A rocky shoreline with a boat, a house, and a forest in the background.

Bailey Island Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Bailey 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, (8 reviews)
"The views from the home were amazing! The home was cozy and had everything we needed for our stay. The host was great with communication and quick to reply. We were very happy with our stay and are grateful for the ability to stay here."
United States
Elizabeth M.
$188 nightly
The price is $190
Nov 16 - Nov 17
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.
$396 nightly
The price is $398
Nov 16 - Nov 17
Total with taxes and fees
Orchid Harbor, Bailey Island 3BR
A modern kitchen with a large island, dark cabinetry, and a view of a lake.

3. Bird Watching Paradise @ Waterfront Harpswell with Private Deck

Bird Watching Paradise @ Waterfront Harpswell with Private Deck
Harpswell
10.0 out of 10, Exceptional, (3 reviews)
"Super location, very private, responsive host, lovely, clean. Very lucky to have been able to stay here!"
United States
Kate K.
$289 nightly
The price is $315
Nov 15 - Nov 16
Total with taxes and fees
Bird Watching Paradise @ Waterfront Harpswell with Private Deck
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

4. 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
$190 nightly
The price is $200
Nov 16 - Nov 17
Total with taxes and fees
Mid Coast Getaway w/ water views
A modern interior with a dining area, a living room, and a kitchen.

5. Studio Apartment in Freeport

Studio Apartment in Freeport
Freeport
10.0 out of 10, Exceptional, (4 reviews)
"The bed was the most comfortable I have ever slept on! Lovely large warm open room. I appreciated the coffee/tea options, and the condiments in the fridge. There was a white noise machine in the room though we did not use it."
United States
Susan S.
$142 nightly
The price is $149
Nov 16 - Nov 17
Total with taxes and fees
Studio Apartment in Freeport
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.

6. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
9.8 out of 10, Exceptional, (7 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.
$214 nightly
The price is $227
Nov 17 - Nov 18
Total with taxes and fees
2 bedroom w/ expansive water views
A covered porch with a view of a lake and trees.

7. 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.
$348 nightly
The price is $350
Nov 16 - Nov 17
Total with taxes and fees
Mere Point Sunrise Views at Eastern Shore!
A wooden deck with outdoor seating and string lights.

8. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (80 reviews)
"Great house! Enjoyed our stay very much. Comfortable, clean, and many nice extra touches i.e. games, books."
United States
Jill J.
$306 nightly
The price is $334
Nov 30 - Dec 1
Total with taxes and fees
Full sized home
A dining area with a wooden table and chairs, a red sofa, and a small round table with a decorative plate.

9. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
$330 nightly
The price is $342
Nov 13 - Nov 14
Total with taxes and fees
Quiet Spot in lovely Freeport neighborhood
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

10. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
8.8 out of 10, Excellent, (3 reviews)
"Such a beautiful stay!! My whole group wished we could have stayed longer. We plan to come back"
United States
Holly G.
$274 nightly
The price is $276
Nov 15 - Nov 16
Total with taxes and fees
Captains Watch: A Coastal Escape
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

11. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
United States
boodu
$423 nightly
The price is $461
Nov 13 - Nov 14
Total with taxes and fees
Fully Updated Airy Historic Home in South Freeport
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
9.4 out of 10, Exceptional, (24 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
$271 nightly
The price is $272
Nov 15 - Nov 16
Total with taxes and fees
Fantastic Waterfront Views
A bathroom with a freestanding bathtub, a wooden ladder, a window with a view of a building, and a painting on the wall.

13. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Classic New England Waterfront House Big Lawn Beautiful Sunrise
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay! "
United States
Ashma B.
$1,398 nightly
The price is $1,524
Nov 30 - Dec 1
Total with taxes and fees
Classic New England Waterfront House Big Lawn Beautiful Sunrise
A two-story house with a covered porch, a garage, and a front yard with potted plants.

14. 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, (176 reviews)
"This is a really lovely place to stay. Clean and very comfortable with lovely hosts."
United Kingdom
Lucinda
$107 nightly
The price is $117
Nov 22 - Nov 23
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Bay
A backyard with a wooden deck, a small staircase, and a wooden fence.

15. Great suburban location close to town!

Great suburban location close to town!
Deering Center
9.4 out of 10, Exceptional, (6 reviews)
"We were staying here for the sake of being able to see a show at Good Theater. The theater itself ended up being within walking distance, and same for a few different places to eat! This worked out great for our plans :)"
United States
Kaley
$68 nightly
The price is $68
Nov 16 - Nov 17
Total with taxes and fees
Great suburban location close to town!
A cabin with two chairs facing a fire pit, surrounded by trees.

16. Cabin w/ bath + kitchenette | Hot tub add-on - 03

Cabin w/ bath + kitchenette | Hot tub add-on - 03
Freeport
9.8 out of 10, Exceptional, (10 reviews)
"A lovely glamping facility with several different types of structure in a quiet, wooded area just a couple miles from downtown Freeport. They've built a beautiful spa with sauna, cold plunge, hot tub, and soaking pool, the unit we stayed in was bright and airy, had an outdoor fire pit. We stayed three nights, will definitely stop here again!"
United States
Kirt v.
$306 nightly
The price is $333
Nov 17 - Nov 18
Total with taxes and fees
Cabin w/ bath + kitchenette | Hot tub add-on - 03
A modern kitchen with white cabinets, a wooden dining table, and a vase with green leaves.

17. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (19 reviews)
"The place was clean, bright, and exactly as shown in the pictures. There were fresh towels (4), toiletries, dishsoap/dishwasher tablets, and an in window AC. The table and bed are both lovely and roomy for two people. Plenty of places to plug in devices. The Seadog brewery was walking distance and would recommend for dinner and a pint. Also enjoyed Dutchman's bagels and Baked on Main (marginally longer walk). We were really happy with our stay!"
United States
Stefanie M.
$210 nightly
The price is $212
Nov 15 - Nov 16
Total with taxes and fees
King Size Sun Rise Midcoast Lovely Stay
A living room with a sofa, a coffee table, a TV, a fireplace, and a kitchen area.

18. 1st FL Downtown Grand Brunswick

1st FL Downtown Grand Brunswick
Brunswick
10.0 out of 10, Exceptional, (2 reviews)
"Great location, one block off main street, 4 or 5 blocks from grocery store."
United States
william h.
$248 nightly
The price is $270
Nov 18 - Nov 19
Total with taxes and fees
1st FL Downtown Grand Brunswick
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a granite countertop.

19. Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Freeport
10.0 out of 10, Exceptional, (12 reviews)
"Our whole family was impressed by this house!"
United States
Gary B.
$594 nightly
The price is $647
Nov 23 - Nov 24
Total with taxes and fees
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
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, (8 reviews)
"Perfect place and location for visiting Bowdoin."
United States
Kristen S.
$237 nightly
The price is $239
Nov 16 - Nov 17
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 Bailey Island Hotel Reviews

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"We had a great stay!"
Aliza 1-night trip
Posted 7 hours ago
Portland Harbor Hotel

Find out more about Bailey Island

Everything you need to know about Bailey 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 Bailey 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 Bailey Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Bailey Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bailey 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 Bailey 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 $68 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 Bailey Island rentals

At Expedia, we put the best Bailey 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 Bailey 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 Bailey 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 Bailey 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 a vacation rental in Bailey Island?

Yes, we give you a choice of vacation rentals in Bailey Island near Land's End Gift Shop, or you can choose a secluded option if you're looking for extra privacy while you relax. 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 vacation rentals that Bailey Island has to offer?

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

How many vacation rentals are there in Bailey Island?

With 34 Expedia vacation rentals, you're sure to find just the right place for your Bailey Island stay.

What can I see and do in Bailey Island?

Mackerel Cove and Ragged Island 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 vacation rentals like in Bailey Island?

Vacation rentals are private properties you can reserve for several days or longer in Bailey Island. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a small group gathering.