A sunset over a lake surrounded by dense forests and a distant shoreline.

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Check prices for these dates

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Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
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Dec 4 - Dec 6
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Jan 1 - Jan 3

Our top choices for Long Island bed & breakfast

A multi-story building with a stone facade, multiple windows, and awnings.

1. Inn at St John Portland In-Town

Inn at St John Portland In-Town
2.5 star property
Valley Street
8.6 out of 10, Excellent, (1,176 reviews)
"Great location and exactly what we needed for our time in Portland"
United States
Darbi
The price is CA $93
CA $101 total
includes taxes & fees
Nov 22 - Nov 23
Inn at St John Portland In-Town
A breakfast setup with a tiered tray holding fruits, cups, and a coffee pot.

2. The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (185 reviews)
"Great place"
United States
Mark
The price is CA $186
CA $203 total
includes taxes & fees
Dec 1 - Dec 2
The Orchard House: Inn & Cafe
Exterior

3. West End Collection at 146 Pine

West End Collection at 146 Pine
3.0 star property
West End
9.6 out of 10, Exceptional, (100 reviews)
"This was a super cute boutique inn and the location was ideal. The staff was super friendly!"
United States
Stephanie
The price is CA $303
CA $331 total
includes taxes & fees
Nov 30 - Dec 1
West End Collection at 146 Pine
A two-story house with a red roof, a front porch, and a well-maintained lawn.

4. Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (498 reviews)
"Great stay in a historic home."
United States
Richard
The price is CA $200
CA $218 total
includes taxes & fees
Nov 9 - Nov 10
Candlebay Inn
A garden with a stone wall, various plants, and flowers.

5. Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (150 reviews)
"Close location to airport. Sweet Neighbhorhood Good shower and breakfast was delish. Loved eating on the houses China"
United States
caia
The price is CA $320
CA $363 total
includes taxes & fees
Nov 9 - Nov 10
Fleetwood House Bed & Breakfast
A well-lit living room with a fireplace, comfortable seating, and a large mirror.

6. Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (137 reviews)
"Beautiful place"
United States
Samuel
The price is CA $288
CA $314 total
includes taxes & fees
Nov 17 - Nov 18
Blind Tiger Portland – Carleton Street
A covered porch with white railings and a view of a well-maintained lawn and pathway.

7. The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (169 reviews)
"The breakfasts were so tasty! The Inn is so charming! We loved our stay and hope to return next year!"
United States
Justin Terry
The price is CA $227
CA $247 total
includes taxes & fees
Dec 6 - Dec 7
The Kendall Inn
A spacious kitchen with a central island, wooden bar stools, and a long dining table.

8. Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (204 reviews)
"Very helpful and friendly staff"
United States
paul k
The price is CA $341
CA $372 total
includes taxes & fees
Nov 22 - Nov 23
Blind Tiger Portland - Danforth Street.
A two-story house with a balcony, a front porch, and a snow-covered landscape.

9. The Nicholson Inn

The Nicholson Inn
3.0 star property
Freeport
10.0 out of 10, Exceptional, (5 reviews)
"We had a fantastic and lovely, although quick, stay. The Inn is very charming and John and Loretta are so kind and helpful. Would love to go back and stay with them again.."
United States
alexandre
The price is CA $311
CA $339 total
includes taxes & fees
Dec 6 - Dec 7
The Nicholson Inn
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

10. Experience the History of Portland - The Hope Island Room

Experience the History of Portland - The Hope Island Room
West End
10.0 out of 10, Exceptional, (1 review)
"Really cool home and room was big and clean!"
United States
Daniel
The price is CA $233
CA $263 total
includes taxes & fees
Nov 8 - Nov 9
Experience the History of Portland - The Hope Island Room
A house with a porch, white railings, and hanging flower baskets.

11. Old Orchard Beach Inn

Old Orchard Beach Inn
2.5 star property
Old Orchard Beach
8.2 out of 10, Very good, (1,000 reviews)
"Really nice hotel"
United States
James
The price is CA $172
CA $209 total
includes taxes & fees
Nov 13 - Nov 14
Old Orchard Beach Inn
A house with a sign for The James Place Inn, indicating a vacancy.

12. The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (196 reviews)
"Sean was amazingly helpful and friendly. The house itself is so well maintained, and the blue room was adorable. Loved the fact that we were within walking distance of all the shops. Would definitely recommend and will plan on staying again the next time we’re in town."
United States
Kim
The price is CA $350
CA $382 total
includes taxes & fees
Nov 9 - Nov 10
The James Place Inn B&B
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

13. Diamond Island | King Room with Private Ensuite

Diamond Island | King Room with Private Ensuite
West End
The price is CA $262
CA $296 total
includes taxes & fees
Nov 8 - Nov 9
Diamond Island | King Room with Private Ensuite
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

14. Experience the History of Portland - The Hope Island Room

Experience the History of Portland - The Hope Island Room
West End
The price is CA $310
CA $350 total
includes taxes & fees
Nov 8 - Nov 9
Experience the History of Portland - The Hope Island Room
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

15. Experience the History of Portland - Two Room Suite w/Private Bath

Experience the History of Portland - Two Room Suite w/Private Bath
West End
The price is CA $371
CA $420 total
includes taxes & fees
Nov 8 - Nov 9
Experience the History of Portland - Two Room Suite w/Private Bath
A modern bathroom with a white tiled shower, a round mirror, and a gold vanity.

16. The Loft - private suite in historic home

The Loft - private suite in historic home
West End
The price is CA $453
CA $659 total
includes taxes & fees
Nov 15 - Nov 16
The Loft - private suite in historic home
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 Long Island Hotel Reviews

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Awesome boutique hotel in the heart of everything and I will definitely be back soon! Actually kinda sad I left."
Aaron 2-night trip
Posted 2 hours ago
Portland Regency Hotel & Spa

Find out more about Long Island

Long Island B&B information

Number of reviews
2,432
Accommodation
29 B&B
Lowest Price
CA $101
Highest Price
CA $659

Frequently asked questions

Searching for B&Bs in Long Island?
If you're looking for something a little more offbeat than your standard hotel experience, 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, opportunities to meet guests from other places, and tasty breakfasts, B&Bs provide a truly one-of-a-kind environment.
What are the best B&Bs in Long Island?
Here are some well-liked B&Bs in the surrounding area: Inn at St John Portland In-Town: 5.8 mi (9.3 km) from the heart of Long Island.Old Orchard Beach Inn: 15.5 mi (24.9 km) from the downtown core. Enjoy the outdoor pool and unique décor. Blind Tiger Portland - Danforth Street.: 9 rooms. Situated 5.2 mi (8.3 km) from the heart of Long Island. The Orchard House: Inn & Cafe: 5 rooms. 13.7 mi (22 km) from the heart of downtown.Blind Tiger Portland – Carleton Street: 6 rooms. Located 5.5 mi (8.8 km) from the core of Long Island. Enjoy the unique décor and patio area.
What's the best time of year to stay at a B&B in Long Island?
When you're dreaming of a stay in Long 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 Long 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 Long Island?
Mapping out your trip in and around Long Island is easy with these transportation options. Fly into Portland Intl. Jetport Airport (PWM), which is located 7.4 mi (11.9 km) away from the heart of the city. Otherwise, you can search for flights to Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 25.9 mi (41.6 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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