Entire home

Conveniently located, spacious home located on Bailey Island in Harpswell!

Photo gallery for Conveniently located, spacious home located on Bailey Island in Harpswell!

A two-story house with a gabled roof, a front porch, and a mailbox marked "2030".
A spacious living area with a dining table, chairs, and a staircase leading to another level.
A white balcony railing with dense green foliage in the background.
A modern kitchen with a central island, dark wooden chairs, white cabinets, and stainless steel appliances.
A dining area with a green tablecloth, white chairs, and a wooden floor.

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 6143 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View map
Bailey Island, ME
  • Place, Casco Bay
    ‪1 min walk‬
  • Place, Cobwork Bridge
    ‪8 min walk‬
  • Place, Bailey Island Bridge
    ‪13 min walk‬
  • Airport, Portland, ME (PWM-Portland Intl. Jetport)
    ‪63 min drive‬

Room options

About the area

Bailey Island

This holiday home places you steps from Casco Bay and within a 10-minute stroll of Bailey Island Bridge. Highlights at this holiday home include a kitchen, a washing machine and free WiFi. .Home features 2.5 bathrooms, a fireplace and a patio. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A living room, a TV and a coffee/tea maker are also available. .In proximity to this Bailey Island holiday home you'll find LL Bean Flagship Store.

What's nearby

  • Casco Bay - 1 min walk - 0.0 km
  • Cobwork Bridge - 8 min walk - 0.7 km
  • beach near Channel View Lane - 10 min walk - 0.9 km
  • Bailey Island Bridge - 13 min walk - 1.1 km
  • beach near Merritt House Road - 18 min walk - 1.5 km

Getting around

  • Brunswick Station - 25 min drive
  • Portland, ME (PWM-Portland Intl. Jetport) - 61 min drive

Restaurants

  • ‪Erica's Seafood & Lobster Shop - ‬32 min drive
  • ‪Cook's Lobster & Ale House - ‬13 min walk
  • ‪Dolphin Marina & Restaurant - ‬32 min drive
  • ‪Holbrooks Lobster Wharf - ‬23 min drive
  • ‪Salt Cod Cafe - ‬15 min walk

About this property

Entire place

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

Conveniently located, spacious home located on Bailey Island in Harpswell!

Charming Bailey Island Home | Near the Water & Local Attractions!

Welcome to our cheerful and comfortable coastal home on beautiful Bailey Island, one of the picturesque peninsulas of Harpswell, Maine! Just a short stroll from the water and surrounded by the beauty of Maine's rocky coastline, this charming home is the perfect place to relax, explore, and enjoy all that coastal Maine has to offer. Whether you're planning a family holiday, a getaway with friends, or an extended stay, you'll find a comfortable and inviting place to call home.

This lovely three-bedroom, 2.5-bath home features custom cathedral ceilings, a cosy living room, dining area, and a well-equipped open kitchen with a centre island. The primary bedroom is conveniently located on the main floor and offers a king-size bed, connecting private bath, and walk-in closet. The upstairs sleeping arrangements include one private bedroom with a queen-size bed and an open loft-style sleeping area with two twin beds. Please note that the loft area is not a private, enclosed bedroom. It is located at the top of the stairs, and guests must walk through the loft area to access the second-floor queen bedroom. The home comfortably accommodates family and friends while offering plenty of space to gather and unwind. (professionally managed by Maine Coastal Connections)

Step outside onto the wonderful deck, the perfect spot to enjoy your morning coffee, relax with an evening cocktail, or fire up the grill for a casual barbecue. It's a great place to gather and enjoy the peaceful island atmosphere. Convenient driveway for parking, just off the main road is also provided.

One of the best features of this home is its wonderful location! The home is within walking distance of many of Bailey Island's favourite attractions and is just a short distance from beautiful coastal scenery and oceanfront spots. Explore the spectacular Giant's Stairs, enjoy nearby hiking trails, rent a kayak, browse local art galleries, visit the charming sweets shop and Land's End Gift Shop, or enjoy a delicious meal at Cook's Lobster House. And, of course, you'll find some of the freshest lobster and seafood anywhere on either of the islands!

You'll also want to experience the remarkable Cribstone Bridge, a unique granite bridge built in 1927 that connects Bailey Island to Orr's Island. Listed on the National Register of Historic Places, this incredible structure is a true Maine landmark and offers beautiful coastal scenery as you travel across it.

