Search Vacation Homes in Bailey Island
- Be pickySearch almost a million properties worldwide
- Change your mindBook hotels with free cancellation
Plan, book, stay with confidence
Check availability on Vacation Homes in Bailey Island
Compare 434 Vacation Homes in Bailey Island with updated reviews, rates, and availability.
Stunning oceanfront cottage w/ private deck and Atlantic views
Stunning oceanfront cottage w/ private deck and Atlantic views
9.2 out of 10, Wonderful, (37)
Rent a room in the gorgeous Holt House
Rent a room in the gorgeous Holt House
8.4 out of 10, Very Good, (19)
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
8.8 out of 10, Excellent, (33)
Save an average of 15% on thousands of hotels when you're signed in
Elegant condo - walk to Portland's best restaurants & Old Port
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (45)
The price is AED 742
AED 1,742 total
includes taxes & fees
3 Jun - 4 Jun
Spacious Waterfront Summer Home with Swimming, Kayaking, and Sunsets
Spacious Waterfront Summer Home with Swimming, Kayaking, and Sunsets
10.0 out of 10, Exceptional, (37)
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
8.8 out of 10, Excellent, (48)
The price is AED 415
AED 909 total
includes taxes & fees
29 May - 30 May
Convenient Portland home 3 miles from Downtown
Convenient Portland home 3 miles from Downtown
10.0 out of 10, Exceptional, (8)
The price is AED 1,017
AED 2,594 total
includes taxes & fees
29 May - 30 May
Sunrise Catcher with a Panoramic View!
Sunrise Catcher with a Panoramic View!
10.0 out of 10, Exceptional, (22)
5 Star Back Cove Hide-Away<br>1 bedroom Back Cove apartment with water views!
5 Star Back Cove Hide-Away<br>1 bedroom Back Cove apartment with water views!
10.0 out of 10, Exceptional, (115)
325 Year OldWaterfront Fully Renovated Loaded with Amenities
Bring Your Boat!
325 Year OldWaterfront Fully Renovated Loaded with Amenities Bring Your Boat!
10.0 out of 10, Exceptional, (20)
New home at Popham Beach
New home at Popham Beach
10.0 out of 10, Exceptional, (4)
Riverfront Topsham Home ~ 28 Mi to Portland!
Riverfront Topsham Home ~ 28 Mi to Portland!
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
9.4 out of 10, Exceptional, (19)
Dog-friendly home with deck, pool table, & firepit - walk to downtown Boothbay
Dog-friendly home with deck, pool table, & firepit - walk to downtown Boothbay
9.6 out of 10, Exceptional, (26)
Cute Maine Cottage: Woods & Water View
Cute Maine Cottage: Woods & Water View
10.0 out of 10, Exceptional, (1)
Oceanside escape 🌊 perfect family getaway!
Oceanside escape 🌊 perfect family getaway!
10.0 out of 10, Exceptional, (5)
The price is AED 845
AED 1,557 total
includes taxes & fees
4 Jun - 5 Jun
Beautiful 3BR Home with Office in Town of Brunswick with King beds
Beautiful 3BR Home with Office in Town of Brunswick with King beds
The price is AED 735
AED 1,601 total
includes taxes & fees
26 May - 27 May
Charming 110-year former Inn 10' from the Ocean!
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (99)
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.4 out of 10, Exceptional, (23)
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
10.0 out of 10, Exceptional, (52)
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.
Other property types 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
10.0 out of 10, Exceptional, (94)
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Completely remodeled 2 bedroom apartment in Portland's West End
Completely remodeled 2 bedroom apartment in Portland's West End
10.0 out of 10, Exceptional, (35)
The price is AED 841
AED 1,682 total
includes taxes & fees
13 Jun - 14 Jun
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.
Recent reviews of Bailey Island hotelsExpedia verified reviews
5/5 Excellent
"The hotel was very comfortable and the staff was friendly and helpful."
A verified traveler from Pomona stayed at Portland Harbor Hotel
Posted 2 hours ago
Popular Destinations
More Accommodation Types in Bailey Island
- Apartments in Bailey Island (198)
- Cottages in Bailey Island (150)
- Cabin Rentals in Bailey Island (48)
- Condo Rentals in Bailey Island (39)
- B&B in Bailey Island (27)
- Motels in Bailey Island (10)
- Lodges in Bailey Island (6)
- Guest Houses in Bailey Island (4)
- Farmstay in Bailey Island (3)
- RV Parks in Bailey Island (3)
- Chalets in Bailey Island (2)
- Resorts in Bailey Island (2)
- Inns in Bailey Island (2)
- Aparthotels in Bailey Island (1)
- Villas in Bailey Island (1)
- Hotels (1,641)