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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 dining area with a green tablecloth, white chairs, and a wooden floor.
A modern kitchen with a central island, dark wooden chairs, white cabinets, and stainless steel appliances.
A white balcony railing with dense green foliage in the background.
A spacious living area with a dining table, chairs, and a staircase leading to another level.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Cook, dine, and unwind
    Top-rated for its fully equipped kitchen, perfect for every meal.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Casco Bay

Popular amenities

  • Patio
  • Dog-friendly
  • Barbecue grill
  • Air-conditioning
  • Refrigerator
  • Internet

Explore the area

View in a map
Bailey Island, ME
  • Place, Casco Bay
    ‪1 min walk‬
  • Place, Cobwork Bridge
    ‪8 min walk‬
  • Place, Bailey Island Bridge
    ‪13 min walk‬
  • Airport, Auburn, ME (LEW-Auburn - Lewiston Municipal)
    ‪57 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Single Beds

Bedroom 3

1 King Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Soap · Towels provided · Bathtub · Toilet · Shower only · Hair dryer

Bathroom 2

Soap · Towels provided · Toilet

Bathroom 3

Soap · Towels provided · Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Dining area

Add dates for prices

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Similar properties

Property grounds
Orchid Harbor, Bailey Island 3BR
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  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
10.0 out of 10, Exceptional, (13 reviews)
Orchid Harbor, Bailey Island 3BR

About the area

Bailey Island

Located in Bailey Island, this holiday home is near the beach. Bailey Island Bridge and Cobwork Bridge are local landmarks, and the area's natural beauty can be seen at Brunswick Town Commons and Casco Bay. Land's End Gift Shop and Ash Cove Pottery are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cycling and hiking/biking trails.
View more Holiday homes in Bailey IslandOpens in a new window
Map
Bailey Island, ME

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

  • ‪Dolphin Marina & Restaurant - ‬32 min drive
  • ‪Cook's Lobster & Ale House - ‬13 min walk
  • ‪Erica's Seafood & Lobster Shop - ‬32 min drive
  • ‪Holbrooks Lobster Wharf - ‬23 min drive
  • ‪Sundrenched - ‬10 min walk

Frequently asked questions

Is Conveniently located, spacious home located on Bailey Island in Harpswell! pet-friendly?

Yes, this property allows dogs (limit 1 total).

How much does it cost to stay at Conveniently located, spacious home located on Bailey Island in Harpswell!?

As of 24 Oct 2026, prices found for a 1-night stay for 2 adults at Conveniently located, spacious home located on Bailey Island in Harpswell! on 4 Nov 2026 start from £701, 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.

How much is parking at Conveniently located, spacious home located on Bailey Island in Harpswell!?

On-site parking is available at the property.

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

Check-in begins at 4:00 PM.

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

Checkout is at 9:30 AM.

Where is Conveniently located, spacious home located on Bailey Island in Harpswell! located?

Situated by the sea, this holiday home is within a 10-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

9.8

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. 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

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

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
Response from VrboOwner on 25 Jul 2026
Thank you, we're happy that the lovely, well-equipped home worked well for you!
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
Response from VrboOwner on 1 Aug 2026
Many thanks, we're thrilled that you enjoyed the well-kept home, as well as the location!
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
Response from VrboOwner on 1 Oct 2025
We're thrilled that you enjoyed the great home, and that you had good times during your stay!
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
Response from VrboOwner on 29 May 2026
Thank you!! We're so happy that you enjoyed the clean, relaxing home!
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
Response from VrboOwner on 30 Oct 2025
Thank you! We're pleased that you enjoyed the well-equipped, relaxing home during your stay! Glad the area worked well for you!
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
Response from VrboOwner on 22 Jul 2024
We're so happy you enjoyed our clean, well-accommodating home during your Harpswell visit !
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
Response from VrboOwner on 24 Aug 2023
Thanks so much, Glenn--I'm so glad you found the home peaceful and well-equipped, as well as enjoying the beauty of Bailey Island !
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
Response from VrboOwner on 22 Sept 2023
Thanks so much, Craig ~ I'm so pleased you enjoyed the clean and comfy home, as well as the location ! I'm also happy that the freezer issue turned out okay in the end ! Thanks for being great guests, we'd love to have you return with your pups anytime !
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
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
Response from VrboOwner on 27 Sept 2025
Thank you so much for staying at Fairwinds! We're thrilled that you enjoyed the well equipped home, as well as its location! Happy that you enjoyed the local restaurants and sights!
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
Response from VrboOwner on 16 Aug 2025
So happy to hear that you enjoyed the home as well as the area Nicole, thank you! We hope to see you again!
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
Response from VrboOwner on 31 Jul 2023
Thanks so much, Theresa ! I'm so pleased you enjoyed the home as well as the area ! We'd love to have you return anytime !
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
Response from VrboOwner on 15 Nov 2024
Thank you, Henry and Karen! We appreciate your kindness-- We're so pleased that you enjoyed the home with your pup, and that you were able to explore the area!
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
Response from VrboOwner on 20 Aug 2023
Thanks so much, Nicole ! I'm pleased the home and its location close to hiking trails worked well for you, and that you enjoyed the deck and well-stocked kitchen !
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
Response from VrboOwner on 24 Jul 2024
Thank you, June & Deak ! We're happy you enjoyed the Bailey Island neighborhood, as well as the well equipped home, with its' great deck !
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
Response from VrboOwner on 9 Jul 2026
Thank you! We're so pleased that you enjoyed the home and that it worked well for you- we look forward to your return in the future!
Verified review

10/10 Excellent

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