Bailey Island Holiday Rentals

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Holiday Rentals in Bailey Island

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Terrace/patio
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Fridge, microwave, oven, stovetop
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
9.8 out of 10, Exceptional, (6)
"Overall this location is a great spot for those that dont need many amenities. There is no tv and no ac but the view and the breeze from the water make up for that! The space was clean and there was a grill plus Cooks Lobster house was a quick walk down the street! "
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Adorable Portland getaway on the Eastern Promenade
Interior
Adorable Portland getaway on the Eastern Promenade
9.8 out of 10, Exceptional, (90)
"We really enjoyed our stay. This little third floor walk up was a perfect place for my husband and I to explore Portland. It is homey and comfortable and spotless. If you have any issues with mobility you should look elsewhere, but that is disclosed in the listing. The last set of stairs are very steep, but we found it charming. I highly recommend this rental. Well done! "
The price is HK$864
HK$1,612 total
includes taxes & fees
17 Nov - 18 Nov
Adorable Portland getaway on the Eastern Promenade
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Fridge, microwave, oven, stovetop
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
9.8 out of 10, Exceptional, (98)
"The apartment is just as pictured. Very clean, cute neighborhood, easy access to shops and restaurants. Definitely consider the paid parking because there are so many street parkers even in off season. The kitchen is well set up with pots and pans, silverware, glasses etc. Beds are comfortable and there are plenty of towels. Very easy to get in touch with landlord with questions. Great idea lace!"
The price is HK$1,751
HK$4,114 total
includes taxes & fees
17 Nov - 18 Nov
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Fridge, microwave, oven, stovetop
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Interior
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, (35)
"What a great place! Located in the arts district, this refurbished brownstone has every modern convenience within walking distance of restaurants and museums. Windows on both sides of the apartment provide street views, one active and bustling, one quiet with a view of Casco Bay and sunrises. And the rooftop patio is a dream - we loved being part of Portland history with an up close view of the florist's ad mural!"
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
TV, fireplace
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
8.4 out of 10, Very good, (41)
"GORGEOUS house and view! Very spacious and accommodating. Things you should know before booking is that it is about an hour away from anything and everything. House could use some more TV's if you're going with children, pinball machines did not work and neither did "workout equipment" which was an elliptical and treadmill. One of the showers did not work and some of the fans that were provided did not either. I think its a tad over priced for its distance to do things but the views from...
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
Bayfront home with 270-degree views, large deck & porch - near Popham Beach
TV, fireplace, video games, DVD player
Bayfront home with 270-degree views, large deck & porch - near Popham Beach
8.2 out of 10, Very good, (29)
"The house is beautiful, comfortable and was pristine when we checked in. Decks and screened porch are wonderful. The kids loved the 3rd floor bedroom space, and it was fabulous being so close to Popham Beach. Definitely recommend. Kitchen on 2nd floor ... so have some strong helpers to bring in groceries ;)"
Bayfront home with 270-degree views, large deck & porch - near Popham Beach
Charming 110-year former Inn 10' from the Ocean!
Property grounds
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (110)
"We loved the location of this property. It was far enough away from the hustle and bustle to truly relax and enjoy the ocean sounds and sunrises, but close enough that we could easily hop on over to shopping and restaurants. The property was well-maintained, we loved the deck, and being able to walk right out on the beach. Highly recommend!"
Charming 110-year former Inn 10' from the Ocean!
Cozy, Elegant and Bright 2 bed in the East End
Fridge, microwave, oven, stovetop
Cozy, Elegant and Bright 2 bed in the East End
9.6 out of 10, Exceptional, (35)
"Fabulous location for us as it’s just 1/2 block from our son’s apartment. So close to Casco Bay and the Portland Port area. Walkable to restaurants and shopping. Nice sunny apartment! "
The price is HK$1,556
HK$2,858 total
includes taxes & fees
17 Nov - 18 Nov
Cozy, Elegant and Bright 2 bed in the East End
Popham Beach Direct Oceanfront Cottage Steps to the sand
Interior
Popham Beach Direct Oceanfront Cottage Steps to the sand
9.8 out of 10, Exceptional, (58)
"Beautiful view. The cabin could use a little.TLC but i enjoyed the beach walks and the quiet"
Popham Beach Direct Oceanfront Cottage Steps to the sand
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, (52)
"Beautiful property. Saw seals from living room catching fish. Front door did not lock but it’s a safe neighborhood but a bit isolated. Kitchen is well equipped for cooking. Laundry facilities were a great help! Gorgeous views of the water and excellent service and communication."
