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
The 6-room Hallowell Rooming House is also located approximately 200 metres from the Hallowell Antique Mall. The homestay offers parking on site and modern comforts like Wi-Fi.
The availability of a Jacuzzi and a sauna at the apartment ensures a more enjoyable experience. Sports enthusiasts will appreciate activities like canoeing, horseback riding, and mini golf offered at this apartment.
Hallowell Rooming House
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Sauna
- Sun terrace
Hallowell Rooming House
The 6-room Hallowell Rooming House is also located approximately 200 metres from the Hallowell Antique Mall. The homestay offers parking on site and modern comforts like Wi-Fi.
The availability of a Jacuzzi and a sauna at the apartment ensures a more enjoyable experience. Sports enthusiasts will appreciate activities like canoeing, horseback riding, and mini golf offered at this apartment.
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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
Located about 5 minutes on foot from the Historic New England Nickels-Sortwell House, Lovely Studio W/Full Kitchen/Free Wifi- Next To River/Antique Shops/Restaurants Wiscasset villa offers opportunities for hiking, cycling, and fishing in the area.
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
Located about 5 minutes on foot from the Historic New England Nickels-Sortwell House, Lovely Studio W/Full Kitchen/Free Wifi- Next To River/Antique Shops/Restaurants Wiscasset villa offers opportunities for hiking, cycling, and fishing in the area.
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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 a private parking lot are also available at this apartment.
Access to an ice rink is available for active guests.
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 a private parking lot are also available at this apartment.
Access to an ice rink is available for active guests.
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 3.4 km from the Boothbay Region Land Trust, Brand New Guest Apartment With Furnished Deck, Fast Wifi, Dock, & Water Views Boothbay Harbor villa invites guests to relax at a patio.
Canoeing and fishing are possible in the area.
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 3.4 km from the Boothbay Region Land Trust, Brand New Guest Apartment With Furnished Deck, Fast Wifi, Dock, & Water Views Boothbay Harbor villa invites guests to relax at a patio.
Canoeing and fishing are possible in the 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
Overlooking the sea, the spacious 1-bedroom The Brew House - 2Nd Floor Private Apartment - Located Above Newscapes Brewing Portland is about 25 minutes' walk from the well-respected Portland Museum of Art in Portland. Staying in this 84 m² apartment, nestled within reach of the laid-back Munjoy Hill, guests can relax on a sunbathing terrace.
Access to an ice rink aids guests in body maintainance.
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
Overlooking the sea, the spacious 1-bedroom The Brew House - 2Nd Floor Private Apartment - Located Above Newscapes Brewing Portland is about 25 minutes' walk from the well-respected Portland Museum of Art in Portland. Staying in this 84 m² apartment, nestled within reach of the laid-back Munjoy Hill, guests can relax on a sunbathing terrace.
Access to an ice rink aids guests in body maintainance.
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Private beach
All Points' End
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Located a stone's throw from the Sebago Cove, the 3-bedroom All Points' End Naples villa gives easy access to various tourist attractions in the area. With a maximum capacity of 4 guests, the Naples chalet offers private car parking.
All Points' End
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
All Points' End
Located a stone's throw from the Sebago Cove, the 3-bedroom All Points' End Naples villa gives easy access to various tourist attractions in the area. With a maximum capacity of 4 guests, the Naples chalet offers 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
Situated approximately 5 minutes' walk from Congregation Beth Israel Orthodox Synagogue, the 1-bedroom Sea Shell Villa Old Orchard Beach offers easy access to numerous tourist spots in the area.
Sea Shell
- Free parking
- Air conditioning
- Flat-screen TV
- Golf centre
- Golf course
Sea Shell
Situated approximately 5 minutes' walk from Congregation Beth Israel Orthodox Synagogue, the 1-bedroom Sea Shell Villa Old Orchard Beach offers easy access to numerous tourist spots in the area.
Hasty House Studio
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Situated just 500 metres from Court Street Baptist Church, the 1-room Hasty House Studio Auburn can host up to 2 guests in Auburn. Wi-Fi and private parking are also available at the 23 m² apartment.
Access to an ice rink helps guests maintain their bodies.
Hasty House Studio
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Hasty House Studio
Situated just 500 metres from Court Street Baptist Church, the 1-room Hasty House Studio Auburn can host up to 2 guests in Auburn. Wi-Fi and private parking are also available at the 23 m² apartment.
Access to an ice rink helps guests maintain their bodies.
Cabin At The Beach
- BBQ facilities
- Free parking
- Air conditioning
- Tea and coffee facilities
- Heating
Cabin At The Beach Old Orchard Beach offers swift access to various city sites, such as the miniature Pirate's Cove Golf Course, situated approximately 5 minutes' walk away. Suitable for 6 guests, this 1-bathroom villa offers cycling and fishing to diversify guests' leisure.
