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Upton Vacation Packages

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Upton Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 out of 5
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3.5-star beach hotel in Beverly. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lynch Park and Salem Willows Beach are located nearby.
Guest House Suites

Guest House Suites

2 out of 5
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this hotel in Salisbury. Enjoy free WiFi, free parking, and an in-room coffeemaker. Popular attractions Parker River National Wildlife Refuge and Walsingham Gallery are located nearby.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 5-star luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and New England Aquarium are located nearby.
Cambria Hotel Boston Downtown - Seaport

Cambria Hotel Boston Downtown - Seaport

3.5 out of 5
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3.5-star family-friendly hotel in Boston. Enjoy free WiFi, 2 restaurants, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Common and TD Garden are located nearby.
Sonder at Pierce Boston

Sonder at Pierce Boston

4 out of 5
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star aparthotel in Boston. Enjoy a fitness center, laundry facilities, and in-room washers/dryers. Popular attractions Fenway Park and Copley Square are located nearby.
Hilton Boston Back Bay

Hilton Boston Back Bay

4 out of 5
per person
Mar 9 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star business-friendly 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 Fenway Park and Boston Common are located nearby.
Bay Village Suites

Bay Village Suites

2 out of 5
per person
Apr 2 - Apr 8
just found
Roundtrip flight included
Phoenix (PHX) to Boston (BOS)
Stay at this aparthotel in Boston. Enjoy free WiFi. Popular attractions Boston Common and TD Garden are located nearby.
Hawthorne Hotel

Hawthorne Hotel

3.5 out of 5
per person
Apr 7 - Apr 10
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3.5-star historic hotel in Salem. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Salem Witch Museum and Salem Common are located nearby.

Upton Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Boston - Logan Airport

Hampton Inn Boston - Logan Airport

3 out of 5
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Guest House Suites

Guest House Suites

2 out of 5
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Doubletree By Hilton Boston Logan Airport Chelsea

Doubletree By Hilton Boston Logan Airport Chelsea

4 out of 5
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)

Upton Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
935 Ocean A Beachside Inn

935 Ocean A Beachside Inn

4 out of 5
Save 100% on your flight
per person
Apr 2 - Apr 8
just found
Roundtrip flight included
Phoenix (PHX) to Boston (BOS)
The Hotel Portsmouth

The Hotel Portsmouth

3 out of 5
Downtown
Save 100% on your flight
per person
Apr 2 - Apr 8
just found
Roundtrip flight included
Phoenix (PHX) to Boston (BOS)
YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
per person
Mar 4 - Mar 11
found 1 hour ago
Roundtrip flight included
Phoenix (PHX) to Boston (BOS)
Martin Hill Inn

Martin Hill Inn

3.5 out of 5
West End
per person
Apr 2 - Apr 8
just found
Roundtrip flight included
Phoenix (PHX) to Boston (BOS)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Mon, Feb 10 - Tue, Feb 11
LAX
Los Angeles Intl.
BOS
Logan Intl.
$158 Roundtrip, found 2 days ago
$158
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Mon, Feb 10 from Los Angeles Intl. to Logan Intl., returning Tue, Feb 11, priced at $158 found 2 days ago
Delta
Tue, Sep 16 - Tue, Sep 30
PDX
Portland Intl.
BOS
Logan Intl.
$207 Roundtrip, found 3 days ago
$207
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Sep 16 from Portland Intl. to Logan Intl., returning Tue, Sep 30, priced at $207 found 3 days ago
Breeze Airways
Thu, May 29 - Sun, Jun 1
LAX
Los Angeles Intl.
PVD
T.F. Green
$323 Roundtrip, found 3 days ago
$323
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, May 29 from Los Angeles Intl. to T.F. Green, returning Sun, Jun 1, priced at $323 found 3 days ago
EVA Airways
Sun, May 4 - Wed, May 7
HKG
Hong Kong Intl.
BOS
Logan Intl.
$1,151 Roundtrip, found 3 hours ago
$1,151
Roundtrip
found 3 hours ago
Select EVA Airways flight, departing Sun, May 4 from Hong Kong Intl. to Logan Intl., returning Wed, May 7, priced at $1,151 found 3 hours ago