Bailey Island Vacation Rentals

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In two weeks
Oct 10 - Oct 12
In two months
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Jan 16 - Jan 18

Vacation Rentals in Bailey Island

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

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

10.0 out of 10, Exceptional, (228)
"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
Deluxe Suite, 1 King Bed | Living area | LCD TV, Netflix, streaming services, music library

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (81)
"Absolutely beautiful place to stay. "
The price is ￥52,937
￥68,933 total
includes taxes & fees
Oct 7 - Oct 8
The Weldon Hotel
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
1 bedroom, in-room safe, free WiFi, bed sheets

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

2.0 star property
10.0 out of 10, Exceptional, (3)
"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.
Property grounds

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 ￥11,381
￥22,199 total
includes taxes & fees
Oct 1 - Oct 2
Captain's Guest Room w/private bath & house entrance. Walk to everything.
Full sized home
Terrace/patio

Full sized home

9.8 out of 10, Exceptional, (42)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
The price is ￥29,950
￥54,518 total
includes taxes & fees
Oct 15 - Oct 16
Full sized home
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Interior

Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

10.0 out of 10, Exceptional, (52)
"This cozy cottage is in the beautiful town of Phippsburg, next to the break-taking beach of Popham State Park. With its site on the ocean shore, the sound of waves soothes your soul, and the beach lends all kinds of opportunities for exploring both at low tide and high tide. Our host and hostess were very responsive to our needs, and my daughter and I greatly enjoyed out stay."
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Studio Unit Walkable Everywhere
1 bedroom, bed sheets

Studio Unit Walkable Everywhere

5.2 out of 10, (5)
"We didn't stay there at all. Canceled reservation "
The price is ￥14,063
￥24,910 total
includes taxes & fees
Oct 21 - Oct 22
Studio Unit Walkable Everywhere
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Fridge, microwave, oven, stovetop

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 ￥107,820
￥163,064 total
includes taxes & fees
Sep 29 - Sep 30
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Private Entrance Residential Portland
Fridge, microwave, oven, stovetop

Private Entrance Residential Portland

9.2 out of 10, Wonderful, (5)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
The price is ￥15,724
￥26,803 total
includes taxes & fees
Sep 28 - Sep 29
Private Entrance Residential Portland
Oceanfront Cabin-Castle in Maine Woods
Interior

Oceanfront Cabin-Castle in Maine Woods

9.8 out of 10, Exceptional, (35)
"Place was amazing with an incredible view and fun layout. "
Oceanfront Cabin-Castle in Maine Woods
Updated Long Island Maine Cottage
Fridge, oven, stovetop, coffee/tea maker

Updated Long Island Maine Cottage

10.0 out of 10, Exceptional, (6)
"Great location. Comfortable living room. Well stocked kitchen. Great communication with owner."
Updated Long Island Maine Cottage
Your own private island! Rustic and close to Nature.
Dining

Your own private island! Rustic and close to Nature.

9.4 out of 10, Exceptional, (33)
"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.
Camp Forever cottage
Outdoor dining

Camp Forever cottage

9.6 out of 10, Exceptional, (53)
"Connie and Mike are great hosts. The camp was clean and air conditioned! The view from camp was beautiful. The dock was amazing. "
The price is ￥19,542
￥40,073 total
includes taxes & fees
Oct 1 - Oct 2
Camp Forever cottage
In-town no frills 2 bedroom apt
TV

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 ￥15,724
￥26,803 total
includes taxes & fees
Oct 6 - Oct 7
In-town no frills 2 bedroom apt
Enjoyable 1-bedroom rustic cottage in Southport.
Terrace/patio

Enjoyable 1-bedroom rustic cottage in Southport.

10.0 out of 10, Exceptional, (16)
"Lovely location, quiet, serene, and the cottage is totally cute and comfortable. "
Enjoyable 1-bedroom rustic cottage in Southport.
Spacious Historic Home | 7BR West End for Groups
Marina

Spacious Historic Home | 7BR West End for Groups

10.0 out of 10, Exceptional, (6)
"Seven of us stayed at this beautiful home in a perfect location by the Western Promenade. Everyone had a comfortable bed, bathrooms and showers were plentiful, and the kitchen was perfectly appointed. Both cars we had fit into the garage (an added luxury). The beds were very comfortable and had soft sheets and fluffy towels. We loved every minute of our stay and made great use of the family room. Can't thank our hosts enough...very easy to work with and I would certainly rent from them again...
The price is ￥105,125
￥240,222 total
includes taxes & fees
Sep 28 - Sep 29
Spacious Historic Home | 7BR West End for Groups
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, (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
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C
Property grounds

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

10.0 out of 10, Exceptional, (103)
"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
Large, light filled 4 bedroom house - walk to ocean and ferry
Terrace/patio

Large, light filled 4 bedroom house - walk to ocean and ferry

10.0 out of 10, Exceptional, (34)
"I stayed here for a weekend with a group of friends and it was a dream! So lovely!"
Large, light filled 4 bedroom house - walk to ocean and ferry
Beautiful Oceanfront House- Stunning Water Views
Interior

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
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

Inn at St John Portland In-Town

Inn at St John Portland In-Town

10/10 Excellent
"Hotel in great old Victorian house."
Stacia 1-night trip
Posted 1 day ago
Inn at St John Portland In-Town

Find out more about Bailey Island

Find out more about Bailey Island

Search for holiday rentals in Bailey Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Bailey Island using one of the methods below:

  • View our selection of featured holiday rentals in Bailey Island
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  • Enter your travel dates to view the best deals on holiday rentals in Bailey Island while they last

Look no further and take a look at our great range of rental properties in Bailey Island!

Frequently asked questions

Can I find a vacation rental in Bailey Island?

Yes, we give you a choice of vacation rentals in Bailey Island near Land's End Gift Shop, or you can choose a secluded option if you're looking for extra privacy while you relax. 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 vacation rentals that Bailey Island has to offer?

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This highly rated vacation home rental in Bailey Island is located on the beach and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Bailey Island?

With 26 Expedia vacation rentals, you're sure 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 vacation rentals like in Bailey Island?

Vacation rentals are private properties you can reserve for several days or longer in Bailey Island. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a small group gathering.