Cabin At The Beach
- BBQ facilities
- Free parking
- Air conditioning
- Tea and coffee facilities
- Heating
Cabin At The Beach
Cabin At The Beach Old Orchard Beach offers swift access to various city sites, such as the miniature Pirate's Cove Golf Course, situated approximately 5 minutes' walk away. Suitable for 6 guests, this 1-bathroom villa offers cycling and fishing to diversify guests' leisure.
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
Coastal Bungalow With Large Yard, Beautiful Kitchen, & Great Location Boothbay Harbor offers quick access to such city attractions as Sea Pier Aquarium, located approximately 5 minutes' walk away. Providing guests with Wi-Fi and private car parking, this property is 2.7 km from the Boothbay Region Land Trust.
Nearby activities include snorkelling, diving, and cycling.
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
Coastal Bungalow With Large Yard, Beautiful Kitchen, & Great Location Boothbay Harbor offers quick access to such city attractions as Sea Pier Aquarium, located approximately 5 minutes' walk away. Providing guests with Wi-Fi and private car parking, this property is 2.7 km from the Boothbay Region Land Trust.
Nearby activities include snorkelling, diving, and cycling.
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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 overlooks the garden and is situated 5 minutes' walk from Saint Judes Catholic Church. This homestay also offers a car park 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 overlooks the garden and is situated 5 minutes' walk from Saint Judes Catholic Church. This homestay also offers a car park 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
Staying at Dog-Friendly, Bayfront Home - Gorgeous Ocean Views, Private Balcony & Fireplace East Boothbay, guests can visit the privately owned Squirrel Island, which is approximately a 10-minute ride away. Guests can enjoy snorkelling, diving, and cycling at the East Boothbay holiday home, located 3.7 km from the 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
Staying at Dog-Friendly, Bayfront Home - Gorgeous Ocean Views, Private Balcony & Fireplace East Boothbay, guests can visit the privately owned Squirrel Island, which is approximately a 10-minute ride away. Guests can enjoy snorkelling, diving, and cycling at the East Boothbay holiday home, located 3.7 km from the 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
Nestled 4.4 km from the Split Rock Distilling, Water-View Condo At Sheepscot Harbour Resort With Deck, Full Kitchen, And Wifi Edgecomb villa entices guests to explore various tourist destinations nearby. Guests can enjoy hiking, cycling, and fishing at this property, located around 10 minutes by car from the Maine Heritage Village.
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
Nestled 4.4 km from the Split Rock Distilling, Water-View Condo At Sheepscot Harbour Resort With Deck, Full Kitchen, And Wifi Edgecomb villa entices guests to explore various tourist destinations nearby. Guests can enjoy hiking, cycling, and fishing at this property, located around 10 minutes by car from the Maine Heritage Village.
'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 the Marshall Point Lighthouse Museum, located nearly a 15-minute ride away. The Tenants Harbor holiday home can sleep 2 guests and provides bicycles 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 the Marshall Point Lighthouse Museum, located nearly a 15-minute ride away. The Tenants Harbor holiday home can sleep 2 guests and provides bicycles for rent.
East End. Walk To Food, Beer And Downtown Fun.
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Situated nearly a 20-minute walk from the well-respected Portland Museum of Art, the 102 m² East End. Walk To Food, Beer And Downtown Fun. Apartment Portland can host up to 4 guests in Portland. To keep up with sports routine, access to an ice rink is 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.
Situated nearly a 20-minute walk from the well-respected Portland Museum of Art, the 102 m² East End. Walk To Food, Beer And Downtown Fun. Apartment Portland can host up to 4 guests in Portland. To keep up with sports routine, access to an ice rink is provided.
Eastwind Elegance
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Billiard tables
Eastwind Elegance Villa Ogunquit is located nearly 25 minutes on foot from the beloved 1933 theater "Ogunquit Playhouse" and allows guests to enjoy hiking, cycling, and billiards.
Eastwind Elegance
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Billiard tables
Eastwind Elegance
Eastwind Elegance Villa Ogunquit is located nearly 25 minutes on foot from the beloved 1933 theater "Ogunquit Playhouse" and allows guests to enjoy hiking, cycling, and billiards.
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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 the Panther Pond and offers guests to enjoy canoeing and hiking. With a capacity for 6 guests, the 3-bedroom holiday home offers bicycles available for renting.
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 the Panther Pond and offers guests to enjoy canoeing and hiking. With a capacity for 6 guests, the 3-bedroom holiday home offers bicycles available for renting.
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.