Bailey Island Holiday Rentals

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Holiday Rentals in Bailey Island

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

10.0 out of 10, Exceptional, (223)
"We had a wonderful stay at this cottage. Great location to explore the surrounding areas."
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (69)
"Absolutely beautiful place to stay. "
The price is NZ$810
includes taxes & fees
25 Aug - 26 Aug
The Weldon Hotel

Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

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

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

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 Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

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

9.6 out of 10, Exceptional, (75)
"We loved our stay here. This is a fantastic location and has everything you need to enjoy your stay in Boothbay. Bring eye masks though, the futon sleeper is going to get a lot of light from the windows."
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers

Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

7.4 out of 10, Good, (12)
"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 NZ$276
includes taxes & fees
17 Aug - 18 Aug
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

Private Entrance Residential Portland

9.0 out of 10, Wonderful, (2)
"This apartment is great- the furnishings are cute and the bed is comfy. It has a kitchen with all of the cookware I needed, and off-street parking is awesome. I liked that it was really convenient to downtown, but outside of the busy, touristy parts of town. The owners were communicative, but not intrusive. It was overall a great experience. I would definitely stay here again."
The price is NZ$341
includes taxes & fees
18 Aug - 19 Aug
Private Entrance Residential Portland

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (109)
"Unit was very clean"
The price is NZ$525
includes taxes & fees
1 Sept - 2 Sept
Adorable Portland getaway on the Eastern Promenade

Studio Unit Walkable Everywhere

6.0 out of 10, (1)
"Before check in the host was kind and incredibly communicative. Upon check out they asked how our stay was and I wrote them a message saying I’d rather discuss this before leaving a bad review but they left me on read… When we arrived there were so many unhoused folx outside the apt we didn’t feel safe entering. we literally saw a woman being chased/harassed while we were pulling up. If I wasn’t with my partner I would’ve had to cancel due to feeling unsafe. I have no bad feelings about unhoused...
The price is NZ$352
includes taxes & fees
24 Aug - 25 Aug
Studio Unit Walkable Everywhere

Walkable near downtown 1 Bedroom

The price is NZ$343
includes taxes & fees
10 Sept - 11 Sept
Walkable near downtown 1 Bedroom

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.

Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist

10.0 out of 10, Exceptional, (47)
"This was a great property and even better host. We had a great time staying in downtown Portland. The apartment has great finishes. I will definitely plan to stay here again."
Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist

Elegant and efficient Island home 4 miles from downtown Portland

8.0 out of 10, Very good, (1)
"Historic and charming home in a most interesting setting-- the community was a former military fort and barracks. Chat with neighbors on the front porch or watch wildlife and hang out in the backyard picnic tables. Comfortable beds and two full baths makes it good for group of 4-6 people. The golf cart is a godsend but there are bicycles and kayaks for land and water exploration. We didn't make it to the lovely looking pool or rec center for gym/bowling but they look like lots of fun. Rental and...
Elegant and efficient Island home 4 miles from downtown Portland

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

10.0 out of 10, Exceptional, (100)
"Adorable place, roomy, quiet, upscale yet felt just like home. Will definitely stay again! "
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

Modern woodland privacy with ocean, trails, and lobster all in walking distance.

10.0 out of 10, Exceptional, (48)
"My friend and I felt very relaxed at this house. The beds were comfortable and the kitchen was stocked with most every cooking equipment needed. The host answered any question I had very quickly and supplied information about the surrounding area. It was a great place to unwind!"
Modern woodland privacy with ocean, trails, and lobster all in walking distance.

Studio Apartment near downtown Walkable!

6.0 out of 10, (1)
"The listing said "Studio Apartment," but it is really just a bedroom with a bath. A mini-fridge, coffeemaker and microwave oven do not make this a "Studio" in the sense that I understand that word (i.e., a one-room apartment with kitchen and bath). When I went back and looked at the photos in the listing, that should have been obvious to me, but I got hung up on the word "Studio."That said, it was a comfortable room, although the bathroom was stingy on towels (no face cloths, only one hand...
The price is NZ$352
includes taxes & fees
7 Sept - 8 Sept
Studio Apartment near downtown Walkable!

Modern Getaway by the Sea

The price is NZ$982
includes taxes & fees
25 Aug - 26 Aug
Modern Getaway by the Sea

Knock on Wood | Airy Charm in Heart of Downtown

9.0 out of 10, Wonderful, (19)
"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 NZ$810
includes taxes & fees
8 Sept - 9 Sept
Knock on Wood | Airy Charm in Heart of Downtown

City Amenities, Casco Bay Sunrises and Natural Beauty

9.8 out of 10, Exceptional, (112)
"While minutes away from the Old Port, our stay on Casco Bay allowed us to relax and unwind."
The price is NZ$675
includes taxes & fees
20 Aug - 21 Aug
City Amenities, Casco Bay Sunrises and Natural Beauty

Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

8.8 out of 10, Excellent, (38)
"This was our second stay here. We love the comfort of this home and the location is perfect."
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK
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

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.