Holiday Rentals in Bailey Island

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Holiday Rentals in Bailey Island

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

10.0 out of 10, Exceptional, (220)
"We enjoyed everything about our place!"
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (64)
"We had a wonderful stay. The room was super clean, spacious, cool and comfortable. The self check in process was easy and although there is no front desk, the staff was very responsive."
The price is €384
includes taxes & fees
22 Jul - 23 Jul
The Weldon Hotel

Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

3.0 star property
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Charming cottage near the beach with balcony, deck, grill, fireplace - dogs OK

9.2 out of 10, Wonderful, (7)
"This was a wonderful place to stay!"
Charming cottage near the beach with balcony, deck, grill, fireplace - dogs OK

Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun

6.4 out of 10, (6)
"Nice and quiet. Beautiful view of the water"
Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun

Cozy and Quiet Beautiful Home One Bedroom Private Bathroom in Portland Maine.

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
Cozy and Quiet Beautiful Home One Bedroom Private Bathroom in Portland Maine.

In-town no frills 2 bedroom apt

6.0 out of 10, (2)
"The frills of the neighborhood carried into the apartment. Floors and bathrooms seemed clean. Dishes and Keurig filthy - broken window a/c on floor. Broken chairs. No tlc for the property. Neighborhood beyond the stated description- would not recommend . Best to say is that rental car made it out with all windows and tires. Very disappointed "
The price is €178
includes taxes & fees
10 Aug - 11 Aug
In-town no frills 2 bedroom apt

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (103)
"Perfect location. Wonderful accommodations"
The price is €260
includes taxes & fees
13 Jul - 14 Jul
Adorable Portland getaway on the Eastern Promenade

Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town

9.8 out of 10, Exceptional, (25)
"The cabin was very clean and a nice quiet location. Had everything we needed for a comfortable stay."
Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town

Private Contemporary Artist's Tree House on two acres with perennial gardens.

10.0 out of 10, Exceptional, (38)
"Great stay. Unique place with lots of character. Clean and pleasant. Loved the geese that greeted us each time we walked in/out (fenced not loose) !"
Private Contemporary Artist's Tree House on two acres with perennial gardens.

Unique oceanfront home with a deck, tons of natural light, & amazing views

8.6 out of 10, Excellent, (56)
"Beautiful lcation, private & quiet"
Unique oceanfront home with a deck, tons of natural light, & amazing views

Private Entrance Residential Portland

8.0 out of 10, Very good, (1)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
The price is €199
includes taxes & fees
8 Aug - 9 Aug
Private Entrance Residential Portland

Your own private island! Rustic and close to Nature.

9.4 out of 10, Exceptional, (32)
"wonderful place, glamping, wildlife all around, you can't but enjoy the beauty of Mid Coast Maine. Thanks for sharing your island with all of us !"
Your own private island! Rustic and close to Nature.

Captain's House 2BR Apartment. Walk to Everything!

8.8 out of 10, Excellent, (3)
"Nice, clean, cosy, conveniently located and easy enough to find. Great communication with host, comfortable beds and plenty of hot water. very responsive and would definitely consider using again. "
The price is €216
includes taxes & fees
13 Jul - 14 Jul
Captain's House 2BR Apartment. Walk to Everything!

Ocean view Victorian

9.8 out of 10, Exceptional, (90)
"Everything about the stay was fantastic. Great location and responsive host. "
Ocean view Victorian

Luxury on Back Cove - Three Gables

10.0 out of 10, Exceptional, (2)
"GoodLocation, very clean. Would stay again "
The price is €582
includes taxes & fees
4 Aug - 5 Aug
Luxury on Back Cove - Three Gables

Oceanfront Cabin-Castle in Maine Woods

10.0 out of 10, Exceptional, (24)
"This place was amazing and so special- incredible views, great cabin, and amazing access to the water. "
Oceanfront Cabin-Castle in Maine Woods

1BR Guest Suite w/Private Bath & Entrance. Best Value in Town!

7.0 out of 10, Good, (10)
"Clean, well maintained, slighly funky in an historical way . Very convenient to great breakfast spots and downtown Bath. Would stay there again."
The price is €143
includes taxes & fees
13 Jul - 14 Jul
1BR Guest Suite w/Private Bath & Entrance. Best Value in Town!

Beautiful Oceanfront House- Stunning Water Views

9.6 out of 10, Exceptional, (4)
"This house is absolutely fantastic! Better than the photos!Bookmark this house right now! We were amazed at the view of the inlet. We saw seals and American bald eagles. We had such a peaceful stay in this spacious home.It is actually 4 levels and 5 bedrooms. Would be perfect for a group or large family! If you want to experience “real” Maine , this is it !! Absolutely would stay here again and recommend highly to everyone. "
Beautiful Oceanfront House- Stunning Water Views
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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Frequently asked questions

Can I find a holiday rental in Bailey Island?

Yes, there are holiday rentals in Bailey Island close to Land's End Gift Shop, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Bailey Island has to offer?

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This highly rated holiday home rental in Bailey Island is located on the beach, and has a patio, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Bailey Island?

With 26 Expedia holiday rentals, you're guaranteed to find just the right place for your Bailey Island stay.

What can I see and do in Bailey Island?

Ragged Island and Mackerel Cove 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 holiday rentals like in Bailey Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Bailey Island. Holiday rentals feature amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips or small group gatherings.