Cheap Vacations in Bailey Island

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3-night Bailey Island vacations

Price found within the past 48 hours. Click for updated prices.
The Beach Rose Inn

The Beach Rose Inn

2.5 out of 5
Price was $525, price is now $468 per person
$468
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

3.5 out of 5
Price was $731, price is now $689 per person
$689
per person
Apr 17 - Apr 20
found 18 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Portland (PWM)
84 Main

84 Main

4 out of 5
Price was $765, price is now $611 per person
$611
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Price was $704, price is now $563 per person
$563
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $958, price is now $766 per person
$766
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $654, price is now $533 per person
$533
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
The McKernan Inn

The McKernan Inn

3 out of 5
Price was $729, price is now $597 per person
$597
per person
Apr 29 - May 2
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Price was $692, price is now $568 per person
$568
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $657, price is now $559 per person
$559
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $785, price is now $690 per person
$690
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
And.N Lodging

And.N Lodging

2 out of 5
Price was $706, price is now $625 per person
$625
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
AWOL Kennebunkport

AWOL Kennebunkport

3 out of 5
Price was $812, price is now $747 per person
$747
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)

4-night Bailey Island vacations

Price found within the past 48 hours. Click for updated prices.
The Beach Rose Inn

The Beach Rose Inn

2.5 out of 5
Price was $567, price is now $507 per person
$507
per person
Apr 8 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The McKernan Inn

The McKernan Inn

3 out of 5
Price was $870, price is now $703 per person
$703
per person
Apr 8 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
84 Main

84 Main

4 out of 5
Price was $950, price is now $771 per person
$771
per person
Apr 8 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Price was $911, price is now $741 per person
$741
per person
Apr 13 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,071, price is now $892 per person
$892
per person
Apr 13 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Price was $882, price is now $736 per person
$736
per person
Apr 13 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $837, price is now $700 per person
$700
per person
Apr 13 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $853, price is now $739 per person
$739
per person
Apr 13 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Price was $736, price is now $650 per person
$650
per person
Apr 13 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Spinneys Guesthouse & Beach Cottages

Spinneys Guesthouse & Beach Cottages

3 out of 5
Price was $802, price is now $715 per person
$715
per person
Apr 19 - Apr 23
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Comfort Inn & Suites Scarborough - Portland

Comfort Inn & Suites Scarborough - Portland

2.5 out of 5
Price was $585, price is now $525 per person
$525
per person
Apr 8 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
Price was $873, price is now $787 per person
$787
per person
Apr 13 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)

5-night Bailey Island vacations

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

HomeAwhile

4 out of 5
Price was $681, price is now $589 per person
$589
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Price was $1,154, price is now $854 per person
$854
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
84 Main

84 Main

4 out of 5
Price was $994, price is now $748 per person
$748
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $964, price is now $744 per person
$744
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Price was $1,051, price is now $813 per person
$813
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,276, price is now $997 per person
$997
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $997, price is now $805 per person
$805
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Price was $794, price is now $664 per person
$664
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
Price was $1,240, price is now $1,075 per person
$1,075
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
Price was $893, price is now $775 per person
$775
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Dormir

Dormir

3 out of 5
Price was $795, price is now $691 per person
$691
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Best Western Merry Manor Inn

Best Western Merry Manor Inn

2.5 out of 5
Price was $805, price is now $706 per person
$706
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)

6-7 night Bailey Island vacations

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Hotel & Suites Freeport by IHG

Holiday Inn Express Hotel & Suites Freeport by IHG

2.5 out of 5
Price was $1,086, price is now $1,009 per person
$1,009
per person
Apr 26 - May 3
found 5 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Price was $1,704, price is now $1,397 per person
$1,397
per person
Apr 26 - May 3
found 5 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Price was $1,587, price is now $1,332 per person
$1,332
per person
Apr 26 - May 3
found 5 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $1,428, price is now $1,207 per person
$1,207
per person
Apr 26 - May 3
found 5 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,952, price is now $1,657 per person
$1,657
per person
Apr 26 - May 3
found 5 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
The McKernan Inn

The McKernan Inn

3 out of 5
Price was $1,489, price is now $1,297 per person
$1,297
per person
Apr 26 - May 3
found 5 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Dormir

Dormir

3 out of 5
Price was $1,168, price is now $1,019 per person
$1,019
per person
Apr 26 - May 3
found 5 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Waldo Emerson Inn

Waldo Emerson Inn

3 out of 5
Price was $1,594, price is now $1,404 per person
$1,404
per person
Apr 26 - May 3
found 5 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Holiday Inn Express Biddeford by IHG

Holiday Inn Express Biddeford by IHG

2.5 out of 5
Price was $1,198, price is now $1,101 per person
$1,101
per person
Apr 26 - May 3
found 5 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Best Western Merry Manor Inn

Best Western Merry Manor Inn

2.5 out of 5
Price was $1,137, price is now $1,051 per person
$1,051
per person
Apr 26 - May 3
found 5 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Price was $1,191, price is now $1,104 per person
$1,104
per person
Apr 26 - May 3
found 5 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

3 out of 5
Price was $1,095, price is now $1,039 per person
$1,039
per person
Apr 26 - May 3
found 5 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)

Flight deals to Bailey Island

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Sep 1 - Sat, Sep 5
TPA
Tampa
PWM
Portland
$177 Roundtrip, found 4 days ago
$177
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Tue, Sep 1 from Tampa to Portland, returning Sat, Sep 5, priced at $177 found 4 days ago
Mon, Mar 23 - Fri, Mar 27
RDU
Raleigh
PWM
Portland
$204 Roundtrip, found 6 days ago
$204
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Mon, Mar 23 from Raleigh to Portland, returning Fri, Mar 27, priced at $204 found 6 days ago
Sat, Jun 6 - Thu, Jun 11
MCO
Orlando
PWM
Portland
$213 Roundtrip, found 1 day ago
$213
Roundtrip
found 1 day ago
Select United flight, departing Sat, Jun 6 from Orlando to Portland, returning Thu, Jun 11, priced at $213 found 1 day ago

Top rated hotels for your Bailey Island vacation

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
14.62 mi from city center
$98 nightly
The price is $108 total per night
$108 total
Mar 29 - Mar 30
Total with taxes and fees
With a stay at The Westin Portland Harborview, you'll be centrally located in Portland, steps from State Theatre and Portland Museum of Art.
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
15.79 mi from city center
$77 nightly
The price is $85 total per night
$85 total
Mar 24 - Mar 25
Total with taxes and fees
With a stay at Clarion Hotel Portland Airport ME in Portland, you'll be near the airport, within a 15-minute walk of Thompson's Point and Portland Exposition Building.
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
14.05 mi from city center
$153 nightly
The price is $169 total per night
$169 total
Mar 9 - Mar 10
Total with taxes and fees
With a stay at Portland Regency Hotel & Spa, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Fore Street Gallery.
Don't see what you're looking for?
See all available properties in Bailey Island
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.