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Nov 21 - Nov 23
In two weeks
Nov 28 - Nov 30
In one month
Dec 12 - Dec 14
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Jan 9 - Jan 11

B&B in Chebeague Island

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

Inn at St John Portland In-Town

2.5 star property
Valley Street
8.8 out of 10, Excellent, (1137)
"Great place to stay. Would highly recommend "
United States
Benjamin
$80 nightly
The price is $87
Dec 1 - Dec 2
Total with taxes and fees
Inn at St John Portland In-Town
Exterior
Old Orchard Beach Inn

Old Orchard Beach Inn

2.5 star property
Old Orchard Beach
8.2 out of 10, Very Good, (1000)
"My family had a cozy and memorable stay. The staff was incredibly helpful and my daughter enjoyed the historical look and feel to the Inn."
United States
Christopher
$100 nightly
The price is $110
Nov 22 - Nov 23
Total with taxes and fees
Old Orchard Beach Inn
Porch
Candlebay Inn

Candlebay Inn

3.0 star property
Freeport
9.6 out of 10, Exceptional, (457)
"The Inn was great and the staff was very hospitable "
United States
Timothy
$154 nightly
The price is $168
Nov 16 - Nov 17
Total with taxes and fees
Candlebay Inn
Front of property - evening/night
The Orchard House & Cafe

The Orchard House & Cafe

3.0 star property
Freeport
9.6 out of 10, Exceptional, (161)
"Wonderful place to stay! The room was very clean and the beds super comfortable. Will most definitely be returning for another visit in Maine."
United States
Shannon
$167 nightly
The price is $182
Nov 16 - Nov 17
Total with taxes and fees
The Orchard House & Cafe
Exterior
Benjamin F. Packard House

Benjamin F. Packard House

3.0 star property
Bath
10.0 out of 10, Exceptional, (102)
"Wonderful place to stay in Bath. The breakfast is terrific!"
United States
William
$229 nightly
The price is $250
Nov 24 - Nov 25
Total with taxes and fees
Benjamin F. Packard House
Exterior
The Kendall Inn

The Kendall Inn

3.5 star property
Freeport
9.8 out of 10, Exceptional, (144)
"Quaint stay. Enjoyed our stay. "
United States
Linda
$189 nightly
The price is $206
Nov 17 - Nov 18
Total with taxes and fees
The Kendall Inn
Property entrance
Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast

3.0 star property
Rosemont
9.0 out of 10, Wonderful, (132)
"This was a beautiful old house in excellent condition. The hosts were very nice. The breakfast was excellent. "
United States
Linda
$229 nightly
The price is $250
Nov 16 - Nov 17
Total with taxes and fees
Fleetwood House Bed & Breakfast
Baxter | 1 bedroom, premium bedding, individually decorated
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 star property
West End
9.6 out of 10, Exceptional, (161)
" Beautiful historic building. The common areas and our room were stunning! Breakfast in the morning was great. Make sure to go to the widow’s walk in the evening for a view. "
United States
John
$235 nightly
The price is $257
Dec 14 - Dec 15
Total with taxes and fees
Blind Tiger Portland - Danforth Street.
Outdoor dining
The James Place Inn B&B

The James Place Inn B&B

3.5 star property
Freeport
10.0 out of 10, Exceptional, (182)
"Wish we could have stayed longer. It has the ambiance of an older inn but the rooms are very clean and well maintained. "
United States
Melissa
$218 nightly
The price is $238
Dec 1 - Dec 2
Total with taxes and fees
The James Place Inn B&B
Stovall | Living area
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 star property
West End
9.6 out of 10, Exceptional, (119)
"One of the best hotel/bnb experiences I’ve had in my past year of travels. Would recommend to anyone going to Maine. "
United States
Cristian
$236 nightly
The price is $258
Nov 20 - Nov 21
Total with taxes and fees
Blind Tiger Portland – Carleton Street
Garden
Brewster House Bed & Breakfast

Brewster House Bed & Breakfast

4.0 star property
Freeport
9.8 out of 10, Exceptional, (114)
"Nice inn - a bit noisy as it's on a main street and I had a front facing room. "
United States
lorna
$379 nightly
The price is $413
Dec 3 - Dec 4
Total with taxes and fees
Brewster House Bed & Breakfast
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Lovely hotel, great location, great staff, valet parking."
Elizabeth 1-night trip
Posted 11 hours ago
Portland Regency Hotel & Spa

Find out more about Chebeague Island

Chebeague Island B&B information

Number of reviews
3,646
Accommodation
24 B&B
Lowest Price
$87
Highest Price
$413

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Chebeague Island?
Prices for B&Bs in Chebeague Island often vary, but you can find a great deal from $87 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chebeague Island B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Chebeague Island?
The best time to book a B&B in Chebeague Island is during the summer months, particularly from June to August. This vibrant season draws visitors eager to enjoy the island's stunning coastal scenery, partake in water activities, and bask in the warm weather, with temperatures typically ranging from the mid-60s to low 80s Fahrenheit.

July stands out as the peak month, where the island comes alive with festivals, outdoor concerts, and bustling local markets. It's an ideal time for families and couples looking to soak in the lively atmosphere, as well as explore the picturesque beaches and charming walking trails that showcase the island's natural beauty.

For those seeking a more tranquil experience, consider visiting in September. During this time, you can still enjoy pleasant weather, along with the added bonus of fewer crowds. The summer bustle gives way to a quieter charm, allowing for leisurely walks along the shoreline and peaceful moments watching the sunset.
What is the difference between a Chebeague Island Bed & Breakfast and a hotel?
Every Chebeague Island B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chebeague Island B&Bs.

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