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, (229)
"Beautiful views, very clean and enjoyed the oceanside vibe both inside and out! Easy walk to general store and walkable to Giant Stairs trail and Cedar Beach."
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, (81)
"Absolutely beautiful place to stay. "
The price is NZ$615
includes taxes & fees
31 Oct - 1 Nov
The Weldon Hotel

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.

8.2 out of 10, Very good, (17)
"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$264
includes taxes & fees
15 Oct - 16 Oct
Captain's Guest Room w/private bath & house entrance. Walk to everything.

Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

10.0 out of 10, Exceptional, (52)
"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

Full sized home

9.8 out of 10, Exceptional, (43)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
Full sized home

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 NZ$1,859
includes taxes & fees
14 Oct - 15 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

In-town no frills 2 bedroom apt

7.8 out of 10, Good, (9)
"The Apt is very old but nice. Wasn’t aware of stairs as we were on the 3rd floor and had to go up very narrow stairs with no hand rails. The outdoors had bums sitting around and people across the street partying and coming up to us . Didn’t feel safe and would never have kids here. The place was nice to lay your head down but that’s it"
The price is NZ$310
includes taxes & fees
6 Oct - 7 Oct
In-town no frills 2 bedroom apt

Studio Unit Walkable Everywhere

5.2 out of 10, (5)
"We didn't stay there at all. Canceled reservation "
The price is NZ$288
includes taxes & fees
19 Oct - 20 Oct
Studio Unit Walkable Everywhere

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

9.2 out of 10, Wonderful, (5)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
Private Entrance Residential Portland

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

8.8 out of 10, Excellent, (39)
"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

Knock on Wood | Airy Charm in Heart of Downtown

8.8 out of 10, Excellent, (23)
"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$730
includes taxes & fees
29 Oct - 30 Oct
Knock on Wood | Airy Charm in Heart of Downtown

1 room luxury ocean front studio cottage

9.6 out of 10, Exceptional, (160)
"Quaint with a great view."
1 room luxury ocean front studio cottage

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

10.0 out of 10, Exceptional, (104)
"If you plan to visit Boothbay Harbor, you won't find a better place! The lakefront property is very close to town but offers a quiet location in a private neighborhood. Beautiful and bright interior in a natural setting. One of the best places I've stayed at. Great for kayaking and fishing too! "
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

Beautiful Oceanfront House- Stunning Water Views

9.6 out of 10, Exceptional, (16)
"The Host and his wife were so pleasant and accommodating. We enjoyed watching seals, fish and birds during our visit. Highly recommend."
Beautiful Oceanfront House- Stunning Water Views

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

9.6 out of 10, Exceptional, (79)
"Great stay, wonderful location"
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers

Captain's Quarters 2BR Apartment. Walk to Everything!

8.6 out of 10, Excellent, (7)
"Nice, clean, cosy, conveniently located and easy enough to find. Great communication with host, comfortable beds and plenty of hot water. very responsive and would definitely consider using again. "
The price is NZ$428
includes taxes & fees
8 Oct - 9 Oct
Captain's Quarters 2BR Apartment. Walk to Everything!

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

8.8 out of 10, Excellent, (6)
Charming 2-bedroom house with AC, WiFi in lovely Falmouth

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
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

Find out more about Bailey Island

Find out more about Bailey Island

Everything you need to know about Bailey Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Bailey Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bailey Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Bailey Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bailey Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Bailey Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Bailey Island holiday rentals we have selected for you start as low as NZ$264 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Bailey Island rentals

At Expedia, we put the best Bailey Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Bailey Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bailey Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bailey Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 24 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.