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10 Oct - 12 Oct
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17 Oct - 19 Oct
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31 Oct - 2 Nov
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B&B in Chebeague Island

Inn at St John Portland In-Town
Front of property - evening/night

Inn at St John Portland In-Town

2.5 star property
8.8 out of 10, Excellent, (1121)
"Enjoyed our stay."
The price is AED 327
AED 356 total
includes taxes & fees
27 Oct - 28 Oct
Inn at St John Portland In-Town
Old Orchard Beach Inn
Exterior

Old Orchard Beach Inn

2.5 star property
8.2 out of 10, Very Good, (1030)
"Good place to stay and convenient to walk to the beach "
Old Orchard Beach Inn
Blind Tiger Portland - Danforth Street.
Baxter | 1 bedroom, premium bedding, individually decorated

Blind Tiger Portland - Danforth Street.

3.5 star property
9.6 out of 10, Exceptional, (152)
"Everything was wonderful, we highly recommend staying here to anyone considering it."
The price is AED 1,267
AED 1,381 total
includes taxes & fees
29 Oct - 30 Oct
Blind Tiger Portland - Danforth Street.
Candlebay Inn
Porch

Candlebay Inn

3.0 star property
9.6 out of 10, Exceptional, (446)
"Great location and hospitality."
The price is AED 731
AED 797 total
includes taxes & fees
7 Oct - 8 Oct
Candlebay Inn
Fleetwood House Bed & Breakfast
Property entrance

Fleetwood House Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (128)
"The breakfasts and friendly conversations were amazing. We thoroughly enjoyed our stay at the Fleetwood Bed and Breakfast "
The price is AED 841
AED 917 total
includes taxes & fees
2 Oct - 3 Oct
Fleetwood House Bed & Breakfast
The Orchard House & Cafe
Front of property - evening/night

The Orchard House & Cafe

3.0 star property
9.6 out of 10, Exceptional, (156)
"Lovely home outside the congestion of Freeport but close for easy visit. Breakfast was perfect. "
The price is AED 767
AED 837 total
includes taxes & fees
1 Oct - 2 Oct
The Orchard House & Cafe
Blind Tiger Portland – Carleton Street
Stovall | Living area

Blind Tiger Portland – Carleton Street

3.5 star property
9.8 out of 10, Exceptional, (115)
"Loved the place "
The price is AED 1,012
AED 1,103 total
includes taxes & fees
30 Oct - 31 Oct
Blind Tiger Portland – Carleton Street
The James Place Inn B&B
Outdoor dining

The James Place Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (178)
"Great place. Comfortable and welcoming. Great proprietors and great location. "
The price is AED 1,116
AED 1,216 total
includes taxes & fees
1 Oct - 2 Oct
The James Place Inn B&B
And. N B&B
Front of property

And. N B&B

3.0 star property
9.8 out of 10, Exceptional, (73)
"Really lovely place and great hospitality from the owners!"
The price is AED 620
AED 676 total
includes taxes & fees
14 Oct - 15 Oct
And. N B&B
Brewster House Bed & Breakfast
Garden

Brewster House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (113)
"Wonderful hosts. Enjoyed quiet evening and lovely gourmet breakfast. Truly memorable stay. We look forward to returning in the future."
The price is AED 1,098
AED 1,197 total
includes taxes & fees
8 Oct - 9 Oct
Brewster House Bed & Breakfast
Benjamin F. Packard House
Exterior

Benjamin F. Packard House

3.0 star property
10.0 out of 10, Exceptional, (102)
"Beautiful house, the breakfast food was amazing, and the owners were so personable and welcoming. "
The price is AED 915
AED 997 total
includes taxes & fees
20 Oct - 21 Oct
Benjamin F. Packard House
The Kendall Inn
Exterior

The Kendall Inn

3.5 star property
9.8 out of 10, Exceptional, (139)
"Quaint stay. Enjoyed our stay. "
The price is AED 774
AED 843 total
includes taxes & fees
1 Oct - 2 Oct
The Kendall Inn
West End Inn
Exterior

