Best Chebeague Island Vacation Rentals
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Guest favorite
Hallowell Rooming House
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Sauna
- Sun terrace
Historic Hallowell Aptviewshot Tubwalk Downtown hotel sits approximately 200 metres from Hallowell Antique Mall and offers luggage storage. This Hallowell inn is within 10 minutes' drive of Maine State Museum and provides guests with a hot tub and a sauna.
A selection of activities are offered in the area, such as canyoning, fisheries, and darts.
Hallowell Rooming House
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Sauna
- Sun terrace
Hallowell Rooming House
Historic Hallowell Aptviewshot Tubwalk Downtown hotel sits approximately 200 metres from Hallowell Antique Mall and offers luggage storage. This Hallowell inn is within 10 minutes' drive of Maine State Museum and provides guests with a hot tub and a sauna.
A selection of activities are offered in the area, such as canyoning, fisheries, and darts.
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Great deal
Lovely Studio W/Full Kitchen/Free Wifi- Next To River/Antique Shops/Restaurants
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Golf centre
The 1-bedroom Lovely Studio W/Full Kitchen/Free Wifi- Next To River/Antique Shops/Restaurants Wiscasset villa entices guests to enjoy hiking, mini golf, and cycling and offers proximity to Historic New England Nickels-Sortwell House, located just 400 metres away. The Wiscasset holiday home can host up to 2 guests and offers quick access to 1790 Tiny House, located only a 6-minute walk away.
Lovely Studio W/Full Kitchen/Free Wifi- Next To River/Antique Shops/Restaurants
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Golf centre
Lovely Studio W/Full Kitchen/Free Wifi- Next To River/Antique Shops/Restaurants
The 1-bedroom Lovely Studio W/Full Kitchen/Free Wifi- Next To River/Antique Shops/Restaurants Wiscasset villa entices guests to enjoy hiking, mini golf, and cycling and offers proximity to Historic New England Nickels-Sortwell House, located just 400 metres away. The Wiscasset holiday home can host up to 2 guests and offers quick access to 1790 Tiny House, located only a 6-minute walk away.
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Best-rated
Island View House Bnb Self Check-In
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
Island View House Bnb Self Check-In Portland lies in a prime location in Portland, a 6-minute walk from the laid-back Munjoy Hill. Wi-Fi and private parking are provided for guests' utmost comfort.
Island View House Bnb Self Check-In
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
Island View House Bnb Self Check-In
Island View House Bnb Self Check-In Portland lies in a prime location in Portland, a 6-minute walk from the laid-back Munjoy Hill. Wi-Fi and private parking are provided for guests' utmost comfort.
Cheap Chebeague Island Vacation Rentals
Brand New Guest Apartment With Furnished Deck, Fast Wifi, Dock, & Water Views
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Garden area
Situated 4.7 km from McFarland Island, the 1-bedroom Brand New Guest Apartment With Furnished Deck, Fast Wifi, Dock, & Water Views Boothbay Harbor villa offers guests to enjoy a patio and a golf course. Offering canyoning, snow skiing, and cycling, the holiday home is suitable for 4 guests.
Brand New Guest Apartment With Furnished Deck, Fast Wifi, Dock, & Water Views
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Garden area
Brand New Guest Apartment With Furnished Deck, Fast Wifi, Dock, & Water Views
Situated 4.7 km from McFarland Island, the 1-bedroom Brand New Guest Apartment With Furnished Deck, Fast Wifi, Dock, & Water Views Boothbay Harbor villa offers guests to enjoy a patio and a golf course. Offering canyoning, snow skiing, and cycling, the holiday home is suitable for 4 guests.
The Brew House - 2Nd Floor Private Apartment - Located Above Newscapes Brewing
- Picnic area/ Tables
- Free parking
- Air conditioning
- Flat-screen TV
- Live entertainment
- Sun terrace
Nestled about 25 minutes' walk from the well - respected Portland Museum of Art, the spacious 1-bedroom The Brew House - 2Nd Floor Private Apartment - Located Above Newscapes Brewing Portland allows guests to explore numerous tourist destinations in the vicinity. Entertainment and leisure options include live performances, as well as a sun deck and a picnic area.
The Brew House - 2Nd Floor Private Apartment - Located Above Newscapes Brewing
- Picnic area/ Tables
- Free parking
- Air conditioning
- Flat-screen TV
- Live entertainment
- Sun terrace
The Brew House - 2Nd Floor Private Apartment - Located Above Newscapes Brewing
Nestled about 25 minutes' walk from the well - respected Portland Museum of Art, the spacious 1-bedroom The Brew House - 2Nd Floor Private Apartment - Located Above Newscapes Brewing Portland allows guests to explore numerous tourist destinations in the vicinity. Entertainment and leisure options include live performances, as well as a sun deck and a picnic area.
