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.
Best Western Freeport Inn

Best Western Freeport Inn

3 out of 5
Price was $533, price is now $487 per person
$487
per person
Apr 16 - Apr 19
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $908, price is now $770 per person
$770
per person
Apr 16 - Apr 19
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 $982, price is now $857 per person
$857
per person
Apr 23 - Apr 26
found 4 hours ago
Roundtrip flight included
Charlotte (CLT) 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 $1,010, price is now $894 per person
$894
per person
Apr 23 - Apr 26
found 4 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,211, price is now $1,073 per person
$1,073
per person
Apr 23 - Apr 26
found 4 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $894, price is now $801 per person
$801
per person
Apr 23 - Apr 26
found 4 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $918, price is now $843 per person
$843
per person
Apr 23 - Apr 26
found 4 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

3 out of 5
Price was $684, price is now $634 per person
$634
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
The McKernan Inn

The McKernan Inn

3 out of 5
Price was $890, price is now $826 per person
$826
per person
Apr 23 - Apr 26
found 4 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
Danemead Cottage - For 10ppl

Danemead Cottage - For 10ppl

3.5 out of 5
Price was $1,597, price is now $1,491 per person
$1,491
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Old Orchard Beach Inn

Old Orchard Beach Inn

2.5 out of 5
Price was $619, price is now $580 per person
$580
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Price was $792, price is now $748 per person
$748
per person
Apr 23 - Apr 26
found 4 hours ago
Roundtrip flight included
Charlotte (CLT) 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 $584, price is now $522 per person
$522
per person
Apr 19 - Apr 23
found 1 day 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 $911, price is now $741 per person
$741
per person
Apr 13 - Apr 17
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,037, price is now $863 per person
$863
per person
Apr 19 - Apr 23
found 1 day 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 $1,071, price is now $892 per person
$892
per person
Apr 13 - Apr 17
found 3 hours 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 3 hours 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 3 hours 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 3 hours 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 $903, price is now $786 per person
$786
per person
Apr 19 - Apr 23
found 1 day 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 $736, price is now $650 per person
$650
per person
Apr 13 - Apr 17
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Best Western Freeport Inn

Best Western Freeport Inn

3 out of 5
Price was $589, price is now $526 per person
$526
per person
Apr 13 - Apr 17
found 23 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
HomeAwhile

HomeAwhile

4 out of 5
Price was $679, price is now $614 per person
$614
per person
Apr 13 - Apr 17
found 3 hours 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.
USA Inn

USA Inn

2.5 out of 5
Price was $606, price is now $517 per person
$517
per person
Apr 11 - Apr 16
found 16 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)

6-7 night Bailey Island vacations

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

HomeAwhile

4 out of 5
Price was $675, price is now $573 per person
$573
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
84 Main

84 Main

4 out of 5
Price was $981, price is now $710 per person
$710
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip flight included
Denver (DEN) 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 $1,039, price is now $778 per person
$778
per person
Apr 13 - Apr 18
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 $969, price is now $751 per person
$751
per person
Apr 13 - Apr 18
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 $901, price is now $705 per person
$705
per person
Apr 13 - Apr 18
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 $1,214, price is now $954 per person
$954
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,228, price is now $993 per person
$993
per person
Apr 13 - Apr 18
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 $923, price is now $750 per person
$750
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Price was $724, price is now $597 per person
$597
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip flight included
Denver (DEN) to Portland (PWM)
White Barn Inn & Spa, Auberge Collection

White Barn Inn & Spa, Auberge Collection

5 out of 5
Save 100% on your flight
Price was $2,546, price is now $2,114 per person
$2,114
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip flight included
Denver (DEN) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $1,023, price is now $852 per person
$852
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip flight included
Denver (DEN) to Portland (PWM)
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Price was $764, price is now $639 per person
$639
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) 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 2 days ago
$177
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Tue, Sep 1 from Tampa to Portland, returning Sat, Sep 5, priced at $177 found 2 days ago
Wed, Apr 15 - Wed, Apr 29
RDU
Raleigh
PWM
Portland
$178 Roundtrip, found 6 days ago
$178
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Apr 15 from Raleigh to Portland, returning Wed, Apr 29, priced at $178 found 6 days ago
Wed, Apr 1 - Wed, Apr 8
MCO
Orlando
PWM
Portland
$224 Roundtrip, found 1 day ago
$224
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Apr 1 from Orlando to Portland, returning Wed, Apr 8, priced at $224 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 22 - Mar 23
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
$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.
Pool
Hot Tub
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Free Cancellation
13.74 mi from city center
$116 nightly
The price is $128 total per night
$128 total
Mar 22 - Mar 23
Total with taxes and fees
With a stay at Cambria Hotel Portland Downtown-Old Port in Portland (East Bayside), you'll be within a 10-minute drive of Maine Mall and Maine Jewish Museum.
Pet friendly
Free WiFi
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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.