Hot Bailey Island Cottage Rates

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Featured Cottages in Bailey Island

Bayfront Cottage on Mill Cove w/ Private Dock & Furnished Deck - Walk Downtown

Bayfront Cottage on Mill Cove w/ Private Dock & Furnished Deck - Walk Downtown

Boothbay Harbor
Book a stay at this beach cottage in Boothbay Harbor. Enjoy a beach locale, patios, and an in-room coffeemaker. Popular attractions Boothbay Harbor Memorial ...
Bayfront Cottage on Mill Cove w/ Private Dock & Furnished Deck - Walk Downtown
Private Contemporary Artist's Tree House on two acres with perennial gardens.

Private Contemporary Artist's Tree House on two acres with perennial gardens.

Cape Elizabeth
Book a stay at this ski cottage in Cape Elizabeth. Enjoy free WiFi, a garden, and ski-in/ski-out access. Popular attractions Maine Mall and Goddard Mansion are ...
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Unique oceanfront home with a deck, tons of natural light, & amazing views

Unique oceanfront home with a deck, tons of natural light, & amazing views

Wiscasset
Book a stay at this beach cottage in Wiscasset. Enjoy a beach locale, a garden, and patios. Popular attractions Long Ledge and Brooks Point are located ...
Unique oceanfront home with a deck, tons of natural light, & amazing views
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Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe

Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe

Boothbay Harbor
Stay at this cottage in Boothbay Harbor. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Barrett Park and Boothbay Region Land Trust ...
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

Bailey Island
Stay at this cottage in Bailey Island. Enjoy a garden, patios, and in-room jetted tubs. Popular attractions Land's End Gift Shop and Casco Bay are located ...
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.

Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.

Bailey Island
Stay at this cottage in Bailey Island. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Land's End Gift Shop and Casco Bay are located ...
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Beaches, Boating, Cool Ocean Breezes, Trails & Incredible Views! Max 2 people.

Beaches, Boating, Cool Ocean Breezes, Trails & Incredible Views! Max 2 people.

Harpswell
Book a stay at this beach cottage in Harpswell. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Cobwork Bridge and Ash Cove Pottery are located ...
Beaches, Boating, Cool Ocean Breezes, Trails & Incredible Views! Max 2 people.
WATERFRONT ON HIGHLAND LAKE.  LESS THAN 30 MINUTES TO PORTLAND

WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND

WINDHAM
Stay at this cottage in Windham. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Maine Wildlife Park and MAGAN Trailhead are located ...
WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.

Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.

Harpswell
Stay at this cottage in Harpswell. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Thomas Point Beach and Brunswick Naval Aviation ...
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
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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.

Bailey Island Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Bailey Island will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Bailey Island definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Bailey Island, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Bailey Island Cottages essential information

Accommodation
143 Cottages
Lowest Price
NZ$133
Highest Price
NZ$301
Popular accommodation
Bayfront Cottage on Mill Cove w/ Private Dock & Furnished Deck - Walk Downtown, Private Contemporary Artist's Tree House on two acres with perennial gardens. , Unique oceanfront home with a deck, tons of natural light, & amazing views, Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe, PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room, Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island., Beaches, Boating, Cool Ocean Breezes, Trails & Incredible Views! Max 2 people., WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND, Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.

Top trending hotels in Bailey Island

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

Bailey Island
Stay at this cottage in Bailey Island. Enjoy a garden, patios, and in-room jetted tubs. Popular attractions Land's End Gift Shop and Casco Bay are located ...
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
La Quinta Inn & Suites by Wyndham Portland

La Quinta Inn & Suites by Wyndham Portland

2.5 out of 5
340 Park Ave, Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$156 per night from 5 Dec to 6 Dec
NZ$156
includes taxes & fees
5 Dec - 6 Dec
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
La Quinta Inn & Suites by Wyndham Portland
Casco Bay Hotel, Ascend Hotel Collection

Casco Bay Hotel, Ascend Hotel Collection

3.5 out of 5
80 John Roberts Rd., South Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$133 per night from 8 Dec to 9 Dec
NZ$133
includes taxes & fees
8 Dec - 9 Dec
Stay at this 3.5-star business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Casco Bay Hotel, Ascend Hotel Collection
Save an average of 15% on thousands of hotels when you're signed in
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$301 per night from 5 Dec to 6 Dec
NZ$301
includes taxes & fees
5 Dec - 6 Dec
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the ...
Portland Harbor Hotel
Don't see what you're looking for?
See all available properties in Bailey Island
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.