Search Deals onSouth Side Vacation Packages
South Side Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
InnSeason Resorts HarborWalk
Falmouth Heights
per person
May 30 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) to Boston (BOS)
Stay at this hotel in Falmouth. Enjoy free parking, an outdoor pool, and a sauna. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Woods Hole Ferry Terminal and Island Queen Ferry are located nearby.
Lighthouse Inn
Save 100% on your flight
per person
May 30 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) to Boston (BOS)
Stay at this 3-star beach hotel in West Dennis. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Hyannis Harbor and Bass River Lighthouse are located nearby.
InnSeason Resorts Surfside
per person
May 30 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) to Boston (BOS)
Stay at this 3-star beach hotel in East Falmouth. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Woods Hole Ferry Terminal and Menauhant Beach are located nearby.
Sesuit Harbor House
Save 100% on your flight
per person
May 30 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) to Boston (BOS)
Stay at this 3-star hotel in Dennis. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Scargo Tower and Corporation Beach are located nearby.
DoubleTree by Hilton Hotel Boston - Westborough
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Stay at this 4-star business-friendly hotel in Westborough. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lake Chauncy Public Beach and Westborough Country Club are located nearby.
By the Sea Guests Bed & Breakfast & Suites
per person
May 30 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) to Boston (BOS)
Stay at this 3.5-star beach guesthouse in Dennis Port. Enjoy free WiFi, free parking, and a private beach. Popular attractions Sea Street Beach and Pleasant Road Beach are located nearby.
All Seasons Resort, Trademark Collection by Wyndham
Bass River
per person
May 30 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) to Boston (BOS)
Stay at this 3-star business-friendly hotel in South Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Hyannis Harbor and Cape Cod Melody Tent are located nearby.
Blue Rock Resort
per person
May 30 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) to Boston (BOS)
Book a stay at this golf hotel in South Yarmouth. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hyannis Harbor and Bass River Golf Course are located nearby.
3-4 Night Vacations in South Side
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in South Side
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in South Side
citizenM Boston Back Bay
408 Newbury street, Boston, MA
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Fenway Park and Copley Square ...
The Revolution Hotel
40 Berkeley Street, Boston, MA
Stay at this 3.5-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful ...
Harborside Inn Of Boston
185 State St, Boston, MA
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the restaurant in ...
Save an average of 15% on thousands of hotels when you're signed in
Omni Boston Hotel at the Seaport
450 Summer Street, Boston, MA
Stay at this 4-star spa hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
The Godfrey Hotel Boston
505 Washington Street, Boston, MA
Stay at this 4-star boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the ...
Four Points by Sheraton Boston Newton
320 Washington Street, Newton, MA
Book a stay at this business-friendly hotel in Newton. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
The Dagny Boston
89 Broad Street, Boston, MA
Stay at this 4-star luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the restaurant in our ...
Copley Square Hotel, a FOUND Hotel
47 Huntington Ave, Boston, MA
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the restaurant and the ...
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.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Jun 3 - Mon, Jun 9
LAX
Los Angeles Intl.
BOS
Logan Intl.
$174 Roundtrip, found 1 day ago
$174
Roundtrip
found 1 day ago
Wed, Aug 13 - Tue, Aug 19
PDX
Portland Intl.
BOS
Logan Intl.
$215 Roundtrip, found 1 day ago
$215
Roundtrip
found 1 day ago
Fri, Apr 18 - Mon, Apr 28
FOC
Changle Intl.
BOS
Logan Intl.
$1,212 Roundtrip, found 1 day ago
$1,212
Roundtrip
found 1 day ago
Mon, May 5 - Sat, May 10
HKG
Hong Kong Intl.
BOS
Logan Intl.
$1,212 Roundtrip, found 2 days ago
$1,212
Roundtrip
found 2 days ago
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