Highlands Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Photo by Tiffany Zhou
Highlands Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel
South End
Save 100% on your flight
Price was $848, price is now $572 per person
$572
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), 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.
Boston Harbor Hotel
North End
Price was $3,469, price is now $1,755 per person
$1,755
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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 Common are located nearby.
Fairmont Copley Plaza, Boston
Back Bay
Save 100% on your flight
Price was $1,614, price is now $1,069 per person
$1,069
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The Colonnade Hotel Back Bay
Back Bay
Save 100% on your flight
Price was $1,515, price is now $1,075 per person
$1,075
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
Hotel Commonwealth
Fenway–Kenmore
Save 100% on your flight
Price was $1,547, price is now $1,101 per person
$1,101
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fenway Park and Copley Square are located nearby.
The Bostonian Boston
Government Center
Save 100% on your flight
Price was $1,049, price is now $759 per person
$759
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, room service, and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions New England Aquarium and TD Garden are located nearby.
Top Hotel Deals
Four Points by Sheraton Boston Newton
320 Washington Street Newton MA
32.66 km from Highlands
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 ...
DoubleTree by Hilton Boston North Shore
50 Ferncroft Rd Danvers MA
30.26 km from Highlands
Book a stay at this golf hotel in Danvers. Enjoy free parking, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
Bedford Plaza Hotel - Boston
340 Great Road Bedford MA
17.07 km from Highlands
Stay at this hotel in Bedford. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Burlington Mall and Lexington Battle Green are located ...
Hampton Inn & Suites Boston/Waltham
135 2nd Ave Waltham MA
26.97 km from Highlands
Book a stay at this business-friendly hotel in Waltham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Holiday Inn Express Boston - Saugus by IHG
999 Broadway Saugus MA
30.91 km from Highlands
Book a stay at this business-friendly hotel in Saugus. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
AC Hotel by Marriott Boston Cambridge
10 Acorn Park Drive Cambridge MA
29.97 km from Highlands
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Hyatt Place Boston/Medford
116 Riverside Ave Medford MA
30.23 km from Highlands
Book a stay at this business-friendly hotel in Medford. Enjoy free breakfast, free WiFi, and a free area shuttle. Our guests praise the breakfast and the helpful ...
Hampton Inn Boston Woburn
371 Washington Street Woburn MA
22.41 km from Highlands
Book a stay at this business-friendly hotel in Woburn. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
La Quinta Inn & Suites by Wyndham Boston-Andover
131 River Rd Andover MA
12.38 km from Highlands
Book a stay at this business-friendly hotel in Andover. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Best Western Plus New Englander
1 Rainin Road Woburn MA
24.27 km from Highlands
Book a stay at this business-friendly hotel in Woburn. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Sonesta Simply Suites Boston Burlington
130 Middlesex Tpke Burlington MA
18.55 km from Highlands
Book a stay at this business-friendly hotel in Burlington. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and ...
The Westin Waltham-Boston
70 Third Avenue Waltham MA
26.86 km from Highlands
Book a stay at this business-friendly hotel in Waltham. Enjoy breakfast (surcharge), room service, and a health club. Our guests praise the helpful staff and ...
Best Western Plus Waltham Boston
380 Winter Street Waltham MA
26.49 km from Highlands
Book a stay at this business-friendly hotel in Waltham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
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, Apr 22 - Tue, May 5
LAX
Los Angeles Intl.
BOS
Logan Intl.
$179 Roundtrip, found 3 days ago
$179
Roundtrip
found 3 days ago
Wed, Apr 15 - Mon, Apr 27
LAX
Los Angeles Intl.
BOS
Logan Intl.
$179 Roundtrip, found 3 days ago
$179
Roundtrip
found 3 days ago
Thu, Mar 12 - Tue, Mar 17
LAX
Los Angeles Intl.
BOS
Logan Intl.
$185 Roundtrip, found 2 days ago
$185
Roundtrip
found 2 days ago
Fri, Jan 16 - Sat, Jan 17
LAX
Los Angeles Intl.
BOS
Logan Intl.
$199 Roundtrip, found 2 days ago
$199
Roundtrip
found 2 days ago
Wed, Mar 18 - Mon, Mar 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$199 Roundtrip, found 2 days ago
$199
Roundtrip
found 2 days ago