Find a Bed and Breakfast in Five Islands from CA $265

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Five Islands bed & breakfast

A balcony with two wooden chairs and a small table, overlooking a body of water with houses in the background.

1. Harborage Inn on the Oceanfront

Harborage Inn on the Oceanfront
3.5 star property
Boothbay 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!"
United States
Michele
The price is CA $266
CA $290 total
includes taxes & fees
Nov 10 - Nov 11
Harborage Inn on the Oceanfront
A serene lakeside setting with two rocking chairs, a fire pit, and a view of boats on the water.

2. The Snug: Cozy Ground-Floor Queen at Admiral's Quarters, Boothbay Harbor

The Snug: Cozy Ground-Floor Queen at Admiral's Quarters, Boothbay Harbor
Boothbay 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."
United States
Rhonda L.
The price is CA $302
CA $359 total
includes taxes & fees
Nov 9 - Nov 10
The Snug: Cozy Ground-Floor Queen at Admiral's Quarters, Boothbay Harbor
A wooden deck with three white Adirondack chairs facing a marina with boats and houses in the background.

3. Penthouse B: Top-Floor King Suite, Shared Sky Deck, Greenleaf Inn, Boothbay

Penthouse B: Top-Floor King Suite, Shared Sky Deck, Greenleaf Inn, Boothbay
Boothbay Harbor
10.0 out of 10, Exceptional, (3 reviews)
"We had such a great time at The Greenleaf. Jersey is an incredible host and will make sure your visit is amazing."
United States
Karen G.
The price is CA $431
CA $510 total
includes taxes & fees
Nov 28 - Nov 29
Penthouse B: Top-Floor King Suite, Shared Sky Deck, Greenleaf Inn, Boothbay
A deck with three chairs and a table, overlooking a marina with boats and a lighthouse.

4. 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, Boothbay
Boothbay Harbor
8.0 out of 10, Very good, (1 review)
"Friendly"
United States
Amy
The price is CA $377
CA $434 total
includes taxes & fees
Nov 27 - Nov 28
Second-Floor King Suite with a Deck Toward the Harbor, Greenleaf Inn, Boothbay
A wooden deck with three chairs and a table, overlooking a marina with boats and a lighthouse.

5. Ground-Level King with a Harbor-View Deck, Greenleaf Inn, Boothbay Harbor

Ground-Level King with a Harbor-View Deck, Greenleaf Inn, Boothbay Harbor
Boothbay 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."
United States
Kaitlyn H.
The price is CA $357
CA $423 total
includes taxes & fees
Nov 9 - Nov 10
Ground-Level King with a Harbor-View Deck, Greenleaf Inn, Boothbay Harbor
A balcony with a table set for two, a vase with flowers, and a view of a residential area.

6. 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, Boothbay
Boothbay Harbor
9.4 out of 10, Exceptional, (3 reviews)
"What a beautiful place! We loved staying here and will definitely be back."
United States
Anonymous traveller
The price is CA $496
CA $587 total
includes taxes & fees
Nov 9 - Nov 10
Room to Breathe: 800 sq ft Harbor-View King Suite, Admiral's Quarters, Boothbay
A balcony with two white wicker chairs and a small table, overlooking a waterfront with boats and houses.

7. Your Own Balcony: King Room at Waterfront Admiral's Quarters, Boothbay Harbor

Your Own Balcony: King Room at Waterfront Admiral's Quarters, Boothbay Harbor
Boothbay 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."
United States
Eileen O.
The price is CA $393
CA $465 total
includes taxes & fees
Nov 27 - Nov 28
Your Own Balcony: King Room at Waterfront Admiral's Quarters, Boothbay Harbor
A serene lakeside setting with two rocking chairs, a fire pit, and a view of boats on the water.

8. Penthouse with Ocean Views over Boothbay Harbor, Sleeps 4, Admiral's Quarters

Penthouse with Ocean Views over Boothbay Harbor, Sleeps 4, Admiral's Quarters
Boothbay 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."
United States
Harrison S.
The price is CA $446
CA $528 total
includes taxes & fees
Nov 9 - Nov 10
Penthouse with Ocean Views over Boothbay Harbor, Sleeps 4, Admiral's Quarters
A serene lakeside setting with two rocking chairs, a fire pit, and a view of boats on the water.

