Book Exclusive Bailey Island Vacation Packages

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Bailey Island flight + hotel packages

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

The Meadowmere Resort

2.5 out of 5
Price was CA $921, price is now CA $770 per person
CA $770
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Portland (PWM)
Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Marginal Way and Ogunquit Beach are located nearby.
The Kendall Inn

The Kendall Inn

3.5 out of 5
Price was CA $2,055, price is now CA $1,641 per person
CA $1,641
per person
Nov 2 - Nov 9
found 1 hour ago
Roundtrip non-stop flight included
Edmonton (YEA) to Portland (PWM)
Stay at this B&B in Freeport. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LL Bean Flagship Store and Freeport Historical Society are located nearby.
The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Downtown Portland
Price was CA $1,332, price is now CA $1,137 per person
CA $1,137
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Cross Insurance Arena and Thompson's Point are located nearby.
The Francis

The Francis

3.5 out of 5
Parkside
Price was CA $1,297, price is now CA $1,120 per person
CA $1,120
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was CA $1,183, price is now CA $1,021 per person
CA $1,021
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Thompson's Point and Portland Head Light are located nearby.

Top Bailey Island hotels deals

Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
Free cancellation
The price is CA $117 per night
CA $117
CA $127 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Maine Mall and Cross Insurance Arena are located nearby.
Breakfast included
Pet-friendly
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

3.5 out of 5
80 John Roberts Rd. South Portland ME
Free cancellation
The price is CA $119 per night
CA $119
CA $130 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Maine Mall and Cross Insurance Arena are located nearby.
Breakfast included
Free airport shuttle
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Free cancellation
Reserve now, pay when you stay
The price is CA $132 per night
CA $132
CA $146 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
Pool
Hot tub
Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
Free cancellation
The price is CA $72 per night
CA $72
CA $79 total
Oct 27 - Oct 28
includes taxes & fees
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's Point are located nearby.
Pool
Breakfast included
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 $308 per night
CA $308
CA $395 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Thompson's Point are located nearby.
Pet-friendly
Free WiFi
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Free cancellation
Reserve now, pay when you stay
The price is CA $127 per night
CA $127
CA $141 total
Oct 20 - Oct 21
includes taxes & fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
Pool
Hot tub
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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.

Stay near popular Bailey Island attractions

Bailey Island Bridge

9.2/10 (10 reviews)
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.
See properties

Frequently asked questions

How much are vacation packages to Bailey Island?
Vacation packages, which provide both flights and hotels in Bailey Island, start at just CA $770. Make your travel fantasies come to life and secure your vacation with Travelocity today.
Where can I get the best vacation package deals for Bailey Island?
With around 400 partner airlines and 1,000,000 properties across the globe, you can't beat Travelocity. Browse our comprehensive range and score an incredible Bailey Island package deal. Don't you love it when travel is that easy?
Why should I book my Bailey Island vacation bundle with Travelocity?
With exceptional service, customer support available 24/7 and some of the most perfect escapes on offer, you'll never wander alone. And if you find a better price, we'll match it. That's our Price Match Guarantee.
Can I save money on my Bailey Island car rental if I bundle it with my hotel or flight?
Bundling your bookings into a Bailey Island vacation package will leave you with a nice chunk of spare change. You can bundle a car and flight; a hotel, flight and car; or a hotel and car. You won't find a better way to explore the greater Bailey Island region than with your own ride. You can also add experiences and tours to your Travelocity package.

Photos of local treasures

Browse Bailey Island vacation photos for more inspiration

A rocky shoreline with a boat, a house, and a forest in the background.
A wooden pier extending into calm waters with a red and white boat docked at the end.
A green netted buoy attached to a wooden post by a curved metal hook, with a wooden fence and a body of water in the background.
A sign for Morse Lobster, open Monday to Sunday, with a lobster and lobster traps displayed.
A wooden bridge over water with a yellow kayak, boats, and a motel in the background.