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Private beach
All Points' End
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Situated just around the corner from Sebago Cove, the 3-bedroom All Points' End Naples villa offers easy access to numerous tourist spots in the area. The Naples chalet hosts up to 4 guests and provides them with private car parking.
All Points' End
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
All Points' End
Situated just around the corner from Sebago Cove, the 3-bedroom All Points' End Naples villa offers easy access to numerous tourist spots in the area. The Naples chalet hosts up to 4 guests and provides them with private car parking.
Pet Friendly Vacation Rentals Chebeague Island
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Beach access
Sea Shell
- Free parking
- Air conditioning
- Flat-screen TV
- Golf centre
- Golf course
Located approximately 5 minutes' walk from Congregation Beth Israel Orthodox Synagogue, the 1-bedroom Sea Shell Villa Old Orchard Beach gives easy access to various tourist attractions in the area. Providing guests with Wi-Fi and parking, the accommodation is within 3 km of Dunegrass Golf Club.
Sea Shell
- Free parking
- Air conditioning
- Flat-screen TV
- Golf centre
- Golf course
Sea Shell
Located approximately 5 minutes' walk from Congregation Beth Israel Orthodox Synagogue, the 1-bedroom Sea Shell Villa Old Orchard Beach gives easy access to various tourist attractions in the area. Providing guests with Wi-Fi and parking, the accommodation is within 3 km of Dunegrass Golf Club.
Hasty House Studio
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
To enjoy your vacation in Auburn, stay at the 1-bedroom Hasty House Studio Auburn, which is just 500 metres from Court Street Baptist Church and just 1.3 km from Museum L-A. The 23 m² apartment capacity is based on up to 2 guests.
Hasty House Studio
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Hasty House Studio
To enjoy your vacation in Auburn, stay at the 1-bedroom Hasty House Studio Auburn, which is just 500 metres from Court Street Baptist Church and just 1.3 km from Museum L-A. The 23 m² apartment capacity is based on up to 2 guests.
Cabin At The Beach
- BBQ facilities
- Free parking
- Air conditioning
- Tea and coffee facilities
- Heating
The 2-bedroom Cabin At The Beach Old Orchard Beach provides easy access to various city attractions, such as the miniature Pirate's Cove Golf Course, situated approximately 5 minutes' walk away. Suitable for up to 6 guests, this 1-bathroom villa offers opportunities for cycling and fisheries.
Cabin At The Beach
- BBQ facilities
- Free parking
- Air conditioning
- Tea and coffee facilities
- Heating
Cabin At The Beach
The 2-bedroom Cabin At The Beach Old Orchard Beach provides easy access to various city attractions, such as the miniature Pirate's Cove Golf Course, situated approximately 5 minutes' walk away. Suitable for up to 6 guests, this 1-bathroom villa offers opportunities for cycling and fisheries.
Chebeague Island Vacation Rentals Oceanfront
Coastal Bungalow With Large Yard, Beautiful Kitchen, & Great Location
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Golf centre
- Garden area
The 3-bedroom Coastal Bungalow With Large Yard, Beautiful Kitchen, & Great Location Boothbay Harbor offers swift access to various city sites, such as Sea Pier Aquarium, situated approximately 5 minutes' walk away. Providing guests with Wi-Fi and private car parking, this holiday home is 2.7 km from Boothbay Region Land Trust.
Snorkelling, diving, and cycling can be enjoyed in the area.
Coastal Bungalow With Large Yard, Beautiful Kitchen, & Great Location
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Golf centre
- Garden area
Coastal Bungalow With Large Yard, Beautiful Kitchen, & Great Location
The 3-bedroom Coastal Bungalow With Large Yard, Beautiful Kitchen, & Great Location Boothbay Harbor offers swift access to various city sites, such as Sea Pier Aquarium, situated approximately 5 minutes' walk away. Providing guests with Wi-Fi and private car parking, this holiday home is 2.7 km from Boothbay Region Land Trust.
Snorkelling, diving, and cycling can be enjoyed in the area.
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Top location
Casa Alchimia
- Free parking
- VIP check-in/ -out
- Air conditioning
- Leisure/ TV room
- Mini-bar
- Sun terrace
Casa Alchimia Apartment Freeport includes offers a sun terrace and is situated 5 minutes' walk from Saint Judes Catholic Church. Guests will enjoy Wi-Fi, and parking provided on site.
Casa Alchimia
- Free parking
- VIP check-in/ -out
- Air conditioning
- Leisure/ TV room
- Mini-bar
- Sun terrace
Casa Alchimia
Casa Alchimia Apartment Freeport includes offers a sun terrace and is situated 5 minutes' walk from Saint Judes Catholic Church. Guests will enjoy Wi-Fi, and parking provided on site.
