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Highland Vacation Packages

Highland Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Boston - Westborough

DoubleTree by Hilton Hotel Boston - Westborough

4 out of 5
Save 100% on your flight
Price was $1,013, price is now $641 per person
$641
per person
May 27 - Jun 3
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this business-friendly hotel in Westborough. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lake Chauncy Public Beach and Westborough Country Club are located nearby.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $2,423, price is now $1,485 per person
$1,485
per person
Jun 9 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this 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 Boston Common are located nearby.
The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
Price was $1,317, price is now $817 per person
$817
per person
Jun 2 - Jun 9
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Fenway Park and Harvard Square are located nearby.
Studio Allston Hotel

Studio Allston Hotel

4 out of 5
Brighton
Save 100% on your flight
Price was $1,500, price is now $997 per person
$997
per person
May 27 - Jun 3
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
The Inn on Arsenal

The Inn on Arsenal

2.5 out of 5
Save 100% on your flight
Price was $1,382, price is now $925 per person
$925
per person
Jun 9 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in Watertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
The Mansion at Ocean Edge

The Mansion at Ocean Edge

4 out of 5
Save 100% on your flight
Price was $2,393, price is now $1,603 per person
$1,603
per person
Jun 9 - Jun 13
found 1 day ago
Roundtrip flight included
Nashville (BNA) to Boston (BOS)
Book a stay at this luxury hotel in Brewster. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Ocean Edge Golf Club and Linnell Landing Beach are located nearby.
The Hotel Salem

The Hotel Salem

3 out of 5
Downtown Salem
Save 100% on your flight
Price was $1,765, price is now $1,190 per person
$1,190
per person
Jun 9 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in Salem. Enjoy free WiFi, a rooftop terrace, and a 24-hour front desk. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Witch History Museum and Salem Museum are located nearby.
Hampton Inn & Suites Portsmouth Downtown

Hampton Inn & Suites Portsmouth Downtown

3 out of 5
Downtown
Save 100% on your flight
Price was $1,355, price is now $916 per person
$916
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
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 staff in our reviews. Popular attractions Market Square and Water Country are located nearby.

3-4 Night Vacations in Highland

Price found within the past 48 hours. Click for updated prices.
The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
Price was $783, price is now $555 per person
$555
per person
Jun 4 - Jun 7
found 23 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,846, price is now $1,073 per person
$1,073
per person
Jun 10 - Jun 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Mansion at Ocean Edge

The Mansion at Ocean Edge

4 out of 5
Save 100% on your flight
Price was $2,393, price is now $1,603 per person
$1,603
per person
Jun 9 - Jun 13
found 1 day ago
Roundtrip flight included
Nashville (BNA) to Boston (BOS)
Beachside Village Resort

Beachside Village Resort

3 out of 5
Price was $1,042, price is now $730 per person
$730
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)

5-7 Night Vacations in Highland

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Boston - Westborough

DoubleTree by Hilton Hotel Boston - Westborough

4 out of 5
Save 100% on your flight
Price was $1,013, price is now $641 per person
$641
per person
May 27 - Jun 3
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $2,423, price is now $1,485 per person
$1,485
per person
Jun 9 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
Price was $1,317, price is now $817 per person
$817
per person
Jun 2 - Jun 9
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
enVision Hotel Boston Everett

enVision Hotel Boston Everett

2 out of 5
Save 100% on your flight
Price was $1,269, price is now $793 per person
$793
per person
Jun 2 - Jun 9
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)

Cheap Hotel Deals in Highland

Best Western Merry Manor Inn

Best Western Merry Manor Inn

2.5 out of 5
700 Main St South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool ...
Opens in a new windowBest Western Merry Manor Inn
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff ...
Opens in a new windowPortland Harbor Hotel
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
Opens in a new windowCambria Hotel Portland Downtown-Old Port
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HomeAwhile

HomeAwhile

4 out of 5
205 Southborough Drive Scarborough ME
Stay at this aparthotel in Scarborough. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Maine Mall and Thompson's Point are located ...
Opens in a new windowHomeAwhile
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowPortland Regency Hotel & Spa
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Opens in a new windowClarion Hotel Portland Airport ME
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

4 out of 5
88 Spring St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Opens in a new windowHoliday Inn Portland-By the Bay by IHG
Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

3 out of 5
433 Fore St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast ...
Opens in a new windowHyatt Place Portland Downtown - Old Port Square
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

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

JetBlue Airways
Sat, May 9 - Thu, May 21
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$161 Roundtrip, found 4 days ago
$161
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sat, May 9 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Thu, May 21, priced at $161 found 4 days ago
United
Tue, Jun 16 - Wed, Jun 17
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$161 Roundtrip, just found
$161
Roundtrip
just found
Select United flight, departing Tue, Jun 16 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Wed, Jun 17, priced at $161 just found
Delta
Sun, May 17 - Sat, May 23
LGA
LaGuardia
PWM
Portland Intl. Jetport
$161 Roundtrip, found 5 days ago
$161
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, May 17 from LaGuardia to Portland Intl. Jetport, returning Sat, May 23, priced at $161 found 5 days ago
Breeze Airways
Wed, May 27 - Sat, May 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$179 Roundtrip, found 2 days ago
$179
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 30, priced at $179 found 2 days ago