Find Family Hotels in Bailey Island, ME

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Check availability on Bailey Island Family Hotels

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Bailey Island Family Hotels

Exclusive Apartment, 2 Bedrooms | Dining room
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 star property
Downtown Portland
9.6 out of 10, Exceptional, (256)
"Excellent property and the staff was so wonderful, would definitely come back here!"
United States
ERIC
The price is SAR 540
SAR 588 total
includes taxes & fees
8 Dec - 9 Dec
The Docent’s Collection – Thompson Block
Reception
Longfellow Hotel

Longfellow Hotel

4.0 star property
Parkside
9.6 out of 10, Exceptional, (133)
"Best hotel ever!! "
United States
Heather
Longfellow Hotel
Standard Room, 1 King Bed, Non Smoking | In-room safe, desk, laptop workspace, blackout drapes
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3.0 star property
East Bayside
9.4 out of 10, Exceptional, (1126)
"Excellent room and accommodations in nice location near so much of downtown Portland’s charms"
United States
NEWELL
The price is SAR 372
SAR 514 total
includes taxes & fees
25 Dec - 26 Dec
Cambria Hotel Portland Downtown-Old Port
Dinner served
Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

3.5 star property
Portland
9.4 out of 10, Exceptional, (1128)
"Hotel was great."
United States
Joshua
The price is SAR 351
SAR 389 total
includes taxes & fees
14 Dec - 15 Dec
Embassy Suites by Hilton Portland Maine
Garden
The Harraseeket Inn & Event House Freeport Downtown

The Harraseeket Inn & Event House Freeport Downtown

3.5 star property
Freeport
9.4 out of 10, Exceptional, (869)
"Great stay "
United States
Sofia
The price is SAR 409
SAR 446 total
includes taxes & fees
14 Dec - 15 Dec
The Harraseeket Inn & Event House Freeport Downtown
Bar (on property)
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4.0 star property
Downtown Portland
9.4 out of 10, Exceptional, (1003)
"Yes great stay great staff"
United States
Douglas
The price is SAR 459
SAR 507 total
includes taxes & fees
17 Dec - 18 Dec
Canopy by Hilton Portland Waterfront
Royal Suite, 1 Bedroom | Frette Italian sheets, hypo-allergenic bedding, pillowtop beds
The Press Hotel, Marriott Autograph Collection

The Press Hotel, Marriott Autograph Collection

4.0 star property
Downtown Portland
9.4 out of 10, Exceptional, (1000)
"Beautiful hotel, good & convenient restaurant and very short walk to Merrill Auditorium"
United States
PETER
The price is SAR 587
SAR 649 total
includes taxes & fees
4 Jan - 5 January 2026
The Press Hotel, Marriott Autograph Collection
Premium bedding, desk, blackout drapes, iron/ironing board
Portland Harbor Hotel

Portland Harbor Hotel

4.0 star property
Downtown Portland
9.2 out of 10, Wonderful, (1696)
"The location is perfect and the rooms are so comfortable. We enjoyed our stay! "
United States
Lisa
The price is SAR 413
SAR 601 total
includes taxes & fees
14 Dec - 15 Dec
Portland Harbor Hotel
Aerial view
Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

3.0 star property
Downtown Portland
9.2 out of 10, Wonderful, (1001)
"Beautiful hotel"
United States
Lauren
The price is SAR 402
SAR 445 total
includes taxes & fees
11 Dec - 12 Dec
Hilton Garden Inn Portland Downtown Waterfront
Lounge
Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

3.0 star property
Downtown Portland
9.0 out of 10, Wonderful, (1275)
"Room was great, awesome location!"
United States
Erick
The price is SAR 409
SAR 453 total
includes taxes & fees
7 Dec - 8 Dec
Hyatt Place Portland Downtown - Old Port Square
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.
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Top Bailey Island Hotel Reviews

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"room fabulous - we love this place. BUT -- we booked through Expedia for $157 and hotel charged us $257 -- what's up?"
barbara 1-night trip
Posted 2 days ago
Portland Harbor Hotel

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Frequently asked questions

What's Bailey Island like for family-friendly vacations?
The destination of Bailey Island is a good option if you've been considering a getaway with the kids. The island setting, local tours, and notable monuments are just a few things that make this an attractive place for families. Arrange a flight into Portland Intl. Jetport Airport (PWM), which is located 17 mi (27.3 km) from the city center.
When's the best time to book a family-friendly vacation in Bailey Island?
The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Bailey Island are January, March, February, and December, with each month seeing an average of 7 inches of snowfall.
What's there to see and do with your family in Bailey Island?
While you are visiting Bailey Island, you might want to round up the kiddos and make time to see interesting attractions such as Land's End Gift Shop, LL Bean Flagship Store, and Maine Street. Make sure you have lots of time for activities like Casco Bay Lines Ferry Terminal and Fore Street Gallery.