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Check prices for these dates

Next weekend
14 Saf. - 16 Saf.
In two weeks
21 Saf. - 23 Saf.
In one month
7 Rab. I - 9 Rab. I
In two months
4 Rab. II - 6 Rab. II

Compare 422 Vacation Homes in Bailey Island with updated reviews, rates, and availability.

Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.
Newly renovated 3 bedroom, 2 bath bungalow.

Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.

10.0 out of 10, Exceptional, (70)
"One of our best stays at a vacation rental. Cosy, immaculate and well equipped house with everything needed for a comfortable family stay. A short walk into town is a bonus. "
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.
Oceanfront Cabin-Castle in Maine Woods
Fall View from Porch

Oceanfront Cabin-Castle in Maine Woods

9.8 out of 10, Exceptional, (12)
"Absolutely loved this property! My family and I enjoyed every minute of our stay! Listening to the waves crashing on the rocks, hanging out by the fire and just relaxing made for the perfect after Christmas getaway! I look forward to coming again! Highly recommend "
Oceanfront Cabin-Castle in Maine Woods
Charming 110-year former Inn 10' from the Ocean!
A cruise ship goes by at sunset

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (116)
"Stunning location. Dog friendly beach. Lighthouse in walking distance. "
Charming 110-year former Inn 10' from the Ocean!
The Globe House on Munjoy Hill - Walk to Breweries
Living area

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (74)
"The Globe House was a wonderful Plato spend a couple of days while exploring Portland. The house itself was immaculate and well appointed, with extra touches that put it a step above: the fresh scent from a diffuser welcomed us, a complimentary bottle of wine awaited us in the refrigerator, and luxe amenities like L’Occitane moisturizer were provided. Great location with easily walkable and excellent restaurants. Our hosts left a fabulous “guide to Portland” for us, with many of their favorite...
The Globe House on Munjoy Hill - Walk to Breweries
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Outdoor spa tub

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
Oceanfront home & guesthouse w/ incredible ocean views, deck & location

Oceanfront home & guesthouse w/ incredible ocean views, deck & location

9.6 out of 10, Exceptional, (65)
"We loved this place. Even better in person than the pictures. Gorgeous setting on Ocean Point in a quiet neighborhood. Very nicely appointed, it meets all your needs and when the thermostat acted up the property manager was quick to respond and provide space heaters until hvac could come the next morning. We highly recommend and will stay here again. "
Oceanfront home & guesthouse w/ incredible ocean views, deck & location
Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Dining Room Seating for ten, extra dining also available

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (68)
"Great house very comfortable and well appointed. Very roomy for our entire family. Nice to have en suite bathrooms with all the bedrooms. The host was very good with communication. Located on a busy road and the driveway is on a curve which made it a little challenging entering and exiting the property. "
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Beautiful, Spacious Home, minutes to the Old Port!
Private kitchen

Beautiful, Spacious Home, minutes to the Old Port!

10.0 out of 10, Exceptional, (1)
"We stayed for night with couples and friends. We had an amazing time and the place was so clean and exactly as described. "
The price is SAR 413
SAR 1,321 total
includes taxes & fees
5 Mar - 6 Mar
Beautiful, Spacious Home, minutes to the Old Port!
Charming ocean-view cottage just 10 minutes from downtown Freeport shops
Living area

Charming ocean-view cottage just 10 minutes from downtown Freeport shops

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a fantastic stay with our family (including our 3yo). The home was exactly as described/photos show, and the view is simply amazing. Everything worked as expected, and the kids toys were an added bonus. Great communication with the host, would happily stay here again!"
Charming ocean-view cottage just 10 minutes from downtown Freeport shops
The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor with private dock
View from the dock

The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor with private dock

10.0 out of 10, Exceptional, (5)
"Six of us stayed at Sea Eagle and enjoyed every minute of this well appointed and thoughtfully decorated house. If you are considering Boothbay, I highly recommend. The location can’t be beat, the house has everything you need to include comfy beds and nice linens, plenty of places to enjoy the company of others or enjoy some solitude. It really is a gem. We look forward to returning. "
The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor with private dock
Bayfront home with 270-degree views, large deck & porch - near Popham Beach

