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7 bedrooms7 bathroomsSleeps 123000 sq ft

Rooms & beds

7 bedrooms (sleeps 12)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Twin Bed and 1 Double Bed

Bedroom 4

2 Twin Beds

Bedroom 5

1 King Bed

Bedroom 6

1 Twin Bunk Bed

Bedroom 7

1 Queen Bed

7 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Bathtub or shower · Toilet

Bathroom 4

Toilet · Shower only

Bathroom 5

Bathtub or shower · Toilet

Bathroom 6

Bathtub or shower · Toilet

Bathroom 7

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Kitchenette
Separate dining area
Garden
Dining area

About this property

The Captain York House

The Historic Captain York House in a unique New England home that was originally one home built along side another. This allows for the house to split into a duplex. The historic Captain York House has been on Bailey Island for more than 100 years. It is a 7 bedroom, 7 bathroom house that can accommodate families of up to 12 adults.
ALL SUMMER RENTALS ARE SATURDAY TO SATURDAY - NO EXCEPTIONS
This house provides a great home base for exploring Bailey Island and the surrounding coastal areas. With 7 bedrooms and 7 baths everyone has their own area! Beds include: two king, two queen, one full trundle with twin, twin bunk beds, and two twins.
Sheets, linens and towels included in linen closet - beds are not made. We have board games throughout the house and a mini foosball, ping-pong, air-hockey, pool table.
There are many outdoor activities on and within a short drive, including; beaches, boating, kayaking, hiking trails, Bailey Island General Store, Land's End Gift Shop, Cook's Lobster and Ale House, and Morse's Cribstone Restaurant on the island (with both restaurants in walking distance). Come explore, relax and enjoy the Maine coast!

There are absolutely no pets allowed at this property. There are two external cameras monitoring the driveway and road. If a pet is seen at the property your party will be asked to remove the pet the same day. If this is not done your reservation will be forfeited and your entire party will be asked to leave immediately. We appreciate it when our property is treated like your own, with respect to its owner’s house rules.

*** Please note, upon booking you will be asked to sign a contract agreeing to all house rules. Your reservation will not be confirmed until this is received ***
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Air conditioning
Outdoor Space
Ocean view

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock

We should mention

A car is recommended for transportation to and from this property

About the neighborhood

Bailey Island

Located in Bailey Island, this vacation home is by the sea. Maine Street and LL Bean Flagship Store are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Brunswick Town Commons and Casco Bay. Traveling with kids? Consider Paddleworks and Land's End Gift Shop. Be sure to check out the area's animals with activities such as game walks and birdwatching.
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Map
Bailey Island, ME

What's nearby

  • Cobwork Bridge - 5 min walk - 0.5 km
  • Bailey Island Bridge - 6 min walk - 0.6 km
  • Mackerel Cove - 2 min drive - 1.5 km
  • Paddleworks - 5 min drive - 2.9 km
  • LL Bean Flagship Store - 43 min drive - 50.2 km

Getting around

  • Brunswick Station - 25 min drive
  • Portland Intl. Jetport Airport (PWM) - 59 min drive

Restaurants

  • ‪Cook's Lobster & Ale House - ‬8 min walk
  • ‪Erica's Seafood & Lobster Shop - ‬32 min drive
  • ‪Dolphin Marina & Restaurant - ‬32 min drive
  • ‪Holbrooks Lobster Wharf - ‬23 min drive
  • ‪B.I.G.S. Bailey Island General Store - ‬14 min walk

Frequently asked questions

Is The Captain York House pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at The Captain York House ?

As of Mar 21, 2026, prices found for a 1-night stay for 2 adults at The Captain York House on Mar 23, 2026 start from $648, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at The Captain York House ?

Check-in begins at 3:00 PM.

What time is check-out at The Captain York House ?

Check-out is at 10:00 AM.

Where is The Captain York House located?

This family-friendly Bailey Island vacation home is located by the sea, within a 5-minute walk of Casco Bay and Bailey Island Bridge. Mackerel Cove and Cobwork Bridge are also within 1 mi (2 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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Rating 10 - Excellent. 22 out of 28 reviews
Rating 8 - Good. 6 out of 28 reviews
Rating 6 - Okay. 0 out of 28 reviews
Rating 4 - Poor. 0 out of 28 reviews
Rating 2 - Terrible. 0 out of 28 reviews

9.4/10

Cleanliness

9.8/10

Check-in

9.4/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Julie R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fun in Maine

Property was just as described. We enjoyed all the space, walking to the restaurant and the cove at the bottom of the hill. Even caught some striper bass one evening. Air conditioning and WiFi worked well and owner responded to emails in a timely manner.
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Rebecca M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic break!

