Photo by The Maine Way of Life

Orrs Island Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Vacation Rentals in Orrs Island

Downtown Boothbay Harbor, 2-Story Cottage

9.4 out of 10, Exceptional, (17)
"Loved how walkable this property is! "
The price is ¥21,967
¥45,638 total
includes taxes & fees
Aug 10 - Aug 11
Downtown Boothbay Harbor, 2-Story Cottage

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 ¥58,972
¥107,347 total
includes taxes & fees
Jul 20 - Jul 21
Downtown Boothbay Harbor, The Francis Greene House

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 ¥34,985
¥45,494 total
includes taxes & fees
Jul 21 - Jul 22
Greenleaf Inn Room 4 – Gorgeously Renovated Corner King w/ Harbor & Island Views!

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 ¥39,010
¥50,704 total
includes taxes & fees
Jul 17 - Jul 18
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!

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 ¥44,428
¥57,335 total
includes taxes & fees
Jul 20 - Jul 21
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!

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 ¥37,307
¥48,450 total
includes taxes & fees
Jul 21 - Jul 22
Boothbay Harbor King Suite - Room 1 at Greenleaf Inn - Balcony, Harbor Views!

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 ¥43,035
¥55,755 total
includes taxes & fees
Jul 15 - Jul 16
Greenleaf Inn Room 6 | Private Entry Executive King Suite, Large Balcony, Harbor Views!

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 ¥55,574
¥72,076 total
includes taxes & fees
Jul 28 - Jul 29
Greenleaf Inn Penthouse King w/ Panoramic Ocean views off Rooftop Deck

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

The price is ¥37,462
¥48,625 total
includes taxes & fees
Jul 15 - Jul 16
Boothbay Harbor 2 Room King Suite - Room 2 at Greenleaf Inn - Balcony, Harbor Views, 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 ¥42,570
¥55,227 total
includes taxes & fees
Jul 16 - Jul 17
Room 14 at Admiral's Quarters Penthouse | Stunning Views + King Bed + Trundle

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 ¥39,474
¥51,232 total
includes taxes & fees
Jul 17 - Jul 18
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

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 ¥38,700
¥50,192 total
includes taxes & fees
Jul 15 - Jul 16
Boothbay Harbor King Suite – Room 11 at Admiral's Quarters Inn

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 ¥44,738
¥58,010 total
includes taxes & fees
Jul 15 - Jul 16
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!

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 ¥39,629
¥51,407 total
includes taxes & fees
Jul 21 - Jul 22
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

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 ¥47,834
¥62,166 total
includes taxes & fees
Jul 25 - Jul 26
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

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 ¥58,051
¥74,888 total
includes taxes & fees
Aug 7 - Aug 8
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

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 ¥59,171
¥85,089 total
includes taxes & fees
Jul 14 - Jul 15
Premium Family Suite - 2 Double Beds, 1 King Bed

More then a Motel With Garden , Renovated Rooms at heart of Boothbay

2.0 star property
8.0 out of 10, Very Good, (2)
"clean, affordable accomadations. Manager helpful and responsive"
The price is ¥49,094
¥66,690 total
includes taxes & fees
Jul 14 - Jul 15
More then a Motel With Garden , Renovated Rooms at heart of Boothbay

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

The price is ¥17,102
¥26,837 total
includes taxes & fees
Jul 19 - Jul 20
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

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 ¥17,544
¥52,921 total
includes taxes & fees
Jul 16 - Jul 17
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome
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.
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

Can I find vacation rentals in Orrs Island?

Yes, there are vacation rentals in Orrs Island close to Paddleworks, or you can go with a more secluded option if you want a relaxing stay. Orrs Island is known for its ski areas and mountain views. Make sure you have time to check out the seafood restaurants while you're in the area.

What are some of the best vacation home rentals that Orrs Island has to offer?

Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun: This vacation home rental outside of Orrs Island is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals will I find in Orrs Island?

Expedia has 17 vacation rentals for your stay in Orrs Island.

What’s there to see and do in Orrs Island?

Enjoy the area's cultural attractions such as Brunswick Naval Aviation Museum, or get outdoors into nature at a spot like Casco Bay. In the larger area, you’ll find Paddleworks and Bailey Island Bridge.

What’s a vacation rental in Orrs Island like?

Vacation rentals are private properties you can book for a few days or a quick weekend in Orrs Island. Vacation rentals feature amenities like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips.