Falmouth Vacations

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Falmouth Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was $1,180, price is now $1,020 per person
$1,020
per person
Dec 28 - Jan 2
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
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 our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $2,560, price is now $1,975 per person
$1,975
per person
Dec 28 - Jan 2
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions State Theatre and Cross Insurance Arena 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 $1,705, price is now $1,413 per person
$1,413
per person
Dec 28 - Jan 2
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions State Theatre and Thompson's Point are located nearby.

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,548, price is now $1,295 per person
$1,295
per person
Dec 28 - Jan 2
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach 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 $1,921, price is now $1,626 per person
$1,626
per person
Dec 28 - Jan 2
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions State Theatre and Thompson's Point are located nearby.
room was very modern, however some areas did not look well cleaned (edge if the bed had some dried white liquid). the surrounding area has nice shops but is very sketchy at night. did not feel comfortable with the parking situation. also at 6am sounded like maintenance or cleaning crew was constantly in and out of the elevator making tons of noise. was good for a night but wouldnt stay again.

Reviewed on Oct 27, 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $1,646, price is now $1,447 per person
$1,447
per person
Dec 28 - Jan 2
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Cross Insurance Arena and State Theatre are located nearby.

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Top Hotel Deals

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
9.9 km from city center
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 ...
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
10.01 km from city center
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 ...
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
14.47 km from city center
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 ...
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
8.93 km from city center
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 ...
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
9.82 km from city center
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 ...
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St Portland ME
8.79 km from city center
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 ...
Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 out of 5
939 Congress St Portland ME
10.11 km from city center
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
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
13.73 km from city center
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 ...
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
10.01 km from city center
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 ...
Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
14.19 km from city center
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 ...
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
13.95 km from city center
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 ...
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
9.6 km from city center
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 ...
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
209 Fore St Portland ME
9.41 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Motel 6 Portland, ME

Motel 6 Portland, ME

2 out of 5
1 Riverside St Portland ME
9.14 km from city center
Stay at this motel in Portland. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Thompson's Point and Maine Mall are located ...
Grand Beach Inn

Grand Beach Inn

3 out of 5
198 East Grand Avenue Old Orchard Beach ME
24.79 km from city center
Stay at this hotel in Old Orchard Beach. Enjoy free WiFi, free parking, and room service. Our guests praise the restaurant and the helpful staff in our reviews. ...
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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.

Delta
Wed, Dec 16 - Mon, Dec 21
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$272 Roundtrip, found 6 days ago
$272
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Dec 16 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Mon, Dec 21, priced at $272 found 6 days ago
Delta
Wed, Dec 16 - Sun, Dec 20
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$293 Roundtrip, found 6 days ago
$293
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Dec 16 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Sun, Dec 20, priced at $293 found 6 days ago
American Airlines
Thu, Nov 12 - Sun, Nov 15
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$349 Roundtrip, found 5 days ago
$349
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Nov 12 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Sun, Nov 15, priced at $349 found 5 days ago
United
Thu, Nov 12 - Sun, Nov 15
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$457 Roundtrip, found 5 days ago
$457
Roundtrip
found 5 days ago
Select United flight, departing Thu, Nov 12 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Sun, Nov 15, priced at $457 found 5 days ago