9. Coffee on the Harbor Patio: Queen Room at Admiral's Quarters, Boothbay Harbor

Coffee on the Harbor Patio: Queen Room at Admiral's Quarters, Boothbay Harbor
Boothbay Harbor
9.0 out of 10, Wonderful, (2 reviews)
"No cups aka for water no coffee maker in room wasn’t, given WiFi password or password to tv room was clean plenty heat and ac nice view nice deck outside our slider had a small fridge so we had cold water drinks no cups!!!!!!"
United States
Marjorie
The price is CA $363
CA $430 total
includes taxes & fees
Nov 9 - Nov 10
Coffee on the Harbor Patio: Queen Room at Admiral's Quarters, Boothbay Harbor
A wooden deck with three chairs and a table, overlooking a marina with boats and a lighthouse.

10. Tugboats at the Window: Direct Harbor-View King, Greenleaf Inn, Boothbay Harbor

Tugboats at the Window: Direct Harbor-View King, Greenleaf Inn, Boothbay Harbor
Boothbay Harbor
10.0 out of 10, Exceptional, (2 reviews)
"Jearsy was great! Will stay again."
United States
Sara S.
The price is CA $329
CA $390 total
includes taxes & fees
Nov 9 - Nov 10
Tugboats at the Window: Direct Harbor-View King, Greenleaf Inn, Boothbay Harbor
A wooden deck with three chairs and a table, overlooking a marina with boats and a lighthouse.

11. Private-Entrance King, Covered Harbor Balcony, Greenleaf Inn, Boothbay Harbor

Private-Entrance King, Covered Harbor Balcony, Greenleaf Inn, Boothbay Harbor
Boothbay Harbor
10.0 out of 10, Exceptional, (3 reviews)
"Loved the amenities and views! Great location… walking distance to everything. The staff was very friendly and accommodating!"
United States
Melissa
The price is CA $389
CA $460 total
includes taxes & fees
Nov 9 - Nov 10
Private-Entrance King, Covered Harbor Balcony, Greenleaf Inn, Boothbay Harbor
A serene lakeside setting with two rocking chairs, a fire pit, and a view of boats on the water.

12. Waterfront 2BR Suite, Three Balconies, Admiral's Quarters, Boothbay Harbor

Waterfront 2BR Suite, Three Balconies, Admiral's Quarters, Boothbay Harbor
Boothbay Harbor
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful Inn so close to many activities to choose from."
United States
Diana C.
The price is CA $441
CA $522 total
includes taxes & fees
Nov 9 - Nov 10
Waterfront 2BR Suite, Three Balconies, Admiral's Quarters, Boothbay Harbor
A serene lakeside setting with two rocking chairs, a fire pit, and a view of boats on the water.

13. Easy In, Easy Out: Ground-Floor King Suite at Admiral's Quarters, Boothbay Harbor

Easy In, Easy Out: Ground-Floor King Suite at Admiral's Quarters, Boothbay Harbor
Boothbay Harbor
9.8 out of 10, Exceptional, (6 reviews)
"This is a great property. You have full access to a kitchen that is stocked with snacks and breakfast. There are lots of rocking chairs and outdoor chairs to lounge and look at the harbor. Jersey was great. He even lit a fire every evening. Everything is walkable from here. Would definitely stay here again."
United States
Kelli H.
The price is CA $389
CA $460 total
includes taxes & fees
Nov 9 - Nov 10
Easy In, Easy Out: Ground-Floor King Suite at Admiral's Quarters, Boothbay Harbor
A deck with three chairs and a table, overlooking a marina with boats and a lighthouse.

14. Penthouse A: Top-Floor King, Shared Sky Deck, Greenleaf Inn, Boothbay Harbor

Penthouse A: Top-Floor King, Shared Sky Deck, Greenleaf Inn, Boothbay Harbor
Boothbay Harbor
10.0 out of 10, Exceptional, (1 review)
"The room was very new and clean. The view was unbelievable. Would stay again without question. Jersey is a delightful host."
United States
Mark H.
The price is CA $483
CA $573 total
includes taxes & fees
Nov 27 - Nov 28
Penthouse A: Top-Floor King, Shared Sky Deck, Greenleaf Inn, Boothbay Harbor
A serene lakeside setting with two rocking chairs facing a calm body of water, a fire pit in the center, and a clear view of boats and distant land.

15. 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, Boothbay
Boothbay Harbor
8.0 out of 10, Very good, (1 review)
The price is CA $374
CA $444 total
includes taxes & fees
Nov 9 - Nov 10
Your Own Deck Over the Harbor: Second-Floor King at Greenleaf Inn, Boothbay
A serene lakeside setting with two rocking chairs facing a calm body of water, a fire pit in the center, and a clear view of boats and distant land.

