Pleasantdale Vacation Packages for 2026

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Top Hotel Deals

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
3.46 km from Pleasantdale
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 ...
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
2.7 km from Pleasantdale
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
7.38 km from Pleasantdale
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 ...
Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
3.4 km from Pleasantdale
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 ...
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
3.72 km from Pleasantdale
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
2.91 km from Pleasantdale
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 ...
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
3.18 km from Pleasantdale
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

2.5 out of 5
90 Maine Mall Rd South Portland ME
5.47 km from Pleasantdale
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
Old Orchard Beach Inn

Old Orchard Beach Inn

2.5 out of 5
6 Portland Ave Old Orchard Beach ME
15.39 km from Pleasantdale
Stay at this B&B in Old Orchard Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. ...
Waves Oceanfront Resort

Waves Oceanfront Resort

3 out of 5
87 W Grand Ave Old Orchard Beach ME
16.19 km from Pleasantdale
Book a stay at this beach hotel in Old Orchard Beach. Enjoy free parking, an outdoor pool, and a beach locale. Our guests praise the helpful staff and the clean ...
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

4 out of 5
88 Spring St Portland ME
2.61 km from Pleasantdale
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St Portland ME
7.62 km from Pleasantdale
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff ...
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
5.13 km from Pleasantdale
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 ...
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
3.1 km from Pleasantdale
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...
Spark by Hilton Portland Airport Maine Mall

Spark by Hilton Portland Airport Maine Mall

2 out of 5
461 Maine Mall Rd South Portland ME
6.03 km from Pleasantdale
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Wed, Sep 2 - Wed, Sep 16
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$157 Roundtrip, found 4 days ago
$157
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Sep 2 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Wed, Sep 16, priced at $157 found 4 days ago
JetBlue Airways
Wed, Aug 26 - Tue, Sep 1
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$179 Roundtrip, found 4 days ago
$179
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, Aug 26 from Tampa Intl. to Portland Intl. Jetport, returning Tue, Sep 1, priced at $179 found 4 days ago
Delta
Sat, Aug 29 - Tue, Sep 1
LGA
LaGuardia
PWM
Portland Intl. Jetport
$191 Roundtrip, found 4 days ago
$191
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Aug 29 from LaGuardia to Portland Intl. Jetport, returning Tue, Sep 1, priced at $191 found 4 days ago
United
Sun, Aug 23 - Sat, Aug 29
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$191 Roundtrip, found 4 days ago
$191
Roundtrip
found 4 days ago
Select United flight, departing Sun, Aug 23 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Sat, Aug 29, priced at $191 found 4 days ago
American Airlines
Sat, Aug 29 - Wed, Sep 2
LGA
LaGuardia
PWM
Portland Intl. Jetport
$211 Roundtrip, found 1 day ago
$211
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Aug 29 from LaGuardia to Portland Intl. Jetport, returning Wed, Sep 2, priced at $211 found 1 day ago