Bailey Island Holiday Rentals

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Check prices for these dates

Tonight
11 Jul - 12 Jul
Tomorrow
12 Jul - 13 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Holiday Rentals in Bailey Island

Downtown Boothbay Harbor, 2-Story Cottage
Exterior

Downtown Boothbay Harbor, 2-Story Cottage

9.4 out of 10, Exceptional, (17)
"Loved how walkable this property is! "
The price is HK$1,170
HK$2,430 total
includes taxes & fees
10 Aug - 11 Aug
Downtown Boothbay Harbor, 2-Story Cottage
Downtown Boothbay Harbor, The Francis Greene House
Fridge, microwave, oven, stovetop

Downtown Boothbay Harbor, The Francis Greene House

9.4 out of 10, Exceptional, (41)
"We had a blast, home was just the local place we needed for our weekend! Home was beautiful and nice and clean! Would love to stay again!"
The price is HK$3,140
HK$5,767 total
includes taxes & fees
27 Jul - 28 Jul
Downtown Boothbay Harbor, The Francis Greene House
Greenleaf Inn Room 4 – Gorgeously Renovated Corner King w/ Harbor & Island Views!
Property grounds

Greenleaf Inn Room 4 – Gorgeously Renovated Corner King w/ Harbor & Island Views!

2.5 star property
10.0 out of 10, Exceptional, (2)
"As soon as we got there we felt welcome. John was amazing, showing us around the whole property & explaining all that was offered. We got there late & had not had a chance to eat so we asked him if there was any suggestions. He immediately got on the phone & got us a reservation for the Thistle Inn. He was amazing & could not do enough for us, including bringing us pastries every morning & having campfires at night so that we could get to know the other guests staying at the inn.The room was...
The price is HK$1,797
HK$2,330 total
includes taxes & fees
13 Jul - 14 Jul
Greenleaf Inn Room 4 – Gorgeously Renovated Corner King w/ Harbor & Island Views!
Greenleaf Inn 3 - Gorgeously Renovated King Suite, Large Bath, Balcony, Harbor Views!
Property grounds

Greenleaf Inn 3 - Gorgeously Renovated King Suite, Large Bath, Balcony, Harbor Views!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Our host did a tremendous job making us feel welcome. "
The price is HK$2,085
HK$2,709 total
includes taxes & fees
17 Jul - 18 Jul
Greenleaf Inn 3 - Gorgeously Renovated King Suite, Large Bath, Balcony, Harbor Views!
Greenleaf Inn 5 - Alyson's Room - Main House King, Ocean views, Large Bath!
Property grounds

Greenleaf Inn 5 - Alyson's Room - Main House King, Ocean views, Large Bath!

2.5 star property
10.0 out of 10, Exceptional, (1)
"This was one of our very favorite places we have visited. The Greenleaf Inn was perfect and we lacked for nothing. Make sure you relax on the roof top deck with a coffee or glass of wine!"
The price is HK$2,366
HK$3,053 total
includes taxes & fees
20 Jul - 21 Jul
Greenleaf Inn 5 - Alyson's Room - Main House King, Ocean views, Large Bath!
Boothbay Harbor King Suite - Room 1 at Greenleaf Inn - Balcony, Harbor Views!
1 bedroom, iron/ironing board, free WiFi, bed sheets

Boothbay Harbor King Suite - Room 1 at Greenleaf Inn - Balcony, Harbor Views!

8.0 out of 10, Very good, (2)
"The property was on a great location and the service was excellent! We will definitely stay here again!"
The price is HK$1,986
HK$2,580 total
includes taxes & fees
13 Jul - 14 Jul
Boothbay Harbor King Suite - Room 1 at Greenleaf Inn - Balcony, Harbor Views!
Greenleaf Inn Penthouse King w/ Panoramic Ocean views off Rooftop Deck
Property grounds

Greenleaf Inn Penthouse King w/ Panoramic Ocean views off Rooftop Deck

10.0 out of 10, Exceptional, (2)
"Great room. Friendly staff. Ocean views. Had a fantastic weekend!"
The price is HK$2,827
HK$3,671 total
includes taxes & fees
28 Jul - 29 Jul
Greenleaf Inn Penthouse King w/ Panoramic Ocean views off Rooftop Deck
Greenleaf Inn Room 6 | Private Entry Executive King Suite, Large Balcony, Harbor Views!
Outdoor dining

Greenleaf Inn Room 6 | Private Entry Executive King Suite, Large Balcony, Harbor Views!

