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Perched on the rugged cliffs of beautiful Bailey Island.

Photo gallery for Perched on the rugged cliffs of beautiful Bailey Island.

A wooden deck with outdoor furniture, including chairs and a table, overlooking a body of water.
A cabin surrounded by dense forest, with a clear view of the surrounding landscape.
A window with a view of trees and a body of water.
A wooden cabin bedroom with a bed, two bedside tables with lamps, a window with curtains, and a view of the sea.
A wooden interior with a staircase, large windows, and a view of the outdoors.

Reviews

10 out of 10
Exceptional

Highlights

  • Bring your furry friends
    Top-rated for creating memorable stays with your pets.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Air conditioning
  • Barbecue grill
  • Deck or patio

Explore the area

View in a map
Bailey Island, ME
  • Place, Land's End Gift Shop
    ‪3 min walk‬
  • Place, Mackerel Cove
    ‪6 min walk‬
  • Place, beach near Mackerel Cove Lot
    ‪2 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

2 twin size beds

2 Twin Beds

Queen size bed

1 Queen Bed

1 bathroom

Full bathroom

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Dining area

About this property

Perched on the rugged cliffs of beautiful Bailey Island.

Welcome to Captain's Watch!

Perched on the rugged cliffs of beautiful Bailey Island, this charming 2-bedroom, 1-bath Maine vacation getaway offers breathtaking easterly views of Casco Bay, where you can enjoy spectacular sunrises over the Atlantic each morning.

Inside, the home features a warm and inviting living space complete with a cozy fireplace, perfect for relaxing after a day of exploring the coast. Air conditioning ensures your comfort during the warmer summer months, while large ocean-facing windows bring in natural light and stunning water views throughout the day.

Step outside onto the expansive oceanfront deck, ideal for sipping your morning coffee as the sun rises, dining al fresco with family and friends, or simply unwinding to the soothing sounds of the waves below.

Conveniently located in the heart of Bailey Island, this property is within easy walking distance to the iconic Land's End Gift Shop and nearby beach access, allowing you to enjoy local shopping, scenic strolls, and the natural beauty of Maine's coastline without ever needing to get in the car.

Whether you're planning a peaceful retreat or a memorable seaside getaway, this cliffside escape offers the perfect blend of comfort, location, and unforgettable ocean views.
PLEASE NOTE: FIREPLACE IS NOT FOR TENANT'S USE!
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
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

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 5133173
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
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Bailey Island

Located in Bailey Island, this vacation home is on the waterfront. Bailey Island Bridge and Cobwork Bridge are local landmarks, and the area's natural beauty can be seen at Brunswick Town Commons and Casco Bay. Land's End Gift Shop and Ash Cove Pottery are also worth visiting. Kayaking and snorkeling offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and mountain climbing nearby.
View more Vacation Homes in Bailey IslandOpens in a new window
Map
Bailey Island, ME

What's nearby

  • Land's End Gift Shop - 3 min walk - 0.3 km
  • Mackerel Cove - 6 min walk - 0.6 km
  • beach near Mackerel Cove Lot - 2 min drive - 1.5 km
  • beach near Bailey Island - 4 min drive - 2.9 km

Getting around

  • Brunswick Station - 28 min drive
  • Portland Intl. Jetport Airport (PWM) - 70 min drive

Restaurants

  • ‪Cook's Lobster & Ale House - ‬5 min drive
  • ‪Dolphin Marina & Restaurant - ‬36 min drive
  • ‪Erica's Seafood & Lobster Shop - ‬35 min drive
  • ‪Bailey Island General Store - ‬2 min drive
  • ‪Morse’s - ‬22 min drive

Frequently asked questions

Is Perched on the rugged cliffs of beautiful Bailey Island. pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Perched on the rugged cliffs of beautiful Bailey Island.?

As of Aug 14, 2026, prices found for a 1-night stay for 2 adults at Perched on the rugged cliffs of beautiful Bailey Island. on May 31, 2027 start from $1,136, 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 Perched on the rugged cliffs of beautiful Bailey Island.?

Check-in begins at 4:00 PM.

What time is check-out at Perched on the rugged cliffs of beautiful Bailey Island.?

Check-out is at 10:00 AM.

Where is Perched on the rugged cliffs of beautiful Bailey Island. located?

Situated on the waterfront, this vacation home is within a 5-minute walk of Casco Bay and Land's End Gift Shop. Mackerel Cove and Bailey Island Bridge are also within 3 mi (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Becky D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Place was spotless and the view was incredible! We brought our dog Owen and the three of us had a ball. Would definitely rent here again.
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Greg W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place with amazing views! The cabin is a little dark and some bulbs were out but otherwise, everything was great! I have never barbequed with a better view!
Stayed 5 nights in Jun 2026
Verified review

10/10 Excellent

Adam B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was not just a rental—this was an experience! The privacy and beauty of staying on this little corner of Bailey Island overlooking the ocean made for the perfect getaway. Our dog loved exploring the rocks with us and playing fetch in the yard. The host was wonderfully communicative and made everything a breeze, from check-in to check-out. I could not recommend a place more.
Stayed 3 nights in Jun 2026

About the host

Hosted by Your Island Connection, LLC

Host profile image

Languages:

English
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