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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Browse Select Bailey Island Condo Rentals

Elegant condo - walk to Portland's best restaurants & Old Port
Fridge, microwave, oven, stovetop

Elegant condo - walk to Portland's best restaurants & Old Port

9.4 out of 10, Exceptional, (62)
"Right off a Main Street with tons of food and drink options. Loved the area, felt safe and fun. Close to walking trails as well. Inside decor was nice. "
The price is £324
includes taxes & fees
17 Aug - 18 Aug
Elegant condo - walk to Portland's best restaurants & Old Port
Walking Distance To Shops, Restaurants And Footbridge
Fridge, microwave, oven, stovetop

Walking Distance To Shops, Restaurants And Footbridge

10.0 out of 10, Exceptional, (39)
"This is a great place right downtown which makes for easy walking access. Would definitely stay again!"
Walking Distance To Shops, Restaurants And Footbridge
Charming 3-bedroom 3-bath condo with WiFi, in quaint Yarmouth
Property grounds

Charming 3-bedroom 3-bath condo with WiFi, in quaint Yarmouth

10.0 out of 10, Exceptional, (3)
"Beautiful place to stay. We are planning on doing this again next year. "
Charming 3-bedroom 3-bath condo with WiFi, in quaint Yarmouth
Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location
Outdoor dining

Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location

9.4 out of 10, Exceptional, (16)
"Loved the location, lots of activity but also very private and relaxing. Great place, everyone was really nice and friendly"
Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location
Cozy, Elegant and Bright 2 bed in the East End
Smart TV

Cozy, Elegant and Bright 2 bed in the East End

9.8 out of 10, Exceptional, (42)
"Excellent stay and location"
The price is £264
includes taxes & fees
7 Sept - 8 Sept
Cozy, Elegant and Bright 2 bed in the East End
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo
Exterior

Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo

10.0 out of 10, Exceptional, (15)
"We had a lovely weekend staying at this condo! It was clean, cozy, and the coffee bar was amazing! "
The price is £551
includes taxes & fees
17 Aug - 18 Aug
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo
Brand New Listing! 3 Bedrooms, all En Suite- Yellow Door Guesthouse
Fridge, microwave, oven, stovetop

Brand New Listing! 3 Bedrooms, all En Suite- Yellow Door Guesthouse

10.0 out of 10, Exceptional, (1)
"Magnificent find in Freeport! Every bedroom is an en suite, which is super-convenient. Decor is absolutely beautiful! It has a washer/dryer, BBQ grill, a porch out back and split units. The split units were whisper-quiet and allowed my relatives from Florida to be toasty at night while the rest of us enjoyed a cool night’s sleep. Jennifer, the host, was very kind, gracious, and accommodating. I look forward to more stays at this charming condo that felt more like a house."
Brand New Listing! 3 Bedrooms, all En Suite- Yellow Door Guesthouse
Centrally located off Back Cove, 2nd floor 4 bedroom, 2 Bath condo w/ deck
Exterior

Centrally located off Back Cove, 2nd floor 4 bedroom, 2 Bath condo w/ deck

2.0 star property
10.0 out of 10, Exceptional, (5)
"This place was perfect for our weekend getaway! The unit was huge with plenty of space for everyone. It was clean and nicely stocked, with easy access to downtown Portland. "
Centrally located off Back Cove, 2nd floor 4 bedroom, 2 Bath condo w/ deck
Waterfront Condo in Boothbay Harbor
Property grounds

Waterfront Condo in Boothbay Harbor

10.0 out of 10, Exceptional, (1)
"This home was fully stocked and organized. Beautiful view and a great location. Easy walk to restaurants and shops. Would stay again!!"
Waterfront Condo in Boothbay Harbor
City Amenities, Casco Bay Sunrises and Natural Beauty
Interior

City Amenities, Casco Bay Sunrises and Natural Beauty

9.8 out of 10, Exceptional, (112)
"While minutes away from the Old Port, our stay on Casco Bay allowed us to relax and unwind."
The price is £298
includes taxes & fees
14 Aug - 15 Aug
City Amenities, Casco Bay Sunrises and Natural Beauty
Elegant Oceanfront Condo with Stunning Harbor Views & Spectacular Sunsets
Fridge, microwave, oven, stovetop

