Jamaica Plain Vacations
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Your Jamaica Plain Vacation
Book a Jamaica Plain vacation package and immerse yourself in the rhythm and vibe of this captivating neighborhood. With all your travel plans worked out, the only thing you need to focus on here is having an absolute ball. Kick off your trip to Jamaica Plain with a visit to nearby attractions such as Fenway Park, Copley Place and Boston Museum of Fine Arts. Whatever your travel goals or the size of your budget, booking your perfect Jamaica Plain vacation is simple with Expedia.
Price found within the past 48 hours. Click for updated prices.
- The Inn at Hastings Park, Relais & Chateaux - Boston
Aug 18 - Aug 22The Inn at Hastings Park, Relais & Chateaux - Boston + Flight
Lexington4 nights9.6/10 - Exceptional (256 reviews)"Splendid bed and breakfast"Reviewed April 29, 2026Roundtrip • Atlanta (ATL) - Boston (BOS)ATL - BOS • 1 stop BOS - ATL • 1 stop - The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Aug 2 - Aug 9The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat + Flight
East Wareham7 nights10/10 - Exceptional (9 reviews)"I can't express how much I appreciate the hosts very fine people Indeed, the property is just awesome! The view gorgeous clearly they went out of their way to think of everything highly recommended. Tim Lawler "Reviewed October 8, 2025Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)ATL - MVY • 1 stop MVY - ATL • 1 stop - Boston Harbor Hotel
Aug 27 - Aug 29Boston Harbor Hotel + Flight
North End2 nights9.8/10 - Exceptional (1,000 reviews)"Wonderful classic harbor front hotel. Very nice front desk. Would stay again"Reviewed May 25, 2026Roundtrip • Atlanta (ATL) - Boston (BOS)ATL - BOS • Nonstop BOS - ATL • Nonstop - By the Sea Guests Bed & Breakfast & Suites
Jul 10 - Jul 16By the Sea Guests Bed & Breakfast & Suites + Flight
Dennis Port6 nights9.2/10 - Wonderful (187 reviews)"Such a cute place to stay and the staff are so helpful and welcoming!!"Reviewed May 31, 2026Roundtrip • Atlanta (ATL) - Boston (BOS)ATL - BOS • Nonstop BOS - ATL • Nonstop - Nantucket Inn
Aug 1 - Aug 8Nantucket Inn + Flight
Nantucket6 nights9.2/10 - Wonderful (698 reviews)"Do yourself a favor and stay here the rooms are not incredibly updated, but they are incredibly clean and well-maintained and the overall aesthetic of the place is top shelf, but the glowing star of the entire place are the Jamaican staff that run the place you will not find nicer people that are more accommodating and friendly not to mention the café is a 10 out of 10 highly recommend this place also lots of parking"Reviewed May 28, 2026Roundtrip • Denver (DEN) - Boston (BOS)DEN - BOS • Nonstop BOS - DEN • Nonstop
Where to stay in Jamaica Plain
Find the best Jamaica Plain areas and neighborhoods for the activities you enjoy most. Learn more about Jamaica Plain
Downtown Boston
Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.
Jamaica Plain Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$258 nightly
The price is $301 total per night from Jun 7 to Jun 8
$301 total
Jun 7 - Jun 8
Total with taxes and fees
9.2/10 Wonderful! (4,669 reviews)
"The room was very nice and had useful amenities and features. I wish there was a microwave for guests to use. The water pressure wasn’t the greatest, but everything else was great."
Reviewed on Jun 1, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $177 total per night from Jun 7 to Jun 8
$177 total
Jun 7 - Jun 8
Total with taxes and fees
9/10 Wonderful! (2,638 reviews)
"A unique hotel that we enjoyed. Very clean."
Reviewed on May 31, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$287 nightly
The price is $333 total per night from Jun 28 to Jun 29
$333 total
Jun 28 - Jun 29
Total with taxes and fees
9.6/10 Exceptional! (4,397 reviews)
"Clean, updated , friendly staff"
Reviewed on May 31, 2026
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.
Discover the most popular places to visit in Jamaica Plain
Arnold Arboretum
Escape the city bustle and soak up the serenity in this beloved park that doubles as a respected Harvard University research center.
Axiom
You can study the exhibits at Axiom, a museum with a story of its own, during your travels to Boston. Experience the acclaimed art scene and fascinating museums in this vibrant area.
Things to do
Boston CityPASS®: Admission to Top 4 Attractions
$84
per adult
92% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
$45
per adult
98% of travellers recommend
Harvard University Campus Guided Walking Tour
$23
per adult
92% of travellers recommend
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- Boston Vacations
- Boston Museum of Fine Arts
- Axiom
- Samuel Adams Brewery
- Isabella Stewart Gardner Museum
- Arnold Arboretum
- Forest Hills Cemetery
- Larz Anderson Auto Museum
- Frederick Law Olmsted National Historic Site
- Franklin Park Zoo
- Brookline Vacations
- Brigham and Women's Hospital
- Warren Anatomical Museum
- Visit Roxbury
- Dana-Farber Cancer Institute
- Children's Hospital Boston
- Visit Brookline
- Car rentals near Boston
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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.