16. Fireside Corner King, Harbor Views, Electric Fireplace, Greenleaf Inn, Boothbay

Fireside Corner King, Harbor Views, Electric Fireplace, Greenleaf Inn, Boothbay
Boothbay Harbor
The price is CA $328
CA $388 total
includes taxes & fees
Nov 10 - Nov 11
Fireside Corner King, Harbor Views, Electric Fireplace, Greenleaf Inn, Boothbay
A wooden deck with outdoor seating and a view of the water.

17. The Corner Suite: Two Rooms, One Harbor Balcony, Greenleaf Inn, Boothbay Harbor

The Corner Suite: Two Rooms, One Harbor Balcony, Greenleaf Inn, Boothbay Harbor
Boothbay Harbor
10.0 out of 10, Exceptional, (2 reviews)
"The property was amazing! The staff are very helpful. This wasn't a very relaxing and enjoyable stay. We definitely would come back"
United States
Robert S.
The price is CA $411
CA $487 total
includes taxes & fees
Nov 9 - Nov 10
The Corner Suite: Two Rooms, One Harbor Balcony, Greenleaf Inn, Boothbay Harbor
A serene lakeside setting with two rocking chairs, a fire pit, and a view of boats on the water.

18. Top of the Inn: Penthouse King Suite with Balcony, Admiral's Quarters, Boothbay

Top of the Inn: Penthouse King Suite with Balcony, Admiral's Quarters, Boothbay
Boothbay Harbor
10.0 out of 10, Exceptional, (8 reviews)
"Great spot"
United States
Jarrett
The price is CA $459
CA $544 total
includes taxes & fees
Nov 9 - Nov 10
Top of the Inn: Penthouse King Suite with Balcony, Admiral's Quarters, Boothbay
A wooden deck with three chairs and a table, overlooking a marina with boats and a lighthouse.

19. Step-Free King with Your Own Harbor Balcony, Greenleaf Inn, Boothbay Harbor

Step-Free King with Your Own Harbor Balcony, Greenleaf Inn, Boothbay Harbor
Boothbay Harbor
9.6 out of 10, Exceptional, (4 reviews)
"Great spot, details were handled by property very well"
United States
John H.
The price is CA $367
CA $436 total
includes taxes & fees
Nov 9 - Nov 10
Step-Free King with Your Own Harbor Balcony, Greenleaf Inn, Boothbay Harbor
An outdoor patio with a covered seating area, a brick pathway, and potted plants.

20. Benjamin F. Packard House

Benjamin F. Packard House
3.0 star property
Bath
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!"
United States
Tina
The price is CA $278
CA $303 total
includes taxes & fees
Nov 9 - Nov 10
Benjamin F. Packard House
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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Frequently Asked Questions

Searching for B&Bs in Five Islands?

If you're looking for something a little different than your standard hotel, a bed and breakfast might be the perfect option for your trip.

How do you know if a B&B is the right choice for your stay?

Every B&B has its own unique feel. Whether it's a cozy reading space or a beautiful breakfast room, the little details are what make bed and breakfasts a fun place to get away.

What are the top B&Bs in Five Islands?

Here are some B&Bs in the surrounding area: Five Gables Inn: 16 rooms. 6.4 mi (10.2 km) from the heart of Five Islands.Harborage Inn on the Oceanfront: 11 rooms. 4.7 mi (7.6 km) from the downtown core. Enjoy the free cooked breakfast and designer toiletries. Captain Sawyer's Bed & Breakfast: 9 rooms. Situated 4.5 mi (7.2 km) from the heart of Five Islands. Enjoy the free full breakfast and patio area. Boothbay Harbor King Suite - Room 16 at AQ Inn: 4.4 mi (7.1 km) from the heart of downtown. Boothbay Harbor Penthouse Suite - Room 15 at AQ Inn - Fireplace, Ocean View: Located 4.4 mi (7.1 km) from the core of Five Islands.

When is the best time to stay at a B&B in Five Islands?

When you're planning your escape to Five Islands, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 64°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Five Islands are January, March, December, and February, with each month seeing an average of 6 inches of snowfall.

How can I get to and around Five Islands?

You can map out your trip in and around Five Islands ahead of time with these transportation options. Fly into Wiscasset, ME (ISS), which is located 9.7 mi (15.5 km) away from the city center. You can also search for flights into Augusta, ME (AUG-Augusta State), which is 34.4 mi (55.3 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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