Boston Vacations from $990

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Your Boston Vacation

Lock in a Boston vacation package and get set for a fantastic getaway. Well known for its rich history and cultural experiences, there's tons to love about this captivating city. Every trip to Boston needs a well-designed itinerary. Fill yours with attractions like St Botolphs Church, York Street and Maud Foster Windmill. A couple of clicks is all it takes to build your ideal Boston vacation on Expedia.

The Latest Boston vacation packages

Price found within the past 48 hours. Click for updated prices.
Nottingham City Centre by Sunday

Nottingham City Centre by Sunday

4 out of 5
Nottingham City Centre
Price was $1,092, price is now $990 per person
$990
per person
Aug 23 - Aug 28
found 13 hours ago
Roundtrip flight included
New York (NYC) to East Midlands (EMA)
7.8/10 Good! (1,002 reviews)
Ideal location with comfortable rooms and an amazing shower

Reviewed on Jun 20, 2026

Oaklands Hall Hotel Grimsby

Oaklands Hall Hotel Grimsby

3 out of 5
Price was $1,462, price is now $1,275 per person
$1,275
per person
Sep 10 - Sep 15
found 3 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to East Midlands (EMA)
8.6/10 Excellent! (303 reviews)
Very helpful staff and so friendly. Found us a room with aircon -much appreciated during the heatwave. Room had everything you needed. Breakfast was reasonably priced and great.

Reviewed on Jun 30, 2026

Healing Manor Hotel

Healing Manor Hotel

4 out of 5
Price was $1,443, price is now $1,336 per person
$1,336
per person
Sep 10 - Sep 15
found 3 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to East Midlands (EMA)
8.8/10 Excellent! (299 reviews)
No wifi in room was terrible other than that everything okay but no wifi in this day and age is terrible especially when you are paying top dollar

Reviewed on Jun 25, 2026

The White Swan

The White Swan

4 out of 5
Price was $1,282, price is now $1,206 per person
$1,206
per person
Sep 10 - Sep 15
found 3 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to East Midlands (EMA)
9.2/10 Wonderful! (338 reviews)
Brilliant hotel

Reviewed on Jun 30, 2026

Millfields hotel

Millfields hotel

3 out of 5
Price was $1,308, price is now $1,259 per person
$1,259
per person
Sep 10 - Sep 15
found 3 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to East Midlands (EMA)
8.8/10 Excellent! (452 reviews)
Warm welcome and service, good size room and comfortable bed. Room was a little warm and curtains did not close fully, not great for summer.

Reviewed on Jul 1, 2026

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Stay near popular Boston attractions

St Botolph's Church

9.6/10 (16 reviews)
Climb the tower of this large 14th-century church for superb views across the small port town of Boston and beyond.
See properties

Boston Hotel Deals

The White Hart Hotel, Boston, Lincolnshire

The White Hart Hotel, Boston, Lincolnshire

4 out of 5
1-5 High Street Boston England
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $90 total per night from Jul 3 to Jul 4
$90 total
Jul 3 - Jul 4
Total with taxes and fees
8.6/10 Excellent! (566 reviews)
"Small, rather airless room. No airconditioning or fan. Drawer in (very small) bathroom was broken. Access to second floor room (205) was not easy. Reception desk appeared not be staffed most of the day. Space was limited in the hotel carpark. Breakfast was adequate, but limited (no coffee ..."

Reviewed on Jun 28, 2026

The White Hart Hotel, Boston, Lincolnshire
Boston West Hotel

Boston West Hotel

3 out of 5
Hubbert's Bridge Boston England
Fully refundableReserve now, pay when you stay
$50 nightly
The price is $60 total per night from Jul 5 to Jul 6
$60 total
Jul 5 - Jul 6
Total with taxes and fees
8.4/10 Very Good! (783 reviews)
"Really good quality of room and very spacious. Great bed comfort and better secure doors to when I last stayed two years ago. The resort did decent food in a western style of meals. However they did not offer any breakfast options. Good all round WiFi but it was very slow. Good parking also."

Reviewed on Jun 30, 2026

Boston West Hotel
The Arundell Hotel

The Arundell Hotel

3 out of 5
1 Church Close Boston England
$94 nightly
The price is $113 total per night from Jul 3 to Jul 4
$113 total
Jul 3 - Jul 4
Total with taxes and fees
8.8/10 Excellent! (146 reviews)
"As usual it was a very nice stay."

Reviewed on Jun 18, 2026

The Arundell Hotel
See all 3,594 properties in Boston
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 Boston Vacation Packages

Boston Essential Information

Language
English
Currency
British pounds sterling
Population
41,300
Max Temp Winter
45ºF
Max Temp Summer
70ºF
Top Sights
Lincolnshire Aviation Heritage Centre, Tattershall Castle and Lincolnshire Wildlife Park

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Frequently asked questions

How much does a Boston vacation package cost?
Offering excellent value package deals from $990 on Expedia, you'll be pleasantly surprised at how much a vacation to Boston costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Boston?
You're likely to find reduced prices and greater availability in September, October and December. Browse our cheap Boston vacation packages and you could land some great off-season discounts.
How many days is enough for Boston?
With a well-organized itinerary, you can easily hit the top Boston sights in a handful of days. But if you prefer to explore off the beaten track or take day trips, consider booking your Boston vacation for longer.
Is it worth booking a vacation package to Boston?
Whether you want to visit top attractions such as St Botolph's Church and York Street on your Boston vacation, or coming for its excellent history, markets and walking trails, there's something for everyone here. With so many things to see and do, you'll quickly learn why so many visitors think Boston is a good vacation destination.
How to find the best Boston package deals?
Begin your search for a Boston package deal by entering your destination and travel dates under our "Packages" tab. Then select some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Boston package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Boston adventure underway.
Is it cheaper to book a Boston vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations separately. Better still, you can customize your Boston getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Boston?
If you've got your Boston vacation dates finalized, book as early as you can to grab some unbeatable deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Boston?

  1. Choose the perfect time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to travel to Boston.
  2. Set your budget: Consider costs such as transportation, flights and meals when working out how much to put aside for your trip to Boston. Then, select a hotel that works with your budget, whether that's an affordable option or a deluxe retreat.
  3. Organize your Boston escape with Expedia's trip planning tool: Search for and book accommodations and things to do all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Boston together.
  4. Work out your trip length: Think about how long you want to spend exploring Boston. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  5. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a tailored Boston vacation package.
  6. Book any day trips or activities: Now to the fun part — locking in everything you want to see and do. Browse some of the best things to do in Boston and book your tickets in advance to save time (and maybe some money too!).

Does Expedia offer Book Now, Pay Later Boston vacation packages?
Jet off on your dream trip to Boston with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait for your next paycheck — we've partnered with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to budget for your trip and snap up cheap deals before they sell out.

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.