An aerial view of a river with a series of floating docks and a small island with trees.

Orrs Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Orrs Island vacation rentals

A wooden deck with outdoor seating and string lights.

1. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (71 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is CA $289
CA $518 total
includes taxes & fees
Oct 14 - Oct 15
Full sized home
A lakeside property with a deck, picnic table, and barbecue grill.

2. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (70 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is CA $299
CA $520 total
includes taxes & fees
Oct 15 - Oct 16
Camp Forever cottage
A wooden deck with a view of a lake, surrounded by trees and shrubs.

3. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (73 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
The price is CA $420
CA $683 total
includes taxes & fees
Oct 15 - Oct 16
Centerview cottage
A two-story house with a covered porch, a garage, and a front yard with potted plants.

4. Large suite/private bath/private entrance on quiet street near Thomas Bay

Large suite/private bath/private entrance on quiet street near Thomas Bay
Brunswick
10.0 out of 10, Exceptional, (172 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
The price is CA $135
CA $179 total
includes taxes & fees
Nov 3 - Nov 4
Large suite/private bath/private entrance on quiet street near Thomas Bay
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

5. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
The price is CA $235
CA $266 total
includes taxes & fees
Oct 7 - Oct 8
Captains Watch: A Coastal Escape
A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

6. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (12 reviews)
The price is CA $633
CA $1,410 total
includes taxes & fees
Nov 5 - Nov 6
Three bedroom in United States of America, Freeport
A multi-story building with a stone facade, large windows, and a corner entrance.

7. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (14 reviews)
"This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class."
United States
Rick
The price is CA $497
CA $756 total
includes taxes & fees
Nov 3 - Nov 4
Evalina Hotel
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

8. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (123 reviews)
"Really nice room and location"
United States
Victoria
The price is CA $290
CA $424 total
includes taxes & fees
Nov 2 - Nov 3
The Weldon Hotel
A covered porch with a view of a lake and trees.

9. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
The price is CA $250
CA $613 total
includes taxes & fees
Oct 13 - Oct 14
Mere Point Sunrise Views at Eastern Shore!
A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

10. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (20 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is CA $262
CA $301 total
includes taxes & fees
Oct 25 - Oct 26
Fantastic Waterfront Views
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

11. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is CA $150
CA $306 total
includes taxes & fees
Nov 1 - Nov 2
Mid Coast Getaway w/ water views
A spacious room with a wooden floor, a dining area with chairs and a table, a sofa, a TV, and a balcony with a view of the sea.

12. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (5 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is CA $180
CA $346 total
includes taxes & fees
Nov 1 - Nov 2
2 bedroom w/ expansive water views
A wooden house with a deck and a stone pathway leading to a grassy area.

13. Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
Freeport
10.0 out of 10, Exceptional, (18 reviews)
"Hosts were very responsive with messages. The stay was clean and comfortable."
United States
Hana L.
The price is CA $152
CA $321 total
includes taxes & fees
Oct 20 - Oct 21
Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
A spacious living room with large windows, a sofa, a chair, and a small table.

14. 1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is CA $214
CA $461 total
includes taxes & fees
Oct 20 - Oct 21
1 Mi to Maine Street! Mcm-style Home in Brunswick
A modern kitchen with white cabinets, a wooden dining table, and a vase with green leaves.

15. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (18 reviews)
"Perfect for a my husband and I. Close to everything!"
United States
Tabcline S.
The price is CA $178
CA $367 total
includes taxes & fees
Oct 7 - Oct 8
King Size Sun Rise Midcoast Lovely Stay
A cabin with two chairs facing a fire pit, surrounded by trees.

16. Modern cabin w/ full bath & kitchenette - 03

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (8 reviews)
"Easy check in process. More than clean, it looked brand new. Overall a great stay. Kitchen was well stocked with plates, utensils, and cookware. "
United States
Michael H.
The price is CA $344
CA $549 total
includes taxes & fees
Oct 8 - Oct 9
Modern cabin w/ full bath & kitchenette - 03
A hallway with a large, rustic mirror leaning against the wall, a potted plant in the foreground, and a glimpse of a bed with a yellow blanket in the background.

17. Lush Coastal Downtown Home - Beaches & Shopping

Lush Coastal Downtown Home - Beaches & Shopping
Freeport
10.0 out of 10, Exceptional, (6 reviews)
"Our stay was very comfortable and easy to navigate. The host was very communicative. We had everything we needed and more. It was nice to be in walking distance from downtown Freeport. Although the price was higher than we wanted, our family of four (2 teens) enjoyed having a clean, comfortable and seamless stay."
United States
Alana K.
The price is CA $488
CA $860 total
includes taxes & fees
Oct 7 - Oct 8
Lush Coastal Downtown Home - Beaches & Shopping
A modern kitchen with white cabinetry, a central island with stools, a refrigerator, and a microwave.

18. Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Brunswick
9.6 out of 10, Exceptional, (34 reviews)
"Perfect for what we needed for the week. All that was missing was some oven mitts and maybe a pair of scissors but we made it work!! Great little spot - thank you!! "
United States
Britta M.
The price is CA $257
CA $581 total
includes taxes & fees
Nov 2 - Nov 3
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
A geodesic dome structure in a forest setting with a visible interior space.

19. Modern dome w/ full bath + spa access - 04

Modern dome w/ full bath + spa access - 04
Freeport
10.0 out of 10, Exceptional, (5 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
The price is CA $270
CA $476 total
includes taxes & fees
Oct 7 - Oct 8
Modern dome w/ full bath + spa access - 04
A treehouse with a wooden staircase and a small building with a colorful mural.

20. Perfect stopover, getaway, base to explore the area, or to simply stay in town.

Perfect stopover, getaway, base to explore the area, or to simply stay in town.
Bath
8.0 out of 10, Very good, (31 reviews)
"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"
United States
Esther
The price is CA $159
CA $251 total
includes taxes & fees
Oct 7 - Oct 8
Perfect stopover, getaway, base to explore the area, or to simply stay in town.
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 Orrs Island Hotel Reviews

Inn at St John Portland In-Town

Inn at St John Portland In-Town

8/10 Good
"The inn itself was beautifully kept. The water pressure was great. There was plenty of hot water except very early in the morning (before 6am). I didn’t walk in the area but if I had too, I wouldn’t feel comfortable in the evening. There was parking behind the hotel and I was lucky to get a spot both nights that I was there otherwise you would have to park in their other lot somewhere around the corner. They had lemon water, fruit, cookies, tea and coffee out all the time. The included breakfast was just an easy grab a toasted bagel and go. Nothing special but it was a nice offer. The beds were soft, the AC worked well and our room was very large. Our room was on the second floor, no elevator and extremely steep steps, but staff was always available to help with bags or luggage. Overall, a very nice stay and less expensive than closer to town."
Jane 2-night trip
Posted less than an hour ago
Inn at St John Portland In-Town

Find out more about Orrs Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Orrs Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Orrs Island?

Yes, there are vacation rentals close to the most popular points of interest in Orrs Island, or you can select a more remote option if you're looking for 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?

Charming 110-year former Inn 10' from the Ocean!: This vacation home rental outside of Orrs Island is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

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?

Explore the area and family-friendly sights such as Maine Maritime Museum, or get out into nature at a spot like Casco Bay. In the larger area, you’ll find Bailey Island Bridge and Wolfe's Neck Woods State Park.

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.