Bolton Vacations from $363

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Your Bolton Vacation

Our vacation packages to Bolton give you the power to customize your own adventure. Tailor your getaway to your needs and interests and make the most of your time in this fantastic city. If taking in sights is part of the plan during your trip to Bolton, check out well-known attractions like The Silver Buffalo Gallery, Harvard Town Beach and Thurstons Beach. Check out Expedia's extensive range of travel options and begin planning your ideal vacation to Bolton today.

The Latest Bolton vacation packages

Price found within the past 48 hours. Click for updated prices.
The Cove At Yarmouth

The Cove At Yarmouth

3 out of 5
Save 100% on your flight
Price was $587, price is now $363 per person
$363
per person
Feb 19 - Feb 23
found 9 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Boston (BOS)
9.2/10 Wonderful! (243 reviews)
The unit on or suite units are on second floor with no elevator. In addition, the bedroom is on another level. For those with physical issues only.insist on first floor I found 1st floor bath dirty. This is a time share rental which suits families with young kids.

Reviewed on Oct 6, 2025

DoubleTree by Hilton Manchester Downtown

DoubleTree by Hilton Manchester Downtown

4 out of 5
Downtown Manchester
Save 100% on your flight
Price was $545, price is now $364 per person
$364
per person
Jan 26 - Jan 31
found 15 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Boston (BOS)
9/10 Wonderful! (1,061 reviews)
Rooms clean, staff nice, good location

Reviewed on Dec 14, 2025

citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
Fenway–Kenmore
Save 100% on your flight
Price was $556, price is now $381 per person
$381
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Boston (BOS)
9.4/10 Exceptional! (2,013 reviews)
Always enjoy staying there

Reviewed on Dec 13, 2025

Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

3.5 out of 5
Newton Corner
Save 100% on your flight
Price was $718, price is now $500 per person
$500
per person
Feb 10 - Feb 15
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
8.4/10 Very Good! (2,907 reviews)
Signage to get to it is horrible!

Reviewed on Dec 12, 2025

The Club at New Seabury

The Club at New Seabury

3.5 out of 5
New Seabury
Save 100% on your flight
Price was $683, price is now $482 per person
$482
per person
Feb 19 - Feb 23
found 9 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Boston (BOS)
9/10 Wonderful! (337 reviews)
Stayed in one of the cottages. It was so cute. Had everything you needed. Only stood overnight wished we had more time.

Reviewed on Sep 22, 2025

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Discover the most popular places to visit in Bolton

Nashoba Valley Winery

You can enjoy a tasting or tour at Nashoba Valley Winery during your travels to Bolton. You can attend a sporting event while in the area.

Nashoba Valley Winery

Bolton Hotel Deals

Bedford Plaza Hotel - Boston

Bedford Plaza Hotel - Boston

3 out of 5
340 Great Road Bedford MA
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $87 total per night from Jan 4 to Jan 5
$87 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
7/10 Good! (685 reviews)
Great room. Well equipped for the type of travel we do each month. Staff is knowledgeable and helpful.

Reviewed on Dec 7, 2025

Bedford Plaza Hotel - Boston
Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham

2.5 out of 5
135 2nd Ave Waltham MA
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $109 total per night from Dec 24 to Dec 25
$109 total
Dec 24 - Dec 25
Total with taxes and fees
9.2/10 Wonderful! (1,576 reviews)
Been there a few times, doctor appointments in Boston. Easy in and out, clean, friendly staff and PARKING INCLUDED! As well as a quick bite in the morning. Now I book every time we are out there.

Reviewed on Dec 13, 2025

Hampton Inn & Suites Boston/Waltham
Red Roof Inn Boston - Southborough/ Worcester

Red Roof Inn Boston - Southborough/ Worcester

2 out of 5
367 Turnpike Rd Southborough MA
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $69 total per night from Dec 18 to Dec 19
$69 total
Dec 18 - Dec 19
Total with taxes and fees
7/10 Good! (1,009 reviews)
I liked this Red Roof motel much. The room is clean and not to far from Clinton, MA. I recommend this place to anyone that want to come around this area.

Reviewed on Dec 14, 2025

Red Roof Inn Boston - Southborough/ Worcester
See all 579 properties in Bolton
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.

Find the Best Bolton Vacation Packages

Bolton Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Worcester Regional Airport (ORH)
Population
4,200
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Harvard Town Beach, Thurstons Beach and Lake Chauncy Public Beach

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Frequently asked questions

How much does a Bolton vacation package cost?
Offering great value package deals from $363 on Expedia, you'll be pleasantly surprised at how much a vacation to Bolton costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Bolton?
December, January and February are the best times to look for cheap Bolton vacation packages. Traveling in quieter months means you can usually find reduced prices on flights and hotels.
How many days is enough for Bolton?
Typically, a handful of days is enough to see the top sights during your Bolton vacation. However, if you want to have time to relax or go on day trips, think about extending your trip.
How to find the best Bolton package deals?
Use Expedia's filters to help you find some great Bolton package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Bolton package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Bolton vacation as a package?
You can enjoy significant savings on your next Bolton break by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to view some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Bolton?
If you have your Bolton vacation dates confirmed, book as early as you can to bag some unbeatable deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Bolton vacation packages?
Your Bolton trip should be a relaxing escape from your daily routine, not a source of money-related stress. So to allow you that extra flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

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