Main South Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Main South Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
YOTEL Boston
Seaport District
Save 100% on your flight
per person
Sep 8 - Sep 12
found 16 hours ago
Roundtrip non-stop flight included
Chicago (MDW) to Boston (BOS)
Stay at this 4-star hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and a rooftop terrace. Our guests praise the restaurant and the bar in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
Raffles Boston
Back Bay
Save 100% on your flight
per person
Sep 8 - Sep 12
found 16 hours ago
Roundtrip non-stop flight included
Chicago (MDW) to Boston (BOS)
Stay at this 5-star 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.
Boston Harbor Hotel
North End
Save 100% on your flight
per person
Sep 8 - Sep 12
found 16 hours ago
Roundtrip non-stop flight included
Chicago (MDW) to Boston (BOS)
Stay at this 5-star 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 Faneuil Hall Marketplace are located nearby.
The Ritz-Carlton, Boston
Downtown Boston
Save 100% on your flight
per person
Sep 8 - Sep 12
found 16 hours ago
Roundtrip non-stop flight included
Chicago (MDW) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a health club. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.
Hotel AKA Back Bay
Back Bay
Save 100% on your flight
per person
Sep 8 - Sep 12
found 16 hours ago
Roundtrip non-stop flight included
Chicago (MDW) to Boston (BOS)
Stay at this 4.5-star luxury hotel in Boston. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The Langham, Boston
Downtown Boston
Save 100% on your flight
per person
Sep 8 - Sep 12
found 16 hours ago
Roundtrip non-stop flight included
Chicago (MDW) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
Top Hotel Deals
Motel 6 Framingham, MA - Boston West
1668 Worcester Rd, Framingham, MA
28.27 km from Main South
Stay at this motel in Framingham. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
DoubleTree by Hilton Hotel Boston - Westborough
5400 Computer Dr, Westborough, MA
20.81 km from Main South
Stay at this 4-star business-friendly hotel in Westborough. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Publick House Historic Inn and Country Motor Lodge
277 Main Street (RT 131), Sturbridge, MA
26.67 km from Main South
Book a stay at this spa resort in Sturbridge. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the clean ...
Sonesta Select Boston Milford
10 Fortune Blvd, Milford, MA
27.51 km from Main South
Stay at this 3-star business-friendly hotel in Milford. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Wellsworth Hotel
14 Mechanic St, Southbridge, MA
25.98 km from Main South
Stay at this 3-star business-friendly hotel in Southbridge. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Best Western Royal Plaza Hotel & Trade Center
181 Boston Post Rd W, Marlborough, MA
21.41 km from Main South
Book a stay at this business-friendly hotel in Marlborough. Enjoy free breakfast, free parking, and 2 restaurants. Our guests praise the breakfast and the helpful ...
Extended Stay America Suites Boston Westborough Computer Dr
1800 Computer Dr, Westborough, MA
20.19 km from Main South
Book a stay at this business-friendly hotel in Westborough. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Embassy Suites by Hilton Boston Marlborough
123 Boston Post Rd W, Marlborough, MA
21.57 km from Main South
Book a stay at this business-friendly hotel in Marlborough. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hilton Garden Inn Boston/Marlborough
170 Forest St, Marlborough, MA
21.93 km from Main South
Stay at this 3-star business-friendly hotel in Marlborough. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the helpful staff ...
Comfort Inn Auburn - Worcester
426 Southbridge St, Auburn, MA
5.72 km from Main South
Book a stay at this business-friendly hotel in Auburn. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Hyatt Place Marlborough/Apex Center
169 Apex Drive, Marlborough, MA
21.08 km from Main South
Stay at this 3-star business-friendly hotel in Marlborough. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
DoubleTree by Hilton Boston - Milford
11 Beaver Street, Milford, MA
29.52 km from Main South
Stay at this 4-star hotel in Milford. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions ...
Red Roof Inn Boston - Southborough/ Worcester
367 Turnpike Rd, Southborough, MA
21.81 km from Main South
Stay at this hotel in Southborough. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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.
Wed, Sep 24 - Wed, Oct 1
LAX
Los Angeles Intl.
BOS
Logan Intl.
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Tue, Sep 23 - Tue, Sep 30
LAX
Los Angeles Intl.
BOS
Logan Intl.
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Mon, Sep 8 - Fri, Sep 12
LAX
Los Angeles Intl.
BOS
Logan Intl.
$191 Roundtrip, found 4 days ago
$191
Roundtrip
found 4 days ago
Mon, Sep 15 - Fri, Sep 19
PDX
Portland Intl.
BOS
Logan Intl.
$211 Roundtrip, found 3 days ago
$211
Roundtrip
found 3 days ago
Fri, Sep 5 - Tue, Sep 9
LAX
Los Angeles Intl.
BOS
Logan Intl.
$228 Roundtrip, found 5 days ago
$228
Roundtrip
found 5 days ago
Best points of interest in Worcester
- Clark University Vacations
- Burnside Fountain Vacations
- DCU Center Vacations
- Union Station Vacations
- Old Sturbridge Village Vacations
- Wachusett Mountain Ski Area Vacations
- UMass Memorial Medical Center Vacations
- New England Sports Center Vacations
- College of the Holy Cross Vacations
- Apex Entertainment Center Vacations
More AARP Member Vacation Packages
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Chicago Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations