Jamaica Plain Vacations from $351
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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.
The Latest Jamaica Plain Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Sunbird ANNEX Resort
Price was $489, price is now $351 per person
$351
per person
May 28 - Jun 1
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
7.8/10 Good! (825 reviews)
Everything was good.
The room was very plain, but it had everything we needed which was bed, TV, fridge, iron, WiFi. The staff was very gracious.
Reviewed on Oct 19, 2025
The Cove at Yarmouth by Westgate Resorts
Save 100% on your flight
Price was $845, price is now $511 per person
$511
per person
May 28 - Jun 1
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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
Beachside Village Resort
Save 100% on your flight
Price was $1,621, price is now $1,095 per person
$1,095
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (101 reviews)
Very clean and quiet place to relax. Very friendly and professional! We will come back!
Reviewed on Nov 10, 2025
Sunbird Cape Cod Resort
Price was $537, price is now $383 per person
$383
per person
May 28 - Jun 1
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
7.8/10 Good! (533 reviews)
It's definitely not a resort but it's is clean and peaceful. You get watched very closely at breakfast.
Reviewed on Nov 13, 2025
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
$189 nightly
The price is $220 total per night from Apr 5 to Apr 6
$220 total
Apr 5 - Apr 6
Total with taxes and fees
9.2/10 Wonderful! (4,547 reviews)
This hotel is clean, the staff are friendly - just a great experience every time I stay here.
Reviewed on Apr 2, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $182 total per night from Apr 5 to Apr 6
$182 total
Apr 5 - Apr 6
Total with taxes and fees
9.6/10 Exceptional! (4,122 reviews)
I enjoyed the comfort of my room, the bar and evening meal, and my breakfast in the morning.
Reviewed on Apr 2, 2026
Hilton Boston Park Plaza
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
$213 nightly
The price is $248 total per night from Apr 6 to Apr 7
$248 total
Apr 6 - Apr 7
Total with taxes and fees
8.4/10 Very Good! (3,124 reviews)
The heater was so loud, I couldn’t sleep well.
Reviewed on Apr 1, 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
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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.