Exclusive Paddleworks Vacation Deals

Paddleworks vacation package deals

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

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $559, price is now $415 per person
$415
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $918, price is now $688 per person
$688
per person
Mar 6 - Mar 8
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center, laundry service, and valet parking. Relax with a drink at one of the 2 poolside bars and enjoy perks like free self parking.
The McKernan Inn

The McKernan Inn

3 out of 5
Price was $651, price is now $507 per person
$507
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
This inn features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A garden, a picnic area, and luggage storage are also on offer.
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $609, price is now $479 per person
$479
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
This hotel features free WiFi in public areas, a virtual front desk, and self parking. Express check-out is provided and the front desk is staffed around-the-clock.
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $599, price is now $491 per person
$491
per person
Mar 6 - Mar 8
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. Luggage storage and concierge services are also provided.
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $710, price is now $584 per person
$584
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Families will appreciate the playground, onsite laundry facilities, and free supervised childcare. Enjoy the outdoor pool and perks like free valet parking.

Frequently asked questions

How much are vacation packages to Paddleworks?
You'll want to check out Travelocity's awesome $415 Paddleworks package deal. With the extra cash saved on your hotel and return flights, you can treat yourself to some local travel experiences. Paddleworks, here you come!
Where can I get the best vacation package deals for Paddleworks?
Travelocity has everything you need to score an amazing Paddleworks package deal. Choose from as many as 400 partner airlines and 1,000,000 properties across the globe and craft a vacation package that's suited to you. With so many options, it's easy to organize your next great escape.
Why should I book my Paddleworks vacation bundle with Travelocity?
Fantastic savings, an abundance of exciting destinations and 24/7 customer service — that's why. And with our Price Match Guarantee, you can rest assured knowing that you'll always score the best possible deal with Travelocity.

Top Paddleworks hotel deals

Charming, comfortable 2 Bedroom, One Bath, home, gorgeous views of Lowell's Cove--A great homeba...

Charming, comfortable 2 Bedroom, One Bath, home, gorgeous views of Lowell's Cove--A great homeba...

Orr's Island ME
This vacation home featured laundry facilities and barbecue grills.
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The Little House - Gorgeous Views of Lowell's Cove and Casco Bay

The Little House - Gorgeous Views of Lowell's Cove and Casco Bay

Orrs Island Maine
This cottage includes a garden and barbecue grills.
Kitchen
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Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.

Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.

Harpswell ME
This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
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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.