Hot Bailey Island Cottage Rates

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

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!
Save an average of 15% on thousands of hotels when you're signed in
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
Located in Brunswick, this cottage is by the ocean, a 1-minute drive from Casco Bay and 5 minutes from Thomas Point Beach.
Waterfront Cottage
Cute 2+ Bedroom Cottage

Cute 2+ Bedroom Cottage

Portland
When you a stay at this cottage in Peaks Island, you'll be near the beach, within a 5-minute walk of Casco Bay and Richard Boyd Art Gallery.
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
This cottage is in the heart of Freeport, within a 10-minute walk of Casco Bay and LL Bean Flagship Store.
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
Don't see what you're looking for?
See all available properties in Bailey Island
View all properties
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$146
Highest Price
AU$352
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

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$237 per night from 26 May to 27 May
AU$237
includes taxes & fees
26 May - 27 May
With a stay at The Westin Portland Harborview, you'll be centrally located in Portland, steps from State Theatre and Portland Museum of Art.
The Westin Portland Harborview
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$352 per night from 4 May to 5 May
AU$352
includes taxes & fees
4 May - 5 May
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
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$146 per night from 30 Apr to 1 May
AU$146
includes taxes & fees
30 Apr - 1 May
With a stay at Clarion Hotel Portland in Portland, you'll be near the airport, within a 15-minute walk of Thompson's Point and Portland Exposition Building.
Clarion Hotel Portland
Save an average of 15% on thousands of hotels when you're signed in
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$300 per night from 30 Apr to 1 May
AU$300
includes taxes & fees
30 Apr - 1 May
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
Don't see what you're looking for?
See all available properties in Bailey Island
View all properties
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.