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Beautifully landscaped, Spacious home, conveniently located in Harpswell

Holiday home in Bailey Island with kitchen and patio

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Exterior - Beautifully landscaped, Spacious home, conveniently located in Harpswell (Bailey Island)
Interior - Beautifully landscaped, Spacious home, conveniently located in Harpswell (Bailey Island)
Property grounds - Beautifully landscaped, Spacious home, conveniently located in Harpswell (Bailey Island)
Fridge, microwave, oven, stovetop - Beautifully landscaped, Spacious home, conveniently located in Harpswell (Bailey Island)
TV, fireplace - Beautifully landscaped, Spacious home, conveniently located in Harpswell (Bailey Island)
On Bailey Island, Maine, this charming 3-bedroom home invites you to unwind with its cozy living room and fully equipped kitchen. Enjoy fresh Maine seafood and scenic ocean views just a stone's throw away. The master bedroom has an en-suite bath, while the second floor features two more bedrooms.

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 61540 sq ft

Popular amenities

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

Add dates for prices

About this property

Entire place

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

Beautifully landscaped, Spacious home, conveniently located in Harpswell

Holiday home in Bailey Island with kitchen and patio
This smoke-free holiday home features laundry facilities and barbecues. The holiday home has 3 bedrooms and offers free WiFi and a patio. Guests can enjoy a fireplace, and other amenities include a kitchen with a fridge and an oven.
Air-conditioned accommodation at this holiday home offers fireplaces and coffee/tea makers. Rooms open to patios. Kitchens offer fridges, stovetops, microwaves and kitchenware and utensils.

Bathrooms include baths or showers and hairdryers. Guests can surf the web using complimentary wireless Internet access.

The recreational activities listed below are available either on-site or nearby; fees may apply.

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
  • Microwave
  • Oven
  • Refrigerator
  • 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

  • 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

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  • Dryer
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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 allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
1 total pets

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

We should mention

A car is required for transport to and from this property

Property is also known as

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About the area

Located in Bailey Island, this holiday home is near the beach. Brunswick Naval Aviation Museum and Joshua L. Chamberlain Museum are cultural highlights, and some of the area's activities can be experienced at Gulf of Maine and Brunswick Golf Course. Land's End Gift Shop and Paddleworks are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching. Visit our Bailey Island travel guide
View more Holiday homes in Bailey Island
Map
Bailey Island, ME

What's nearby

  • LL Bean Flagship Store showing outdoor art and signage
    LL Bean Flagship Store
    43 min drive - 50.2 km
  • State Theatre showing street scenes as well as an individual female
    State Theatre
    61 min drive - 82.0 km
  • Cobwork Bridge
    8 min walk - 0.7 km
  • Bailey Island Bridge
    10 min walk - 0.9 km
  • Mackerel Cove
    19 min walk - 1.7 km

Getting around

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

Restaurants

  • Cook's Lobster & Ale House
    13 min walk
  • Erica's Seafood & Lobster Shop
    32 min drive
  • Dolphin Marina & Restaurant
    32 min drive
  • B.I.G.S. Bailey Island General Store
    8 min walk
  • Allen's Seafood
    19 min drive

Frequently asked questions

Is Beautifully landscaped, Spacious home, conveniently located in Harpswell pet-friendly?

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

How much is parking at Beautifully landscaped, Spacious home, conveniently located in Harpswell?

On-site parking is available at the property.

What time is check-in at Beautifully landscaped, Spacious home, conveniently located in Harpswell?

Check-in begins at 4:00 PM.

What time is check-out at Beautifully landscaped, Spacious home, conveniently located in Harpswell?

Checkout is at 9:30 AM.

Where is Beautifully landscaped, Spacious home, conveniently located 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).

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Beautifully landscaped, Spacious home, conveniently located in Harpswell Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 16 out of 18 reviews
Rating 8 - Good. 2 out of 18 reviews
Rating 6 - Okay. 0 out of 18 reviews
Rating 4 - Poor. 0 out of 18 reviews
Rating 2 - Terrible. 0 out of 18 reviews

9.8

Cleanliness

9.6

Location

Reviews

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

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

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

10/10 Excellent

Glenn R., Alexandria

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

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

10/10 Excellent

Craig I., Waterbury Vermont

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

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

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

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

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

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

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

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

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

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

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

10/10 Excellent

Kerry A.

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