Entire home

Perched on the rugged cliffs of beautiful Bailey Island.

Choose dates to view prices

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

Welcome to Captain's Watch!
Arial view from the cliffs of Casco Bay.
Street view with parking.
Manicured path overlooking the crashing surf at Captain's Watch!.
Arial view of Captain's Watch.
2 bedrooms1 bathroomSleeps 468.7 sq m

Popular amenities

  • Ocean view
  • Kitchen
  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space
NZ$638
avg per night

Explore the area

View map
Bailey Island, ME
  • Place, Land's End Gift Shop
    ‪3 min walk‬
  • Place, Mackerel Cove
    ‪6 min walk‬
  • Place, LL Bean Flagship Store
    ‪47 min drive‬
  • Airport, Portland, ME (PWM-Portland Intl. Jetport)
    ‪72 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

2 twin size beds

2 Single Beds

Queen size bed

1 Queen Bed

1 bathroom

Full bathroom

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Dining area
The current price is NZ$638
avg per night

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

About the area

Bailey Island

Located in Bailey Island, this holiday 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 Paddleworks are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

What's nearby

  • Land's End Gift Shop - 3 min walk - 0.3 km
  • Mackerel Cove - 6 min walk - 0.6 km
  • Bailey Island Bridge - 8 min drive - 4.7 km
  • Bowdoin College - 36 min drive - 30.4 km
  • LL Bean Flagship Store - 47 min drive - 53.4 km

Getting around

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

Restaurants

  • ‪Cook's Lobster & Ale House - ‬5 min drive
  • ‪Erica's Seafood & Lobster Shop - ‬35 min drive
  • ‪Dolphin Marina & Restaurant - ‬36 min drive
  • ‪B.I.G.S. Bailey Island General Store - ‬2 min drive
  • ‪Allen's Seafood - ‬22 min drive

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.

Amenities

Kitchen
Pet-friendly
Free WiFi
Air conditioning
Outdoor space
Parking available

House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

Pets allowed
default

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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that 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 and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

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 23 March 2026, prices found for a 1-night stay for 2 adults at Perched on the rugged cliffs of beautiful Bailey Island. on 9 June 2026 start from NZ$638, 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 at Perched on the rugged cliffs of beautiful Bailey Island.?

On-site 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.?

Checkout is at 10:00 AM.

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

Situated on the waterfront, this holiday 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 miles (5 km).

Perched on the rugged cliffs of beautiful Bailey Island. Reviews