Weston 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 Weston Vacation
Say bye-bye to planning hassles and hello to a Weston vacation package. With everything organized before you take off, you can focus on discovering this city, starting with East Cambridge, which is great for shopping, markets and bars and pubs. Fill your days with tours of Walden Pond, Bentley College and Wellesley College, some of the top attractions you really should see during your trip to Weston. A few clicks is all it takes to craft your ideal Weston vacation on Expedia.
Top Weston Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
Dorchester
CA $810
per person
Oct 21 - Oct 23
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
Chatham Bars Inn
CA $4,357
per person
Oct 7 - Oct 12
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.2/10 Wonderful! (857 reviews)
The food wasn’t great. It’s not like it looks in the pictures We stayed in the cottage. It really was not a difference to any room. The kids club was great.
I don’t feel I need to go back
Reviewed on Aug 21, 2026
Pier 7 Condominiums
Bass River
CA $936
per person
Sep 26 - Oct 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (22 reviews)
The property was small and very intimate. Close to downtown Hyannis, Barnstable, and Dennis.........I, definitely, got a great experience with seeing alot in such a small community. Piers are a hop, skip, and a jump away!
The room was nice, upgraded, and super clean! The only thing missing from the kitchenette was a stove. Other than that, I would stay here again!
Reviewed on Aug 24, 2026
Ready to book your vacation to Weston?
Weston Hotel Deals
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $260
CA $350 total
Sep 6 - Sep 7
includes taxes & fees
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $187
CA $218 total
Aug 25 - Aug 26
includes taxes & fees
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
CA $285
CA $388 total
Aug 27 - Aug 28
includes taxes & fees
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 Weston attractions
Cat Rock Park
Explore the great outdoors at Cat Rock Park, a lovely green space in Weston. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
What to do in Weston
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $72
per adult
90% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
CA $65
per adult
80% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $118
per adult
92% of travellers recommend
Frequently asked questions
How much does a Weston vacation package cost?
You'll find cheap prices from CA $810 on Expedia for your Weston break. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Weston costs.
What are the cheapest months to go to Weston?
You can usually find lower prices and greater availability in January, February and November. Check out our cheap Weston vacation packages and you could get some great off-season discounts.
How many days is enough for Weston?
With about 2 days, you'll have enough time to visit popular neighbourhoods such as North Waltham and Auburndale during your Weston vacation. Remember to also add Moody Street Historic District and Cochituate State Park to your must-see list. Looking for more adventures? Consider exploring outside of Weston on tours and day trips.
How to find the best Weston package deals?
Landing a cheap Weston package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply a few filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Weston package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Weston vacation as a package?
You can enjoy significant savings on your Weston retreat by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Weston?
If you're planning a spur-of-the-moment Weston vacation, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Weston?
- Choose when to get away: Check your diary and pack your bags. Your preferred time of year and the activities on offer will also help you decide when to visit Weston.
- Budget wisely: In addition to the cost of your accommodations, you should factor in other expenses too. These include food, transportation and flights. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Weston.
- Work out your trip length: Think about how much time you'd like to spend exploring Weston. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Weston vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
