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Compare 434 Vacation Homes in Bailey Island with updated reviews, rates, and availability.

Stunning oceanfront cottage w/ private deck and Atlantic views
9.2 out of 10, Wonderful, (37)
"The view was exceptional "
Stunning oceanfront cottage w/ private deck and Atlantic views
Exterior
Rent a room in the gorgeous Holt House
8.4 out of 10, Very Good, (19)
"It was a great trip up to Portland and the property met our needs."
Rent a room in the gorgeous Holt House
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
8.8 out of 10, Excellent, (33)
"Great views. House pretty clean & supplies were fine except only 3 coffee cups for 6 adults. VACasa said they would get more cups. They failed, never received. Some lights didn't work & lots of dead bugs in light fixtures."
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
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Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (45)
"The kitchen was very well equipped. Living room was so cozy with the fire. Bed was super comfortable. The unit has really tall ceilings and is cozy. Only issue was the dog upstairs. They kept barking and whining."
The price is AED 742
AED 1,742 total
includes taxes & fees
3 Jun - 4 Jun
Elegant condo - walk to Portland's best restaurants & Old Port
Exterior
Spacious Waterfront Summer Home with Swimming, Kayaking, and Sunsets
10.0 out of 10, Exceptional, (37)
"What a wonderful home in a fantastic location! It has everything you need for a getaway: open and inviting communal spaces including a spacious wraparound deck, stocked kitchen for meals, comfy beds, working fireplace, and so much more. Wouldn't hesitate to stay again!"
Spacious Waterfront Summer Home with Swimming, Kayaking, and Sunsets
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
8.8 out of 10, Excellent, (48)
"This was a great old townhouse. Great parking and very clean. Easy walk to attractions and a charming neighborhood bar just around the corner. "
The price is AED 415
AED 909 total
includes taxes & fees
29 May - 30 May
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Living room with oversized leather reclining couch, recliner and 60" smart tv
Convenient Portland home 3 miles from Downtown
10.0 out of 10, Exceptional, (8)
"The house was spotless and comfortable. We arrived in the middle of a snowstorm, and it was great to have the one-car attached garage, a heating system that worked well, someone who plowed the driveway and shoveled the snow shortly after we arrived, and a comfortable hot shower. Grocery stores and restaurants are nearby. Beds are comfortable, and there is a lot of closet space and drawer space. We would stay here again."
The price is AED 1,017
AED 2,594 total
includes taxes & fees
29 May - 30 May
Convenient Portland home 3 miles from Downtown
Third or top floor lounge- spectacular ocean views.
Sunrise Catcher with a Panoramic View!
10.0 out of 10, Exceptional, (22)
"Very clean property. Amazing views. Well appointed. Enjoyed our stay."
Sunrise Catcher with a Panoramic View!
Private kitchen
5 Star Back Cove Hide-Away<br>1 bedroom Back Cove apartment with water views!
10.0 out of 10, Exceptional, (115)
"Perfect little place just outside of downtown, very convenient to everything. Very clean & nicely decorated. Exactly as shown. Excellent communication from host, easy check in. Will def re-book if/when we return to Portland!"
5 Star Back Cove Hide-Away<br>1 bedroom Back Cove apartment with water views!
It’s going to be an amazing summer!
325 Year OldWaterfront Fully Renovated Loaded with Amenities Bring Your Boat!
10.0 out of 10, Exceptional, (20)
"The property and home were very charming, lovely views from every room of the tawny late November marsh landscape. Recent renovations provided creature comforts, and getting out to explore in-town Bath or out to Reid was a short car ride away. Accessibility for older family was great with the single level and low entry thresholds. Tina was great for communicating with- our best wishes!"
325 Year OldWaterfront Fully Renovated Loaded with Amenities Bring Your Boat!
Dining
New home at Popham Beach
10.0 out of 10, Exceptional, (4)
"Wonderful way to decompress and walk the sandy beaches at Popham. The property, the views, our host, and all details were great!"
New home at Popham Beach
Topsham Vacation Rental | 2BR | 1BA | 775 Sq Ft | Step-Free Access
Riverfront Topsham Home ~ 28 Mi to Portland!
Riverfront Topsham Home ~ 28 Mi to Portland!
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