Elegant Oceanfront Condo with Stunning Harbor Views & Spectacular Sunsets

2.0 star property
9.6 out of 10, Exceptional, (5)
"This was a great condo. We really enjoyed watching the action on the harbor from the covered deck. The furnishings and appliances were brand new. There was plenty of room for a group with the layout of the bedrooms. It was very convenient to have the restaurant in the same building and it was a short drive to downtown. Our only suggestions would be to add a coffeemaker and directions for the dishwasher and garbage removal.Also it would be helpful to explain the parking situation and that the...
Elegant Oceanfront Condo with Stunning Harbor Views & Spectacular Sunsets
Seabed @ The Offshore House
Outdoor dining

Seabed @ The Offshore House

10.0 out of 10, Exceptional, (12)
"This was a great place to stay that let me explore the area I wanted to."
Seabed @ The Offshore House
Penthouse Two Master Waterfront Suite with Rooftop
Property grounds

Penthouse Two Master Waterfront Suite with Rooftop

10.0 out of 10, Exceptional, (248)
"Enjoyed our 2nd stay..great location "
The price is £1,087
includes taxes & fees
25 Aug - 26 Aug
Penthouse Two Master Waterfront Suite with Rooftop
USM Area. Great location.
Living area

USM Area. Great location.

USM Area. Great location.
Renovated condo with prime West End location, 2 en suite bathrooms, & HGTV style
Fridge, microwave, oven, stovetop

Renovated condo with prime West End location, 2 en suite bathrooms, & HGTV style

9.8 out of 10, Exceptional, (41)
"Perfect two bedroom for us to stay in during our work event."
Renovated condo with prime West End location, 2 en suite bathrooms, & HGTV style
Spacious 4 bedroom luxury Condo
Exterior

Spacious 4 bedroom luxury Condo

10.0 out of 10, Exceptional, (32)
"A great place to stay minutes from downtown Freeport and a short ride to Portland. Had a great time visiting family and the house was perfect for our getaway! Very close to all the Freeport attractions but quiet enough to rest and relax!"
Spacious 4 bedroom luxury Condo
Waterfront Two Master Suite Penthouse with Rooftop
Exterior

Waterfront Two Master Suite Penthouse with Rooftop

10.0 out of 10, Exceptional, (183)
"My family and I enjoyed our stay at the Cornelia apartment and very much appreciate the cleanliness of the space and responsiveness of the hosts. "
The price is £1,051
includes taxes & fees
19 Aug - 20 Aug
Waterfront Two Master Suite Penthouse with Rooftop
Walk to Old Port ♦ West End Condo ♦ Parking
Microwave, oven, coffee/tea maker, cookware/dishes/utensils

Walk to Old Port ♦ West End Condo ♦ Parking

9.6 out of 10, Exceptional, (76)
"Cute place, close to old port! We brought our pup and she was happy as well. We would definitely stay there again! "
The price is £250
includes taxes & fees
3 Sept - 4 Sept
Walk to Old Port ♦ West End Condo ♦ Parking
The perfect seaside retreat overlooking scenic Mackerel Cove on Bailey Island
Outdoor dining

The perfect seaside retreat overlooking scenic Mackerel Cove on Bailey Island

9.8 out of 10, Exceptional, (21)
"We thoroughly enjoyed a long weekend on Bailey Island. The condo was clean and new, very nicely furnished. It was a quiet easy to access property, very good experience."
The perfect seaside retreat overlooking scenic Mackerel Cove on Bailey Island
Shipwright @ The Offshore House
Smart TV

Shipwright @ The Offshore House

9.4 out of 10, Exceptional, (11)
"Luv the area and the room location was great A few steps from Bets fish and chips short drive into town "
The price is £276
includes taxes & fees
18 Aug - 19 Aug
Shipwright @ The Offshore House
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

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

10/10 Excellent
"Great place "
Ruben 1-night trip
Posted 21 hours ago
Days Inn by Wyndham Airport/Maine Mall