West End Inn

3.0 star property
9.6 out of 10, Exceptional, (94)
"Wonderful staff and scrumptious breakfast "
West End Inn
PineCrest Inn
Street view

PineCrest Inn

4.0 star property
9.8 out of 10, Exceptional, (103)
"Lovely home, great breakfast. Kathy is a very gracious hostess and really helped us to thoroughly enjoy the Portland area."
PineCrest Inn
Stonehouse Manor -Popham Beach B&B - Pond Island Room
Interior

Stonehouse Manor -Popham Beach B&B - Pond Island Room

10.0 out of 10, Exceptional, (1)
"The place is quiet, breakfast was so good and Jane the host is a very kind, knowledgeable person. "
Stonehouse Manor -Popham Beach B&B - Pond Island Room
"SABINO" 1 Bdrm Suite
Property grounds

"SABINO" 1 Bdrm Suite

10.0 out of 10, Exceptional, (14)
"Will definitely stay again."
"SABINO" 1 Bdrm Suite
Kennebec Room - King Bed, Private Bath
Interior

Kennebec Room - King Bed, Private Bath

9.0 out of 10, Wonderful, (7)
"What a lovely place. My wife and I were able to relax and recharge. The home and property are an experience themselves. Then the beach right here for long walks was so rejuvenating. Rachel our host was a picture of hospitality and breakfast was so yummy. Thanks for the loving care, just what we needed!"
Kennebec Room - King Bed, Private Bath
Lake View Suite with wall of windows w south exposure, Large King, Ensuite Bath
Interior

Lake View Suite with wall of windows w south exposure, Large King, Ensuite Bath

9.4 out of 10, Exceptional, (3)
"Clean and enjoyable"
Lake View Suite with wall of windows w south exposure, Large King, Ensuite Bath
The Chadwick Bed & Breakfast
Terrace/patio

The Chadwick Bed & Breakfast

3.5 star property
9.8 out of 10, Exceptional, (48)
"Great getaway within Portland. The breakfast is first rate!"
The Chadwick Bed & Breakfast
Harpswell Inn
Exterior

Harpswell Inn

2.0 star property
10.0 out of 10, Exceptional, (3)
"Had a great stay. The owner was SO welcoming. The setting is beautiful!!!!"
Harpswell Inn
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 Chebeague Island Hotel Reviews

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

10/10 Excellent
"Everything about the stay was perfect!"
Heath 2-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

Frequently asked questions

Searching for B&Bs in Chebeague Island?
If you're looking for something a little different than your standard hotel, a bed and breakfast could be the perfect alternative for your trip.
Why would you choose a B&B over a traditional hotel room?
With attentive service, an atmosphere suited to mingling with other guests, and top-rated breakfasts, B&Bs all have a truly one-of-a-kind environment.
What are the best B&Bs in Chebeague Island?
Here are some well-liked B&Bs in the surrounding area: Inn at St John Portland In-Town: 10.5 mi (16.9 km) from the heart of Chebeague Island.Fleetwood House Bed & Breakfast: 3 rooms. Situated 10.9 mi (17.6 km) from the heart of Chebeague Island. Enjoy the free full breakfast and unique décor. Blind Tiger Portland - Danforth Street.: 9 rooms. 10 mi (16.1 km) from the heart of downtown.The Orchard House & Cafe: 5 rooms. Located 9.1 mi (14.7 km) from the core of Chebeague Island.
When should I stay at a B&B in Chebeague Island?
When you're dreaming of a escape to Chebeague Island, year-round temperatures and rainfall may be important factors to consider. 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 Chebeague Island are January, March, February, and December, with each month seeing an average of 7 inches of snowfall.
How can I get to and around Chebeague Island?
Planning your excursions in and around Chebeague Island is easier with these transportation options. Fly into Portland Intl. Jetport Airport (PWM), which is located 12.1 mi (19.4 km) away from the city center. You can also search for flights into Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 23 mi (37.1 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.