Jamaica Plain Vacations from $806
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The Latest Jamaica Plain Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Thomas Sea Suites
Aug 21 - Aug 23Thomas Sea Suites + Flight
Plymouth Downtown Waterfront District2 nights3.5 star property9.0/10 - Wonderful (110 reviews)"Great location, clean and the room setup is perfect for family."Reviewed July 13, 2026Roundtrip • New York (EWR) - Boston (BOS)EWR - BOS • Nonstop BOS - EWR • Nonstop - Good Hotels Boston
Sep 24 - Sep 29Good Hotels Boston + Flight
South End5 nights2.0 star property8.0/10 - Very Good (55 reviews)"This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order."Reviewed May 23, 2026Roundtrip • Chicago (CHI) - Boston (BOS)ORD - BOS • Nonstop BOS - RFD • 1 stop - Boston Harbor Hotel
Aug 17 - Aug 20Boston Harbor Hotel + Flight
North End2 nights5.0 star property9.8/10 - Exceptional (1,001 reviews)"Great location and very helpful staff"Reviewed July 16, 2026Roundtrip • Burbank (BUR) - Boston (BOS)BUR - BOS • 1 stop BOS - BUR • 1 stop - The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Aug 26 - Sep 1The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat + Flight
East Wareham6 nights3.0 star property10/10 - Exceptional (10 reviews)"It was an amazing relaxing place. Very family friendly"Reviewed July 12, 2026Roundtrip • Dallas (DFW) - Boston (BOS)DAL - BOS • Nonstop BOS - DFW • 1 stop - Boston Lodge and Suites
Sep 3 - Sep 7Boston Lodge and Suites + Flight
Dorchester4 nights4.0 star property8.4/10 - Very Good (190 reviews)"Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles."Reviewed May 19, 2026Roundtrip • Dallas (DFW) - Boston (BOS)DFW - BOS • Nonstop BOS - DFW • Nonstop
Discover the most popular places to visit in Jamaica Plain
What to do near Jamaica Plain
Boston Haunted Tour : Ghosts & Gravestones
$47
per adult
80% of travelers recommend
Boston CityPASS®: Admission to Top 4 Attractions
$84
per adult
92% of travelers recommend
Boston Summer Nights Tour and River Cruise
$50
per adult
100% of travelers recommend
Jamaica Plain Hotel Deals
3.4 out of 10, (58 reviews)
3.4/10
(58 reviews)
"When I arrived the room was all messy and with trash. It smelled really bad and felt insecure as if someone could enter randomly to it. I entered the room and left straight away, didn’t even stay there."
$139 nightly
The price is $159
$159 total
Jul 25 - Jul 26
Total with taxes and fees
2.8 out of 10, (29 reviews)
2.8/10
(29 reviews)
"Never ever book this dump. We couldn’t contact the owner to get in to the place . No reply to days of messages. Some of the residents let us into the property but we didn’t know what rooms were ours and we didn’t have codes to get in. The place was dirty . I have never seen an airb&b as bad as this . The stair carpet was rotten ,the stair had expanding foam blocking the mouse or rat holes.we saw 2 rats scurry under the front door porch. The place was so bad ,if you had a shower ,you would come...
$259 nightly
The price is $298
$298 total
Jul 25 - Jul 26
Total with taxes and fees
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.
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.
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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.