Upton Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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 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

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,411, price is now CA $706 per person
CA $706
per person
Jan 29 - Feb 1
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,406, price is now CA $1,579 per person
CA $1,579
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,383, price is now CA $1,635 per person
CA $1,635
per person
Jan 29 - Feb 1
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,657, price is now CA $2,633 per person
CA $2,633
per person
Dec 24 - Dec 28
found 6 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was CA $1,870, price is now CA $1,353 per person
CA $1,353
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (744 reviews)

Ready to book your vacation to Upton?

 

Choose your dates

Upton Hotel Deals

Sonesta Select Boston Milford

Sonesta Select Boston Milford

3 out of 5
10 Fortune Blvd Milford MA
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Nov 10 to Nov 11
CA $132
CA $147 total
Nov 10 - Nov 11
includes taxes & fees
Sonesta Select Boston Milford
Motel 6 Framingham, MA - Boston West

Motel 6 Framingham, MA - Boston West

2 out of 5
1668 Worcester Rd Framingham MA
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Nov 8 to Nov 9
CA $131
CA $149 total
Nov 8 - Nov 9
includes taxes & fees
7/10 Good! (1,283 reviews)
"B"

Reviewed on Nov 7, 2026

Motel 6 Framingham, MA - Boston West
enVision Hotel & Conference Center Mansfield-Foxboro

enVision Hotel & Conference Center Mansfield-Foxboro

2.5 out of 5
31 Hampshire St Mansfield MA
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Nov 9 to Nov 10
CA $138
CA $154 total
Nov 9 - Nov 10
includes taxes & fees
7.4/10 Good! (1,414 reviews)
"First room was dirty but second room was clean make sure you check your room soon as you enter"

Reviewed on Nov 7, 2026

enVision Hotel & Conference Center Mansfield-Foxboro
See all 582 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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.
See properties

Frequently asked questions

How much does an Upton vacation package cost?
Offering excellent value package deals from CA $706 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?

  1. Choose your dates: The things you'd like to do in Upton and your favourite season will help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.