Hot Bailey Island Cottage Rates

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Featured Cottages in Bailey Island

Popham Beach Direct Oceanfront Cottage Steps to the sand

Popham Beach Direct Oceanfront Cottage Steps to the sand

Phippsburg
When you a stay at this cottage in Phippsburg, you'll be on the beach, just steps from Casco Bay and Popham Beach State Park.
Popham Beach Direct Oceanfront Cottage Steps to the sand
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

Bailey Island
When you a stay at this cottage in Bailey Island, you'll be on the waterfront, just steps from Casco Bay and Land's End Gift Shop.
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Waterfront Log Cabin Private Community Beach. CLOSEST TO TOWN less 10 min walk!

Waterfront Log Cabin Private Community Beach. CLOSEST TO TOWN less 10 min walk!

Boothbay Harbor
With a stay at this cottage in Boothbay Harbor, you'll be on the waterfront, just a 1-minute walk from Linekin Bay and 5 minutes by foot from Barrett Park.
Waterfront Log Cabin Private Community Beach. CLOSEST TO TOWN less 10 min walk!
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Charming Cottage on the Great Pond in Boothbay Harbor, Maine

Charming Cottage on the Great Pond in Boothbay Harbor, Maine

Boothbay Harbor
Located in Boothbay Harbor, this cottage is within a 5-minute drive of Boothbay Harbor Marina and Burnt Island Living Lighthouse.
Charming Cottage on the Great Pond in Boothbay Harbor, Maine
Waterfront Cottage

Waterfront Cottage

Brunswick
With a stay at this cottage in Brunswick, you'll be on the waterfront, within a 10-minute drive of Bowdoin College and Casco Bay.
Waterfront Cottage
Cute 2+ Bedroom Cottage

Cute 2+ Bedroom Cottage

Portland
With a stay at this cottage in Peaks Island, you'll be near the beach, just a 1-minute walk from Casco Bay and 5 minutes by foot from Umbrella Cover Museum.
Cute 2+ Bedroom Cottage
Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More

Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More

Boothbay Harbor
With a stay at this cottage in Boothbay Harbor, you'll be by the sea, just a 4-minute walk from Linekin Bay and 14 minutes by foot from Barrett Park.
Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More
The Outlet House, Comfortable Cottage

The Outlet House, Comfortable Cottage

Freeport
With a stay at this cottage, you'll be centrally located in Freeport, a 2-minute drive from LL Bean Flagship Store and 14 minutes from Bowdoin College.
The Outlet House, Comfortable Cottage
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
When you stay at this cottage in Boothbay Harbor, you'll be on the beach, within a 10-minute walk of Boothbay Harbor Memorial Library and Burnt Island Living ...
Bayfront Cottage on Mill Cove w/ Private Dock & Furnished Deck - Walk Downtown
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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
179 Cottages
Lowest Price
AU$150
Highest Price
AU$315
Popular accommodation
Popham Beach Direct Oceanfront Cottage Steps to the sand, PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room, Waterfront Log Cabin Private Community Beach. CLOSEST TO TOWN less 10 min walk!, Charming Cottage on the Great Pond in Boothbay Harbor, Maine, Waterfront Cottage, Cute 2+ Bedroom Cottage, Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More, The Outlet House, Comfortable Cottage, Bayfront Cottage on Mill Cove w/ Private Dock & Furnished Deck - Walk Downtown

Top trending hotels in Bailey Island

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 AU$150 per night from 6 Apr to 7 Apr
AU$150
includes taxes & fees
6 Apr - 7 Apr
Located in Portland, La Quinta Inn & Suites by Wyndham Portland is a 5-minute walk from Portland Exposition Building and 5 minutes by foot from Hadlock ...
La Quinta Inn & Suites by Wyndham Portland
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 AU$315 per night from 6 Apr to 7 Apr
AU$315
includes taxes & fees
6 Apr - 7 Apr
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, a 5-minute drive from Thompson's Point and 9 minutes from Maine Mall.
Portland Harbor Hotel
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$266 per night from 13 Apr to 14 Apr
AU$266
includes taxes & fees
13 Apr - 14 Apr
Located in Portland (East Bayside), Cambria Hotel Portland Downtown-Old Port is within a 10-minute drive of Thompson's Point and Maine Mall.
Cambria Hotel Portland Downtown-Old Port
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Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
9 Center Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$269 per night from 20 Apr to 21 Apr
AU$269
includes taxes & fees
20 Apr - 21 Apr
With a stay at Canopy by Hilton Portland Waterfront in Portland (Downtown Portland), you'll be a 5-minute drive from Thompson's Point and 9 minutes from Maine ...
Canopy by Hilton Portland Waterfront
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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.

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^Subject to availability and chosen travel dates.