Jamaica Plain Vacations from $614
Book a Hotel + Flight or Car together to unlock savings
Photo by throwingsofas
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
The Latest Jamaica Plain Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Cove at Yarmouth by Westgate Resorts
Price was $867, price is now $614 per person
$614
per person
May 18 - May 22
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (254 reviews)
From the moment we arrived, we was welcomed with warm hospitality and genuine friendliness
The room was spotless, comfortable, and beautifully maintained, and I especially appreciated the attention to detail throughout the property. The indoor pool a plus in these cold months -
The location was perfect as well—close to everything I wanted to explore, yet peaceful and relaxing.
Your staff went above and beyond to ensure a pleasant experience, and it did not go unnoticed. It’s clear that you take great pride in providing exceptional service, and it made my trip all the more memorable.
Thank you for such a wonderful stay. I will absolutely be recommending your hotel to friends and family, and I look forward to returning in the future.
Reviewed on Mar 29, 2026
D. Hotel Suites & Spa
Price was $1,147, price is now $711 per person
$711
per person
May 29 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Boston (BOS)
9.2/10 Wonderful! (2,225 reviews)
If you have a kid at one of the five colleges and you are looking for a good place to stay a night or two for a reasonable price, this is a very good option. Nice sized rooms, clean, well maintained and friendly staff.
Reviewed on Apr 5, 2026
The Inn at Hastings Park, Relais & Chateaux - Boston
Price was $1,470, price is now $960 per person
$960
per person
Jun 14 - Jun 17
found 9 hours ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
9.6/10 Exceptional! (252 reviews)
Excellent experience- clean and very helpful staff
Reviewed on Mar 9, 2026
The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was $3,033, price is now $2,064 per person
$2,064
per person
Jun 11 - Jun 15
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (1,004 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
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
4.5/5(2,438 area reviews)
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
$218 nightly
The price is $254 total per night from Apr 10 to Apr 11
$254 total
Apr 10 - Apr 11
Total with taxes and fees
9.2/10 Wonderful! (4,555 reviews)
Staff welcoming, great location for Boston convention center tournament. Clean room and hotel areas.
Reviewed on Apr 5, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $210 total per night from Apr 9 to Apr 10
$210 total
Apr 9 - Apr 10
Total with taxes and fees
9.6/10 Exceptional! (4,133 reviews)
Pros: Convenient location near convention center and Silver Line. Excellent gym. Cons: limited takeout and late night dining options nearby. Destination fee not well disclosed when I made the reservation. Hit my head on the shower door every time I got out.
Reviewed on Apr 5, 2026
Hilton Boston Park Plaza
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
$218 nightly
The price is $254 total per night from Apr 9 to Apr 10
$254 total
Apr 9 - Apr 10
Total with taxes and fees
8.4/10 Very Good! (3,134 reviews)
Room is Too small .
Reviewed on Apr 5, 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 fascinating museums and acclaimed art scene in this vibrant area.
Things to do
Boston CityPASS®: Admission to Top 4 Attractions
$84
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
$23
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
$56
per adult
92% of travellers recommend
Explore a world of travel with Expedia
- Boston Hotels
- Hotels near Fenway Park
- Hotels near Downtown Boston
- Cheap Hotels in Boston
- Hotels near Logan Intl.
- Hotels near Green Street Station
- Apartments in Green Street Station
- Hotels near Axiom
- Hotels near Samuel Adams Brewery
- Hotels near Stony Brook Station
- Houseboats in Stony Brook Station
- Motels in Stony Brook Station
- Hotels near Egleston Square
- Hotels near Boston Forest Hills Station
- Houseboats in Boston Forest Hills Station
- Apartments in Boston Forest Hills Station
- Brookline Hotels
- Hotels near Forest Hills Cemetery
- Hotels near Arnold Arboretum
- Hotels near Larz Anderson Auto Museum
- Hotels near Larz Anderson Park
- Condo Rentals in Jackson Square Station
- Hotels near Jackson Square Station
- Hotels near High Street Hill
- Hotels near Back of the Hill Station
- Hotels near Frederick Law Olmsted National Historic Site
- Hotels near Franklin Park Zoo
- Hotels near Roxbury
- Best Western Hotels in Roxbury
- 5 Star Hotels in Roxbury
- 4 Star Hotels in Roxbury
- Romantic Hotels in Roxbury
- Cheap Hotels in Brookline
- Hotels near GASP
- B&B in Brookline
- Boutique Hotels in Brookline
- Apartments in Brookline
- Beach Hotels in Brookline
- Pet-Friendly Hotels in Brookline
- Resorts & Hotels with Spas in Brookline
- Extended Stay Hotels in Brookline
- Hotels with an Indoor Pool in Brookline
- 5 Star Hotels in Brookline
- Hotels with Free Breakfast in Brookline
- Hotels with Bars in Brookline
- Hotels with Restaurants in Brookline
- Hotels with Hot Tubs in Brookline
- 4 Star Hotels in Brookline
- Best Western Hotels in Brookline
- 3 Star Hotels in Brookline
- Condo Rentals in Brookline
- Luxury Hotels in Brookline
- Hotels with Balconies in Brookline
- Hotels with Free Parking in Brookline
- Guest Houses in Brookline
- Hotels with Connecting Rooms in Brookline
- Hotels with a Gym in Brookline
- Hotels with Suites in Brookline
- Golf Hotels in Brookline
- Family Hotels in Brookline
- Hyatt Hotels in Brookline
- Hotel Wedding Venues Hotels in Brookline
- 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
- Car rental Boston Airport (BOS)
- Car rentals near Axiom
- Car rentals near Larz Anderson Auto Museum
- Car rentals near Larz Anderson Park
- Car rentals near Brookline
- Car rentals near Roxbury
- Enterprise Rental Cars in Brookline
- Car rentals near Franklin Park Zoo
- Hertz Rental Cars in Brookline
- Budget Rental Cars in Brookline
- Sixt Rental Cars in Brookline
- Alamo Rent A Car Rental Cars in Brookline
- Thrifty Car Rental Rental Cars in Brookline
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.