Search Vacation Homes in Bailey Island

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Compare 430 Vacation Homes in Bailey Island with updated reviews, rates, and availability.

Admiral's Quarters - Room 12
8.8 out of 10, Excellent, (5)
"We had a wonderful time at Admiral’s Quarters and wish we’d had one more night to spend in Boothbay Harbor. Our room was cozy and the two levels made it perfect for our family of four. The location was fantastic and John always had great recommendations for things to do or places to eat. "
The price is AED 1,350
AED 1,723 total
includes taxes & fees
17 Nov - 18 Nov
Admiral's Quarters - Room 12
Oceanfront Cabin-Castle in Maine Woods
9.8 out of 10, Exceptional, (8)
"We had a great time during our stay. Very fun and unique placeb to stay. We had a little pine squirrel make his way into the house with us somehow, but the host was very understanding and it didnt take away from our stay at all. Thanks, Micah, we hope to be back. "
Oceanfront Cabin-Castle in Maine Woods
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (110)
"We loved the location of this property. It was far enough away from the hustle and bustle to truly relax and enjoy the ocean sounds and sunrises, but close enough that we could easily hop on over to shopping and restaurants. The property was well-maintained, we loved the deck, and being able to walk right out on the beach. Highly recommend!"
Charming 110-year former Inn 10' from the Ocean!
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.
10.0 out of 10, Exceptional, (66)
"We have stayed at several VRBO and this one was the best. Great location and great house."
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.
Luxurious Penthouse with Modern Design in Downtown
9.2 out of 10, Wonderful, (5)
"Just as advertised, would definitely stay here again. Great location!"
Luxurious Penthouse with Modern Design in Downtown
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Full sized home
9.6 out of 10, Exceptional, (22)
"Short visit but fun little cottage off the beaten path. Most comfortable beds ever and very responsive host and caretaker. Would stay here again. Loved the nearby waterfront restaurants."
The price is AED 826
AED 1,365 total
includes taxes & fees
18 Nov - 19 Nov
Full sized home
The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor
10.0 out of 10, Exceptional, (4)
"I can’t say enough about the house and our wonderful hosts. They’ve created a wonderful memory for our friends and family that will last a lifetime. The house, the views, boothbay harbor and all that it has to offer. Best vacation ever!! THANK YOU SO MUCH!! Paul"
The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor
Oceanside escape 🌊 perfect family getaway!
9.8 out of 10, Exceptional, (10)
"Beautiful home! Well kept, clean and very comfortable. A little touch of history in this wonderful house and neighborhood. Great location, quick to Portland and the airport. We loved it!!!! Owner communication is a 10+++. "
Oceanside escape 🌊 perfect family getaway!
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (56)
"We really enjoyed this home and the location. The upgrades were beautiful and the restaurants nearby were amazing. When we checked out and took out our trash the outside bin had a lock on it so our only issue was not being able to access that but that wasn’t anyone’s fault. "
The price is AED 599
AED 1,543 total
includes taxes & fees
18 Nov - 19 Nov
Elegant condo - walk to Portland's best restaurants & Old Port
Rent a room in the gorgeous Holt House
8.2 out of 10, Very Good, (22)
"We loved staying at the Holt House. It's a truly beautiful building. It's like staying in a hotel from another era. The room was beautifully decorated with victorian decor and we loved it. It was also handy to have access to a full kitchen on the first floor where we washed some of our dishes. Overall, it was a cozy and quiet place to stay."
Rent a room in the gorgeous Holt House
Bayside House Near Portland with Water Views, Fast WiFi, & Patio - Dogs OK
8.6 out of 10, Excellent, (12)
"This is owners first year renting. It needs a complete review by electrician because there are several outlets not working. We also had trouble with the thermostats and heat. So that needs help too. The 1800 salt box portion of the home was charming to us. The addition added a great number of beds and baths. The kitchen was marginally stocked with bowls, etc so bring your own.. kitchen could have been cleaner too. So not smooth sailing but a comfy no fuss second home"
Bayside House Near Portland with Water Views, Fast WiFi, & Patio - Dogs OK
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.
9.6 out of 10, Exceptional, (33)
"The house we stayed in was wonderful. It met all of our expectations. I highly recommend it!"
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.
5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!
10.0 out of 10, Exceptional, (134)
"This property is fantastic and I would prioritize staying there each and every time I visit Portland."
5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!
Beautiful house on the Harpswell Peninsula over looking Casco Bay
9.8 out of 10, Exceptional, (59)
"Comfortable, peaceful. Everything we needed for mussels, steamers and lobster Nice to have working dock in front of us for lobsters"
Beautiful house on the Harpswell Peninsula over looking Casco Bay
New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!
9.8 out of 10, Exceptional, (174)
"Great house, big enough for our family group ranging from 1 year old to 70 year old. :) Home was clean & spacious & cozy - with a beautiful view. "
New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
9.6 out of 10, Exceptional, (32)
"Great location, very easy to get to harbor, and a great view. Check-in was easy, not having to keep a key on you was also nice. The house was very cozy, perfect for doing puzzles or drinking coffee in the morning. Lots of appliances and home goods to make it easy to cook, iron clothes, hang stuff, etc. Overall we would definitely stay again!"
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
Back yard paradise
9.8 out of 10, Exceptional, (19)
"I live in California, but my son was married in Portland (our home state). We spent a long weekend close to family and wedding activities. This is a comfortable home, in a great location. I feel fortunate to have chosen the perfect VRBO."
Back yard paradise
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome
9.0 out of 10, Wonderful, (56)
"Beautiful house with lots of charm….. gorgeous views from the deck. I was texted when we arrived to make sure we were happy with the cleanliness of the home and we were . House was supplied with plenty of towels, blankets, toiletries, cushions for outdoor furniture and games. We stayed here with our dogs who loved it as well. We would stay here again"
The price is AED 378
AED 1,166 total
includes taxes & fees
17 Nov - 18 Nov
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome
Shady Potts Point Cottage Cooled by Ocean Breezes
9.6 out of 10, Exceptional, (77)
"Great stay in very clean house in a very quiet ocean side community. Perfect getaway!"
Shady Potts Point Cottage Cooled by Ocean Breezes
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 property types 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
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
9.8 out of 10, Exceptional, (6)
"Overall this location is a great spot for those that dont need many amenities. There is no tv and no ac but the view and the breeze from the water make up for that! The space was clean and there was a grill plus Cooks Lobster house was a quick walk down the street! "
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Adorable Portland getaway on the Eastern Promenade
9.8 out of 10, Exceptional, (90)
"We really enjoyed our stay. This little third floor walk up was a perfect place for my husband and I to explore Portland. It is homey and comfortable and spotless. If you have any issues with mobility you should look elsewhere, but that is disclosed in the listing. The last set of stairs are very steep, but we found it charming. I highly recommend this rental. Well done! "
The price is AED 408
AED 761 total
includes taxes & fees
17 Nov - 18 Nov
Adorable Portland getaway on the Eastern Promenade
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.