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
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
Lakefront House
Interior

Lakefront House

10.0 out of 10, Exceptional, (21)
" Thank you so much for sharing your lovely home with us. We had the perfect bachelorette weekend getaway! We would all definitely stay again! "
The price is HK$1,516
HK$6,009 total
includes taxes & fees
20 Jan - 21 Jan 2025
Lakefront House
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, (114)
"This location is EVERYTHING!!! Right on the beach, cozy accommodations with spacious bedrooms was perfect for the 4 of us - with the 3rd bedroom, we could've included another couple! Host John was lovely!!!"
Charming 110-year former Inn 10' from the Ocean!
Amazing riverfront home with private deck, views, private dock, & fireplace
Aerial view

Amazing riverfront home with private deck, views, private dock, & fireplace

9.4 out of 10, Exceptional, (40)
"Beautiful place! Perfect fit for us"
Amazing riverfront home with private deck, views, private dock, & fireplace
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
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, (81)
"This house is in perfect spot in Boothbay Harbor. Easy walk to town, right on the water. Everything about the house was perfect and exactly what we needed. "
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
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)
"Well taken care of and maintained. Comfortable."
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, (53)
"Property was great. But we had no water for one of our three days of our stay. We had to call to get someone out to fix it, and they didn’t know how. It set the tone for our stay."
Unique oceanfront home with a deck, tons of natural light, & amazing views
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
Rent a room in the gorgeous Holt House
Exterior

Rent a room in the gorgeous Holt House

8.0 out of 10, Very good, (24)
"This was a perfect place, close to everything in Portland! "
Rent a room in the gorgeous Holt House
Glorious getaway on Portland's Eastern Promenade.
Property grounds

Glorious getaway on Portland's Eastern Promenade.

10.0 out of 10, Exceptional, (142)
"We had a wonderful night in Portland! We spent the afternoon shopping in Freeport and arrived at the apartment around 5. Very easy finding parking on the street and no trouble getting inside. The apartment is absolutely adorable! Between the colors and decorations, it just gives off this girly, cozy vibe. There were 4 of us and we all had room to sleep comfortably. Wish we could have stayed another night! "
The price is HK$988
HK$1,983 total
includes taxes & fees
2 Jan - 3 Jan 2025
Glorious getaway on Portland's Eastern Promenade.
Full sized home
Interior

Full sized home

9.6 out of 10, Exceptional, (24)
"The house is very clean, and it's very well situated. There are plenty of room in and out. Will come again."
The price is HK$1,750
HK$2,890 total
includes taxes & fees
23 Dec - 24 Dec
Full sized home
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$1,555
HK$2,856 total
includes taxes & fees
26 Dec - 27 Dec
Cozy, Elegant and Bright 2 bed in the East End
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, (57)
"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$1,267
HK$3,282 total
includes taxes & fees
26 Dec - 27 Dec
Elegant condo - walk to Portland's best restaurants & Old Port
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, (31)
"Very cozy house in an absolutely lovely spot. We really enjoyed the outdoor space and the peace and quiet. "
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
Rent a room in the gorgeous Holt House
Exterior

Rent a room in the gorgeous Holt House

8.0 out of 10, Very good, (14)
"Really cool room and in a great location only a short walk from restaurants and sights. "
Rent a room in the gorgeous Holt House
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
The Westin Portland Harborview
View from room

The Westin Portland Harborview

4.0 star property
8.8 out of 10, Excellent, (1003)
"I had an incredible stay! This was my first time at the Westin Harborview. Upon check-in I was awarded “Guest of the Day” status with a top floor upgrade. It was such a sweet surprise and a wonderful experience. The harbor view is quite lovely and the next morning I watched a couple of cargo ships move through the draw bridge while sipping delicious in room Starbucks coffee. From check-in to upgrade, which included a complimentary breakfast in C2 (delicious options and friendly warm service), to...
The price is HK$762
HK$855 total
includes taxes & fees
7 Jan - 8 Jan 2025
The Westin Portland Harborview
Ramada Plaza by Wyndham Portland
Exterior

Ramada Plaza by Wyndham Portland

3.0 star property
7.6 out of 10, Good, (1010)
"This was a great place to stay at. Very easy to locate and close enough to everything. The room was very clean and stocked perfectly. It was a breeze to check in and out. There are 2 hot tubs on site. Definately a great place to stay especially for the money."
The price is HK$727
HK$804 total
includes taxes & fees
29 Dec - 30 Dec
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?

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub: This holiday home rental outside of Bailey Island is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

How many holiday rentals are there in Bailey Island?

With 27 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.