Bailey Island Vacation Rentals

Name: A yurt in the trees. Close to Portland but close to nature. Treeyurt Maine
Address: Cumberland

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Vacation Rentals in Bailey Island

Full sized home

$250

per night

Jun 6 - Jun 7

With a stay at this vacation home in Harpswell, you'll be by the sea, just steps from Casco Bay and a 3-minute drive from Ash Cove Pottery.

Lakefront home with sunrise views, private dock, kayaks, paddle boards, WFH desk

With a stay at this vacation home in Windham, you'll be on the waterfront, within a 15-minute drive of Sebago Lake and Mercy Primary Care.

Coastal home with new, full kitchen, walkable downtown location

With a stay at this vacation home, you'll be centrally located in Boothbay Harbor, just a 3-minute walk from Boothbay Railway Village and 6 minutes by foot from Opera House at Boothbay Harbor.

Charming Remodeled Home with Deck overlooking Land Trust Nature - Dog Friendly!

With a stay at this vacation home in Boothbay Harbor, you'll be within a 15-minute walk of Carousel Music Theater and Boothbay Region Land Trust.

Elegant condo - walk to Portland's best restaurants & Old Port

$202

per night

Jun 16 - Jun 17

With a stay at this vacation home, you'll be centrally located in Portland, within a 5-minute drive of State Theatre and Thompson's Point.

Downtown Boothbay Harbor, 2-story house.

With a stay at this vacation home in Boothbay Harbor, you'll be within a 5-minute walk of Opera House at Boothbay Harbor and Boothbay Region Historical Society Museum.

Modern & Sunny House Steps from the Promenade. Private Parking!

$297

per night

Jun 10 - Jun 11

With a stay at this vacation home, you'll be centrally located in Portland, a 2-minute drive from State Theatre and 5 minutes from Thompson's Point.

Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

Located in Wiscasset, this vacation home is by the ocean, a 4-minute drive from Long Ledge and 6 minutes from Brooks Point.

Rent a room in the gorgeous Holt House

With a stay at this vacation home in Portland (Parkside), you'll be within a 5-minute drive of State Theatre and Thompson's Point.

Private Oceanfront Home on 10 Acres -- 2 Fireplaces, 4 Decks & Grill

With a stay at this vacation home in East Boothbay (Ocean Point), you'll be within a 5-minute drive of Grimes Cove Beach and Linekin Bay.

5 Star Back Cove Hide-Away<br>1 bedroom Back Cove apartment with water views!

With a stay at this vacation home in Portland (Back Cove), you'll be within a 5-minute drive of State Theatre and Thompson's Point.

A yurt in the trees. Close to Portland but close to nature. Treeyurt Maine

When you stay at this vacation home in Cumberland Center, you'll be 10 minutes by car from Spring Meadows Golf Course.

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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.