South End Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
South End Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Lakeside Inn
Save 100% on your flight
Price was $652, price is now $448 per person
$448
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this business-friendly hotel in Wakefield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attraction MarketStreet Lynnfield is located nearby.
Hotel Ivy Boston Common
Bay Village
Save 100% on your flight
Price was $2,080, price is now $1,224 per person
$1,224
per person
Jul 12 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, a 24-hour front desk, and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $2,860, price is now $1,774 per person
$1,774
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Boston Harbor are located nearby.
Raffles Boston
Back Bay
Save 100% on your flight
Price was $5,703, price is now $3,946 per person
$3,946
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Club Quarters Hotel Faneuil Hall, Boston
Downtown Boston
Save 100% on your flight
Price was $1,936, price is now $1,357 per person
$1,357
per person
Jul 12 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Common and New England Aquarium are located nearby.
Cambridge Common House
West Cambridge
Save 100% on your flight
Price was $2,313, price is now $1,630 per person
$1,630
per person
Jul 12 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Boston (BOS)
Stay at this guesthouse in Cambridge. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions Harvard Square and Fenway Park are located nearby.
Top Hotel Deals
Hilton Garden Inn-Springfield, MA
800 Hall of Fame Avenue Springfield MA
0.37 km from South End
Book a stay at this business-friendly hotel in Springfield. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff in our reviews. ...
Hampton Inn & Suites Springfield/Downtown
851 East Columbus Ave Springfield MA
0.11 km from South End
Book a stay at this business-friendly hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
MGM Springfield
One MGM Way Springfield MA
0.76 km from South End
Stay at this hotel in Springfield. Enjoy free parking, an outdoor pool, and 8 restaurants. Our guests praise the helpful staff and the convenient parking in ...
La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport
64 Ella Grasso Turnpike Windsor Locks CT
20.87 km from South End
Book a stay at this business-friendly hotel in Windsor Locks. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Sheraton Hartford Hotel at Bradley Airport
1 Bradley International Airport Windsor Locks CT
20.21 km from South End
Book a stay at this business-friendly hotel in Windsor Locks. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
20.07 km from South End
Book a stay at this spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ...
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
5.9 km from South End
Book a stay at this golf hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Comfort Inn & Suites Hadley - Amherst
400 Russell St Hadley MA
29.83 km from South End
Book a stay at this business-friendly hotel in Hadley. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport
185 Ella Grasso Turnpike Windsor Locks CT
19.97 km from South End
Book a stay at this business-friendly hotel in Windsor Locks. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Motel 6 Enfield, CT - Hartford
11 Hazard Ave Enfield CT
11.49 km from South End
Stay at this motel in Enfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Six Flags New England and Enfield Square are located ...
Fairfield Inn & Suites Hartford Airport
2 Loten Dr Windsor Locks CT
20.63 km from South End
Book a stay at this business-friendly hotel in Windsor Locks. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Quality Inn & Suites Northampton - Amherst
117 Conz St Northampton MA
24.42 km from South End
Book a stay at this business-friendly hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Motel 6 Windsor Locks, CT - Hartford
3 National Dr Windsor Locks CT
20.21 km from South End
Stay at this motel in Windsor Locks. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. Popular attractions ...
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
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Fri, May 29 - Tue, Jun 2
PDX
Portland Intl.
BOS
Logan Intl.
$217 Roundtrip, just found
$217
Roundtrip
just found
Wed, Aug 12 - Tue, Sep 1
LAX
Los Angeles Intl.
BOS
Logan Intl.
$227 Roundtrip, found 4 hours ago
$227
Roundtrip
found 4 hours ago
Thu, Jul 9 - Tue, Jul 14
LAX
Los Angeles Intl.
BOS
Logan Intl.
$240 Roundtrip, found 22 hours ago
$240
Roundtrip
found 22 hours ago
Fri, May 29 - Tue, Jun 2
PDX
Portland Intl.
BOS
Logan Intl.
$247 Roundtrip, just found
$247
Roundtrip
just found
Tue, Jul 14 - Thu, Jul 16
LAX
Los Angeles Intl.
BOS
Logan Intl.
$257 Roundtrip, found 4 hours ago
$257
Roundtrip
found 4 hours ago