A snow-covered park with a gazebo, a bench, and bare trees.

Boston Road Vacations from $482

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The Latest Boston Road Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Jan 6 - Jan 11
Boston Lodge and Suites + Flight
Dorchester
5 nights
4.0 star property
8.4/10 - Very good (194 reviews)
"The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The..."
Reviewed October 17, 2026
Roundtrip • Los Angeles (LAX) - Boston (BOS)
LAX - BOS • Nonstop BOS - LAX • 1 stop
~~$1,473~~
$482
per traveler
found 1 day ago
Boston Lodge and Suites
Jan 15 - Jan 18
Delamar West Hartford + Flight
West Hartford
3 nights
4.0 star property
9.8/10 - Exceptional (1,000 reviews)
"Very clean and the staff was very friendly"
Reviewed November 10, 2026
Roundtrip • San Juan (SJU) - Hartford (BDL)
SJU - BDL • Nonstop BDL - SJU • Nonstop
~~$1,194~~
$795
per traveler
found 1 day ago
Delamar West Hartford
Jan 27 - Jan 31
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat + Flight
East Wareham
4 nights
3.0 star property
10/10 - Exceptional (11 reviews)
"We had a great experience staying in the crab house. The cottage was well maintained and had everything we needed to enjoy our stay. The staff was friendly, helpful, and genuinely care. Ken was fantastic, you can really tell he cares about ensuring guests have a great experience. 10/10 experience, would recommend this spot to anyone looking for a great stay on the cape."
Reviewed July 27, 2026
Roundtrip • Chicago (ORD) - Boston (BOS)
ORD - BOS • Nonstop BOS - ORD • Nonstop
~~$1,431~~
$1,014
per traveler
found 13 hours ago
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Jan 14 - Jan 18
Raffles Boston + Flight
Back Bay
4 nights
5.0 star property
9.6/10 - Exceptional (357 reviews)
Roundtrip • Los Angeles (LAX) - Boston (BOS)
LAX - BOS • Nonstop BOS - LAX • Nonstop
Save 100% on your flight
~~$2,037~~
$1,445
per traveler
found 1 day ago
Raffles Boston
Jan 14 - Jan 18
Four Seasons Hotel Boston + Flight
Bay Village
4 nights
5.0 star property
9.4/10 - Exceptional (497 reviews)
"The best location and the beat service! The best swimming pool"
Reviewed November 9, 2026
Roundtrip • Los Angeles (LAX) - Boston (BOS)
LAX - BOS • Nonstop BOS - LAX • Nonstop
~~$2,083~~
$1,530
per traveler
found 1 day ago
Four Seasons Hotel Boston

Where to stay in Boston Road

Find the best Boston Road areas and neighborhoods for the activities you enjoy most.

A river with a bridge, a large dome-shaped building, and a cityscape with various buildings and roads.

Metro Center

Explore Springfield Armory National Park, Quadrangle museums, and enjoy over 70 clubs, bars, and restaurants in the Club Quarter. Exceptionally walkable, with easy access to I-91, I-291, and Union Station.

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A basketball court with spectators, a scoreboard, and a wall of portraits.

South End

If you're spending some time in South End, Naismith Memorial Basketball Hall of Fame and Titanic Museum are top sights worth seeing.

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A dense forest with a stream, moss-covered rocks, and ferns.

Forest Park

While visiting Forest Park, you might make a stop by sights like Forest Park Branch Springfield City Library and Forest Park.

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East Springfield

While there might not be top attractions in East Springfield, you can explore the larger area and discover places like Lake Lorraine State Park and Chicopee Memorial State Park.

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A calm lake surrounded by autumn-colored trees.

Liberty Heights

While visiting Liberty Heights, you might make a stop by sights like Health Sciences Library and Gilman Health Sciences Library.

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Boston Road Hotel Deals

A reception area with a reception desk, two green armchairs, a patterned rug, and a chandelier.

Howard Johnson by Wyndham Springfield

Boston Road

"DIRTY. DISGUSTING. NOTHING WAS CHANGED OR CLEANED FROM PREVIOUS STAYS. SHEETS FULL OF STAINS AND BODY HAIRS CARPET HASN'T BEEN VACUUMED IN WEEKS. TOILET WAS ABSOLUTELY DISGUSTING. SHOWER HASN'T BEEN DISINFECTED PROBABLY EVER. SHOWER HEAD WAS NASTY. SHOWED DRAIN WAS MOSTLY CLOGGED SO WATER WOULDN'T DRAIN PROPERLY. FURNITURE WAS ALL STAINED AND FALLING APART.. SOME LIGHTING DIDN'T WORK IN ROOM. HOWEVER, THE EMPLOYEE WAS GREAT. NOT THE PLACE TO STAY AND RELAX, AT ALL"

$80 nightly

Nov 12 - Nov 13

Total with taxes and fees