableReserve now, pay when you stay
CA $132
CA $147 total
Aug 10 - Aug 11
includes taxes & fees
7.8/10 Good! (1,015 reviews)
"Very clean room"
Reviewed on Aug 7, 2026
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.
Stay near popular Upton attractions
Dean Pond
6.0/10 (1 review)
Commune with nature and explore the great outdoors at Dean Pond during your travels in Upton. Discover the lively bars and great live music in this family-friendly area.
Frequently asked questions
How much does an Upton vacation package cost?
Offering excellent value package deals from CA $665 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?
If you'd like to score a cheap Upton vacation package, consider visiting in January, February and November. You'll typically find lower rates on airfares and hotels during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Upton?
Typically, a handful of days is enough to visit the top attractions during your Upton vacation. But if you want to have more time to kick back or take day trips, consider extending your trip.
How to find the best Upton package deals?
Bagging a cheap Upton package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Upton package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book an Upton vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and stays separately. Better still, you can personalize your Upton escape to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Upton?
If you're planning a spontaneous Upton getaway, 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 incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Upton?
- Choose your dates: The things you'd like to do in Upton and your favourite season will help you decide when to travel.
- Figure out your budget: Make sure you have enough money to cover everything from food and transportation to experiences and flights. Your hotel will likely be the biggest expense during your trip to Upton.
- Decide how long to go away for: Now that you're up to speed on Upton, you can figure out the right length of your break. Put together a rough itinerary and allocate enough time for all the things you want to do.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customized Upton vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
