See all properties
Entire home

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

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

Terrace/patio
Property grounds
Beach
Property grounds
Outdoor dining

Reviews

10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 61574 sq ft

Popular amenities

  • Ocean view
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Outdoor space

Explore the area

View in a map
Bailey Island, ME
  • Place, Cobwork Bridge
    ‪10 min walk‬
  • Place, Bailey Island Bridge
    ‪11 min walk‬
  • Place, Mackerel Cove
    ‪19 min walk‬
  • Airport, Portland, ME (PWM-Portland Intl. Jetport)
    ‪68 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Separate dining area
Garden

About this property

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
Our prices include all fees. No hidden fees.

Add dates for prices

Have a question?

AI iconBeta

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

Similar properties

Cottage on the point
Sunny Cottage on Private Oceanfront Point
Harpswell
  • Ocean view
  • Kitchen
  • Free Wi-Fi
  • Air-conditioning
10.0 out of 10, Exceptional, (131 reviews)
Sunny Cottage on Private Oceanfront Point

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

No pets allowed
default

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

About the area

Bailey Island

Located in Bailey Island, this holiday home is on the waterfront. Brunswick Naval Aviation Museum and Pickard Theater are cultural highlights, and some of the area's landmarks include Bailey Island Bridge and Cobwork Bridge. Land's End Gift Shop and Paddleworks are also worth visiting. Discover the area's water adventures with sailing, fishing and swimming nearby, or enjoy the great outdoors with hiking/biking trails.
View more Holiday homes in Bailey IslandOpens in a new window
Map
Bailey Island, ME

What's nearby

  • Cobwork Bridge - 10 min walk - 0.9 km
  • Bailey Island Bridge - 11 min walk - 1.0 km
  • Mackerel Cove - 19 min walk - 1.7 km
  • Bowdoin College - 32 min drive - 27.5 km
  • LL Bean Flagship Store - 44 min drive - 50.6 km

Getting around

  • Brunswick Station - 32 min drive
  • Portland, ME (PWM-Portland Intl. Jetport) - 67 min drive

Restaurants

  • ‪Cook's Lobster & Ale House - ‬12 min walk
  • ‪Erica's Seafood & Lobster Shop - ‬32 min drive
  • ‪Dolphin Marina & Restaurant - ‬33 min drive
  • ‪Holbrooks Lobster Wharf - ‬24 min drive
  • ‪B.I.G.S. Bailey Island General Store - ‬9 min walk

Frequently asked questions

Is The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home?

As of 3 Apr 2026, prices found for a 1-night stay for 2 adults at The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home on 6 Jun 2026 start from £431, 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.

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.

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

Checkout is at 10:00 AM.

Where is The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home located?

Situated on the waterfront, this holiday home is within a 15-minute walk of Casco Bay, Bailey Island Bridge and Cobwork Bridge. Mackerel Cove and Land's End Gift Shop are also within 2 miles (3 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 16 out of 16 reviews
Rating 8 - Good. 0 out of 16 reviews
Rating 6 - Okay. 0 out of 16 reviews
Rating 4 - Poor. 0 out of 16 reviews
Rating 2 - Terrible. 0 out of 16 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Michelle R.

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

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
Verified

10/10 Excellent

John F.

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

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
Verified

10/10 Excellent

Matthew D.

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

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
Verified

10/10 Excellent

Danita K.

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

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
From a partner site

10/10 Excellent

Ervin B.

Our 5th year at The Overlook

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: As in prior years, everything was perfect, including the weather.
From a partner site

10/10 Excellent

Greg M.

Perfect Home, Perfect Spot

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: I was traveling with older relatives who needed an accessible home right on the water. The home was spectacularly well-furnished and the view before us including a veritable lobster farm was stunning, sunrise to sunset.
From a partner site

10/10 Excellent

Austina F.

Beautiful Stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The house is in a great location on Baileys Island and is decorated so you feel comfortable and right at home. There was a lot of outdoor seating for us to watch the water/sunset. The kitchen has everything you will need. It is also really simple to contact management since they text you and are available for any questions. The only downside is if you stay in the hotter months, there is no AC, but they do have fans throughout. I would definitely stay here again!
Verified

10/10 Excellent

Jennifer T.

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

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
From a partner site

10/10 Excellent

Polly O.

Wonderful!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a spectacular time at The Overlook. The house was impeccable, and the views are exquisite. Cannot say enough good things.
From a partner site

10/10 Excellent

Bev B.

best of bailey

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: lovely house with fantastic water views from lots of windows. house very clean-lovely bed linens-nice kitchen
From a partner site

10/10 Excellent

Ervin B.

2024 Stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: For the fourth year in a row, it was excellent!
From a partner site

10/10 Excellent

Cathy C.

Girls weekend

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Everything was perfect, just as described!
From a partner site

10/10 Excellent

Ervin B.

Our third stay at The Overlook

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Everything was excellent, except the weather. Even with the rain and clouds, it is still such a beautiful location we enjoy it no matter what.
From a partner site

10/10 Excellent

Tanya B.

Wonderful vacation!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We loved everything about the property. Much appreciated the lawn games, indoor games, and having basic spices on hand. Beautiful views, clean and inviting
Verified

10/10 Excellent

Paul G.

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

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
Verified

10/10 Excellent

K M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Aug 2025

About the host

Hosted by MaineStay Vacations

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback