Exclusive Dock Square Vacation Deals

Dock Square vacation package deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Portland Airport

Hilton Garden Inn Portland Airport

3 out of 5
Price was $281, price is now $244 per person
$244
per person
Jan 10 - Jan 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. There's a gym on site, and a 24-hour front desk and a terrace are also provided.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $339, price is now $255 per person
$255
per person
Jan 10 - Jan 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $614, price is now $509 per person
$509
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. A garden, luggage storage, and concierge services are also on offer.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $560, price is now $476 per person
$476
per person
Jan 10 - Jan 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
This bed & breakfast doesn't skimp on freebies - guests receive free breakfast and free WiFi. Luggage storage and concierge services are also provided.
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Price was $741, price is now $640 per person
$640
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Free WiFi in public areas, a terrace, and a garden are available at this bed & breakfast. Enjoy the free on-the-go breakfast each morning. Concierge services are provided for your convenience.
AWOL Kennebunkport

AWOL Kennebunkport

3 out of 5
Price was $515, price is now $448 per person
$448
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
This hotel features free WiFi in public areas, concierge services, and free self parking. Enjoy the free buffet breakfast each morning. Express check-out and luggage storage are also provided.

Frequently asked questions

How much are vacation packages to Dock Square?
Save on your visit to Dock Square by combining your hotel and return flights into a $244 package. With all that extra money in your pocket, why not stay longer and explore even more?
Where can I get the best vacation package deals for Dock Square?
Look no further than Travelocity. With access to 400 air carriers and at least 1,000,000 hotels around the world, finding the best Dock Square package deal couldn't be simpler.
Why should I purchase my Dock Square vacation bundle via Travelocity?
With exceptional service, support available 24/7 and some of the most perfect escapes money can buy, you'll never wander alone. And if you find a cheaper price, we'll match it. That's our Price Match Guarantee.

Top Dock Square hotel deals

White Barn Inn & Spa, Auberge Collection

White Barn Inn & Spa, Auberge Collection

5 out of 5
37 Beach Ave Kennebunk ME
$501 nightly
The price is $546 total per night
$546 total
Dec 21 - Dec 22
Total with taxes and fees
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and airport shuttle. Enjoy the seasonal outdoor pool and perks like free valet parking.
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
6 Pleasant Street Kennebunkport ME
$164 nightly
The price is $179 total per night
$179 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. A garden, luggage storage, and concierge services are also on offer.
Breakfast included
Parking included
The Boathouse Waterfront Hotel & Marina

The Boathouse Waterfront Hotel & Marina

3 out of 5
21 Ocean Ave Kennebunkport ME
Free Cancellation
Reserve now, pay when you stay
$178 nightly
The price is $195 total per night
$195 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free on-the-go breakfast, free WiFi, and free valet parking. Free self parking, a terrace, and luggage storage are also offered.
Breakfast included
Parking included
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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.