Holiday Rentals in Bailey Island

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Holiday Rentals in Bailey Island

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

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (68)
"Great house very comfortable and well appointed. Very roomy for our entire family. Nice to have en suite bathrooms with all the bedrooms. The host was very good with communication. Located on a busy road and the driveway is on a curve which made it a little challenging entering and exiting the property. "
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

The Weldon Hotel

4.0 star property
9.4 out of 10, Exceptional, (36)
"The full kitchen and appliances were perfect for my stay so that I did not have to eat out while I was there and save money "
The price is €151
includes taxes & fees
2 Mar - 3 Mar
The Weldon Hotel

Glorious getaway on Portland's Eastern Promenade.

10.0 out of 10, Exceptional, (144)
"This rental is adorable with so many thoughtful touches from the host. From the personalized card and snacks to the labels explaining most everything you'd like to know about the space, everything has been considered. A great base from which to explore a fun town."
The price is €214
includes taxes & fees
17 Feb - 18 Feb
Glorious getaway on Portland's Eastern Promenade.

1 room luxury ocean front studio cottage

9.6 out of 10, Exceptional, (149)
"Very clean, amazinv views, perfect weekend!!!! "
1 room luxury ocean front studio cottage

Oceanfront Cabin-Castle in Maine Woods

9.8 out of 10, Exceptional, (12)
"Absolutely loved this property! My family and I enjoyed every minute of our stay! Listening to the waves crashing on the rocks, hanging out by the fire and just relaxing made for the perfect after Christmas getaway! I look forward to coming again! Highly recommend "
Oceanfront Cabin-Castle in Maine Woods

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

9.8 out of 10, Exceptional, (103)
"A great place for people looking to explore Portland. Clean, comfortable and with great communication by our host, we’d recommend it for any group looking for a home base in the area."
The price is €476
includes taxes & fees
17 Feb - 18 Feb
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (74)
"The Globe House was a wonderful Plato spend a couple of days while exploring Portland. The house itself was immaculate and well appointed, with extra touches that put it a step above: the fresh scent from a diffuser welcomed us, a complimentary bottle of wine awaited us in the refrigerator, and luxe amenities like L’Occitane moisturizer were provided. Great location with easily walkable and excellent restaurants. Our hosts left a fabulous “guide to Portland” for us, with many of their favorite...
The Globe House on Munjoy Hill - Walk to Breweries

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (93)
"Perfect location. Wonderful accommodations"
The price is €183
includes taxes & fees
17 Feb - 18 Feb
Adorable Portland getaway on the Eastern Promenade

Fall In Love With Portland!

9.6 out of 10, Exceptional, (110)
"We had a great time at Nick's apartment, it is spaceous and tastefully furnished. We were able to feel right at home and used the kitchen every day, the dining room had space for all of us which made for some great holiday meals together. The location is nearly unbeatable with just two blocks to the promenade by the water and a short walk to downtown. Congress Street, which is 50 yards from the front door, has a really cool vibe with bars, cafes and restaurants. Yet, you are clearly nestled in a...
The price is €476
includes taxes & fees
17 Feb - 18 Feb
Fall In Love With Portland!

Cozy, Elegant and Bright 2 bed in the East End

9.8 out of 10, Exceptional, (36)
"Very clean. Nice walk along bikepath to downtown. Will look to stay here again. Loved the neighborhood and parking was easy. Kitchen had everything we needed to cook. "
The price is €352
includes taxes & fees
18 Feb - 19 Feb
Cozy, Elegant and Bright 2 bed in the East End

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (116)
"Stunning location. Dog friendly beach. Lighthouse in walking distance. "
Charming 110-year former Inn 10' from the Ocean!

Lakefront House

10.0 out of 10, Exceptional, (22)
" 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 €713
includes taxes & fees
24 Feb - 25 Feb
Lakefront House

Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

3.0 star property
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

9.8 out of 10, Exceptional, (177)
"What a beautiful home and location! Second time we have stayed here and love it. "
New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

Prime City Living Townhouse by RedAwning

2.0 star property
8.0 out of 10, Very good, (1)
"It was very convenient. "
The price is €487
includes taxes & fees
19 Feb - 20 Feb
Prime City Living Townhouse by RedAwning

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 €358
includes taxes & fees
17 Mar - 18 Mar
Full sized home

Waterfront Log Cabin Private Community Beach. CLOSEST TO TOWN less 10 min walk!

10.0 out of 10, Exceptional, (9)
"This is a charming log cabin in an historic log cabin development minutes from town, grocery shopping and within walking distance to a lovely park (Barrett). The "great room" has a wonderful fireplace, high ceilings, and comfortable couches and chairs. The large deck facing the water is beautiful, offering a spectacular view of Lewes Cove in Linekin Bay. You can hear loons, watch cormorants fishing and drying their wings on lobster trap platforms, and see bald eagles fly by and roost in nearby...
Waterfront Log Cabin Private Community Beach. CLOSEST TO TOWN less 10 min walk!

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

Beautiful, Spacious Home, minutes to the Old Port!

10.0 out of 10, Exceptional, (1)
"We stayed for night with couples and friends. We had an amazing time and the place was so clean and exactly as described. "
The price is €338
includes taxes & fees
5 Mar - 6 Mar
Beautiful, Spacious Home, minutes to the Old Port!
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

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (68)
"Great house very comfortable and well appointed. Very roomy for our entire family. Nice to have en suite bathrooms with all the bedrooms. The host was very good with communication. Located on a busy road and the driveway is on a curve which made it a little challenging entering and exiting the property. "
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

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

Portland Harbor Hotel

4.0 star property
9.2 out of 10, Wonderful, (1470)
"Awesome place to get cozy for a few days. Great staff, restaurant, and lots of free waters/coffee and snacks. "
The price is €173
includes taxes & fees
2 Mar - 3 Mar
Portland Harbor Hotel
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?

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary: This highly rated holiday home rental in Bailey Island is located in the city centre, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 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 garden and 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?

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.