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Wiscasset Vacation Packages

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Wiscasset Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
Save 100% on your flight
Price was $989, price is now $738 per person
$738
per person
Oct 26 - Oct 29
found 5 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions Thompson's Point and Maine Mall are located nearby.
Beautiful place

Reviewed on Sep 20, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $1,381, price is now $1,003 per person
$1,003
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Portland (PWM)
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 and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Thompson's Point are located nearby.

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Price was $1,394, price is now $1,083 per person
$1,083
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Thompson's Point and Portland Head Light are located nearby.
The loft was wonderful! Really great location for old port! Really enjoyed our stay! Felt homely! We relaxed and felt so comfortable there! Would recommend!

Reviewed on Sep 24, 2026

The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Price was $1,473, price is now $1,146 per person
$1,146
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Cross Insurance Arena and Thompson's Point are located nearby.
This loft was perfect! We will be back and stay longer!!

Reviewed on Sep 25, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,323, price is now $1,069 per person
$1,069
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,738, price is now $1,405 per person
$1,405
per person
Nov 4 - Nov 8
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions Thompson's Point and Portland Head Light are located nearby.
Place was charming and quirky. Very comfortable and well located.

Reviewed on Sep 18, 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Price was $1,250, price is now $1,013 per person
$1,013
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
Better than expected. This new property was in a great location. Easy to walk to restaurants and shopping. Comfortable bed, nice bathroom and a sitting area with sofa, chair and tv. I was a little concerned because we could hear music from a nearby bar, but everything stopped by 10 o’clock. Would return.

Reviewed on Sep 25, 2026

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Price was $1,219, price is now $1,023 per person
$1,023
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Portland (PWM)
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 rooms in our reviews. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.

Wiscasset Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $709, price is now $556 per person
$556
per person
Oct 26 - Oct 29
found 5 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
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 $777, price is now $562 per person
$562
per person
Oct 26 - Oct 29
found 5 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Save 100% on your flight
Price was $989, price is now $738 per person
$738
per person
Oct 26 - Oct 29
found 5 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $1,738, price is now $1,405 per person
$1,405
per person
Nov 4 - Nov 8
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)

Wiscasset Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 out of 5
Valley Street
Price was $550, price is now $407 per person
$407
per person
Dec 11 - Dec 16
found 19 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,176, price is now $732 per person
$732
per person
Dec 11 - Dec 16
found 19 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $759, price is now $547 per person
$547
per person
Dec 11 - Dec 16
found 19 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,793, price is now $1,318 per person
$1,318
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Portland (PWM)

Top Flight Deals

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

Breeze Airways
Sat, Nov 7 - Sat, Nov 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$144 Roundtrip, found 1 hour ago
$144
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Nov 7 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Nov 14, priced at $144 found 1 hour ago
Breeze Airways
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$185 Roundtrip, found 2 hours ago
$185
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Wed, Oct 28 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $185 found 2 hours ago
Breeze Airways
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$213 Roundtrip, found 10 hours ago
$213
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Wed, Nov 11 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $213 found 10 hours ago
Delta
Tue, Oct 20 - Sat, Oct 31
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$301 Roundtrip, found 2 days ago
$301
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Oct 20 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Sat, Oct 31, priced at $301 found 2 days ago