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Dock Square Vacation Packages

Dock Square Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
per person
Jun 23 - Jun 27
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thompson's Point and Portland Head Light are located nearby.
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
per person
Jun 16 - Jun 21
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this 3.5-star B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thompson's Point and Maine Mall are located nearby. Discover genuine guest reviews for Blind Tiger Portland – Carleton Street, in West End neighborhood, along with the latest prices and availability – book now.
The Inn at English Meadows

The Inn at English Meadows

4 out of 5
per person
Jun 28 - Jul 2
Roundtrip flight included
Washington (WAS) to Portland (PWM)
Stay at this 4-star B&B in Kennebunk. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Art Gallery Framing and Kennebunkport Harbor are located nearby. Discover genuine guest reviews for The Inn at English Meadows along with the latest prices and availability – book now.
White Barn Inn & Spa, Auberge Resorts Collection

White Barn Inn & Spa, Auberge Resorts Collection

5 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 25
Roundtrip flight included
Washington (DCA) to Portland (PWM)
Stay at this 5-star luxury hotel in Kennebunk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions St. Anthony's Franciscan Monastery and Kennebunkport Village Green are located nearby. Discover genuine guest reviews for White Barn Inn & Spa, Auberge Resorts Collection along with the latest prices and availability – book now.
River View Resort

River View Resort

2.5 out of 5
per person
Jun 18 - Jun 22
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this motel in Bethel. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Sunday River and Bethel Chamber of Commerce are located nearby. Discover genuine guest reviews for River View Resort along with the latest prices and availability – book now.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 10
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the breakfast and the bar in our reviews. Popular attractions Thompson's Point and Portland Head Light are located nearby.
Admiral Peary Inn Bed and Breakfast

Admiral Peary Inn Bed and Breakfast

2 out of 5
per person
Jun 18 - Jun 22
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Fryeburg. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Saco Valley Sports Center and Sherman Farm are located nearby. Discover genuine guest reviews for Admiral Peary Inn Bed and Breakfast along with the latest prices and availability – book now.
And. N B&B

And. N B&B

2 out of 5
per person
Jun 19 - Jun 25
Roundtrip flight included
Washington (DCA) to Portland (PWM)
Stay at this B&B in Gray. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the clean rooms in our reviews. Popular attractions Spring Meadows Golf Course and Little Sebago Lake are located nearby. Discover genuine guest reviews for And. N B&B along with the latest prices and availability – book now.
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
per person
Jun 19 - Jun 25
Roundtrip flight included
Washington (DCA) to Portland (PWM)
Stay at this 3-star 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 Thompson's Point and Portland Head Light are located nearby.
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 10
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Stay at this 4-star beach hotel in Cape Elizabeth. Enjoy free valet parking, a beach locale, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby. Discover genuine guest reviews for Inn By The Sea along with the latest prices and availability – book now.
Hidden Pond

Hidden Pond

4 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 25
Roundtrip flight included
Washington (DCA) to Portland (PWM)
Stay at this 4-star beach hotel in Kennebunkport. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Goose Rocks Beach and Seashore Trolley Museum are located nearby. Discover genuine guest reviews for Hidden Pond along with the latest prices and availability – book now.
The Press Hotel, Marriott Autograph Collection

The Press Hotel, Marriott Autograph Collection

4 out of 5
per person
Jun 18 - Jun 22
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Thompson's Point and Portland Head Light are located nearby.

3-4 Night Vacations in Dock Square

Price found within the past 48 hours. Click for updated prices.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
per person
Jun 23 - Jun 27
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
River View Resort

River View Resort

2.5 out of 5
per person
Jun 18 - Jun 22
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Admiral Peary Inn Bed and Breakfast

Admiral Peary Inn Bed and Breakfast

2 out of 5
per person
Jun 18 - Jun 22
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
And. N B&B

And. N B&B

2 out of 5
per person
Jun 6 - Jun 10
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)

5-7 Night Vacations in Dock Square

Price found within the past 48 hours. Click for updated prices.
White Barn Inn & Spa, Auberge Resorts Collection

White Barn Inn & Spa, Auberge Resorts Collection

5 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 25
Roundtrip flight included
Washington (DCA) to Portland (PWM)
And. N B&B

