Search Deals on
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
just found
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.
HYATT house Boston/Waltham

HYATT house Boston/Waltham

3 out of 5
Save 100% on your flight
Price was $1,230, price is now $687 per person
$687
per person
Jun 2 - Jun 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in Waltham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attraction Walden Pond is located nearby.
The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Save 100% on your flight
Price was $2,447, price is now $1,471 per person
$1,471
per person
Jun 2 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Popular attractions Harvard Square and Fenway Park are located nearby.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $1,786, price is now $1,087 per person
$1,087
per person
Jun 2 - Jun 8
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 Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $2,029, price is now $1,268 per person
$1,268
per person
Jun 2 - Jun 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Common and New England Aquarium are located nearby.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $2,101, price is now $1,336 per person
$1,336
per person
Jun 2 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Lexington. Enjoy room service, free bicycles on site, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions Lexington Battle Green and Burlington Mall are located nearby.
Studio Allston Hotel

Studio Allston Hotel

4 out of 5
Brighton
Save 100% on your flight
Price was $1,326, price is now $878 per person
$878
per person
Jun 2 - Jun 8
found 1 day 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 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 Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
Price was $1,216, price is now $817 per person
$817
per person
Jun 2 - Jun 9
found 1 day 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.

3-4 Night Vacations in Highland

Price found within the past 48 hours. Click for updated prices.
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

3 out of 5
Price was $801, price is now $573 per person
$573
per person
May 28 - May 31
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was $870, price is now $618 per person
$618
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Nantucket Inn

Nantucket Inn

3.5 out of 5
Price was $2,435, price is now $1,668 per person
$1,668
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
HYATT house Boston/Waltham

HYATT house Boston/Waltham

3 out of 5
Save 100% on your flight
Price was $1,230, price is now $687 per person
$687
per person
Jun 2 - Jun 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was $2,816, price is now $863 per person
$863
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Save 100% on your flight
Price was $2,447, price is now $1,471 per person
$1,471
per person
Jun 2 - Jun 8
found 1 day ago
Roundtrip 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 $1,786, price is now $1,087 per person
$1,087
per person
Jun 2 - Jun 8
found 1 day 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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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 3 days ago
$161
Roundtrip
found 3 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 3 days ago
United
Sun, May 17 - Sat, May 23
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$161 Roundtrip, found 1 day ago
$161
Roundtrip
found 1 day ago
Select United flight, departing Sun, May 17 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Sat, May 23, priced at $161 found 1 day ago
Delta
Sun, May 17 - Sat, May 23
LGA
LaGuardia
PWM
Portland Intl. Jetport
$161 Roundtrip, found 4 days ago
$161
Roundtrip
found 4 days ago
Select Delta flight, departing Sun, May 17 from LaGuardia to Portland Intl. Jetport, returning Sat, May 23, priced at $161 found 4 days ago
Breeze Airways
Wed, May 27 - Sat, May 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 30, priced at $179 found 1 day ago