Dog-Friendly, Bayfront Home - Gorgeous Ocean Views, Private Balcony & Fireplace
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Garden area
Accommodating up to 10 guests, the 4-bedroom Dog-Friendly, Bayfront Home - Gorgeous Ocean Views, Private Balcony & Fireplace East Boothbay is situated approximately a 10-minute ride from renowned cultural sites such as Boothbay Region Art Foundation. Guests can enjoy hiking, mini golf, and fisheries at the East Boothbay holiday home, located 3.7 km from Maine State Aquarium.
Dog-Friendly, Bayfront Home - Gorgeous Ocean Views, Private Balcony & Fireplace
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Garden area
Dog-Friendly, Bayfront Home - Gorgeous Ocean Views, Private Balcony & Fireplace
Accommodating up to 10 guests, the 4-bedroom Dog-Friendly, Bayfront Home - Gorgeous Ocean Views, Private Balcony & Fireplace East Boothbay is situated approximately a 10-minute ride from renowned cultural sites such as Boothbay Region Art Foundation. Guests can enjoy hiking, mini golf, and fisheries at the East Boothbay holiday home, located 3.7 km from Maine State Aquarium.
Chebeague Island Vacation Rentals with Private Pool
Water-View Condo At Sheepscot Harbour Resort With Deck, Full Kitchen, And Wifi
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Garden area
The 1-bedroom Water-View Condo At Sheepscot Harbour Resort With Deck, Full Kitchen, And Wifi Edgecomb villa is located 4.5 km from Maine Heritage Village and provides snow skiing, mini golf, and cycling for active guests. This property hosts up to 4 guests and provides them with private car parking.
Water-View Condo At Sheepscot Harbour Resort With Deck, Full Kitchen, And Wifi
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Garden area
Water-View Condo At Sheepscot Harbour Resort With Deck, Full Kitchen, And Wifi
The 1-bedroom Water-View Condo At Sheepscot Harbour Resort With Deck, Full Kitchen, And Wifi Edgecomb villa is located 4.5 km from Maine Heritage Village and provides snow skiing, mini golf, and cycling for active guests. This property hosts up to 4 guests and provides them with private car parking.
'Paul'S Cottage' In Tenants Harbor, 1 Min To Shore
- Cookware/ Kitchen utensils
- Free parking
Staying at the 1-bedroom 'Paul'S Cottage' In Tenants Harbor, 1 Min To Shore, guests can easily reach Marshall Point Lighthouse Museum, located nearly a 15-minute ride away. The Tenants Harbor holiday home can sleep 2 guests and provides hire for rent.
'Paul'S Cottage' In Tenants Harbor, 1 Min To Shore
- Cookware/ Kitchen utensils
- Free parking
'Paul'S Cottage' In Tenants Harbor, 1 Min To Shore
Staying at the 1-bedroom 'Paul'S Cottage' In Tenants Harbor, 1 Min To Shore, guests can easily reach Marshall Point Lighthouse Museum, located nearly a 15-minute ride away. The Tenants Harbor holiday home can sleep 2 guests and provides hire for rent.
East End. Walk To Food, Beer And Downtown Fun.
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
The 102 m² East End. Walk To Food, Beer And Downtown Fun. Apartment Portland lies in a convenient location in Portland, about a 5-minute walk from the historic Eastern Cemetery. At this 2-bedroom apartment, Wi-Fi and a car park are also provided.
East End. Walk To Food, Beer And Downtown Fun.
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
East End. Walk To Food, Beer And Downtown Fun.
The 102 m² East End. Walk To Food, Beer And Downtown Fun. Apartment Portland lies in a convenient location in Portland, about a 5-minute walk from the historic Eastern Cemetery. At this 2-bedroom apartment, Wi-Fi and a car park are also provided.
Eastwind Elegance
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Billiard tables
The 2-bedroom Eastwind Elegance Villa Ogunquit is located nearly 25 minutes on foot from the beloved 1933 theater "Ogunquit Playhouse" and allows guests to enjoy windsurfing, snorkelling, and mini golf.
Eastwind Elegance
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Billiard tables
Eastwind Elegance
The 2-bedroom Eastwind Elegance Villa Ogunquit is located nearly 25 minutes on foot from the beloved 1933 theater "Ogunquit Playhouse" and allows guests to enjoy windsurfing, snorkelling, and mini golf.
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Private beach
Quiet & Remote Cottage On Panther Pond!
- Cookware/ Kitchen utensils
- Free parking
- Flat-screen TV
- Sun loungers
Quiet & Remote Cottage On Panther Pond! Raymond is located 9 minutes' walk from Panther Pond and offers guests to enjoy canyoning and hiking. Providing guests with Wi-Fi and parking, the 3-bedroom holiday home is 4.3 km from Good Life Market.
