Milford Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
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Milford Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hilton Boston/Woburn
Save 100% on your flight
Price was $734, price is now $491 per person
$491
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3.5-star business-friendly hotel in Woburn. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attraction Burlington Mall is located nearby.
The Newbury Boston
Back Bay
Price was $2,697, price is now $1,438 per person
$1,438
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
DoubleTree Suites by Hilton Hotel Boston - Cambridge
Allston
Save 100% on your flight
Price was $1,196, price is now $691 per person
$691
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
The Ritz-Carlton, Boston
Downtown Boston
Save 100% on your flight
Price was $2,464, price is now $1,519 per person
$1,519
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Pennyweight Hotel Boston, Curio Collection by Hilton
West End
Save 100% on your flight
Price was $1,453, price is now $978 per person
$978
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Faneuil Hall Marketplace are located nearby.
Maverick Suites at 402 Columbus Ave
South End
Save 100% on your flight
Price was $1,109, price is now $755 per person
$755
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this aparthotel in Boston. Enjoy free WiFi, laundry facilities, and satellite TV channels. Popular attractions Copley Square and Boston Common are located nearby.
Top Hotel Deals
Sonesta Select Boston Milford
10 Fortune Blvd, Milford, MA
2.66 km from city center
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 ...
DoubleTree by Hilton Boston - Milford
11 Beaver Street, Milford, MA
2.68 km from city center
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 ...
Comfort Inn Boston Milford
24 Beaver St, Milford, MA
2.67 km from city center
Book a stay at this business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Fairfield Inn & Suites by Marriott Boston Milford
1 Fortune Blvd, Milford, MA
2.56 km from city center
Book a stay at this business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Motel 6 Framingham, MA - Boston West
1668 Worcester Rd, Framingham, MA
17.65 km from city center
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. ...
Sheraton Boston Needham Hotel
100 Cabot St, Needham, MA
30.48 km from city center
Book a stay at this business-friendly hotel in Needham. Enjoy breakfast (surcharge), a fitness center, and parking (surcharge). Our guests praise the helpful ...
Hampton Inn & Suites Boston/Waltham
135 2nd Ave, Waltham, MA
34.82 km from city center
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 ...
The Verve Hotel Boston Natick, Tapestry Collection by Hilton
1360 Worcester St, Natick, MA
20.49 km from city center
Stay at this 3.5-star business-friendly hotel in Natick. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean ...
DoubleTree by Hilton Hotel Boston - Westborough
5400 Computer Dr, Westborough, MA
17.21 km from city center
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 ...
Crescent Suites Hotel
287 Crescent Street, Waltham, MA
33.54 km from city center
Stay at this 3-star business-friendly aparthotel in Waltham. Enjoy a fitness center, a business center, and a garden. Our guests praise the helpful staff and ...
Boston Marriott Newton
2345 Commonwealth Avenue, Newton, MA
31.29 km from city center
Stay at this 4-star business-friendly hotel in Newton. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the helpful staff and ...
Fairfield Inn & Suites by Marriott Boston Waltham
250 Second Avenue, Waltham, MA
34.64 km from city center
Stay at this 3-star business-friendly hotel in Waltham. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Hampton Inn Boston Natick
319 Speen St, Natick, MA
21.4 km from city center
Book a stay at this business-friendly hotel in Natick. 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.
Fri, Nov 7 - Tue, Nov 11
PDX
Portland Intl.
BOS
Logan Intl.
$188 Roundtrip, found 19 hours ago
$188
Roundtrip
found 19 hours ago
Wed, Nov 5 - Sat, Nov 8
PDX
Portland Intl.
BOS
Logan Intl.
$197 Roundtrip, found 19 hours ago
$197
Roundtrip
found 19 hours ago
Tue, Oct 21 - Wed, Oct 22
LAX
Los Angeles Intl.
BOS
Logan Intl.
$217 Roundtrip, found 3 hours ago
$217
Roundtrip
found 3 hours ago
Mon, Oct 20 - Fri, Oct 24
LAX
Los Angeles Intl.
BOS
Logan Intl.
$217 Roundtrip, found 3 hours ago
$217
Roundtrip
found 3 hours ago
Thu, Oct 30 - Sun, Nov 2
LAX
Los Angeles Intl.
BOS
Logan Intl.
$222 Roundtrip, found 6 days ago
$222
Roundtrip
found 6 days ago