Bailey Island Holiday Rentals

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan

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, (230)
"Tremendous stay, great property and host."
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, (82)
"Great spot, large space, cool design, clean, easy to walk all over town. "
The price is HK$1,436
HK$2,149 total
includes taxes & fees
9 Nov - 10 Nov
The Weldon Hotel
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
1 bedroom, in-room safe, free WiFi, bed sheets

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

2.0 star property
10.0 out of 10, Exceptional, (4)
"Very smooth and easy check-in. Very nice room and bathroom. Thank you so much for letting us stay! "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
Captain's Guest Room w/private bath & house entrance. Walk to everything.
Property grounds

Captain's Guest Room w/private bath & house entrance. Walk to everything.

8.0 out of 10, Very good, (19)
"Dmitri is accommodating and check-in easy. Property details are accurate "
The price is HK$623
HK$1,188 total
includes taxes & fees
2 Nov - 3 Nov
Captain's Guest Room w/private bath & house entrance. Walk to everything.
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Interior

Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

10.0 out of 10, Exceptional, (53)
"The cottage location was beautiful, we had a wonderful time on the beach. The cottage could have been a little more clean than it was, but after letting the property owner know she addressed those issues. "
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Studio Unit Walkable Everywhere
1 bedroom, bed sheets

Studio Unit Walkable Everywhere

5.2 out of 10, (5)
"We didn't stay there at all. Canceled reservation "
The price is HK$654
HK$1,213 total
includes taxes & fees
9 Nov - 10 Nov
Studio Unit Walkable Everywhere
In-town no frills 2 bedroom apt
TV

In-town no frills 2 bedroom apt

8.2 out of 10, Very good, (13)
"Beds were very comfortable. Parking was a little difficult. 3rd floor was a little tough on my 83 year old mother. But it was clean and roomy and close to downtown shopping and touristy attractions."
The price is HK$735
HK$1,294 total
includes taxes & fees
27 Oct - 28 Oct
In-town no frills 2 bedroom apt
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Fridge, microwave, oven, stovetop

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

10.0 out of 10, Exceptional, (64)
"We stayed for a group trip to Portland and this was the perfect spot. Location is fantastic, lots of comfortable sleeping options, and great communication from the host. Highly recommend! "
The price is HK$5,429
HK$8,360 total
includes taxes & fees
15 Oct - 16 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Updated Long Island Maine Cottage
Fridge, oven, stovetop, coffee/tea maker

Updated Long Island Maine Cottage

10.0 out of 10, Exceptional, (7)
"Great location. Comfortable living room. Well stocked kitchen. Great communication with owner."
Updated Long Island Maine Cottage
Private Entrance Residential Portland
Fridge, microwave, oven, stovetop

Private Entrance Residential Portland

9.2 out of 10, Wonderful, (5)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
The price is HK$735
HK$1,303 total
includes taxes & fees
16 Oct - 17 Oct
Private Entrance Residential Portland
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C
Property grounds

Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

10.0 out of 10, Exceptional, (104)
"Our third stay was just as charming as the first two. The beauty of the lake, the serene accommodations and locale cannot be topped. The apartment is so cozy and comfortable. We've stayed in many vacation rentals, but this is our favorite. We'll be back."
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C
Knock on Wood | Airy Charm in Heart of Downtown
Outdoor dining

Knock on Wood | Airy Charm in Heart of Downtown

8.8 out of 10, Excellent, (24)
"This apartment is so well situated to walk to parks, restaurants and shopping. It’s a very large space and quite comfortable. "
The price is HK$1,538
HK$3,127 total
includes taxes & fees
6 Nov - 7 Nov
Knock on Wood | Airy Charm in Heart of Downtown
Back yard paradise
Terrace/patio

Back yard paradise

9.8 out of 10, Exceptional, (21)
"We had a wonderful weekend with family at this nicely appointed space that is close to downtown Portland. We all enjoyed swimming in the pool and hanging out on the deck."
Back yard paradise
Charming 2-bedroom house with AC, WiFi in lovely Falmouth
Property grounds

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

8.8 out of 10, Excellent, (6)
"We had a wonderful stay. Nice comfortable camp. We enjoyed swimming in the lake. "
Charming 2-bedroom house with AC, WiFi in lovely Falmouth
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers

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

9.6 out of 10, Exceptional, (80)
"Great stay, wonderful location"
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers
1 room luxury ocean front studio cottage
Fridge, microwave, oven, stovetop

1 room luxury ocean front studio cottage

9.6 out of 10, Exceptional, (161)
"Quaint with a great view."
1 room luxury ocean front studio cottage
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo
Exterior

Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo

10.0 out of 10, Exceptional, (18)
"We loved the walkable neighborhood & had a great, comfortable stay!"
The price is HK$2,397
HK$4,623 total
includes taxes & fees
14 Oct - 15 Oct
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo
Camp Forever cottage
Outdoor dining

Camp Forever cottage

9.6 out of 10, Exceptional, (55)
"Most enjoyed vacation this year.Location was beautiful. "
The price is HK$925
HK$1,958 total
includes taxes & fees
14 Oct - 15 Oct
Camp Forever cottage
Full sized home
Terrace/patio

Full sized home

9.8 out of 10, Exceptional, (48)
"Great location in Harpswell, close to several trails and restaurants. We stayed for about a month-the yard was fantastic and mowed weekly! We worked while we were here and had plenty of space to spread out-wifi was always fast/reliable and even when the power went out, the generator immediately kicked on! We did bring our senior dog and she loved laying on the deck. The ramp leading up to the back is very nice for older pups and people. "
The price is HK$1,401
HK$2,647 total
includes taxes & fees
15 Oct - 16 Oct
Full sized home
Large, light filled 4 bedroom house - walk to ocean and ferry
Terrace/patio

Large, light filled 4 bedroom house - walk to ocean and ferry

9.8 out of 10, Exceptional, (36)
"I stayed here for a weekend with a group of friends and it was a dream! So lovely!"
Large, light filled 4 bedroom house - walk to ocean and ferry
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

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

10/10 Excellent
"Rooms were nice."
William 2-night trip
Posted 3 days ago
Canopy by Hilton Portland Waterfront

Find out more about Bailey Island

Search for holiday rentals in Bailey Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Bailey Island using one of the methods below:

  • View our selection of featured holiday rentals in Bailey Island
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  • Enter your travel dates to view the best deals on holiday rentals in Bailey Island while they last

Look no further and take a look at our great range of rental properties in Bailey Island!

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 23 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.