Entire home

The Captain York House

Photo gallery for The Captain York House

Exterior
Property grounds
First dining area/formal dining room
Front porch with ocean and sunset views.
Interior

Reviews

9.6 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Arcade/game room
    A rare find - fun for all ages with on-site arcade/game room.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Casco Bay

Popular amenities

  • Patio
  • Toys
  • Kitchenette
  • Air-conditioning
  • Barbecue
  • Refrigerator

Explore the area

View map
Bailey Island, ME
  • Place, Casco Bay
    ‪1 min walk‬
  • Place, Cobwork Bridge
    ‪5 min walk‬
  • Place, Bailey Island Bridge
    ‪10 min walk‬
  • Airport, Portland, ME (PWM-Portland Intl. Jetport)
    ‪63 min drive‬

Rooms & beds

7 bedrooms (sleeps 12)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Single Bed and 1 Double Bed

Bedroom 4

2 Single Beds

Bedroom 5

1 King Bed

Bedroom 6

1 Single 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

Add dates for prices

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About the area

Bailey Island

Located in Bailey Island, this holiday home is by the sea. LL Bean Flagship Store and Maine Street 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. Travelling with kids? Consider Land's End Gift Shop and Ash Cove Pottery. Discover the area's water adventures with kayaking and power boating nearby, or enjoy the great outdoors with hiking/biking trails and rock climbing.
View more Holiday homes in Bailey IslandOpens in a new window
Map
Bailey Island, ME

What's nearby

  • Casco Bay - 1 min walk - 0.0 km
  • Cobwork Bridge - 5 min walk - 0.5 km
  • beach near Channel View Lane - 7 min walk - 0.6 km
  • Bailey Island Bridge - 10 min walk - 0.9 km
  • beach near Merritt House Road - 15 min walk - 1.3 km

Getting around

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

Restaurants

  • ‪Dolphin Marina & Restaurant - ‬32 min drive
  • ‪Cook's Lobster & Ale House - ‬8 min walk
  • ‪Erica's Seafood & Lobster Shop - ‬32 min drive
  • ‪Holbrooks Lobster Wharf - ‬23 min drive
  • ‪Sundrenched - ‬5 min walk

Frequently asked questions

Is The Captain York House pet-friendly?

No, pets are not allowed at this property.

How much is parking at The Captain York House ?

On-site 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 ?

Checkout is at 10:00 AM.

Where is The Captain York House located?

This family-friendly Bailey Island holiday 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 mile (2 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 24 out of 31 reviews
Rating 8 - Good. 7 out of 31 reviews
Rating 6 - Okay. 0 out of 31 reviews
Rating 4 - Poor. 0 out of 31 reviews
Rating 2 - Terrible. 0 out of 31 reviews

9.4/10

Cleanliness

9.8/10

Check-in

9.2/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very comfortable stay for our Extended Family with plenty of room to spread out, games for the kids to play, a side yard for outdoor games, and a welcoming front porch for us to gather together. Walking distance to restaurants, Cedar Beach, and BIGS. Hosts were very responsive to our needs. We would definitely recommend this house for large groups and hope to do so again ourselves!
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was our second stay at the Captain York House. It was as wonderful the second time as it was the first!
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

Liked: Check-in, location
The house is beautiful, with wonderful views in almost every direction.It is, however, byzantine in its layout, kind of like an M.C. Escher drawing. An interesting, very three dimensional space.That being said, a floor plan would have been really helpful in matching rooms and bathrooms with the varying needs of our guests.Great location for our sea kayaking group in terms of ocean access. However, sea kayakers appreciate a fresh water hose with which to rinse the salt from their gear. Hose and spigot were provided, but did not produce any water, and conversations with the property manager were, shall we say, less than effective in getting the water turned on.Finally, although the house seemed at first glance to be well cleaned, the details suggested otherwise. We had to clean some counter surfaces, as they had been left uncleaned, Some knives in the knife block were dirty, and the kitchen sink had not been thoroughly cleaned. The housekeeping staff informed us upon arrival that the trash had not been picked up the previous Monday, leaving us short of trash receptacles, and, that there was only one trash bag left. For eleven guests! On balance the garbage pickup was quickly arranged for the following day. But no additional trash bags were provided.Great house and location, which would benefit from better attention to management details.
Stayed 7 nights in Aug 2026
Response from VrboOwner on 17 August 2026
Thank you for taking the time to share your feedback. We’re glad you enjoyed the home, its views, unique layout, and especially the location for your sea kayaking group. Regarding the trash, unfortunately, we were not aware that the pickup had been missed until you contacted us on Tuesday. Once we were made aware, we promptly arranged for it to be picked up, and it was resolved within 24 hours. I’m sorry that communication regarding the hose and other concerns was frustrating. I did my best to assist remotely, but communication was limited to approximately one message each day, which made it difficult to troubleshoot issues in a timely manner. I also requested photos and provided my cell phone number a second time so that I could better understand and address the concerns. Unfortunately, I never received the requested photos or any further response, which left me unable to determine what needed to be addressed or how best to help. We certainly understand that issues can arise during a stay, and we are always willing to work with guests to resolve them. At the same time, effective communication requires responses from both sides so that we can take appropriate action. We appreciate the positive comments about the house and location and will take your feedback regarding housekeeping and management details into consideration. We wish you better luck and a more enjoyable experience on your future stays.
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

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
Response from VrboOwner on 18 March 2020
I’m sorry for your experience, the cleaning staff and renters are instructed to remove any leftover food from the fridge. Also I was unaware that the toilet seat was not fixed, when I spoke to Carolen she told me that she had fixed the seat not duct taped it. I will be further discussing these issues with our staff. I’m glad you enjoyed the porch as it’s my families favorite part as well. Captain York built the old part of the house from his retired shipmasts and live there for many years.
Verified review

8/10 Good

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 review

10/10 Excellent

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 review

8/10 Good

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 review

10/10 Excellent

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 review

8/10 Good

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

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 review

10/10 Excellent

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 review

8/10 Good

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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
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