Entire home

The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home

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Photo gallery for The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home

Dining
3 bedrooms, desk, iron/ironing board, free WiFi
Dining
Fridge, microwave, oven, stovetop
Beach

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 61574 sq ft

Popular amenities

  • Dryer
  • Washer
  • Kitchen
  • Barbecue grill
  • Outdoor Space
  • Free WiFi

Explore the area

View in a map
Bailey Island, ME
  • Casco Bay
    ‪1 min walk‬
  • Cobwork Bridge
    ‪10 min walk‬
  • Bailey Island Bridge
    ‪11 min walk‬
  • Portland, ME (PWM-Portland Intl. Jetport)
    ‪73 min drive‬

Room options

About the neighborhood

Bailey Island

Seaside stay .You'll find Casco Bay and Bailey Island Bridge within a 15-minute walk of this Bailey Island vacation home. Also, Cobwork Bridge is within half a mile (1 km) and Mackerel Cove is within 2 miles (3 km).

What's nearby

  • Casco Bay - 1 min walk - 0.0 miles
  • Cobwork Bridge - 10 min walk - 0.6 miles
  • Bailey Island Bridge - 11 min walk - 0.6 miles
  • Land's End Gift Shop - 4 min drive - 1.8 miles
  • Ash Cove Pottery - 32 min drive - 16.9 miles

Getting around

  • Brunswick Station - 26 min drive
  • Portland Intl. Jetport Airport (PWM) - 62 min drive

Restaurants

  • ‪Dolphin Marina & Restaurant - ‬33 min drive
  • ‪Erica's Seafood - ‬32 min drive
  • ‪Cook's Lobster House - ‬12 min walk
  • ‪Holbrooks Lobster Wharf - ‬24 min drive
  • ‪Slow Bell Cafe - ‬187 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home

Perched on the water's edge, The Overlook offers commanding views of Merriconeag Sound to Casco Bay and its islands. You'll find yourself waiting to watch the sunset every evening, as the sky is painted with stunning hues and the soft light fills every room. The Overlook offers multiple decks with plenty of seating for dining outdoors or simply relaxing by the sea. Beautiful gardens and trees surround the property, offering great privacy, while being within walking distance to all Bailey Island has to offer.

Inside you'll find a well appointed kitchen with everything you'll need to prepare a delicious Maine meal, a beautiful dining room area with two sliding glass doors opening to the deck, and a spacious living room with comfortable furnishings and panoramic ocean view. The first floor also offers a bedroom with a queen bed and ocean views, as well as a full bathroom with a laundry area just outside. On the second floor you'll find two additional ocean view bedrooms with queen beds and a shared full bathroom with a tile shower. Hardwood and tile floors throughout, modern coastal decor, and an abundance of natural light completes this seaside retreat.

Conveniently located in the West Shore neighborhood of Bailey Island, you'll love being just 0.5mi (8-10min walk) from all of the island's great local restaurants including Cook's Lobster & Ale House (serving lunch and dinner), Sundrenched (serving lunch and dinner), and Bailey Island General Store (convenience store).

Spend your days relaxing by the sea, exploring the shore, sailing out of Cook's Lobster on the Schooner Alert (70-foot tall ship), or soaking up the sun at Cedar Beach (1mi away) and come home to experience the gorgeous sunset over the bay.

The Overlook is the perfect vacation destination and will surely have you coming back for years to come.

Sorry, pets are not allowed at The Overlook.

Bed types/descriptions:
First Floor-
Bedroom with Queen Bed, Closet, and Ocean Views
Second Floor-
Master Bedroom with Queen Bed, Closet, and Ocean Views
Bedroom with Queen Bed, Closet, and Ocean Views

Bathroom setup/description:
First Floor- Full Bath with Shower/Tub Combo
Second Floor- Full Bath with Tile Shower