Bailey Island is the perfect destination for relaxation, yet it's also a wonderful home base for exploring the surrounding Midcoast region. Just a short drive away is Brunswick, home to Bowdoin College, Maine State Music Theatre, art museums, wonderful restaurants, shopping, and supermarkets. Other great destinations for day trips include Freeport, home of the original L.L.Bean flagship store, Portland, Bath, Wiscasset, Boothbay, and beyond. You'll find charming coastal towns, wonderful shops, great restaurants, and plenty of places to explore.

We are also welcoming longer-term bookings for the winter months, November through May! If you're looking for a peaceful place to spend the winter, work remotely, or enjoy an extended stay along the beautiful Maine coast, this comfortable cottage may be just what you're looking for. Please enquire with the property manager for availability and special extended-stay rates.

Whether you're visiting for a summer holiday, a fall getaway, or a longer winter stay, we're sure you'll be delighted with all that Bailey Island and the surrounding area have to offer. Come relax, explore, enjoy the fresh Maine seafood, and experience the charm of island living!

This property can be viewed and booked on Vrbo, AirBnb, and Maine Coastal Connections, Harpswell, Maine.

You are sure to be delighted with all that this area has to offer !

Similar properties

Property amenities

Beach

  • Beach nearby

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Car required
  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Bathtub
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Soap
  • Towels provided

Living spaces

  • Fireplace
  • Living room

Entertainment

  • Games
  • TV

Outdoor areas

  • Barbecue grill
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 2 steps to reach entrance
  • Area rugs in public areas
  • Handrails in stairways
  • Hardwood flooring in public areas
  • Upper floors accessible by stairs only
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the bay
  • Near the marina
  • Near the sea

Things to do

  • Birdwatching nearby
  • Cycling nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Swimming nearby
  • Water tubing nearby
  • Whale watching nearby
  • Wildlife walks nearby
  • Windsurfing 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)
  • First aid kit
  • Fire extinguisher

General

  • Unit size: 1,540 square feet

Policies

Check-in

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

Check-out

Check-out before 9:30 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 1 pets
  • Service animals are exempt from fees.

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
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 and a first aid kit
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 private host, not a professional engaged in trade or business. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector and a first aid kit in all accommodation.

Property is also known as

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Frequently asked questions

Are there any beaches close to Conveniently located, spacious home located on Bailey Island in Harpswell!?

The closest beach to Conveniently located, spacious home located on Bailey Island in Harpswell! is Hunnewell Beach (16.2 km).

Does Conveniently located, spacious home located on Bailey Island in Harpswell! have a pool?

No, this holiday home doesn't have a pool.

Is there a free airport shuttle available at Conveniently located, spacious home located on Bailey Island in Harpswell!?

No, Conveniently located, spacious home located on Bailey Island in Harpswell! does not offer an airport shuttle service.

What time are check-in & check-out at Conveniently located, spacious home located on Bailey Island in Harpswell!?

Check-in begins at 4:00 PM. Check-out time is 9:30 AM.

Conveniently located, spacious home located on Bailey Island in Harpswell! Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 20 out of 23 reviews
Rating 8 - Good. 3 out of 23 reviews
Rating 6 - Okay. 0 out of 23 reviews
Rating 4 - Poor. 0 out of 23 reviews
Rating 2 - Terrible. 0 out of 23 reviews

9.8/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home, equipped with everything you need for a comfortable vacation.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house is beautiful and well kept. Great location to many beautiful sites. Host was highly responsive and great to communicate with for stay needs.
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful place to stay… lots of fun… thank you
Stayed 4 nights in Aug 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
A very nice clean home with beautiful water views. We had all we needed for a relaxing four night stay on Baileys Island.
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Well-stocked kitchen, open concept, lovely deck to relax, dog-friendly. Lots of local recommendations and communication with the host was great!
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

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

Lobster getaway

We had an awesome time at this amazing home. Hope to do it again real soon!!
Stayed 4 nights in Sep 2023
Verified review

10/10 Excellent

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

Fabulous Rental

A fabulous rental for 5 adults over 65 years of age. Close to great hiking and a great fish market. A well-equipped kitchen for people who love to cook. Lovely bathrooms. Would love to stay again.
Stayed 7 nights in Jun 2025
Verified review

8/10 Good

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

Loved it!