The Captain York House was just what we were looking for! We were a large group all wanting to stay in the same place, but we were also worried about feeling crowded. During our stay, we found so many places to gather in twos, threes, fours, or as a whole group, that we never felt like we were in each other's way. We had everything we needed and more!
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Jeff W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

We had 3 families, so the separation of space was great. One suggestion would be to include soap and shampoo in the bathrooms. Air conditioning was nice to have. Kids loved the game room.
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

Rohan J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Must visit the captain york house

We had a lovely stay at this property over new years eve. The house was crystal clean, well furnished and massive! We were a group of 15 people and the house had enough space for everyone. The kitchen was fully equipped with utensils and equipment for cookout sessions. The communication with the host was prompt and accurate which made our stay even more comfortable. Overall 5/5, would totally recommend this oceanfront house.
Stayed 3 nights in Dec 2019
Verified

10/10 Excellent

Rachel Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful house for a group

This house was perfect for 4 families with active children! Plenty of room for everyone to spread out and the kids loved the game room. The view from the porch is gorgeous (we spent most of our time there) as are the flower beds around it. The yard is big enough for kids to run around and play. We enjoyed walking to the cove at the bottom of the hill each night to look for sea glass and shells. The only drawbacks are the kitchen is a touch on the small side and the roads by the house can sometimes be a bit busy. These minor things are good to know but wouldn’t deter us from returning. It is perfect for a group!
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Julee H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic week on Bailey Island

Brianna’s Bailey Island house is spacious, beautiful, and charmingly historic; yet it has been updated to have all of the modern conveniences. Our group had four couples and four very young children. We all had our own spaces and never felt crowded. It is very kid friendly. The kitchen is extremely well supplied and had everything we needed during our stay. There are seven full bathrooms and tons of towels and bed linens. We enjoyed sitting on the spacious porch and strolling down the street to Cook’s Lobster and Ale House to eat or view the boats and shoreline. There were even delicious ripe strawberries in the flower bed! This house is a wonderful jumping off place for the Botanical Garden at Booth Bay, ferry boats to Monhegan island, day trips to Portland and Freeport, and many walking trails. The last afternoon we took a two hour schooner sailing trip in the bay near Cook’s dock. I highly recommend that! Thank you, Brianna, for being such a responsive and helpful host. We all agree that we want to return in the future.
Stayed 7 nights in Jun 2023
Verified

8/10 Good

Richard S.

Liked: Check-in, communication, location, listing accuracy

Great house, but who was Captain York?

Our family spent a wonderful week at the Captain York House. The house was large enough to easily accommodate our family of 13 and was furnished with everything we needed. It is located at the corner of two relatively busy streets and was noisier than I expected (especially the motorcycles.) But it was close to a fine restaurant, marina, general store and a moderately priced gift shop so that more than made up for the noise. My favorite part of the house was the large front porch where I spent most of my time while my children, grandchildren and great grandchild were out and about. There were only two negative aspects of our vacation. When we arrived we found the entire refrigerator door filled with items left by former tenants, plus more food in the cabinet. When I told Brianna her response was that we could use it or dispose of it as we wished. I’m sorry but I don’t use open containers of food if I don’t know where it came from, and I don’t think we should have to dispose of other people’s leftovers. There were also various items of clothing left in some of the rooms. We arrived on Saturday and on Monday one of the plastic bolts on the toilet seat broke. We tried to replace the bolts but they were not standard so we could not fix it. I informed Brianna and she said she would try to take care of it. A day or two later the handle on the refrigerator broke and the handyman’s wife came right over to fix it. When I asked her about the toilet seat she said that she was not authorized to buy a new one. She put duct tape around it but that did little good. I am disappointed that Brianna did not think it important enough to authorize the purchase of a new one. Except for that we had a wonderful week at the Captain York House. By the way, who was Captain York?
Stayed 7 nights in Jul 2019
Verified

8/10 Good

Addy S.

Liked: Check-in, communication, location, listing accuracy

Beautiful location

House is beautiful and spacious I left a message to talk to property manager for a callback
Stayed 4 nights in Sep 2022
Verified

10/10 Excellent

DIANA B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family reunion

We stayed in this house for a recent family get together and had an amazing time. The home is conveniently located walking distance to a few restaurants, the cribstone Bridge, and is a walk or short drive away from a small and beautiful beach. There was so much the island offered, and the liason was ideal. The property has a yard and nice deck space for spending time outdoors. The home has a unique layout that allowed for space for kids to play. Home was equipped with kids games, puzzles, and books for kids and adults.
Stayed 7 nights in Aug 2022
Verified

8/10 Good

Josh E.