Bayfront home with 270-degree views, large deck & porch - near Popham Beach

8.2 out of 10, Very Good, (29)
"The house is beautiful, comfortable and was pristine when we checked in. Decks and screened porch are wonderful. The kids loved the 3rd floor bedroom space, and it was fabulous being so close to Popham Beach. Definitely recommend. Kitchen on 2nd floor ... so have some strong helpers to bring in groceries ;)"
Bayfront home with 270-degree views, large deck & porch - near Popham Beach
Breathtaking 35 Acre Private Oceanfront Compound with countless amenities!
Front Entry

Breathtaking 35 Acre Private Oceanfront Compound with countless amenities!

10.0 out of 10, Exceptional, (2)
"House was perfect for our family vacation and you could not ask for better hosts. We look forward to returning soon."
Breathtaking 35 Acre Private Oceanfront Compound with countless amenities!
Coastal Gathering House - Spacious 4-bedroom house close to Portland
Exterior

Coastal Gathering House - Spacious 4-bedroom house close to Portland

Coastal Gathering House - Spacious 4-bedroom house close to Portland
Luxury Carriage House a short stroll from town!
Private kitchen

Luxury Carriage House a short stroll from town!

2.0 star property
10.0 out of 10, Exceptional, (5)
"Amazing location and beautiful little property. Everything was immaculate and welcoming, and we felt so taken care of, down to the small touches like just the coffee we like! Communication was great and timely, too. We'll definitely be back next time we are in Maine!"
The price is SAR 1,497
SAR 2,277 total
includes taxes & fees
5 Feb - 6 Feb
Luxury Carriage House a short stroll from town!
Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun

Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun

5.6 out of 10, (5)
"The shared driveway was a challenge and the hike from the driveway to the house had was also a challenge. Additionally the window in one of the bathrooms did not work, the dishwasher was not secured and tilted when you put dishes in, one of the commodes ran constantly unless you jiggle. The kitchen garbage can is broken."
Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun
Cottage by the Sea - Steps to Crescent Beach, a Quick Drive to Portland
Living/Dining Room. We add an AC unit in the warmer months.

Cottage by the Sea - Steps to Crescent Beach, a Quick Drive to Portland

10.0 out of 10, Exceptional, (19)
"Our stay was memorable and so enjoyable. There were 5 of us, 4 adults and 1 child. The location is in a nice little neighborhood, only steps from Crescent Beach. We could sit on our deck and see the ocean and sleep by the sounds of the waves. This property has so much to offer with three bedrooms, one of which is downstairs for this older stair challenged lady. It has three parking spots and a lovely fenced yard for the kids to play in. The cottage was very clean and the owner has it stocked...
Cottage by the Sea - Steps to Crescent Beach, a Quick Drive to Portland
Beautiful house on the Harpswell Peninsula over looking Casco Bay
Exterior

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
Full sized home
Private kitchen

Full sized home

9.6 out of 10, Exceptional, (24)
"The house is very clean, and it's very well situated. There are plenty of room in and out. Will come again."
Full sized home
Entire Historic Home - Portland West End
Formal dining for 10-12

Entire Historic Home - Portland West End

10.0 out of 10, Exceptional, (1)
Entire Historic Home - Portland 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.
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Other property types in Bailey Island

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
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, (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
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Dining Room Seating for ten, extra dining also available

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (68)
"Great house very comfortable and well appointed. Very roomy for our entire family. Nice to have en suite bathrooms with all the bedrooms. The host was very good with communication. Located on a busy road and the driveway is on a curve which made it a little challenging entering and exiting the property. "
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
The Weldon Hotel
Front of property

The Weldon Hotel

4.0 star property
9.4 out of 10, Exceptional, (35)
"The full kitchen and appliances were perfect for my stay so that I did not have to eat out while I was there and save money "
The price is SAR 574
SAR 626 total
includes taxes & fees
23 Feb - 24 Feb
The Weldon Hotel
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.