Bailey Island Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

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, (222)
"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, (68)
"Absolutely beautiful place to stay. "
The price is AU$670
includes taxes & fees
14 Aug - 15 Aug
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

Studio Unit Walkable Everywhere

The price is AU$326
includes taxes & fees
4 Aug - 5 Aug
Studio Unit Walkable Everywhere

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

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 Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

Enjoyable 1-bedroom rustic cottage in Southport.

10.0 out of 10, Exceptional, (7)
Enjoyable 1-bedroom rustic cottage in Southport.

Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers

9.6 out of 10, Exceptional, (74)
"Fantastic location, owners were nearby and easy to communicate with for any questions. Perfect views and cozy apartment for our family of 3. Would definitely stay here again!"
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers

Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

7.4 out of 10, Good, (12)
"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 AU$256
includes taxes & fees
7 Aug - 8 Aug
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

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 AU$278
includes taxes & fees
4 Aug - 5 Aug
Private Entrance Residential Portland

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (106)
"Lovely place in the top floor of a multi property house. Everything you need in a cozy space. It is a walk up so pack up light. Clean, charming and comfy. Highly recommend. "
The price is AU$485
includes taxes & fees
1 Sept - 2 Sept
Adorable Portland getaway on the Eastern Promenade

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.

Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer

2.0 star property
10.0 out of 10, Exceptional, (20)
"Beautiful location, comfortable beds and wonderful linens. This place was wonderful"
Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer

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

10.0 out of 10, Exceptional, (2)
"We had a wonderful stay. Nice comfortable camp. We enjoyed swimming in the lake. "
Charming 2-bedroom house with AC, WiFi in lovely Falmouth

In-town no frills 2 bedroom apt

8.0 out of 10, Very good, (6)
The price is AU$318
includes taxes & fees
10 Aug - 11 Aug
In-town no frills 2 bedroom apt

Studio Apartment near downtown Walkable!

6.0 out of 10, (1)
"The listing said "Studio Apartment," but it is really just a bedroom with a bath. A mini-fridge, coffeemaker and microwave oven do not make this a "Studio" in the sense that I understand that word (i.e., a one-room apartment with kitchen and bath). When I went back and looked at the photos in the listing, that should have been obvious to me, but I got hung up on the word "Studio."That said, it was a comfortable room, although the bathroom was stingy on towels (no face cloths, only one hand...
The price is AU$298
includes taxes & fees
5 Aug - 6 Aug
Studio Apartment near downtown Walkable!

Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist

10.0 out of 10, Exceptional, (47)
"This was a great property and even better host. We had a great time staying in downtown Portland. The apartment has great finishes. I will definitely plan to stay here again."
Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist

Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

8.8 out of 10, Excellent, (37)
"This was our second stay here. We love the comfort of this home and the location is perfect."
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

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

9.6 out of 10, Exceptional, (29)
"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

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

9.0 out of 10, Wonderful, (8)
"This was a wonderful place to stay!"
Charming cottage near the beach with balcony, deck, grill, fireplace - dogs OK

Luxury on Back Cove - Three Gables

10.0 out of 10, Exceptional, (2)
"GoodLocation, very clean. Would stay again "
The price is AU$840
includes taxes & fees
26 Aug - 27 Aug
Luxury on Back Cove - Three Gables
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Bailey Island Hotel Reviews

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.