Sterling Vacations from ￥292,318

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The Latest Sterling Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Boston

Hyatt Regency Boston

4 out of 5
Downtown Boston
per person
Sep 25 - Sep 28
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9/10 Wonderful! (1,576 reviews)
Very good service from the check-in to the check-out. Staff were really nice.

Reviewed on Aug 6, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Sep 25 - Sep 28
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.

Reviewed on Aug 5, 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
per person
Sep 25 - Sep 28
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (360 reviews)
The property wasn’t at the level we expected of the Mandarin Oriental, however the location was good and walkable to Bay Bay restaurants and shopping.

Reviewed on Aug 4, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
Sep 25 - Sep 28
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
Very convenient boutique hotel

Reviewed on Aug 5, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Oct 23 - Oct 26
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
Wonderful high end hotel in a fantastic area. Loved being able to walk to the north end!

Reviewed on Aug 3, 2025

Find the Best Sterling Vacation Packages

Sterling Hotel Deals

Chocksett Inn and Restaurant

Chocksett Inn and Restaurant

3.5 out of 5
59 Laurelwood Road, Sterling, MA
Fully refundableReserve now, pay when you stay
The price is ￥27,772 per night from Aug 10 to Aug 11
￥27,772
￥31,021 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (132 reviews)
Short Stay
"Everything went smoothly, but for the noisy air conditioning system and the very noisy toilet!!! Other than that nice, clean, no disturbances at all."

Reviewed on Jun 25, 2025

Chocksett Inn and Restaurant
Extended Stay America Suites Boston Westborough Computer Dr

Extended Stay America Suites Boston Westborough Computer Dr

2.5 out of 5
1800 Computer Dr, Westborough, MA
Fully refundableReserve now, pay when you stay
The price is ￥13,620 per night from Aug 14 to Aug 15
￥13,620
￥15,214 total
Aug 14 - Aug 15
includes taxes & fees
6.4/10 (914 reviews)
"Excellent staff"

Reviewed on Aug 5, 2025

Extended Stay America Suites Boston Westborough Computer Dr
DoubleTree by Hilton Hotel Boston - Westborough

DoubleTree by Hilton Hotel Boston - Westborough

4 out of 5
5400 Computer Dr, Westborough, MA
Fully refundableReserve now, pay when you stay
The price is ￥17,611 per night from Aug 17 to Aug 18
￥17,611
￥19,671 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"The restaurant staff is exceptional."

Reviewed on Aug 4, 2025

DoubleTree by Hilton Hotel Boston - Westborough
See all 356 properties in Sterling
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.

Frequently asked questions

How much does a Sterling vacation package cost?
You'll find cheap prices from ￥292,318 on Expedia for your Sterling escape. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Sterling costs.
What are the cheapest months to go to Sterling?
The off-season is the best time to visit Sterling if you're trying to save. Another tip for finding cheap Sterling vacation packages? Avoid visiting during public holidays and any major events.
How many days is enough for Sterling?
With a well-planned itinerary, you can easily hit the top Sterling attractions in a handful of days. But if you'd like to discover lesser-known spots or take day trips, think about booking your Sterling vacation for longer.
How to find the best Sterling package deals?
Use Expedia's handy filters to help you find some of the best Sterling package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Sterling package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Sterling vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component separately. And you'll still get the freedom to create a tailored Sterling vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Sterling?
Land incredible bargains by reserving your flights in advance with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Sterling vacation.
How to plan a trip to Sterling?

  1. Choose the ideal time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to travel to Sterling.
  2. Set your budget: Consider costs like flights, food and transportation when calculating how much to set aside for your trip to Sterling. Then, choose a property that fits your budget, whether that's an economical stay or a more upscale getaway.
  3. Determine how many days away: Start by making a list of all the sights and activities you'd like to get to in Sterling. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Sterling vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.