Hermit Island Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top Hermit Island vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Portland Harbor Hotel
Downtown Portland
9.2/10 Wonderful! (1,581 reviews)
Nov 14 - Nov 16
2 night stay
Boston (BOS) to Portland (PWM)
Delta • Non-stop • Coach
Portland (PWM) to Boston (BOS)
American Airlines • Non-stop • Coach
Price was $613, price is now $528 per person
$528
per person
found 1 day ago
Great hotel, helpful staff.
Reviewed on Sep 29, 2025
4.5-star property
Cliff House Maine
9.4/10 Exceptional! (1,007 reviews)
Dec 31 - Jan 4
4 night stay
Chicago (ORD) to Portland (PWM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,868, price is now $1,298 per person
$1,298
per person
found 1 day ago
Great pools, staff very friendly, property is beautiful.
Reviewed on Aug 29, 2025
4.5-star property
Kennebunkport Captains Collection
9.4/10 Exceptional! (622 reviews)
Dec 31 - Jan 4
4 night stay
Chicago (ORD) to Portland (PWM)
American Airlines • Non-stop roundtrip • Coach
Price was $950, price is now $769 per person
$769
per person
found 1 day ago
Wonderful time!! Great location close to everything. Amazing staff. Highly recommended!!
Reviewed on Oct 7, 2024
3.5-star property
The Docent's Collection
Downtown Portland
9.6/10 Exceptional! (233 reviews)
Nov 14 - Nov 16
2 night stay
Boston (BOS) to Portland (PWM)
Delta • Non-stop • Coach
Portland (PWM) to Boston (BOS)
American Airlines • Non-stop • Coach
Price was $808, price is now $660 per person
$660
per person
found 1 day ago
This is a beautiful property with amazing, helpful staff at a prime location. Close to lots of dining and activities, a perfect winter wonderland retreat. It is a very relaxing place to stay.
Reviewed on Mar 10, 2023
5.0-star property
White Barn Inn & Spa, Auberge Collection
9.4/10 Exceptional! (102 reviews)
Dec 31 - Jan 4
4 night stay
Chicago (ORD) to Portland (PWM)
American Airlines • Non-stop roundtrip • Coach
Price was $1,423, price is now $1,175 per person
$1,175
per person
found 1 day ago
The property was beautiful & very well kept. The staff was amazing and always happy to be of service. Food was incredible. Will definitely be back!
Reviewed on Jul 11, 2020
Top rated hotels for your Hermit Island vacation package
The Freeport Hotel, an Ascend Collection Hotel
506 Us Route 1, Freeport, ME
Free Cancellation
Reserve now, pay when you stay
15.41 mi from city center
$88 nightly
The price is $96 total per night
$96 total
Nov 2 - Nov 3
Total with taxes and fees
Renovated in 2020, The Freeport Hotel, an Ascend Collection Hotel offers free WiFi in public areas, a 24-hour business center, and free newspapers. If you drive, take advantage of free parking. The 24-hour front desk has staff standing by to help with dry cleaning or laundry, and answer any questions about the accommodations. Additional amenities include laundry facilities, barbecue grills, and a vending machine.
Breakfast included
Parking included
Casco Bay Inn
107 US Route 1, Freeport, ME
Free Cancellation
Reserve now, pay when you stay
15.77 mi from city center
$109 nightly
The price is $119 total per night
$119 total
Nov 7 - Nov 8
Total with taxes and fees
Casco Bay Inn features free WiFi in public areas and a terrace. You can take advantage of free parking if you drive. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours.
Breakfast included
Parking included
Best Western Freeport Inn
31 US Route 1, Freeport, ME
Free Cancellation
Reserve now, pay when you stay
15.92 mi from city center
$88 nightly
The price is $96 total per night
$96 total
Oct 31 - Nov 1
Total with taxes and fees
Guests of Best Western Freeport Inn enjoy free WiFi in public areas, a seasonal outdoor pool, and express check-out. You can put free parking to good use if you drive. Front-desk staff are standing by 24/7 to assist with any requests. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. This hotel also has free newspapers.
Pool
Pet friendly
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.
Explore More Ways to Travel with Travelocity
- Farmstay in Phippsburg
- Apartments in Phippsburg
- Hotels with Pool in Phippsburg
- Hotels with a Gym in Phippsburg
- Phippsburg Hotels
- Rv Parks in Phippsburg
- Resorts in Phippsburg
- Beach Resorts & in Small Point
- Hotels with Bar in Small Point
- Oceanfront Hotels in Small Point
- Spa Resorts & in Small Point
- Hotels near Popham Beach State Park
- Kid Friendly Hotels in West Point
- Hotels near Paddleworks
- Arcade Hotels in Sebasco Estates
- Beach Resorts & in Sebasco Estates
- Fishing Resorts & in Sebasco Estates
- Golf Resorts & in Sebasco Estates
- Spa Resorts & in Sebasco Estates
- Hotels near Bates-Morse Mountain Conservation Area
- Hotels near Hunnewell Beach
- B&B in Orrs Island
- Cabin Rentals in Orrs Island
- Hotels with Tennis Courts in Orrs Island
- Orrs Island Hotels
- Motels in Orrs Island
- 3 Star Hotels in Popham Beach
- Apartments in Popham Beach
- Hotels with Pool in Popham Beach
- Resorts in Popham Beach
- B&B in Cundys Harbor
- Cabin Rentals in Cundys Harbor
- Cundys Harbor Hotels
- Motels in Cundys Harbor
- Resorts in Cundys Harbor
- Apartments in Harpswell
- Extended Stay Hotels in Harpswell
- Gay Friendly Hotels in Harpswell
- Pet Friendly Hotels in Harpswell
- Harpswell Hotels
- Motels in Harpswell
- Vacation Homes in Harpswell
- Flights to Phippsburg
- Flights from Boston to Phippsburg
- Flights from Portland to Phippsburg
- Flights from Bangor to Phippsburg
- Flights from Nashville to Great Island
- Flights from San Francisco to Great Island
- Flights from Popham Beach
- Flights from Escanaba to Harpswell
- Flights from Boston to Harpswell
- Flights from Chicago to Harpswell
- Flights from Houston to Harpswell
- Flights from Las Vegas to Harpswell
- Flights from New York to Harpswell
- Flights from Raleigh to Harpswell
- Flights from Seattle to Harpswell
- Flights from Oakland to Harpswell
- Flights from Santa Barbara to Harpswell
- Flights from Medford to Harpswell
- Flights from Birmingham to Harpswell
- Flights from Colorado Springs to Harpswell
- Flights from Tampa to Harpswell
- Flights from Charleston to Harpswell
- Flights from College Station to Harpswell
- Phippsburg Vacations
- East Boothbay Vacations
- Bath Vacations
- Yarmouth Vacations
- The Boothbay Playhouse
- Cumberland Center Vacations
- Cabbage Island
- Eartha
- Boothbay Vacations
- Fisherman's Memorial Park
- Brunswick Vacations
- Edgecomb Vacations
- Cape Elizabeth Vacations
- Monkey C Monkey Do
- Pemaquid Beach Vacations
- Coastal Maine Botanical Gardens
- Brunswick Golf Course
- Portland Vacations
- Boothbay Harbor Marina
- South Portland Vacations
- Wyler Gallery
- Wiscasset Vacations
- Gulf of Maine
- Casco Bay
- Woolwich Vacations
- Freeport Vacations
- Georgetown Vacations
- Georgetown Historical Society
- Boothbay Harbor Vacations
- Pemaquid Point Lighthouse Park
