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

Bailey Island vacation home with kitchen

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Exterior
TV, fireplace
Outdoor dining
Property grounds
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 61540 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Bailey Island, ME
  • Place, Cobwork Bridge
    ‪8 min walk‬
  • Place, Bailey Island Bridge
    ‪13 min walk‬
  • Place, beach near Water Cove
    ‪16 min walk‬

Room options

About the neighborhood

Bailey Island

Seaside stay .Within a 10-minute walk of the vacation home, you'll find Bailey Island Bridge and Cobwork Bridge. Also, Casco Bay is within half a mile (1 km) and Mackerel Cove is within 2 miles (3 km).
View more Vacation Homes in Bailey IslandOpens in a new window

What's nearby

  • Cobwork Bridge - 8 min walk - 0.5 miles
  • Bailey Island Bridge - 13 min walk - 0.7 miles
  • beach near Water Cove - 16 min walk - 0.9 miles
  • beach near Merritt House Road - 18 min walk - 1.0 mile
  • beach near Mackerel Cove Lot - 19 min walk - 1.0 mile

Getting around

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

Restaurants

  • ‪Cook's Lobster & Ale House - ‬13 min walk
  • ‪Bailey Island General Store - ‬8 min walk
  • ‪Morse’s - ‬19 min drive
  • ‪Dolphin Marina & Restaurant - ‬32 min drive
  • ‪Holbrooks Lobster Wharf - ‬23 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.

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

Charming , comfortable home, 2 full bedrooms plus 1 loft style bedroom, 2.5 bath, Very Close to Fresh Maine seafood!
Now accepting long term bookings for winter months~ November-May. Please inquire with manager for rates !

Cheerful, 3 bedroom, Cottage style home located on Bailey Island, Maine, on one of the peninsulas of Harpswell. Dog friendly, Three bedroom, 2.5 baths, custom cathedral ceilings, cozy living room, dining area, offering a well equipped, open kitchen with an island. The master bedroom is conveniently located on the main floor, presenting a king size bed as well as a connecting master bath and walk in closet ~ Up on the second floor, you will encounter two more sleeping spaces, one full bedroom, with a queen bed, and the other is a loft style bedroom with 2 twin beds. The lovely home has a fantastic outside deck, perfect of course for enjoying your morning coffee, or evening cocktails ! Just a super place to gather, and barbeque on the grill !

Convenient off road parking and is walking distance to many attractions. The quaint home is a stone's throw from magnificent ocean views, close to hiking trails, kayak rentals, candy shop, The Giant Stairs, art galleries, Land's End Gift Shop, Cook's Lobster House and more. You will be astounded with spectacular views while traveling over the world's only granite Cribstone Bridge! The bridge was listed on the National Register of Historic places in 1975, and was built back in 1927 in order to connect Orr's Island to Bailey Island. You are sure to find the freshest lobster on either of the islands !! Bailey Island is the perfect place for relaxation, and the home is perfect for a "base" for exploring the surrounding area. Just a hop away from Brunswick, which features Bowdoin College, The Maine State Music Theater, art museums, many great restaurants, shops, and groceries. Freeport, (home of the mother store for LL Bean), Portland, Boothbay, Bar Harbor, Wiscasset, Bath, are all great day trips with super shops and wonderful places to dine !
Cancellations will receive refund as stated in the policy, less any processing fees. 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 ! We are excited to now be dog friendly,(one only), for an additional fee.
 Rental Property includes but not limited to : 
1 King size bed, 1 Queen bed, 2 single beds 
2 full baths, one half bath 
1 Smart TV, Roku, Internet 
Fully equipped Kitchen/dining area/living room 
Stove/Gas Range/Fridge/Dishwasher/microwave/Toaster/Coffee Maker  
Propane Fireplace, which may or may not be in use at time of stay. 
Linens/Towels /Pillows/Blankets provided / Toiletries to get you started
Outside Deck Chairs
Parking for up to 3 vehicles in driveway   

Similar properties

Front of property
Portland Regency Hotel & Spa
Downtown Portland
  • Hot tub
  • Spa
  • Free airport shuttle
  • Pet friendly
4.7 out of 5, Exceptional, 1,677 reviews
$207 nightly
The price is $230
Jun 7 - Jun 8
Total with taxes and fees
Portland Regency Hotel & Spa

Property amenities

Beach

  • Beach nearby

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Car required
  • Parking on site

Kitchen

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

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

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

Living spaces

  • Fireplace
  • Living room

Entertainment

  • Games
  • TV

Outdoor areas

  • Barbecue grill
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total

Suitability/Accessibility

  • Smoking not allowed

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
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 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. Onsite 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 each accommodation.

Property is also known as

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Frequently asked questions

How close is Conveniently located, spacious home located on Bailey Island in Harpswell! to the airport?

This vacation home is 46 mi (61-min drive) away from the Portland Intl. Jetport Airport (PWM) airport, the closest popular airport to the property.

Does Conveniently located, spacious home located on Bailey Island in Harpswell! have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Conveniently located, spacious home located on Bailey Island in Harpswell! to the beach?

This vacation home is 14.1 mi (33-min drive) from Thomas Point Beach.

Does Conveniently located, spacious home located on Bailey Island in Harpswell! offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Conveniently located, spacious home located on Bailey Island in Harpswell!?

No, there is no casino at this vacation home.

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

Check-in begins at 4:00 PM.

Is there free parking at Conveniently located, spacious home located on Bailey Island in Harpswell!?

Free parking is not available at this vacation home.

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

This vacation home does not have a pool.

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

There are no spa services available at this vacation home.

How close is Conveniently located, spacious home located on Bailey Island in Harpswell! to downtown Bailey Island?

This vacation home is 0.3 mi away from Bailey Island.

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

Reviews

9.8

Exceptional

Rating 10 - Excellent. 16 out of 19 reviews
Rating 8 - Good. 3 out of 19 reviews
Rating 6 - Okay. 0 out of 19 reviews
Rating 4 - Poor. 0 out of 19 reviews
Rating 2 - Terrible. 0 out of 19 reviews

9.8/10

Cleanliness

Reviews

Verified

10/10 Excellent

Richard H.

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

10/10 Excellent

Kerry F.

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

10/10 Excellent

Diane E.

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

10/10 Excellent

Carlo J.

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

8/10 Good

nancy q.

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

10/10 Excellent

Lucas L.

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

10/10 Excellent

Matt K.

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

10/10 Excellent

Dennie C.

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

10/10 Excellent

Glenn R.

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

10/10 Excellent

Nicole A.

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

10/10 Excellent

Teresa C.

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

10/10 Excellent

Craig I.

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

10/10 Excellent

Theresa G.

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

10/10 Excellent

Henry and Karen S.

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

10/10 Excellent

June & Deak D.

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

8/10 Good

Nicole N.

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

10/10 Excellent

Martha A.

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

10/10 Excellent

Kerry A.

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

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