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Bailey Island flight + hotel packages

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Jun. 6 - Jun. 10
Roundtrip non-stop flight included
Québec (YQB) to Portland (PWM)
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast. Our guests praise the breakfast and the bar in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby. Discover genuine guest reviews for Portland Harbor Hotel, in Downtown Portland neighborhood, along with the latest prices and availability – book now.
Admiral Peary Inn Bed and Breakfast

Admiral Peary Inn Bed and Breakfast

2 out of 5
per person
Jun. 6 - Jun. 10
Roundtrip non-stop flight included
Québec (YQB) 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.
River View Resort

River View Resort

2.5 out of 5
per person
Jun. 23 - Jun. 30
Roundtrip flight included
Montreal (YMQ) 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.
Ogunquit Hotel & Suites

Ogunquit Hotel & Suites

2 out of 5
per person
Jul. 2 - Jul. 8
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
Stay at this hotel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Moody Beach and Ogunquit Beach are located nearby. Discover genuine guest reviews for Ogunquit Hotel & Suites along with the latest prices and availability – book now.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
per person
Jun. 6 - Jun. 10
Roundtrip non-stop flight included
Québec (YQB) to Portland (PWM)
Stay at this 3.5-star spa hotel in Portland. Enjoy free WiFi, 2 bars/lounges, and a full-service spa. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby. Discover genuine guest reviews for Portland Regency Hotel & Spa, in Downtown Portland neighborhood, along with the latest prices and availability – book now.
Prices and availability subject to change. Additional terms may apply.

Top Bailey Island hotels deals

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

Get rates
Stay at this cottage in Bailey Island. Enjoy WiFi, onsite parking, and a garden. Popular attractions Land's End Gift Shop and Casco Bay are located nearby. Discover genuine guest reviews for PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room along with the latest prices and availability – book now.
Fireplace
Pet-friendly
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Free cancellation
Reserve now, pay when you stay
The price is CA $187 per night
CA $187
per night
May 12 - May 13
Stay at this spa hotel in Portland. Enjoy a full-service spa, breakfast, and WiFi. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby. Discover genuine guest reviews for The Westin Portland Harborview, in Downtown Portland neighborhood, along with the latest prices and availability – book now.
Pet-friendly
Spa
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Free cancellation
Reserve now, pay when you stay
The price is CA $220 per night
CA $220
per night
Apr. 29 - Apr. 30
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast. Our guests praise the breakfast and the bar in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby. Discover genuine guest reviews for Portland Harbor Hotel, in Downtown Portland neighborhood, along with the latest prices and availability – book now.
Pet-friendly
Breakfast available
Casco Bay Hotel, Ascend Hotel Collection

Casco Bay Hotel, Ascend Hotel Collection

3.5 out of 5
80 John Roberts Rd., South Portland, ME
Free cancellation
Reserve now, pay when you stay
The price is CA $110 per night
CA $110
per night
Apr. 18 - Apr. 19
Stay at this 3.5-star business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby. Discover genuine guest reviews for Casco Bay Hotel, Ascend Hotel Collection along with the latest prices and availability – book now.
Pet-friendly
Breakfast included
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
9 Center Street, Portland, ME
Free cancellation
Reserve now, pay when you stay
The price is CA $258 per night
CA $258
per night
Apr. 21 - Apr. 22
Stay at this 4-star hotel in Portland. Enjoy free WiFi, 2 restaurants, and breakfast. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby. Discover genuine guest reviews for Canopy by Hilton Portland Waterfront, in Downtown Portland neighborhood, along with the latest prices and availability – book now.
Pet-friendly
Breakfast available
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street, Portland, ME
Free cancellation
Reserve now, pay when you stay
The price is CA $209 per night
CA $209
per night
Apr. 23 - Apr. 24
Stay at this 3.5-star spa hotel in Portland. Enjoy free WiFi, 2 bars/lounges, and a full-service spa. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby. Discover genuine guest reviews for Portland Regency Hotel & Spa, in Downtown Portland neighborhood, along with the latest prices and availability – book now.
Hot tub
Pet-friendly
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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.

Popular places to visit

Image for Bailey Island Bridge

Bailey Island Bridge

Find out about the history of Bailey Island when you spend time at Bailey Island Bridge. Stroll along the seaside or seek out the hiking trails.

Bailey Island Bridge
Image for Land's End Gift Shop

Land's End Gift Shop

Enjoy an outing to Land's End Gift Shop during your stay in Bailey Island. While you're in the area, find time to visit its shops.

Land's End Gift Shop
Image for Cobwork Bridge

Cobwork Bridge

You can find out about the history of Bailey Island when you stop by Cobwork Bridge. Stroll along the seaside or seek out the hiking trails.

Cobwork Bridge

Frequently asked questions

How much are vacation packages to Bailey Island?
Your travel fantasies can become a reality in Bailey Island for only CA $1,060. Our packages include flights and hotels, so you’ll find booking is a breeze. The only thing you’ll have to focus on is getting out there and having a great time.
Where can I get the best vacation package deals for Bailey Island?
Travelocity is the place to go to score a terrific Bailey Island package deal. Choose from as many as 400 airlines and 665,000 properties across the globe and craft a travel itinerary that’s suited to you. With so many options at hand, it’s time to start booking your next big getaway.
Why should I book my Bailey Island vacation package via Travelocity?
Because life is one amazing journey, and we’ve got everything you need to help you along the way. With our top-notch service and Price Match Guarantee, you can book with confidence. Plus, you can rest easy on the road knowing we’ve got you covered with our round-the-clock support.
Can I save on my Bailey Island car rental if I combine it with hotels and flights?
You certainly can with our Bailey Island vacation packages. With one of these, there are tons of ways to stretch your budget further. Combine any two or more car, hotel, flight and tour bookings and see the savings pile up. With your own ride, all the popular sights around Bailey Island are an unforgettable road trip away.
What is the best time of year to go to Bailey Island?
If you want to avoid pricey flights, huge crowds and overbooked hotels, plan your escape outside of . The quietest time to travel to Bailey Island is . You’ll find hotel prices are the highest in and the most economical in .
Can I go on vacation to Bailey Island at this time?
Travelocity has the local know-how to ensure your vacation dreams a reality, so before planning your trip to Bailey Island, read through our Covid-19 Travel Advisor. Here you’ll find the latest info about quarantine policies, travel restrictions and other useful advice.