9.4 out of 10, Exceptional, (19)
"Great location!"
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
Dog-friendly home with deck, pool table, & firepit - walk to downtown Boothbay
9.6 out of 10, Exceptional, (26)
"We had a great stay! Close to town and had everything we needed here. Thank you!"
Dog-friendly home with deck, pool table, & firepit - walk to downtown Boothbay
Exterior
Cute Maine Cottage: Woods & Water View
10.0 out of 10, Exceptional, (1)
"Our stay at this beautiful home in Georgetown, Maine was perfect. From the moment we arrived, we were captivated by the views that surrounded us. The property was clean and well-maintained. It was the perfect spot for relaxing and enjoying some quality time with the family. The host went above and beyond to ensure our stay was comfortable and enjoyable, providing clear instructions and recommendations for things to do and places to see in the area. Their hospitality, attention to detail, and...
Cute Maine Cottage: Woods & Water View
Living area
Oceanside escape 🌊 perfect family getaway!
10.0 out of 10, Exceptional, (5)
"Very cute house to rent. Bed options were plentiful. Everything you need. Easy to get to town or local shopping. Nice biking around from here. Local bus route too. Host was a great communicator. Highly recommend!!"
The price is AED 845
AED 1,557 total
includes taxes & fees
4 Jun - 5 Jun
Oceanside escape 🌊 perfect family getaway!
Private kitchen
Beautiful 3BR Home with Office in Town of Brunswick with King beds
The price is AED 735
AED 1,601 total
includes taxes & fees
26 May - 27 May
Beautiful 3BR Home with Office in Town of Brunswick with King beds
 A cruise ship goes by at sunset
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (99)
"Lovely home in a beautiful location. Very welcoming, cozy, and friendly. Easy check-in and check-out process. The owner was very accommodating and helpful. Made amazing memories and look forward to returning soon. Thank you so much!"
Charming 110-year former Inn 10' from the Ocean!
Property grounds
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.4 out of 10, Exceptional, (23)
"This property was perfect for our group of 10 girls!!! It was much bigger than I was even anticipating, beautiful home and very clean. *Very* safe and nice neighborhood, which was incredibly important for us girls. The hot tub was the best part and the fireplace was great too. No complaints with our stay at all, though I wish it was a walking distance to downtown. It was about a 10 minute car ride so we ubered for our stay which worked out pretty good and was still cheap! The host lives upstairs...
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Living area
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
10.0 out of 10, Exceptional, (52)
"Artfully decorated and located walking distance to restaurants and parks. This was the perfect place for me and friends to visit around the table, watch a hockey game on TV, walk to restaurants, heat up take out, and was close to site seeing museums and light houses. The host was quickly available for suggestions. Check in and out was simple."
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
Don't see what you're looking for?
See all available properties in Bailey Island
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.

Other property types in Bailey Island

THE GILLS GROUP has two additional cottages available for larger groups
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
10.0 out of 10, Exceptional, (94)
"We celebrated our Mom’s 70th birthday in this beautiful space. It exceeded our expectations and the property manager David is the best!"
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Interior
Completely remodeled 2 bedroom apartment in Portland's West End
10.0 out of 10, Exceptional, (35)
"We very much enjoyed our stay at this location. The stairs were a bit scary, but with the light on, you'll be fine. :) Cozy spot for the three of us, well appointed and in a fantastic area. Very walkable, even down to the wharf. We are from a very non-walkable area, so it was amazing to see all the activity and places we could go just walking a bit. We enjoyed our first time in Maine, and can't wait to get back for a longer trip. Thanks to the hosts!"
The price is AED 841
AED 1,682 total
includes taxes & fees
13 Jun - 14 Jun
Completely remodeled 2 bedroom apartment in Portland's West End
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.

Recent reviews of Bailey Island hotels
Expedia verified reviews