Bailey Island Holiday Rentals

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Check prices for these dates

Tonight
11 Jul - 12 Jul
Tomorrow
12 Jul - 13 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Holiday Rentals in Bailey Island

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

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
Living area

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (65)
"Absolutely beautiful place to stay. "
The price is HK$2,540
HK$3,358 total
includes taxes & fees
20 Jul - 21 Jul
The Weldon Hotel
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor
Interior

Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

3.0 star property
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor
Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer
Fridge, microwave, oven, stovetop

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

2.0 star property
10.0 out of 10, Exceptional, (19)
"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
Property grounds

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
Fridge, microwave, oven, stovetop

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
Fridge, microwave, oven, stovetop

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.
1 bedroom, in-room safe, free WiFi, bed sheets

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
TV

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 HK$989
HK$1,595 total
includes taxes & fees
10 Aug - 11 Aug
In-town no frills 2 bedroom apt
Adorable Portland getaway on the Eastern Promenade
Interior

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (103)
"Perfect location. Wonderful accommodations"
The price is HK$1,476
HK$2,336 total
includes taxes & fees
13 Jul - 14 Jul
Adorable Portland getaway on the Eastern Promenade
Unique oceanfront home with a deck, tons of natural light, & amazing views
Interior

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
Fridge, microwave, oven, stovetop

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 HK$824
HK$1,405 total
includes taxes & fees
21 Jul - 22 Jul
Private Entrance Residential Portland
Your own private island! Rustic and close to Nature.
Dining

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!
Property grounds

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 HK$1,130
HK$1,788 total
includes taxes & fees
13 Jul - 14 Jul
Captain's House 2BR Apartment. Walk to Everything!
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
Smart TV, video games, ping pong, books

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

8.4 out of 10, Very good, (52)
"We had a large group and had more than enough beds and plenty of space to hang out. Would recommend for a big group or a family looking to spread out!"
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
Ocean view Victorian
Exterior

Ocean view Victorian

9.8 out of 10, Exceptional, (91)
"Everything about the stay was fantastic. Great location and responsive host. "
Ocean view Victorian
Luxury on Back Cove - Three Gables
Property grounds

Luxury on Back Cove - Three Gables

10.0 out of 10, Exceptional, (2)
"GoodLocation, very clean. Would stay again "
The price is HK$2,798
HK$5,197 total
includes taxes & fees
4 Aug - 5 Aug
Luxury on Back Cove - Three Gables
Oceanfront Cabin-Castle in Maine Woods
Interior

Oceanfront Cabin-Castle in Maine Woods

10.0 out of 10, Exceptional, (25)
"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!
Property grounds

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 HK$706
HK$1,283 total
includes taxes & fees
15 Jul - 16 Jul
1BR Guest Suite w/Private Bath & Entrance. Best Value in Town!
Beautiful Oceanfront House- Stunning Water Views
Interior

Beautiful Oceanfront House- Stunning Water Views

9.6 out of 10, Exceptional, (5)
"The Host and his wife were so pleasant and accommodating. We enjoyed watching seals, fish and birds during our visit. Highly recommend."
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.