Unique oceanfront home with a deck, tons of natural light, & amazing views
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
TV, fireplace, books, stereo
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
9.4 out of 10, Exceptional, (30)
"This house was amazing. It was way better than we expected after looking through the pictures online. The outdoor space and the house itself are beautiful and the pictures do it zero justice. We were worried at first about the lack of AC, but the house cooled right down once we opened the windows let the air in. I highly recommend this place if you’re looking to visit Boothbay. It was so close to the main area, but you couldn’t even tell- it felt like you were immersed in nature."
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
Glorious getaway on Portland's Eastern Promenade.
Property grounds
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (139)
"Nice and spacious 2 bedroom unit steps from the promenade. Jennifer was very helpful and accommodating. Easy check in and plenty of parking. Amazing central location. "
The price is HK$1,299
HK$2,383 total
includes taxes & fees
18 Nov - 19 Nov
Glorious getaway on Portland's Eastern Promenade.
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK
Outdoor dining
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK
8.8 out of 10, Excellent, (35)
"Our party of 8 enjoyed our stay. The house is well equipped and stocked to get you started. Conveniently located to town and the Botanical Gardens. Plenty of outside space for kids to run around and play. It has a beautiful view of the cove but is very rocky. This didn't stop us from hunting hermit crabs and catching fish. The house is old but that gives it the Maine charm. "
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK
Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina
Fridge, microwave, oven, stovetop
Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina
9.4 out of 10, Exceptional, (51)
"There were four of us so we each had a bedroom. We have been friends since 1955!!! It was a wonderful getaway! "
Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina
Stunning oceanfront cottage w/ private deck and Atlantic views
TV, DVD player, books, video library
Stunning oceanfront cottage w/ private deck and Atlantic views
9.2 out of 10, Wonderful, (50)
"They thought of everything, including binoculars. We watched seabirds and lobstermen working and didn't leave the house until late in the day for the Botanical Gardens. They only communicate through Vacasa,email, and text. Good communication, though. Final payment is through Vacasa. "
Stunning oceanfront cottage w/ private deck and Atlantic views
Elegant condo - walk to Portland's best restaurants & Old Port
Fridge, microwave, oven, stovetop
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (56)
"We really enjoyed this home and the location. The upgrades were beautiful and the restaurants nearby were amazing. When we checked out and took out our trash the outside bin had a lock on it so our only issue was not being able to access that but that wasn’t anyone’s fault. "
The price is HK$1,268
HK$3,269 total
includes taxes & fees
18 Nov - 19 Nov
Elegant condo - walk to Portland's best restaurants & Old Port
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Fridge, microwave, oven, stovetop
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
9.2 out of 10, Wonderful, (80)
"If you like eclectic you'll love this place. Quite rustic. "
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Beautiful oceanside Castle with private beach and seasonal swimming pool
Outdoor pool
Beautiful oceanside Castle with private beach and seasonal swimming pool
10.0 out of 10, Exceptional, (35)
"It was a wonderful home for a birthday celebration with friends that wanted to experience Maine. The grounds were expansive with lovely water views. The host were very responsive."
Beautiful oceanside Castle with private beach and seasonal swimming pool
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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Other types of properties in Bailey Island you may be interested in

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Terrace/patio
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Casco Bay Hotel, Ascend Hotel Collection
Lobby
Casco Bay Hotel, Ascend Hotel Collection
3.5 star property
8.4 out of 10, Very good, (2364)
"Nice, clean, and close to the airport. "
The price is HK$554
HK$604 total
includes taxes & fees
16 Dec - 17 Dec
Casco Bay Hotel, Ascend Hotel Collection
Ramada Plaza by Wyndham Portland
Exterior
Ramada Plaza by Wyndham Portland
3.0 star property
7.6 out of 10, Good, (1014)
"Room was missing a microwave and the TV remote was broken otherwise the Ramada is a great place thank you "
The price is HK$761
HK$840 total
includes taxes & fees
17 Nov - 18 Nov
Ramada Plaza by Wyndham Portland
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.

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?

Elegant condo - walk to Portland's best restaurants & Old Port: This holiday home rental outside of Bailey Island is in the city centre, and equipped with air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Bailey Island?

With 29 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?

Family-friendly attractions include Land's End Gift Shop, whereas Ragged Island is a spot to enjoy the outdoors. 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.