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.
84 Main

84 Main

4 out of 5
Price was $490, price is now $405 per person
$405
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $777, price is now $608 per person
$608
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Portland (PWM)
The McKernan Inn

The McKernan Inn

3 out of 5
Price was $838, price is now $695 per person
$695
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $719, price is now $601 per person
$601
per person
Mar 5 - Mar 8
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Price was $809, price is now $681 per person
$681
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,088, price is now $921 per person
$921
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,001, price is now $854 per person
$854
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $815, price is now $702 per person
$702
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Portland (PWM)
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
Price was $843, price is now $739 per person
$739
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Portland (PWM)
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Price was $705, price is now $623 per person
$623
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Portland (PWM)
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
Price was $711, price is now $641 per person
$641
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Portland (PWM)
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
Price was $680, price is now $615 per person
$615
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Portland (PWM)

4-night Bailey Island vacations

Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites Scarborough - Portland

Comfort Inn & Suites Scarborough - Portland

2.5 out of 5
Price was $328, price is now $264 per person
$264
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Save 100% on your flight
Price was $556, price is now $354 per person
$354
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
Price was $607, price is now $411 per person
$411
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
84 Main

84 Main

4 out of 5
Save 100% on your flight
Price was $428, price is now $291 per person
$291
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Save 100% on your flight
Price was $546, price is now $384 per person
$384
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Save 100% on your flight
Price was $535, price is now $393 per person
$393
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $794, price is now $601 per person
$601
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
Price was $408, price is now $311 per person
$311
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Save 100% on your flight
Price was $749, price is now $573 per person
$573
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Price was $413, price is now $320 per person
$320
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
The Wolfeboro Inn

The Wolfeboro Inn

3.5 out of 5
Price was $705, price is now $547 per person
$547
per person
Mar 7 - Mar 11
found 19 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Portland (PWM)
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
Price was $395, price is now $310 per person
$310
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)

5-night Bailey Island vacations

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

Casco Bay Inn

2 out of 5
Price was $350, price is now $296 per person
$296
per person
Mar 13 - Mar 18
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
84 Main

84 Main

4 out of 5
Save 100% on your flight
Price was $496, price is now $317 per person
$317
per person
Mar 13 - Mar 18
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $931, price is now $669 per person
$669
per person
Mar 13 - Mar 18
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Save 100% on your flight
Price was $644, price is now $465 per person
$465
per person
Mar 13 - Mar 18
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Save 100% on your flight
Price was $637, price is now $481 per person
$481
per person
Mar 13 - Mar 18
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
Price was $726, price is now $553 per person
$553
per person
Mar 13 - Mar 18
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
Price was $473, price is now $387 per person
$387
per person
Mar 13 - Mar 18
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $616, price is now $517 per person
$517
per person
Mar 13 - Mar 18
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Save 100% on your flight
Price was $863, price is now $724 per person
$724
per person
Mar 13 - Mar 18
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
Price was $728, price is now $616 per person
$616
per person
Mar 13 - Mar 18
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Hilton Garden Inn Freeport Downtown

Hilton Garden Inn Freeport Downtown

3 out of 5
Price was $449, price is now $386 per person
$386
per person
Mar 13 - Mar 18
found 4 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
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
Price was $375, price is now $325 per person
$325
per person
Mar 13 - Mar 18
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)

Flight deals to Bailey Island

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

Fri, Mar 6 - Sun, Mar 8
EWR
New York
PWM
Portland
$110 Roundtrip, found 3 days ago
$110
Roundtrip
found 3 days ago
Select United flight, departing Fri, Mar 6 from New York to Portland, returning Sun, Mar 8, priced at $110 found 3 days ago
Wed, Apr 1 - Sun, Apr 5
JFK
New York
PWM
Portland
$147 Roundtrip, found 3 days ago
$147
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Apr 1 from New York to Portland, returning Sun, Apr 5, priced at $147 found 3 days ago
Fri, Jun 5 - Mon, Jun 8
MCO
Orlando
PWM
Portland
$168 Roundtrip, found 1 day ago
$168
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Jun 5 from Orlando to Portland, returning Mon, Jun 8, priced at $168 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
Feb 8 - Feb 9
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.
Spa
Pet friendly
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
$78 nightly
The price is $87 total per night
$87 total
Jan 22 - Jan 23
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.
Pool
Hot Tub
Long Creek Hotel by IHG

Long Creek Hotel by IHG

2.5 out of 5
171 Philbrook Ave South Portland ME
Free Cancellation
18.54 mi from city center
$78 nightly
The price is $85 total per night
$85 total
Jan 23 - Jan 24
Total with taxes and fees
Located in South Portland, Long Creek Hotel by IHG is in the suburbs, a 1-minute drive from Maine Mall and 9 minutes from University of Southern Maine.
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.

^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.