And. N B&B

2 out of 5
per person
Jun 19 - Jun 25
Roundtrip flight included
Washington (DCA) to Portland (PWM)
River View Resort

River View Resort

2.5 out of 5
per person
Jun 19 - Jun 25
Roundtrip flight included
Washington (DCA) to Portland (PWM)
Admiral Peary Inn Bed and Breakfast

Admiral Peary Inn Bed and Breakfast

2 out of 5
per person
Jun 19 - Jun 25
Roundtrip flight included
Washington (DCA) to Portland (PWM)

Dock Square Last Minute Hotel Deals

The Boathouse Waterfront Hotel & Marina
The Boathouse Waterfront Hotel & Marina
3 out of 5
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 ...
The Boathouse Waterfront Hotel & Marina
Kennebunkport Inn
Kennebunkport Inn
3 out of 5
One Dock Square, Kennebunkport, ME
Stay at this hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Popular attractions First Families Kennebunkport Museum and Dock Square ...
Kennebunkport Inn
Kennebunkport Captains Collection
Kennebunkport Captains Collection
4.5 out of 5
6 Pleasant Street, Kennebunkport, ME
Stay at this 4.5-star luxury hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Kennebunkport Captains Collection
Kings Port Inn
Kings Port Inn
2.5 out of 5
18 Western Ave, Kennebunk, ME
Stay at this hotel in Kennebunk. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Kings Port Inn
AWOL Kennebunkport
AWOL Kennebunkport
3 out of 5
34 Maine St, Kennebunkport, ME
Stay at this hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
AWOL Kennebunkport
White Barn Inn & Spa, Auberge Resorts Collection
White Barn Inn & Spa, Auberge Resorts Collection
5 out of 5
37 Beach Ave, Kennebunk, ME
Stay at this 5-star luxury hotel in Kennebunk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions St. Anthony's Franciscan Monastery and ...
White Barn Inn & Spa, Auberge Resorts Collection
Grand Hotel
Grand Hotel
3 out of 5
1 Chase Hill Rd, Kennebunk, ME
Stay at this 3-star hotel in Kennebunk. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Art Gallery Framing and Kennebunkport Harbor ...
Grand Hotel
The Breakwater Inn and Spa
The Breakwater Inn and Spa
4.5 out of 5
127 Ocean Avenue, Kennebunkport, ME
Stay at this 4.5-star luxury hotel in Kennebunkport. Enjoy free breakfast, free parking, and a full-service spa. Popular attractions Colony Beach and St. Ann’s ...
The Breakwater Inn and Spa
See all 2,263 properties in Dock 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.

Frontier Airlines
Tue, May 21 - Thu, May 30
ATL
Hartsfield-Jackson Atlanta Intl.
PWM
Portland Intl. Jetport
$108 Roundtrip, found 10 hours ago
$108
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Tue, May 21 from Hartsfield-Jackson Atlanta Intl. to Portland Intl. Jetport, returning Thu, May 30, priced at $108 found 10 hours ago
Frontier Airlines
Tue, May 28 - Tue, Jun 4
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$108 Roundtrip, found 1 hour ago
$108
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, May 28 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Tue, Jun 4, priced at $108 found 1 hour ago
Frontier Airlines
Thu, Jun 6 - Sun, Jun 9
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$108 Roundtrip, found 2 hours ago
$108
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Jun 6 from Orlando Intl. to Portland Intl. Jetport, returning Sun, Jun 9, priced at $108 found 2 hours ago
JetBlue Airways
Mon, Jun 17 - Mon, Jun 24
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$137 Roundtrip, found 4 days ago
$137
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Mon, Jun 17 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Mon, Jun 24, priced at $137 found 4 days ago

Book the perfect getaway to Dock Square

With Hotwire, booking your next trip to Kennebunkport is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Dock Square while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Dock Square flight and hotel package for as low as $544.

Living it up in Kennebunkport means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Dock Square, Kennebunkport vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Dock Square for some of the best accommodations and flight deals.

FAQs about cheap Dock Square packages:

How to get cheap vacation deals to Dock Square?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $139.

How much are Dock Square packages?

Vacation packages to Dock Square vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $544.

How to find cheap car rentals near Dock Square?

Hotwire partners with some of the most reliable car rental companies in Kennebunkport to bring you the best car rental deals in Dock Square for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Dock Square now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Dock Square right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

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