Downtown Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Downtown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Lakeside Inn
Price was $677, price is now $498 per person
$498
per person
Sep 24 - Sep 28
found 16 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.
enVision Hotel Boston Everett
Save 100% on your flight
Price was $920, price is now $692 per person
$692
per person
Sep 24 - Sep 28
found 16 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Book a stay at this business-friendly hotel in Everett. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
DoubleTree by Hilton Boston North Shore
Save 100% on your flight
Price was $1,268, price is now $975 per person
$975
per person
Sep 24 - Sep 28
found 16 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Book a stay at this golf hotel in Danvers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Water Park of New England and Putnam House are located nearby.
Holiday Inn Hotel & Suites Boston - Peabody by IHG
Price was $780, price is now $605 per person
$605
per person
Sep 24 - Sep 28
found 16 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Book a stay at this business-friendly hotel in Peabody. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Salem Witch Museum and Salem Common are located nearby.
Holiday Inn Express & Suites Boston - Cambridge by IHG
East Cambridge
Save 100% on your flight
Price was $1,177, price is now $929 per person
$929
per person
Sep 24 - Sep 28
found 16 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Book a stay at this business-friendly hotel in Cambridge. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
Beacon Suites Hotel
Ward Two
Save 100% on your flight
Price was $1,142, price is now $914 per person
$914
per person
Sep 24 - Sep 28
found 16 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Stay at this hotel in Somerville. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Harvard Square and Encore Boston Harbor are located nearby.
Top Hotel Deals
Hilton Garden Inn Portsmouth Downtown
100 High St Portsmouth NH
0.19 km from Downtown
Book a stay at this business-friendly hotel in Portsmouth. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
Hampton Inn & Suites Portsmouth Downtown
23 Portwalk Pl Portsmouth NH
0.23 km from Downtown
Book a stay at this business-friendly hotel in Portsmouth. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
Residence Inn by Marriott Portsmouth Downtown/ Waterfront
100 Deer Street Portsmouth NH
0.3 km from Downtown
Book a stay at this business-friendly hotel in Portsmouth. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff ...
Homewood Suites By Hilton Portsmouth Downtown
165 Deer Street Portsmouth NH
0.4 km from Downtown
Stay at this hotel in Portsmouth. Enjoy free breakfast, a fitness center, and valet parking (surcharge). Popular attractions Market Square and Water Country ...
The Hotel Portsmouth
40 Court St. Portsmouth NH
0.3 km from Downtown
Book a stay at this business-friendly hotel in Portsmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Ashworth by the Sea
295 Ocean Blvd Hampton NH
18.61 km from Downtown
Book a stay at this beach hotel in Hampton. Enjoy 3 restaurants, a beach locale, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms ...
Anchorage Inn and Resort
265 Long Beach Avenue York Beach ME
14.33 km from Downtown
Book a stay at this beach hotel in York Beach. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Ocean Surf at York Beach
780 York Street (Rte 1A) York Beach ME
13.57 km from Downtown
Book a stay at this beach motel in York Beach. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the pool and the helpful staff ...
Ogunquit - The Milestone
687 Main Street Ogunquit ME
24.78 km from Downtown
Book a stay at this business-friendly motel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the pool in ...
Ogunquit River Inn & Suites
17 Post Road Ogunquit ME
25.35 km from Downtown
Book a stay at this business-friendly hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Ogunquit Tides Resort
548 Main Street (U.S. Route 1) Ogunquit ME
24.15 km from Downtown
Book a stay at this beach motel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the pool in our reviews. ...
Cliff House Maine
591 Shore Road Cape Neddick ME
21.64 km from Downtown
Book a stay at this luxury resort in Cape Neddick. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property ...
Janmere Motel
52 Ashworth Ave Hampton NH
19 km from Downtown
Stay at this motel in Hampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff 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.
Thu, Aug 20 - Sat, Sep 5
PDX
Portland Intl.
BOS
Logan Intl.
$237 Roundtrip, found 21 hours ago
$237
Roundtrip
found 21 hours ago
Tue, Sep 22 - Wed, Sep 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$242 Roundtrip, found 21 hours ago
$242
Roundtrip
found 21 hours ago
Mon, Sep 21 - Tue, Sep 29
LAX
Los Angeles Intl.
BOS
Logan Intl.
$247 Roundtrip, found 20 hours ago
$247
Roundtrip
found 20 hours ago
Sat, Oct 17 - Wed, Oct 28
LAX
Los Angeles Intl.
BOS
Logan Intl.
$247 Roundtrip, found 12 hours ago
$247
Roundtrip
found 12 hours ago
Tue, Sep 22 - Wed, Sep 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$267 Roundtrip, found 21 hours ago
$267
Roundtrip
found 21 hours ago