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





Reviews
10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 6146.2 sq m
Popular amenities
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
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
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Free WiFi
Outdoor space
Ocean view
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets 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
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
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.

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
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
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Verified
14 September 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Sep 2024
Verified
10/10 Excellent
John F.
3 August 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house and location
John F.
Stayed 7 nights in Jul 2024
Verified
10/10 Excellent
Danita K.
29 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean and exceptionally appointed kitchen




Danita K.
Stayed 3 nights in Jul 2025
Verified
10/10 Excellent
Matthew D.
21 August 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Relax and Enjoy the View
Matthew D.
Stayed 7 nights in Aug 2024
From a partner site
10/10 Excellent
Ervin B.
30 June 2025
Our 5th year at The Overlook
Ervin B.
From a partner site
10/10 Excellent
Greg M.
5 August 2025
Perfect Home, Perfect Spot
Greg M.
From a partner site
10/10 Excellent
Austina F.
7 August 2025
Beautiful Stay
Austina F.
Verified
10/10 Excellent
Jennifer T.
23 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful view, clean and quiet
Jennifer T.
Stayed 7 nights in Jul 2024
From a partner site
10/10 Excellent
Polly O.
24 September 2024
Wonderful!
Polly O.
From a partner site
10/10 Excellent
Bev B.
29 July 2024
best of bailey
Bev B.
From a partner site
10/10 Excellent
Ervin B.
7 July 2024
2024 Stay
Ervin B.
From a partner site
10/10 Excellent
Cathy C.
10 June 2024
Girls weekend
Cathy C.
From a partner site
10/10 Excellent
Ervin B.
27 August 2023
Our third stay at The Overlook
Ervin B.
From a partner site
10/10 Excellent
Tanya B.
25 July 2023
Wonderful vacation!
Tanya B.
Verified
10/10 Excellent
Paul G.
24 September 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Property and Location
Paul G.
Stayed 7 nights in Sep 2019
Verified
10/10 Excellent
K M.
17 September 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
K M.
Stayed 3 nights in Aug 2025
About the host
Hosted by MaineStay Vacations
Languages:
English
Premier Host
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