Great Diamond Island Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
3.5-star property
The Wolfeboro Inn
8.2/10 Very Good! (644 reviews)
Nov 14 - Nov 16
2 night stay
Dallas (DFW) to Portland (PWM)
Southwest Airlines • Coach
Portland (PWM) to Dallas (DFW)
American Airlines • Coach
Price was $676, price is now $587 per person
$587
per person
found 18 hours ago
The rooms had as much character as a holiday inn express at 3x the price! Just a basic, clean place to spend the night.
Reviewed on Sep 30, 2026
3.0-star property
The Nicholson Inn
10/10 Exceptional! (2 reviews)
Nov 4 - Nov 7
3 night stay
Dallas (DFW) to Portland (PWM)
Southwest Airlines • Non-stop • Coach
Portland (PWM) to Dallas (DFW)
American Airlines • Non-stop • Coach
Price was $925, price is now $812 per person
$812
per person
found 16 hours ago
Just a few steps and you're in the LL Bean shopping center!!! Amazing location! So many places to eat within walking distance! So many shops, not enough time and money!
Great hosts, great breakfast! Such lovely couple who owns the place made sure we're comfortable and happy! Charming house decorated the New England way!
Reviewed on Sep 29, 2026
3.0-star property
AWOL Kennebunkport
9.4/10 Exceptional! (263 reviews)
Nov 13 - Nov 16
3 night stay
Dallas (DFW) to Portland (PWM)
American Airlines • Roundtrip • Coach
Price was $978, price is now $876 per person
$876
per person
found 24 hours ago
great location and hotel configuration
Reviewed on Sep 28, 2026
Top rated hotels for your Great Diamond Island vacation package
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Free Cancellation
6.94 mi from city center
$69 nightly
The price is $75 total per night
$75 total
Nov 1 - Nov 2
Total with taxes and fees
Guests staying at Quality Inn & Suites South Portland enjoy free WiFi in public areas, free newspapers, and a picnic area. If you drive, put free parking to good use. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include a vending machine and a garden.
Breakfast included
Pet friendly
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Free Cancellation
Reserve now, pay when you stay
4.9 mi from city center
$71 nightly
The price is $78 total per night
$78 total
Nov 1 - Nov 2
Total with taxes and fees
Guests staying at Clarion Hotel Portland Airport ME enjoy an indoor pool, a gym, and free WiFi in public areas. There's free parking, as well as a free airport shuttle (available on request). Multilingual staff at the 24-hour front desk can assist with concierge services, luggage storage, and dry cleaning/laundry. Additional amenities include a hot tub, meeting rooms, and conference space.
Pool
Hot Tub
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Free Cancellation
7.42 mi from city center
$81 nightly
The price is $88 total per night
$88 total
Nov 2 - Nov 3
Total with taxes and fees
Renovated in 2022, Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel offers a 24-hour gym, free WiFi in public areas, and coffee in a common area. There's free parking, as well as a free airport shuttle (available 24 hours). The front desk is staffed 24/7 to help with dry cleaning or laundry, and answer any questions about the accommodations. Additional amenities include express check-out and a vending machine.
Breakfast included
Free airport shuttle
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View all propertiesLowest 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.
Things to do
Sunset Windjammer Cruise Along the Coast of Portland Maine
$77
per adult
92% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
$59
per adult
80% of travellers recommend
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