Randolph Vacations from $563

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Your Randolph Vacation

Come and experience this vibrant city for yourself with a Randolph vacation package. Consider spending a few days in the neighborhood of Dorchester, which is great for nature and dining, and your time here is sure to be unforgettable. A trip to Randolph is an ideal opportunity to do some sightseeing. Make sure you visit popular attractions like South Shore Plaza, Blue Hills Ski Area and F1 Boston. Your Randolph vacation is just a few clicks away. Browse hotels, airfares and more on Expedia for an adventure that's tailored to suit your style.

The Latest Randolph 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 $830, price is now $563 per person
$563
per person
May 21 - May 25
found 16 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8.2/10 Very Good! (1,002 reviews)
The hotel is currently being renovated, it's clean, the staff was very kind, and the pool and hot tub are great!

Reviewed on Apr 8, 2026

The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
Seaport District
Save 100% on your flight
Price was $1,213, price is now $772 per person
$772
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.2/10 Wonderful! (2,398 reviews)
Excellent breakfast

Reviewed on Apr 8, 2026

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
MIT
Save 100% on your flight
Price was $1,079, price is now $717 per person
$717
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9/10 Wonderful! (2,291 reviews)
Centrally located, clean facilities.

Reviewed on Apr 9, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $943, price is now $635 per person
$635
per person
Jun 23 - Jun 25
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (253 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,439, price is now $970 per person
$970
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (1,000 reviews)
The rooms were very clean, beds were comfortable, staff friendly and great amenities (I wish the pool was open until 10 pm).

Reviewed on Apr 4, 2026

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Discover the most popular places to visit in Randolph

Fenway Park

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University

Harvard University

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common

Boston Common

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

What to do in Randolph

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$84
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

$23
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
Boston Harbor Cruise boat with the skyscrapers of the city in the background in Boston

City Cruises Boston: Historic Sightseeing Cruise

$56
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
See all activities in Randolph

Randolph Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$230 nightly
The price is $267 total per night from May 8 to May 9
$267 total
May 8 - May 9
Total with taxes and fees
9.2/10 Wonderful! (4,570 reviews)
Clean, good food, good service. Cannot complain!

Reviewed on Apr 9, 2026

Omni Boston Hotel at the Seaport
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $210 total per night from Apr 12 to Apr 13
$210 total
Apr 12 - Apr 13
Total with taxes and fees
9.6/10 Exceptional! (4,153 reviews)
Internet good, staff ok

Reviewed on Apr 9, 2026

Seaport Hotel Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
$221 nightly
The price is $258 total per night from May 10 to May 11
$258 total
May 10 - May 11
Total with taxes and fees
8.4/10 Very Good! (3,141 reviews)
Excellent location, easy access to Boston’s main attractions.

Reviewed on Apr 9, 2026

Hilton Boston Park Plaza
See all 3,932 properties in Randolph
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 Randolph Vacation Packages

Randolph Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
32,100
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
John F. Kennedy Presidential Library and Museum, Franklin Park Zoo and Legacy Place

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Frequently asked questions

How much does a Randolph vacation package cost?
Offering great value package deals from $563 on Expedia, you'll be surprised at how little a vacation to Randolph costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Randolph?
April, May and November are great times to look for cheap Randolph vacation packages. Opting to travel in quieter months means you can usually find reduced prices on flights and hotels.
How many days is enough for Randolph?
Typically, a handful of days is enough to tick off the major sights during your Randolph vacation. But if you prefer to have some time to unwind or go on day trips, think about extending your itinerary.
How to find the best Randolph package deals?
Start your search for a Randolph package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Randolph package deal straight away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Randolph adventure underway.
Is it cheaper to book a Randolph vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still have the flexibility to create a customized Randolph vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Randolph?
If you're considering a spontaneous Randolph vacation, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find awesome deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Randolph vacation packages?
Set off on your dream getaway to Randolph with Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait for the next payday — we've partnered with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans let you split the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to budget for your trip and snap up cheap deals while they last.

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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.