A rocky shoreline with a boat, a house, and a forest in the background.

Bailey Island Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Bailey Island vacation rentals

Property grounds

1. Sunset Hideaway on Bailey Island

Sunset Hideaway on Bailey Island
Harpswell
8.4 out of 10, Very Good, (5 reviews)
"Wonderful views. Comfortable. "
United States
Susy K.
The price is AED 436
AED 905 total
includes taxes & fees
24 Aug - 25 Aug
Sunset Hideaway on Bailey Island
Terrace/patio

2. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (63 reviews)
"Wonderful stay!"
United States
Erika T.
The price is AED 744
AED 1,355 total
includes taxes & fees
24 Aug - 25 Aug
Full sized home
Terrace/patio

3. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (65 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is AED 771
AED 1,349 total
includes taxes & fees
25 Aug - 26 Aug
Camp Forever cottage
TV

4. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.6 out of 10, Exceptional, (7 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is AED 579
AED 1,006 total
includes taxes & fees
13 Sep - 14 Sep
Mid Coast Getaway w/ water views
Property grounds

5. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (68 reviews)
"Great spot to relax and enjoy the beautiful outdoors. Very quiet and amazing views of the water. Everything needed for a comfortable and relaxing getaway. Highly recommend if coming to the area! "
United States
Erin
The price is AED 1,084
AED 1,754 total
includes taxes & fees
29 Aug - 30 Aug
Centerview cottage
TV

6. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (4 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is AED 675
AED 1,127 total
includes taxes & fees
14 Sep - 15 Sep
2 bedroom w/ expansive water views
House (2 Bedrooms) | Interior

7. 1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is AED 375
AED 996 total
includes taxes & fees
25 Aug - 26 Aug
1 Mi to Maine Street! Mcm-style Home in Brunswick
Smart TV, fireplace, foosball, books

8. Cozy and charming coastal retreat

Cozy and charming coastal retreat
West Point
9.8 out of 10, Exceptional, (33 reviews)
"My family and I had an amazing time at the schoolhouse. It is much bigger than the pictures show! Great beds, the couches will force you to nap, and we had so much fun exploring the area. They had everything you need for fun at the beach, and lots of options for kids to keep busy. Highly recommend!"
United Kingdom
Byrony S.
Cozy and charming coastal retreat
Exterior

9. Large suite/private bath/private entrance on quiet street near Thomas Bay

Large suite/private bath/private entrance on quiet street near Thomas Bay
Brunswick
10.0 out of 10, Exceptional, (164 reviews)
"Susan and Jeff were amazing hosts! There were so kind, thoughtful and welcoming. The suite was extremely spacious, well decorated and very comfortable. We were very close to the Air Show which was the reason for our trip. They gave us great instructions for a short cut to the airfield and amazing dinner recommendations. We could not have chosen a better place to stay. We highly recommend this place!"
United States
Asha
The price is AED 474
AED 597 total
includes taxes & fees
2 Sep - 3 Sep
Large suite/private bath/private entrance on quiet street near Thomas Bay
Interior

10. Sweet comfy cottage on Small Point Road

Sweet comfy cottage on Small Point Road
Small Point
9.4 out of 10, Exceptional, (3 reviews)
"Lovely home with plenty of space and seating. Not the most comfortable of beds but we enjoyed the space. Perfect location and would love to stay again. "
United States
Liz J.
The price is AED 1,102
AED 2,058 total
includes taxes & fees
1 Sep - 2 Sep
Sweet comfy cottage on Small Point Road
3 bedrooms, WiFi, bed sheets

11. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (17 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is AED 1,157
AED 1,700 total
includes taxes & fees
9 Sep - 10 Sep
Fantastic Waterfront Views
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

12. Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is AED 990
AED 1,680 total
includes taxes & fees
25 Aug - 26 Aug
Fortland Island Campground
Property grounds

13. Modern cabin w/ full bath & kitchenette - 03

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (8 reviews)
"Easy check in process. More than clean, it looked brand new. Overall a great stay. Kitchen was well stocked with plates, utensils, and cookware. "
United States
Michael H.
The price is AED 1,064
AED 1,653 total
includes taxes & fees
26 Aug - 27 Aug
Modern cabin w/ full bath & kitchenette - 03
Dining

14. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (18 reviews)
"Great location surroundings a little unkept but tis the spring cleanup season. Excellent accommodation and located near town shopping but quiet neighborhood"
United States
Douglas H.
The price is AED 533
AED 1,039 total
includes taxes & fees
7 Sep - 8 Sep
King Size Sun Rise Midcoast Lovely Stay
Outdoor dining

15. Captain's Guest Room. Authenticity. Great Value. Walk to everything.

Captain's Guest Room. Authenticity. Great Value. Walk to everything.
Bath
8.4 out of 10, Very Good, (27 reviews)
"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"
United States
Esther
The price is AED 419
AED 657 total
includes taxes & fees
30 Aug - 31 Aug
Captain's Guest Room. Authenticity. Great Value. Walk to everything.
Property grounds

16. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (9 reviews)
"Lovely location "
United States
Michelle S.
The price is AED 1,437
AED 2,508 total
includes taxes & fees
3 Sep - 4 Sep
Mere Point Sunrise Views at Eastern Shore!
Dining

17. Walk to Town 4BR, 200yr old home! #1

Walk to Town 4BR, 200yr old home! #1
Brunswick
The price is AED 727
AED 1,593 total
includes taxes & fees
24 Aug - 25 Aug
Walk to Town 4BR, 200yr old home! #1
Interior

18. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (7 reviews)
The price is AED 2,041
AED 4,094 total
includes taxes & fees
1 Sep - 2 Sep
Three bedroom in United States of America, Freeport
Interior

19. Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
10.0 out of 10, Exceptional, (11 reviews)
"Great location! We spent very little time in the room, but it was a great place to come back and crash! "
United States
Kristina M.
The price is AED 367
AED 825 total
includes taxes & fees
1 Sep - 2 Sep
Modern style in historic building in downtown Bath
Property grounds

20. Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Bath
8.0 out of 10, Very Good, (18 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is AED 547
AED 684 total
includes taxes & fees
22 Sep - 23 Sep
Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bailey Island Hotel Reviews

Clarion Pointe South Portland

Clarion Pointe South Portland

10/10 Excellent
"Everything was fantastic!! Only downside was we really wanted to use the pool but it looked a little fuzzy at the bottom"
Cailey 2-night trip
Posted less than an hour ago
Clarion Pointe South Portland

Frequently asked questions

Can I find a vacation rental in Bailey Island?

Yes, we give you a choice of vacation rentals in Bailey Island near Land's End Gift Shop, or you can choose a secluded option if you're looking for extra privacy while you relax. Bailey Island is known for its shopping and seafood restaurants. Make sure you have time to check out the local tours and monuments during your trip.

What are some of the best vacation rentals that Bailey Island has to offer?

Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This highly rated vacation home rental in Bailey Island is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Our travelers also rate Johnson Homestead. One level living, ocean view with semi-private beach access. as a favorite home for rent in Bailey Island.

How many vacation rentals are there in Bailey Island?

With 31 Expedia vacation rentals, you're sure to find just the right place for your Bailey Island stay.

What can I see and do in Bailey Island?

Mackerel Cove and Ragged Island are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Land's End Gift Shop. Bailey Island Bridge and Cobwork Bridge are other places to visit while you're in town.

What are vacation rentals like in Bailey Island?

Vacation rentals are private properties you can reserve for several days or longer in Bailey Island. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a small group gathering.