Air Conditioning: No
Beach/Water Access: Direct, on property via private stairs, rocky/pebbly shoreline
Beach Towels: Not included
Departure Cleaning: Included
Cable TV: Uses Xfinity Stream app on TV for cable entertainment channels, Xumo Play app for Live streaming news channels
Closest Shopping Village: Brunswick, 20min away
Coffee Maker: Yes, regular drip
Dishwasher: Yes
Grill: Gas Grill available, Propane provided
Heat Source: Forced hot air
Internet Access: Yes, Xfinity Cable Internet and WiFi
Linens & Bath Towels: Included, beds are made prior to guest arrival and towels remain in their sanitized packaging, placed on each bed
Lobster Pot: Yes
Outdoor Firepit: No
Parking: 2 cars
Stairs to Water: Yes
Trash Removal: Included, picked up weekly (for multi-week stays) or upon departure
TV: Smart TV in Living Room
Usable Fireplaces: No (woodstove in house is NOT for guest use)
Washer & Dryer: Yes, located first floor
Water Frontage: Direct ocean frontage
Water Source: Well water with filtration/softener system, bottled drinking water recommended

Property manager

MaineStay Vacations

Languages

English

Similar properties

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Separate dining area

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Garden
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a hospital
  • Near an outlet shopping mall
  • Near the ocean
  • On the waterfront

Things to do

  • Golf
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Sailing nearby
  • Swimming nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Garden
  • Unit size: 1,574 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation.

Property is also known as

2769-214537

Frequently asked questions

How close is The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home to the airport?

This vacation home is 46.1 mi (62-min drive) away from the Portland Intl. Jetport Airport (PWM) airport, the closest popular airport to the property.

Does The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home to the beach?

This vacation home is 14.1 mi (34-min drive) from Thomas Point Beach.

Does The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home?

No, there is no casino at this vacation home.

What time is check-in at The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home?

Check-in begins at 4:00 PM.

Is there free parking at The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home?

Free parking is not available at this vacation home.

Does The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home have a pool?

This vacation home does not have a pool.

Does The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home have a spa?

There are no spa services available at this vacation home.

How close is The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home to downtown Bailey Island?

This vacation home is 0.3 mi away from Bailey Island.

The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 15 out of 15 reviews
Rating 8 - Good. 0 out of 15 reviews
Rating 6 - Okay. 0 out of 15 reviews
Rating 4 - Poor. 0 out of 15 reviews
Rating 2 - Terrible. 0 out of 15 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Danita K.

Liked: Cleanliness

Clean and exceptionally appointed kitchen

Very clean and comfortable home, with beautiful sunset views. Kitchen is exceptionally appointed. Gorgeous landscaping with cedar wax wings, gold finches and song sparrows flitting about. Lots of Adirondack seating for coastal views with your coffee and book.
Stayed 3 nights in Jul 2025

10/10 Excellent

Michelle R.

Liked: Cleanliness

Wonderful vacation

Gorgeous property and we lucked out with the best weather possible!!! Highly recommend The Overlook and we plan on returning
Stayed 4 nights in Sep 2024

10/10 Excellent

Matthew D.

Liked: Cleanliness

Relax and Enjoy the View

Sunsets, birds, boats, and the sea, magnificent views. Private, hidden, and comfortable place right on the water was perfect for the four of us. We enjoyed every minute of our stay. It's not too far away from many towns like Bath and Boothbay Harbor too.
Stayed 7 nights in Aug 2024

10/10 Excellent

John F.

Liked: Cleanliness

Great house and location

House was very nice for our family of 5. On the water with a great view. Kitchen was well equipped and everything was in good working order. Would definitely stay again.
Stayed 7 nights in Jul 2024

10/10 Excellent

Jennifer T.

Liked: Cleanliness

Beautiful view, clean and quiet

Such a charming property! The house was super clean, quiet, and felt very private....and the view was amazing! It was mid-July and no AC was needed because of the lovely breeze. There are fans available at the property if needed, but we didn't need them. We were able to launch our paddle boards right from the property at high tide. The house was well equipped - had everything we needed.....we even used the Thyme in the herb garden.
Stayed 7 nights in Jul 2024

10/10 Excellent

Paul G.

Liked: Cleanliness

Wonderful Property and Location

The house is very well equipped for travelers, the kitchen has everything you could imagine including a milk steamer for coffee! The setting is wonderful right on the water which create a great canvas for nightly sunsets. Cooks, Morse's and the Giant Stairs restaurants are within walking distance, including the Bailey Island Grocery (BIG's) which serves food from their grill. It is a must to experience BIG's for breakfast and their blueberry pancakes, make sure to order just one because they cover an entire plate...... Great overall experience and the owners have certainly put much thought and care into the property.
Stayed 7 nights in Sep 2019