Liked: Cleanliness, check-in, location, listing accuracy

Vintage New England Great Location

Great house and location for an extended family location on beautiful Bailey Island. The house is older but we viewed it as a vintage, classic house that slept 14 comfortably. We did have some problems with the air conditioning- it was really hot, but we managed. We also had trouble with the oven and while we were able to communicate it to the owners, we did not get it resolved, which was disappointing. There was a small kitchenette in the guest portion of the house with a fridge and small stove, but it was difficult cooking for 14. We also found the tv/dvd player in the basement didn’t work, so we didn’t have that as an option for the kids but we were out exploring most of the week, so not a big deal. I would imagine the owners will have some of the appliances updated and working well for future guests. Despite some of the issues with the appliances, the house was spacious, had a nice deck and patio, a great yard and a great location.
Stayed 7 nights in Aug 2022
Verified

10/10 Excellent

Erik R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location and size

Great place to stay with a big family, lots of space; great location.
Stayed 7 nights in Jul 2022
Verified

8/10 Good

Amanda B.

Liked: Location, listing accuracy
Disliked: Communication

Bailey Island 2022

This is the second time we have stayed at this property. The first visit was super and we had no issues. Unfortunately, when we arrived at check-in time this year we had to wait an hour to enter the home because the two women who were cleaning were not ready. It was 90° outside and we were very hot and tired from the trip. When we were finally able to get into the house there was laundry, clean, set all over the house and it was 85° inside. We had to go outside and figure out how to turn on the AC at the breaker box. There is no Wi-Fi in the in the entire east wing of the house which was very frustrating. We contacted the property owner at the beginning of the week but unfortunately did not hear back from them. The house was very large and fit our three families very comfortably, it was nice having so many bathrooms. The location is amazing and Bailey Island is beautiful.
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Grace C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Experience

If you are looking for a Bailey Island vacation rental that can accommodate a group (refer to property description for size), then the Captain York house is the perfect choice. In the past we have used this perfect Bailey Island location as our home base to make day trips to wonderful Maine locations such as Portland and Freeport, Popham Beach, Damariscotta, Pemaquid Point, Boothbay, Rockland and Camden. This year we totally enjoyed the close to home locations: The Giant Stairs, Lands End, Cedar Beach, Lowell’s Cove, and so conveniently The Captain Cook’s Lobster and Ale House. I
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Tom H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Thank you Captain!!!

We had a fantastic time, we really did! The large house was perfect for our large group - several great family time spaces!! We used every square inch of that house except the bunk Room… we fired up the grill…. The porch was used all the time - if we were awake and home someone was on the porch! We played card games upstairs and on the main level, the kids used the game table in the basement a couple of times .. watched the arrival of the Tour de France into Paris, Watched some Olympics, used the washer and dryer - what a great convenience…. We are All great cooks and each family was responsible for a night of cooking - pretty much found all we needed … there were four families there , and we all loved our bedrooms and bathrooms …so great … and appreciated the parking very much - plenty of room for the vehicles. Easy access to the house too. The island is wonderful …Lots Of fun Island activities - Don’t miss the Giants’ stairs, climbing and wading at Land’s End, wading and skipping stones at the end of street . We went to Popham Beach which is just a wonder. Also a couple trips meeting other family members at Boothbay Harbor and Ocean point…All in all It was a terrific week , and we all wished we had booked two weeks Brianna was great to work with. Easy peasy . We said hello and thank you to Captain York many times during our stay, and that’s where my title of my review came from. Fantastic .
Stayed 7 nights in Jul 2021
Verified

10/10 Excellent

Alan T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Coming Home

We previously owned the Captain York House as a B&B in the late 90’s and early 2000’s. It was like coming home. The house was beautifully decorated and in great shape for a house built in the early 1900’s. The outside deck was great and the butterfly bush by the front door was loaded with butterflies and hummingbirds. Our daughters and granddaughter had a great time exploring the coast of Maine again. This trip was well worth it. The local seafood was outstanding wherever we went.The owner, Brianna, was outstanding in communicating with us and catering to our needs.
Stayed 7 nights in Jul 2021
Verified

