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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Orrs Island vacation rentals

A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

1. Sunset Hideaway on Bailey Island

Sunset Hideaway on Bailey Island
Harpswell
9.0 out of 10, Wonderful, (7 reviews)
"Wonderful views. Comfortable. "
United States
Susy K.
$220 nightly
The price is $223
Oct 19 - Oct 20
Total with taxes and fees
Sunset Hideaway on Bailey Island
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

2. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (13 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
$432 nightly
The price is $437
Oct 27 - Oct 28
Total with taxes and fees
Orchid Harbor, Bailey Island 3BR
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

3. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 reviews)
$203 nightly
The price is $215
Nov 1 - Nov 2
Total with taxes and fees
Mid Coast Getaway w/ water views
A lakeside property with a deck, picnic table, and barbecue grill.

4. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (71 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
$336 nightly
The price is $366
Oct 14 - Oct 15
Total with taxes and fees
Camp Forever cottage
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.

5. 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.
$227 nightly
The price is $241
Nov 1 - Nov 2
Total with taxes and fees
2 bedroom w/ expansive water views
A covered porch with a view of a lake and trees.

6. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
$469 nightly
The price is $474
Oct 25 - Oct 26
Total with taxes and fees
Mere Point Sunrise Views at Eastern Shore!
A bedroom with a bed, a skylight, a window with curtains, and two framed pictures on the wall.

7. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (74 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
$339 nightly
The price is $369
Oct 14 - Oct 15
Total with taxes and fees
Full sized home
A two-story house with a covered porch, a garage, and a front yard with potted plants.

8. 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, (174 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
$115 nightly
The price is $125
Nov 3 - Nov 4
Total with taxes and fees
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.

9. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
$213 nightly
The price is $214
Oct 19 - Oct 20
Total with taxes and fees
Captains Watch: A Coastal Escape
A treehouse with a wooden staircase and a small building with a colorful mural.

10. 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
$163 nightly
The price is $177
Oct 16 - Oct 17
Total with taxes and fees
Perfect stopover, getaway, base to explore the area, or to simply stay in town.
A stone fireplace with a TV mounted above it, a wooden mantel, and a hanging light fixture.

11. The Outlet Studio, Rustic Comfort w Fireplace

The Outlet Studio, Rustic Comfort w Fireplace
Freeport
10.0 out of 10, Exceptional, (15 reviews)
"Cottage is just as described. Great place to stay for a few nights to explore the area.Easy walk to Outlets and Restaurants."
United States
Joanne H.
The Outlet Studio, Rustic Comfort w Fireplace
A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

12. 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.
$208 nightly
The price is $210
Oct 28 - Oct 29
Total with taxes and fees
Fantastic Waterfront Views
A wooden deck with a view of a lake, surrounded by trees and shrubs.

13. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (74 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
$438 nightly
The price is $477
Oct 14 - Oct 15
Total with taxes and fees
Centerview cottage
A wooden house with a deck and a stone pathway leading to a grassy area.

14. 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.
$319 nightly
The price is $341
Oct 20 - Oct 21
Total with taxes and fees
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.

15. 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
$297 nightly
The price is $324
Oct 20 - Oct 21
Total with taxes and fees
1 Mi to Maine Street! Mcm-style Home in Brunswick
A wooden staircase with a wooden railing, surrounded by green foliage.

16. 1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!

1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
Bath
8.2 out of 10, Very good, (21 reviews)
"Cute but aging small space, Near attractions"
United States
michael
$164 nightly
The price is $179
Oct 14 - Oct 15
Total with taxes and fees
1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

17. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (13 reviews)
"All we could say was wow! Words cannot express the view from this house! It looked like a picture! Beautiful view, fully loaded kitchen, spacious, comfortable beds, everything was perfect. I have the worst cell service and I couldn’t get the app to work but David answered my call right away and helped us get in. I’d highly recommend this property and we can’t wait to come back!"
United States
Michael L.
$825 nightly
The price is $899
Nov 4 - Nov 5
Total with taxes and fees
Three bedroom in United States of America, Freeport
A narrow hallway with a window on the right, leading to a room with a visible door.

18. Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
9.8 out of 10, Exceptional, (13 reviews)
"Great location! We spent very little time in the room, but it was a great place to come back and crash! "
United States
Kristina M.
$203 nightly
The price is $221
Oct 18 - Oct 19
Total with taxes and fees
Modern style in historic building in downtown Bath
A modern kitchen with white cabinets, a wooden dining table, and a vase with green leaves.

19. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (19 reviews)
"Perfect for a my husband and I. Close to everything!"
United States
Tabcline S.
$267 nightly
The price is $270
Nov 2 - Nov 3
Total with taxes and fees
King Size Sun Rise Midcoast Lovely Stay
A spacious kitchen with a large island, bar stools, and a dining area with a sofa.

20. King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer

King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer
Topsham
9.6 out of 10, Exceptional, (7 reviews)
"Perfect place and location for visiting Bowdoin."
United States
Kristen S.
$307 nightly
The price is $310
Oct 28 - Oct 29
Total with taxes and fees
King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer
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

Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

8/10 Good
"The room was clean & staff was very friendly & helpful"
Sue 1-night trip
Posted 1 hour ago
Quality Inn & Suites South Portland

Find out more about Orrs Island

Everything you need to know about Orrs Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Orrs Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Orrs Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Orrs Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Orrs Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Orrs Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $111 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Orrs Island rentals

At Expedia, we put the best Orrs Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Orrs Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Orrs Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Orrs Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.