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Highland Vacation Packages

Highland Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Save 100% on your flight
Price was $1,381, price is now $885 per person
$885
per person
Aug 27 - Aug 31
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this beach guesthouse in Dennis Port. Enjoy free WiFi, free parking, and a private beach. Popular attractions West Dennis Beach and Cape Cod Inflatable Park are located nearby.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $1,754, price is now $1,131 per person
$1,131
per person
Aug 30 - Sep 4
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this family-friendly hotel in Boston. Enjoy free WiFi, a garden, and dry cleaning or laundry services. Our guests praise the property condition in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Save 100% on your flight
Price was $1,490, price is now $986 per person
$986
per person
Aug 28 - Sep 2
found 21 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Portland (PWM)
Book a stay at this business-friendly hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $1,851, price is now $1,228 per person
$1,228
per person
Aug 28 - Sep 2
found 21 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Portland (PWM)
Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Marginal Way and Ogunquit Beach are located nearby.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $4,180, price is now $2,818 per person
$2,818
per person
Aug 29 - Sep 5
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $3,280, price is now $2,253 per person
$2,253
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this business-friendly resort in Nantucket. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Nobadeer Beach and Madequecham Pond are located nearby.
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $3,224, price is now $2,234 per person
$2,234
per person
Aug 30 - Sep 4
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
Price was $5,588, price is now $3,904 per person
$3,904
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this beach guesthouse in East Wareham. Enjoy free WiFi, a private beach, and free bicycles on site. Popular attractions Water Wizz and Onset Bay Center - Buzzards Bay Coalition are located nearby.

3-4 Night Vacations in Highland

Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Save 100% on your flight
Price was $1,008, price is now $708 per person
$708
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Price was $1,285, price is now $877 per person
$877
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Beachside Village Resort

Beachside Village Resort

3 out of 5
Save 100% on your flight
Price was $1,239, price is now $878 per person
$878
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,123, price is now $800 per person
$800
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)

5-7 Night Vacations in Highland

Price found within the past 48 hours. Click for updated prices.
Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Save 100% on your flight
Price was $1,697, price is now $1,008 per person
$1,008
per person
Sep 10 - Sep 15
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $1,754, price is now $1,131 per person
$1,131
per person
Aug 30 - Sep 4
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $3,732, price is now $2,435 per person
$2,435
per person
Sep 4 - Sep 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,822, price is now $1,190 per person
$1,190
per person
Sep 4 - Sep 10
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
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
Opens in a new windowFireside Inn & Suites Portland
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...
Opens in a new windowLa Quinta Inn & Suites by Wyndham Portland DT/Maine Med
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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
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
Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's ...
Opens in a new windowClarion Pointe South Portland
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
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
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.

Breeze Airways
Mon, Aug 17 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$207 Roundtrip, found 1 day ago
$207
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Aug 17 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $207 found 1 day ago
Breeze Airways
Tue, Sep 1 - Wed, Sep 2
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$207 Roundtrip, found 1 day ago
$207
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Sep 1 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Wed, Sep 2, priced at $207 found 1 day ago
JetBlue Airways
Wed, Aug 5 - Sat, Aug 22
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$208 Roundtrip, found 6 days ago
$208
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Aug 5 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Aug 22, priced at $208 found 6 days ago
United
Tue, Sep 8 - Sat, Sep 12
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$222 Roundtrip, found 1 day ago
$222
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 8 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Sat, Sep 12, priced at $222 found 1 day ago