10/10 Excellent

Grace C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Stay

Captain York House is a perfect Maine island cottage. It is clean, comfortable, and roomy. You will feel at home whether you decide to stay close by and explore the beautiful sights Bailey Island has to offer, or use it as a base to visit Midcoast Maine beaches, lighthouses, and towns such as Freeport, Bath, and Damariscotta. We have even taken day trips to Rockland and Camden or Portland, and been happy to.return to Captain York to rest our heads. Brianna is an excellent host who makes sure everything goes smoothly. A highly recommended stay!
Stayed 7 nights in Jul 2021
Verified

8/10 Good

Kate K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great House on a Quiet Island

We had a great time at this house with our family and our extended family. There are plenty of bedrooms and bathrooms as well as great gathering areas. It's a quirky place but we loved it. The day we arrived, the power was out (due to a storm) so there was a generator running that provided power to about half of the the house. We all had to sleep in the powered part of the house that first night. The linemen got the power up and running the following day so we were able to utilize all of the living space for the rest of the trip. Brianna was easy to contact and kept us informed of when the power was supposed to come back. The only other minor hiccup was that the oven in the main kitchen didn't function properly. Luckily there was another oven in the extra kitchen that worked great.
Stayed 3 nights in Oct 2019
Verified

10/10 Excellent

Mary-Anne B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spacious house with private areas for large families.

Enjoyed our stay and many activities in the area. Would recommend renting. Only glitch was a finicky oven in the main kitchen, but the oven in the kitchenette worked well.
Verified

8/10 Good

Elisabeth M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Big house, nice spot.

Walk to marina, Cooks lobster, and close to Cedar Beach. Big house, easily fits 2-3 families with privacy. Yard and porch are nice features. Fresh ocean air fills the house with windows open.
Verified

10/10 Excellent

Ross L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place

This property is very well maintained and extremely easy to access. Working with the property manager is a breeze. Will be back again.
Stayed 7 nights in Jul 2019
Verified

10/10 Excellent

Laura M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Family Vacation

First off, we had a hiccup in our plans which left us arriving a little early (hours not days) and after contacting Brianna, she made arrangements for us to be able to check in a little early which was a blessing for us. The home was located in a beautiful spot. We loved the surrounding area with the hiking trails and beach area. The best beach spot for us was Popham beach which was suggested by Brianna. The kids enjoyed the down stairs game room and us parents mainly sat on the porch enjoying the view. Great place to stay if your planning a vacation to Bailey’s Island. We would stay here again in a heartbeat.
Stayed 7 nights in Jul 2019
Verified

10/10 Excellent

Joe M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Place

The property was clean, well maintained and looked just as great as it does in photos. It was a perfect venue for our reunion. Check in/communication was easy and there was a helpful binder with information about the house, the area, and points of interest.
Stayed 7 nights in Jun 2019
Verified

10/10 Excellent

Gina D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacation 2019

This home met our needs for a great family vacation! It was clean, spacious, and comfortable!
Stayed 7 nights in Jun 2019
Verified

10/10 Excellent

Patrick M.

Great place, lots to do.

We had a wonderful, fun family stay. Plenty of room n things to do.
Stayed 7 nights in Aug 2018
Verified

10/10 Excellent

Stephanie M.

What a great house!

The house was spacious enough for 4 families the youngest being 15 years old. A wonderful porch to hang out on and a large dining table for game night. We had lawn space available for yard games. Plenty of parking for 4 four vehicles.
Stayed 7 nights in Jul 2018

About the host

Hosted by Brianna Branch

Host profile image
My family and I love to travel. I believe the best way to feel at home is to stay in a home. I hope travelers enjoy our home and their time in Maine as much as we do.

Why they chose this property

The Captain York House is spacious and has beautiful ocean and sunset views. I have traveled to Bailey Island every year since I was a child. My dream was to someday have a house on the island. The peace and tranquility of the island stays with me year round and draws me back to my home.

What makes this property unique

There are three living areas to provide space and privacy to multiple guests. There are many areas for families to have their own space including two living rooms, a recreational room w mini game table, two laundry rooms, a nice deck and big yard, and kitchen. Three bedrooms have en suite bathrooms.
Everything you need for a perfect vacation can be found within a few miles walking distance and on the island. There is a small general store, a wonderful restaurant serving the freshest seafood (just down the street, Cook's Lobster and Ale House), kids menu as well as inland specialties. There are multiple free beach access points, hiking trails, kayak rentals and lessons, a ferry cruise as well as private charters. Bailey Island also encompasses a unique gift shop at the end of the island, rock climbing at the giant stairs and wonderful open ocean views and sunsets abound.

Languages:

English
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