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Upfront pricingWe are not like the others - we include taxes and fees
Our top choices for Bailey Island bed & breakfast
1. The Orchard House: Inn & Cafe
The Orchard House: Inn & CafeFreeport
9.6 out of 10, Exceptional, (185 reviews)
"Great place"
Mark
$156 nightly
The price is $171
Dec 1 - Dec 2
Total with taxes and fees
2. Candlebay Inn
Candlebay InnFreeport
9.6 out of 10, Exceptional, (500 reviews)
"Great stay in a historic home."
Richard
$159 nightly
The price is $173
Nov 11 - Nov 12
Total with taxes and fees
3. The Kendall Inn
The Kendall InnFreeport
9.8 out of 10, Exceptional, (170 reviews)
"The breakfasts were so tasty! The Inn is so charming! We loved our stay and hope to return next year!"
Justin Terry
$183 nightly
The price is $199
Dec 11 - Dec 12
Total with taxes and fees
4. Inn at St John Portland In-Town
Inn at St John Portland In-TownValley Street
8.6 out of 10, Excellent, (1,179 reviews)
"Great location and exactly what we needed for our time in Portland"
Darbi
$78 nightly
The price is $85
Nov 22 - Nov 23
Total with taxes and fees
5. The Nicholson Inn
The Nicholson InnFreeport
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.."
alexandre
$259 nightly
The price is $282
Nov 11 - Nov 12
Total with taxes and fees
6. The James Place Inn B&B
The James Place Inn B&BFreeport
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."
Kim
$251 nightly
The price is $273
Nov 11 - Nov 12
Total with taxes and fees
7. Benjamin F. Packard House
Benjamin F. Packard HouseBath
10.0 out of 10, Exceptional, (118 reviews)
"This is a wonderful bed and breakfast! I highly recommend and I would stay here again and again!"
Tina
$204 nightly
The price is $222
Nov 13 - Nov 14
Total with taxes and fees
8. Blind Tiger Portland – Carleton Street
Blind Tiger Portland – Carleton StreetWest End
9.6 out of 10, Exceptional, (137 reviews)
"Beautiful place"
Samuel
$146 nightly
The price is $159
Nov 18 - Nov 19
Total with taxes and fees
9. West End Collection at 146 Pine
West End Collection at 146 PineWest End
9.6 out of 10, Exceptional, (101 reviews)
"This was a super cute boutique inn and the location was ideal. The staff was super friendly!"
Stephanie
$217 nightly
The price is $237
Nov 16 - Nov 17
Total with taxes and fees
10. Blind Tiger Portland - Danforth Street.
Blind Tiger Portland - Danforth Street.West End
9.6 out of 10, Exceptional, (206 reviews)
"Very helpful and friendly staff"
paul k
$220 nightly
The price is $239
Nov 17 - Nov 18
Total with taxes and fees
11. Harborage Inn on the Oceanfront
Harborage Inn on the OceanfrontBoothbay Harbor
9.6 out of 10, Exceptional, (241 reviews)
"This little place was excellent! Great views, very convenient to walk everywhere. The morning breakfasts were delicious! Would definitely stay again!"
Michele
$165 nightly
The price is $179
Nov 11 - Nov 12
Total with taxes and fees
12. Fleetwood House Bed & Breakfast
Fleetwood House Bed & BreakfastRosemont
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"
caia
$238 nightly
The price is $260
Nov 11 - Nov 12
Total with taxes and fees
13. The Snug: Cozy Ground-Floor Queen at Admiral's Quarters, Boothbay Harbor
The Snug: Cozy Ground-Floor Queen at Admiral's Quarters, Boothbay HarborBoothbay Harbor
10.0 out of 10, Exceptional, (6 reviews)
"Great location. Shared spaces were comfortable and had beautiful harbor views. Very nice Inn. Would definitely stay here again."
Rhonda L.