Quiet & Remote Cottage On Panther Pond!
- Cookware/ Kitchen utensils
- Free parking
- Flat-screen TV
- Sun loungers
Quiet & Remote Cottage On Panther Pond!
Quiet & Remote Cottage On Panther Pond! Raymond is located 9 minutes' walk from Panther Pond and offers guests to enjoy canyoning and hiking. Providing guests with Wi-Fi and parking, the 3-bedroom holiday home is 4.3 km from Good Life Market.
2 Mi To Drakes Island Beach: Condo W/ Porch!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Indoor swimming pool
The 1-bedroom 2 Mi To Drakes Island Beach: Condo W/ Porch! Wells villa is nestled a mere 650 metres from Congregational Church of Wells and provides an indoor pool.
2 Mi To Drakes Island Beach: Condo W/ Porch!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Indoor swimming pool
2 Mi To Drakes Island Beach: Condo W/ Porch!
The 1-bedroom 2 Mi To Drakes Island Beach: Condo W/ Porch! Wells villa is nestled a mere 650 metres from Congregational Church of Wells and provides an indoor pool.
Are you in a hurry?
Here is a quick list of Vacation Rentals in Chebeague Island, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Hallowell Rooming House |
9.0 / 10 (312 Reviews) |
From 110$ | |
| Lovely Studio W/Full Kitchen/Free Wifi- Next To River/Antique Shops/Restaurants |
9.3 / 10 (20 Reviews) |
From 49$ | |
| Island View House Bnb Self Check-In |
9.2 / 10 (162 Reviews) |
From 334$ | |
| Brand New Guest Apartment With Furnished Deck, Fast Wifi, Dock, & Water Views |
9.3 / 10 (29 Reviews) |
From 117$ | |
| The Brew House - 2Nd Floor Private Apartment - Located Above Newscapes Brewing |
9.4 / 10 (74 Reviews) |
From 360$ |
Frequently Asked Questions
Which dog-friendly vacation rentals are great for families on Chebeague Island?
Two excellent options are the Dog-Friendly, Bayfront Home and Coastal Bungalow. They offer enough space for families and can accommodate pets comfortably.
Book your stay at least a month in advance during summer; pet-friendly rentals fill up quickly.
What rental options have a view of the ocean on Chebeague Island?
Consider the Cabin At The Beach or Water-View Condo At Sheepscot Harbour Resort. Both provide stunning views of the ocean from private decks.
Request ocean-view rooms when booking to ensure the best sea scenery for your stay.
Which Chebeague Island rentals are best for a remote getaway?
The Quiet & Remote Cottage On Panther Pond is ideal for peace and privacy. It's surrounded by nature, suitable for a relaxing experience.
Visit in the fall for colorful foliage and peace and quiet, as fewer visitors come during this season.
Are there vacation rentals with kitchens for families on Chebeague Island?
Yes! The Lovely Studio W/Full Kitchen and Coastal Bungalow both feature full kitchens. This allows families to cook meals together and save on dining costs.
Plan grocery shopping on weekdays for quieter stores, ensuring you find all your favorite ingredients.
Which rentals on Chebeague Island are suitable for a romantic getaway?
The Cabin At The Beach and Dog-Friendly, Bayfront Home offer cozy atmospheres perfect for couples. They both provide private balconies to enjoy the view together.
Visit during sunset for a romantic experience by the water, when the views are most breathtaking.
What Chebeague Island vacation rentals are near the beach?
The Cabin At The Beach and Paul's Cottage offer easy beach access. Both locations are perfect for families who enjoy beach activities.
Arrive at the beach early in the morning to secure the best spot and enjoy calmer waters for young children.
Which Chebeague Island rentals offer a balcony or deck for relaxation?
The Dog-Friendly, Bayfront Home has a private deck, while the Water-View Condo At Sheepscot Harbour Resort features a balcony with stunning views.
Utilize your balcony space for outdoor meals or morning coffee, especially during pleasant weather.
What hiking trails should I explore on Chebeague Island?
The trails at the Chebeague Island Land Trust offer beautiful views and varying difficulty levels. Don't miss the Shoreline Trail for stunning waterfront scenes.
Hike early in the morning for cooler temperatures and fewer crowds, especially in summer.
Where can I find local restaurants on Chebeague Island?
Check out the Chebeague Island Inn and the local cafe for delicious, fresh seafood and local dishes. Both are popular among visitors.
Make reservations during peak season to avoid long wait times and ensure a table with a view.
What is a must-see event on Chebeague Island?
The Chebeague Island Community Church hosts a Summer Fair every August. It includes local crafts, food, and games, perfect for family fun.
Plan your visit around the fair to enjoy local culture and engage with the community.