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Our top choices for Cumberland bed & breakfast

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, (1140)
"Friendly helpful staff and a nice independent location "
United States
Robert
$80 nightly
The price is $87
Dec 14 - Dec 15
Total with taxes and fees
Inn at St John Portland In-Town

And. N B&B

And. N B&B
3.0 star property
Gray
9.8 out of 10, Exceptional, (77)
"Really lovely place and great hospitality from the owners!"
United States
Hunter
$104 nightly
The price is $114
Dec 31 - Jan 1, 2026
Total with taxes and fees
And. N B&B

The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (145)
"Quaint stay. Enjoyed our stay. "
United States
Linda
$167 nightly
The price is $182
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Kendall Inn

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (167)
"The property is beautiful, the staff is kind, and the rooms are spacious and clean. It was great to have a safe place to park the car while having so many things to do within walking distance. Being able to grab a quick breakfast before heading out was great too! We loved our stay here!"
United States
Darby
$204 nightly
The price is $223
Jan 13 - Jan 14, 2026
Total with taxes and fees
Blind Tiger Portland - Danforth Street.

Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (457)
"Great location and hospitality."
United States
Brandon
$154 nightly
The price is $168
Dec 14 - Dec 15
Total with taxes and fees
Candlebay Inn

Brewster House Bed & Breakfast

Brewster House Bed & Breakfast
4.0 star property
Freeport
9.8 out of 10, Exceptional, (114)
"The food was wonderful and the hospitality was great!"
United States
Olivia
$179 nightly
The price is $195
Jan 4 - Jan 5, 2026
Total with taxes and fees
Brewster House Bed & Breakfast

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (120)
"Loved the place "
United States
Stephen
$182 nightly
The price is $198
Jan 13 - Jan 14, 2026
Total with taxes and fees
Blind Tiger Portland – Carleton Street

Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (132)
"Lovely, comfortable stay! So welcoming and accommodating. We only stayed one night but will keep this in mind next time we are in the area :)"
United States
Sadie
$229 nightly
The price is $250
Dec 14 - Dec 15
Total with taxes and fees
Fleetwood House Bed & Breakfast

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 14 - Dec 15
Total with taxes and fees
The James Place Inn B&B
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 Cumberland Hotel Reviews

Find out more about Cumberland

Cumberland B&B information

Number of reviews
2,532
Accommodation
15 B&B
Lowest Price
$87
Highest Price
$250

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Cumberland?
Prices for B&Bs in Cumberland 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 Cumberland 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 & Breakfast in Cumberland?
The most popular time to book a B&B in Cumberland is from July to September, which coincides with the peak travel season. During these months, visitors flock to experience the vibrant summer atmosphere and partake in a plethora of outdoor activities. Whether you're hiking the picturesque trails of the nearby Appalachian Mountains or enjoying the local festivals, there's no shortage of adventures to be had.

July, in particular, is a standout month, boasting warm temperatures typically ranging from the mid-60s to the high 80s Fahrenheit. This inviting climate makes it superb for exploring the scenic beauty of the region, including the lush greenery and breathtaking views that define Cumberland's landscape. The bustling summer schedule also features a variety of events that draw in travelers seeking entertainment and cultural experiences.

If you're looking for a more budget-friendly option, consider visiting in November. While this month may see fewer tourists, it offers a unique charm with the changing seasons, making it a great time for peaceful hikes and enjoying the tranquility of the area. The crisp air and occasional fall colors can provide a refreshing backdrop for outdoor exploration, appealing to those who appreciate nature's beauty without the crowds.
What is the difference between a Cumberland B&B and a hotel?
Every Cumberland 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 Cumberland B&Bs.

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