$226 nightly
The price is $246
Nov 11 - Nov 12
Total with taxes and fees
14. Your Own Deck Over the Harbor: Second-Floor King at Greenleaf Inn, Boothbay
Your Own Deck Over the Harbor: Second-Floor King at Greenleaf Inn, BoothbayBoothbay Harbor
8.0 out of 10, Very good, (1 review)
$278 nightly
The price is $303
Nov 11 - Nov 12
Total with taxes and fees
15. Second-Floor King Suite with a Deck Toward the Harbor, Greenleaf Inn, Boothbay
Second-Floor King Suite with a Deck Toward the Harbor, Greenleaf Inn, BoothbayBoothbay Harbor
8.0 out of 10, Very good, (1 review)
"Friendly"
Amy
$273 nightly
The price is $298
Nov 27 - Nov 28
Total with taxes and fees
16. Ground-Level King with a Harbor-View Deck, Greenleaf Inn, Boothbay Harbor
Ground-Level King with a Harbor-View Deck, Greenleaf Inn, Boothbay HarborBoothbay Harbor
10.0 out of 10, Exceptional, (2 reviews)
"Jersey gave us a tour of the property, got us a reservation for dinner and made us feel right at home! 10/10 we will absolutely be here booking again. Clean room, comfy bed, couldn’t ask for a better stay."
Kaitlyn H.
$266 nightly
The price is $290
Nov 11 - Nov 12
Total with taxes and fees
17. Room to Breathe: 800 sq ft Harbor-View King Suite, Admiral's Quarters, Boothbay
Room to Breathe: 800 sq ft Harbor-View King Suite, Admiral's Quarters, BoothbayBoothbay Harbor
9.4 out of 10, Exceptional, (3 reviews)
"What a beautiful place! We loved staying here and will definitely be back."
Anonymous traveler
$369 nightly
The price is $402
Nov 11 - Nov 12
Total with taxes and fees
18. Your Own Balcony: King Room at Waterfront Admiral's Quarters, Boothbay Harbor
Your Own Balcony: King Room at Waterfront Admiral's Quarters, Boothbay HarborBoothbay Harbor
9.4 out of 10, Exceptional, (3 reviews)
"Very nice place to stay. Boothbay Harbor has so many wonderful restaurants, activities and shops to visit. Jersey was one of a kind. Always wanting to help or recommend things to do."
Eileen O.
$294 nightly
The price is $320
Nov 27 - Nov 28
Total with taxes and fees
19. Penthouse with Ocean Views over Boothbay Harbor, Sleeps 4, Admiral's Quarters
Penthouse with Ocean Views over Boothbay Harbor, Sleeps 4, Admiral's QuartersBoothbay Harbor
9.8 out of 10, Exceptional, (11 reviews)
"Gracious and welcoming host, the property is all about the view. Nice relaxing get away. Beautiful ocean view with peace and quiet."
Harrison S.
$333 nightly
The price is $363
Nov 11 - Nov 12
Total with taxes and fees
20. Tugboats at the Window: Direct Harbor-View King, Greenleaf Inn, Boothbay Harbor
Tugboats at the Window: Direct Harbor-View King, Greenleaf Inn, Boothbay HarborBoothbay Harbor
10.0 out of 10, Exceptional, (2 reviews)
"Jearsy was great! Will stay again."
Sara S.
$246 nightly
The price is $268
Nov 11 - Nov 12
Total with taxes and fees
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.
Learn more about Bailey Island
Hike the Giant's Stairs trail along the rocky coastline for dramatic views of Casco Bay. Seafood lovers shouldn't miss lobster rolls at Cook's Lobster & Ale House on the island's southern tip.
Top reviews in Bailey Island
Candlebay Inn
Candlebay InnFreeport
10/10 Excellent
Very cute B and B. Nice personal touches, snacks and extra amenities, toys for your pet, wonderful breakfast. Connie was very personable and knew alot about surrounding area. Within walking of lots of shops and restaurants. Perfect spot. Clean, would stay again.
Sheree Lee