Sterling Vacations from $496

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Your Sterling Vacation

Our Sterling vacation packages offer countless opportunities to discover new sights, sounds and sensations. And with all the planning taken care of, you can relax and enjoy your city break in the way that you deserve. Tower Hill Botanic Garden, Museum of Russian Icons and Dexter Drumlin are just a few of the sights worth exploring during your trip to Sterling. Expedia is here to help you escape the everyday. Tailor your vacation to Sterling to suit your style of travel, whatever that may be.

The Latest Sterling vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel 1620 Plymouth Harbor

Hotel 1620 Plymouth Harbor

3 out of 5
Plymouth Downtown Waterfront District
Save 100% on your flight
Price was $685, price is now $496 per person
$496
per person
Oct 26 - Oct 30
found 24 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
8.2/10 Very Good! (1,029 reviews)
Hotel 1620 Plymouth Harbor offers a great location near downtown and the waterfront, with friendly staff and a family-friendly atmosphere. Rooms are spacious but can feel dated. There Overall, it’s a solid choice for convenience and amenities, though some aspects need improvement.

Reviewed on Sep 16, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $991, price is now $538 per person
$538
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Falmouth Tides

Falmouth Tides

2.5 out of 5
Falmouth Heights
Price was $829, price is now $623 per person
$623
per person
Oct 26 - Oct 31
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (646 reviews)
This is a motel. All the reviews I read said this place would be the best place to stay in Falmouth. Yes it was on the beach and yes it had a lovely view of the harbour and yes it was convenient for the ferry to MV. But it was the most expensive place we stayed and was just a motel with some beach chairs. A coffee hut outside from 7am. No coffee making facilities in room and a very basic plastic encased shower. Stunning view over the ocean but not worth the money. We used the complimentary bikes (these were a bonus) to ride to town for meal in the evening.

Reviewed on Sep 16, 2025

Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

3 out of 5
Save 100% on your flight
Price was $1,462, price is now $1,113 per person
$1,113
per person
Nov 20 - Nov 25
found 11 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Boston (BOS)
No reviews
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $1,549, price is now $1,182 per person
$1,182
per person
Oct 26 - Oct 30
found 20 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
8.8/10 Excellent! (239 reviews)
The staff especially the new

Reviewed on Sep 14, 2025

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Discover the most popular places to visit in Sterling

Davis' Farmland & Mega Maze

Enjoy an outing to Davis' Farmland & Mega Maze during your stay in Sterling. You can attend a sporting event while in the area.

Davis' Farmland & Mega Maze

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
$189 nightly
The price is $211 total per night from Sep 21 to Sep 22
$211 total
Sep 21 - Sep 22
Total with taxes and fees
8.6/10 Excellent! (134 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
Motel 6 Framingham, MA - Boston West

Motel 6 Framingham, MA - Boston West

2 out of 5
1668 Worcester Rd, Framingham, MA
Fully refundable
$88 nightly
The price is $93 total per night from Sep 21 to Sep 22
$93 total
Sep 21 - Sep 22
Total with taxes and fees
6.6/10 (1,028 reviews)
"Price was right, it’s a Motel 6 so judging on a different scale, not terrible for a one night stay. The marijuana smoke is strong unfortunately, room very basic and relatively clean. Road noise is very high due to location. Again, it’s a motel 6 and you get what you pay for."

Reviewed on Sep 13, 2025

Motel 6 Framingham, MA - Boston West
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 25 to Sep 26
$151 total
Sep 25 - Sep 26
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"The hotel was beautiful, and the staff was extremely friendly."

Reviewed on Sep 15, 2025

Courtyard by Marriott Boston Marlborough
See all 354 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.

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Frequently asked questions

How much does a Sterling vacation package cost?
You'll find cheap prices from $496 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?
If you're hoping to score a cheap Sterling vacation package, consider visiting in May, November and December. You'll generally find lower prices on flights and accommodations during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Sterling?
With a well-organized schedule, you can easily visit the top Sterling sights in a handful of days. But if you prefer to explore off the beaten track or go on 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.
Does Expedia offer Book Now, Pay Later Sterling vacation packages?
Secure your dream getaway to Sterling with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait for the next payday — we've joined forces with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily budget for your trip and snap up cheap deals before they disappear.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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