Dock Square Vacation Deals: Dock Square, Kennebunkport Holidays

Dock Square vacation package deals

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

The Westin Portland Harborview

Downtown Portland

per person

Feb. 8 - Feb. 15

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Portland (PWM)

Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Maine Mall and State Theatre are located nearby.

Inn By The Sea

per person

Feb. 8 - Feb. 15

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Portland (PWM)

Stay at this 4-star beach hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.

Portland Harbor Hotel

Downtown Portland

per person

Feb. 8 - Feb. 15

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) 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 bar and the helpful staff in our reviews. Popular attractions Cross Insurance Arena and Fore Street Gallery are located nearby.

The McKernan Inn

per person

Feb. 8 - Feb. 15

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Portland (PWM)

Stay at this 3-star beach inn in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Fort Preble are located nearby.

The Docent's Collection

Downtown Portland

per person

Feb. 8 - Feb. 15

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Portland (PWM)

Stay at this 3.5-star hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Maine Mall and N.W. Barrett Gallery are located nearby.

The Press Hotel, Marriott Autograph Collection

Downtown Portland

per person

Feb. 8 - Feb. 15

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) 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 Maine Mall and Merrill Auditorium are located nearby.

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 CA $1,323 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 665,000 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.

Can I go on vacation to Dock Square at this time?

Discover all the info you should know about travel restrictions and quarantine policies before you fly to Dock Square. Our Covid-19 Travel Advisor is full of useful advice to help make your trip relaxed and hassle-free.

Top Dock Square hotel deals

The Boathouse Waterfront Hotel & Marina

21 Ocean Ave, Kennebunkport, ME

CA $243

CA $312 total

includes taxes & fees

5 Jan - 6 Jan

Stay at this 3-star hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Dock Square and Northlight Gallery are located nearby.

Breakfast included

Parking included

Kennebunkport Inn

One Dock Square, Kennebunkport, ME

CA $214

CA $280 total

includes taxes & fees

5 Jan - 6 Jan

Stay at this 3-star hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions First Families Kennebunkport Museum and Dock Square are located nearby.

Breakfast included

Parking included

Kennebunkport Captains Collection

6 Pleasant Street, Kennebunkport, ME

CA $282

CA $308 total

includes taxes & fees

3 Feb - 4 Feb

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 in our reviews. Popular attractions Kennebunkport Village Green and W. Robert Paine Gallery are located nearby.

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.