10.0 out of 10, Exceptional, (3)
"Greenleaf Inn was a great place to stay. Staff was friendly and checked on needs of the people staying. We had room 6 which had a good view of the harbor. It overlooked Tugboat Restaurant and was a short walk to the stores downtown and the harbor. Food was delicious anywhere we went. Recommended.Thanks"
The price is HK$2,357
HK$3,052 total
includes taxes & fees
22 Jul - 23 Jul
Greenleaf Inn Room 6 | Private Entry Executive King Suite, Large Balcony, Harbor Views!
Boothbay Harbor 2 Room King Suite - Room 2 at Greenleaf Inn - Balcony, Harbor Views, Fireplace
Property grounds

Boothbay Harbor 2 Room King Suite - Room 2 at Greenleaf Inn - Balcony, Harbor Views, Fireplace

The price is HK$2,019
HK$2,626 total
includes taxes & fees
27 Jul - 28 Jul
Boothbay Harbor 2 Room King Suite - Room 2 at Greenleaf Inn - Balcony, Harbor Views, Fireplace
The legendary Admirals Suite! Boothbay Harbor 2-Room King Suite w/ Bedroom and study
Smart TV, fireplace

The legendary Admirals Suite! Boothbay Harbor 2-Room King Suite w/ Bedroom and study

10.0 out of 10, Exceptional, (1)
"The property was beautiful with a great location. Very inviting."
The price is HK$2,151
HK$2,792 total
includes taxes & fees
14 Jul - 15 Jul
The legendary Admirals Suite! Boothbay Harbor 2-Room King Suite w/ Bedroom and study
Boothbay Harbor King Suite – Room 11 at Admiral's Quarters Inn
Smart TV, fireplace

Boothbay Harbor King Suite – Room 11 at Admiral's Quarters Inn

10.0 out of 10, Exceptional, (3)
"We loved being in the heart of the bay. Jersey was a fabulous host who served me a delicious breakfast in the solarium overlooking the bay. The full kitchen with snacks on hand was nice. We enjoyed relaxing at the end of the day by the fire pit. We're so glad that we found this gem in Boothbay Harbor. "
The price is HK$2,061
HK$2,672 total
includes taxes & fees
15 Jul - 16 Jul
Boothbay Harbor King Suite – Room 11 at Admiral's Quarters Inn
Room 14 at Admiral's Quarters Penthouse | Stunning Views + King Bed + Trundle
Smart TV, fireplace

Room 14 at Admiral's Quarters Penthouse | Stunning Views + King Bed + Trundle

10.0 out of 10, Exceptional, (2)
"Great location. Very nice room. Jersey (manager) was very helpful. "
The price is HK$2,382
HK$3,097 total
includes taxes & fees
13 Jul - 14 Jul
Room 14 at Admiral's Quarters Penthouse | Stunning Views + King Bed + Trundle
Room 15 at Admiral's Quarters Penthouse | Stunning Views + King Bed + Trundle
Smart TV, fireplace

Room 15 at Admiral's Quarters Penthouse | Stunning Views + King Bed + Trundle

10.0 out of 10, Exceptional, (2)
"We loved this property. The views from the premium suites were unbelievable. Property also has shared space that includes a well-stocked, full kitchen (with breakfast food and coffee/nespresso provided), sun room, and outdoor patio. We would definitely stay here again."
The price is HK$2,415
HK$3,126 total
includes taxes & fees
15 Jul - 16 Jul
Room 15 at Admiral's Quarters Penthouse | Stunning Views + King Bed + Trundle
Boothbay Harbors Garden Suite - Admiral's Quarters Room 9 - Fireplace & Stunning Harbor Views!
Smart TV, fireplace

Boothbay Harbors Garden Suite - Admiral's Quarters Room 9 - Fireplace & Stunning Harbor Views!