Perfect accommodations for our family of 6. Upper loft great for kids. Super clean and had everything we needed.
Stayed 3 nights in Jul 2024
Verified review

10/10 Excellent

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

Peaceful property

Quiet and with a partial water view through the trees. Updated interior and spacious living area. We’d love to visit again.
Stayed 4 nights in Jul 2024
Verified review

10/10 Excellent

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

Lovely Views

Perfect location for a peaceful Maine vacation. House is wonderfully equipped and comfortable. Great views of Harpswell Sound. Loved Glen’s Lobsters. $8 a pound and sweet as could be. Would highly recommend Bailey Island and this house!
Stayed 7 nights in Jul 2023
Verified review

10/10 Excellent

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

Loving Maine

Weather was awesome . Spent everyday at the Bluegrass Festival at Thomas Point. Brunswick Is a sweet town. Cribstone Bridge area has a Beautiful view. The Salt Box Cafe has a great breakfast and lunch items. Dont forget while your in Maine to have a Lobster Roll breakfast
Stayed 4 nights in Aug 2024
Verified review

10/10 Excellent

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

Clean and comfortable with great location

Very nice spot on the island private with nice landscaping and clean property and house. The porch was spectacular as we spent most of our time there. Dogs loved it and we had a mishap with the freezer being literally frozen but that was addressed promptly by the manager, Sheri. She was very professional and courteous. We would stay here again!
Stayed 4 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The only complaint is that there was a sulfur smell to the hot whatever.
Stayed 2 nights in Nov 2025
Verified review

10/10 Excellent

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

Bailey Island Paradise

This home exceeded expectations, to the point where I took pictures to use for inspiration on my own home renovation. Bailey Island is not close to the major tourist sites but it is a welcome retreat after a long day in Portland and Boothbay. The two restaurants within walking distance were phenomenal. Sheri was very quick with responses to questions I had. I would love to return upon our next trip to Maine.
Stayed 5 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Highly recommend the Fair Winds as the perfect place to stay in Bailey Island. The place was Home & Gardens picture perfect. The host is a premier host and her property shows it. We loved sitting on the back deck and listening to the ocean and birds. The house was and easy walk to Crib Bridge, Cedar Beach, Mackerel Bay, and the general store. The kitchen is stocked with everything one would need to prepare dinners or there are a few local restaurants within walking distance. We loved the ambience of the house. It was perfect for our group of six.
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

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

Outstanding!

This house is beautiful and spacious - inside and out. Meticulously clean, lights and kitchen cabinets labeled, and key necesseties provided, Our property manager, Sheri, was always extremely responsive and super friendly when we had questions. We love Bailey Island- we will be back and would love to rent this house again!
Stayed 12 nights in Jul 2023
Verified review

10/10 Excellent

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

Fall Trip

This Bailey Island home’s kitchen was well stocked and the space provided us a safe haven with amazing views for the two of us and our 4 year old goldendoodle. We were able to make several day trips that were so worthwhile - Kennebunkport, Booth Harbor, Bar Harbor, and Portland. The communication with Sheri was outstanding! Recommend a few bottles of water to be added to the complimentary wine.
Stayed 5 nights in Oct 2024
Verified review

8/10 Good

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

Great vacation spot!!!

This property was very nice. Comfortable setup and plenty of room for the family- great outdoor deck to enjoy morning coffee or meals. Well stocked kitchen and clean. The house is quite close to the street - really only noticed the street noise in the middle of the night in the upstairs bedroom when cars were passing. Loft was super cute - might be an issue for people with light sleeping kids but our kiddo was exhausted at the end of each day from all the hiking so the noise didn’t bother her at all with us downstairs. Overall great location and wonderful time here!!
Stayed 7 nights in Aug 2023
Verified review

10/10 Excellent

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

Island life

What a sweet neighborhood!! The house is airy, light and was perfectly configured for our family. The kitchen was very well supplied with spices and condiments and was a joy to cook in. I woke up early each morning to the lobster boats heading out. We used the wraparound deck a lot! The beds were very comfortable. The only downside was the distinctly doggy smell of the sofa.
Stayed 6 nights in Jun 2024
Verified review

10/10 Excellent

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

Modern and tasteful. Great Island Vibe. Lovely Owner.

The covered deck is outstanding for enjoying meals alfresco rain or shine. Quiet mornings and beautiful evenings at sunset. Everything you need for kitchen equipment and basics for making great family meals. Fabulous layout for a family including a lovely master suite. Very comfortable. The owner took care of a few small things immediately and he and the property manager were delightful to deal with. Worth noting, as the pictures don’t show, it is right on the main road - but it has great screening and you don’t hear it at all, akd still plenty of property on the sides and back for walking a dog around - just can’t let little kids or pets out of sight outside. Overall, we found it a perfect home for a family vacation.
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was just as described and such a wonderful spot to explore the midcoast from. We will definitely be looking to stay here again during the fall.
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

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