Bailey Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 17 - Oct 19
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28
In four months
Jan 23 - Jan 25

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, (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
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, (82)
"Great spot, large space, cool design, clean, easy to walk all over town. "
The price is ￥27,123
￥40,590 total
includes taxes & fees
Nov 2 - Nov 3
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, (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.
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 ￥11,242
￥21,928 total
includes taxes & fees
Oct 15 - Oct 16
Captain's Guest Room w/private bath & house entrance. Walk to everything.
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)
"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
Terrace/patio

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
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 ￥102,539
￥157,918 total
includes taxes & fees
Oct 6 - Oct 7
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
In-town no frills 2 bedroom apt
TV

In-town no frills 2 bedroom apt

7.8 out of 10, Good, (10)
"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 ￥15,436
￥26,312 total
includes taxes & fees
Oct 6 - Oct 7
In-town no frills 2 bedroom apt
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 ￥13,892
￥24,447 total
includes taxes & fees
Oct 19 - Oct 20
Studio Unit Walkable Everywhere
Updated Long Island Maine Cottage
Fridge, oven, stovetop, coffee/tea maker

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
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."
Private Entrance Residential Portland
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, (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
Outdoor dining

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 ￥28,738
￥58,565 total
includes taxes & fees
Nov 2 - Nov 3
Knock on Wood | Airy Charm in Heart of Downtown
1 room luxury ocean front studio cottage
Fridge, microwave, oven, stovetop

1 room luxury ocean front studio cottage

9.6 out of 10, Exceptional, (161)
"Quaint with a great view."
1 room luxury ocean front studio cottage
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, (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
4 bedrooms, iron/ironing board, WiFi, bed sheets

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

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!
Property grounds

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 ￥23,522
￥36,535 total
includes taxes & fees
Oct 22 - Oct 23
Captain's Quarters 2BR Apartment. Walk to Everything!
Charming 2-bedroom house with AC, WiFi in lovely Falmouth
Property grounds

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
Terrace/patio

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

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

10/10 Excellent
"Whole hotel was immaculate. Frontt desk lady very helpful. Breakfast very good and ample. "
Lynn 1-night trip
Posted 1 day ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

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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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 25 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.