10.0 out of 10, Exceptional, (1)
"The greenleaf/admirals quarters was fantasic! John, was an unbelievable host. He made sure to give us a tour of the whole property, as well as made us feel welcome with an abundance of complementary items to include food and drink, as well as a bonfire at dusk with s’mores. All around fantastic experience. The room was extremely clean and comfortable and the whole place seems to have had brand new renovation. 100% recommend."
The price is HK$2,118
HK$2,755 total
includes taxes & fees
21 Jul - 22 Jul
Boothbay Harbors Garden Suite - Admiral's Quarters Room 9 - Fireplace & Stunning Harbor Views!
Admiral's Quarters Room 13 - PREMIER Ocean View 2 Room King Suite w/ Living Room, Fireplace, Patio
Smart TV, fireplace

Admiral's Quarters Room 13 - PREMIER Ocean View 2 Room King Suite w/ Living Room, Fireplace, Patio

10.0 out of 10, Exceptional, (1)
"The location of the property was awesome, with beautiful Harbor views. The room we stayed in was very clean and a very comfortable size with once again great views. The amenities on the property were much better than we've experienced elsewhere. Kitchen/ eating area and the solarium were large and well stocked.As per most of the reviews you cant leave out "Jersey", who checks you in and runs the place basically. Super nice guy and very accommodating. Great sense of humor and makes everyone feel...
The price is HK$2,563
HK$3,329 total
includes taxes & fees
25 Jul - 26 Jul
Admiral's Quarters Room 13 - PREMIER Ocean View 2 Room King Suite w/ Living Room, Fireplace, Patio
2-Story Harbor View Suite King and Queen w/ 3 Balconies | Admiral's Quarters Inn Room 12
Smart TV, fireplace

2-Story Harbor View Suite King and Queen w/ 3 Balconies | Admiral's Quarters Inn Room 12

9.2 out of 10, Wonderful, (7)
"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 HK$3,214
HK$4,145 total
includes taxes & fees
7 Aug - 8 Aug
2-Story Harbor View Suite King and Queen w/ 3 Balconies | Admiral's Quarters Inn Room 12
Premium Family Suite - 2 Double Beds, 1 King Bed
A heated pool

Premium Family Suite - 2 Double Beds, 1 King Bed

5.0 out of 10, (2)
"Location is close to what we wanted (botanical gardens and Boothbay Harbor shops). The plusses were free breakfast, nice trails connected to property, icecream across the street. The minuses were the pool/hot tub not open as expected,our room was not deep cleaned."
The price is HK$3,150
HK$4,530 total
includes taxes & fees
13 Jul - 14 Jul
Premium Family Suite - 2 Double Beds, 1 King Bed
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome
Property grounds

Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome

9.0 out of 10, Wonderful, (60)
"We stayed in October when the trees were gorgeous and the dome house is nestled in a wooded area. So pretty! Lots of room for everyone. Wish we could have stayed longer."
The price is HK$1,091
HK$3,025 total
includes taxes & fees
16 Jul - 17 Jul
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome
Cozy home on Georgetown Island off the coast of Maine
Exterior

Cozy home on Georgetown Island off the coast of Maine

10.0 out of 10, Exceptional, (55)
"Great location, clean, great commutation. Bonus: Lots of toys my 4 year old loved to play with during our stay. 😆"
The price is HK$4,394
HK$7,913 total
includes taxes & fees
18 Jul - 19 Jul
Cozy home on Georgetown Island off the coast of Maine
Escape to Positive Outlook
Dining

Escape to Positive Outlook

The price is HK$1,648
HK$2,719 total
includes taxes & fees
13 Jul - 14 Jul
Escape to Positive Outlook
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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Frequently asked questions

Can I find a holiday rental in Bailey Island?

Yes, there are holiday rentals in Bailey Island close to Land's End Gift Shop, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Bailey Island has to offer?

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This highly rated holiday home rental in Bailey Island is located on the beach, and has a patio, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Bailey Island?

With 26 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Bailey Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Bailey Island. Holiday rentals feature amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips or small group gatherings.