Search Deals onDock Square Vacation Packages
Dock Square Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Clarion Hotel Portland Airport ME
Price was $473, price is now $440 per person
$440
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
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 clean rooms in our reviews. Popular attractions Children's Museum and Theatre of Maine and Thompson's Point are located nearby.
Portland Harbor Hotel
Price was $694, price is now $561 per person
$561
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
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 and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Fore Street Gallery are located nearby.
The Docent’s Collection – Thompson Block
Price was $766, price is now $664 per person
$664
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Maine Sports Hall of Fame and Cathedral of the Immaculate Conception are located nearby.
Ramada Plaza by Wyndham Portland
Price was $558, price is now $497 per person
$497
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Happy Wheels Skate Center and Fore River Sanctuary are located nearby.
InnSeason Resorts The Falls at Ogunquit
Price was $606, price is now $539 per person
$539
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this motel in Ogunquit. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
Price was $558, price is now $503 per person
$503
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
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 staff in our reviews. Popular attractions Hadlock Field and Home of the Maine Celtics are located nearby.
Super 8 by Wyndham Portland ME
Price was $505, price is now $460 per person
$460
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly motel in Westbrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Happy Wheels Skate Center and Fore River Sanctuary are located nearby.
Hampton Inn Portland Downtown - Waterfront
Price was $537, price is now $496 per person
$496
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. 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 Casco Bay Lines Ferry Terminal and Maine Sports Hall of Fame are located nearby.
Portland Regency Hotel & Spa
Price was $677, price is now $632 per person
$632
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
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 our reviews. Popular attractions N.W. Barrett Gallery and Fore Street Gallery are located nearby.
Embassy Suites by Hilton Portland Maine
Price was $600, price is now $561 per person
$561
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Tate House Museum and Thompson's Point are located nearby.
The Weldon Hotel
Price was $839, price is now $785 per person
$785
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Victoria Mansion and Charles Q. Clapp House are located nearby.
Cambria Hotel Portland Downtown-Old Port
Price was $546, price is now $515 per person
$515
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
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 and the helpful staff in our reviews. Popular attractions Maine Jewish Museum and Maine Narrow Gauge Railroad Company and Museum are located nearby.
3-4 Night Vacations in Dock Square
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Dock Square
Price found within the past 48 hours. Click for updated prices.
Dock Square Last Minute Hotel Deals
White Barn Inn & Spa, Auberge Collection
37 Beach Ave Kennebunk ME
Book a stay at this luxury hotel in Kennebunk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Dock Square and St. Anthony's Franciscan ...
Kennebunkport Captains Collection
6 Pleasant Street Kennebunkport ME
Book a stay at this luxury hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
Kennebunkport Inn
One Dock Square Kennebunkport ME
Stay at this hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Kings Port Inn
18 Western Ave Kennebunk ME
Stay at this hotel in Kennebunk. Enjoy free breakfast, cable TV channels, and housekeeping. Our guests praise the breakfast and the helpful staff in our reviews. ...
The Boathouse Waterfront Hotel & Marina
21 Ocean Ave Kennebunkport ME
Stay at this hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Dock Square and Northlight Gallery are located ...
Grand Hotel
1 Chase Hill Rd Kennebunk ME
Stay at this hotel in Kennebunk. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Dock Square and Maine Art Gallery Framing are located ...
The Colony Hotel
140 Ocean Ave Kennebunkport ME
Book a stay at this business-friendly hotel in Kennebunkport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our ...
Chetwynd House Inn
4 Chestnut St Kennebunkport ME
Stay at this B&B in Kennebunkport. Enjoy free WiFi, free parking, and Netflix. Popular attractions Dock Square and Northlight Gallery are located nearby.
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.
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