Luxury Vacation Rentals Islesboro
-
Great deal
South Point On 700 Acre Island
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Flat-screen TV
- Heating
- Golf centre
Featuring a bicycle trail to make your visit more entertaining, South Point On 700 Acre Island Villa Islesboro is 5 minutes' walk from Seven Hundred Acre Island. The 5-bedroom holiday home hosts up to 8 guests and provides them with a private parking lot.
South Point On 700 Acre Island
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Flat-screen TV
- Heating
- Golf centre
South Point On 700 Acre Island
Featuring a bicycle trail to make your visit more entertaining, South Point On 700 Acre Island Villa Islesboro is 5 minutes' walk from Seven Hundred Acre Island. The 5-bedroom holiday home hosts up to 8 guests and provides them with a private parking lot.
-
Best-rated
-
Private beach
Colonial Gables Oceanfront Village
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Sun terrace
Nestled around a 25-minute walk from Moose Point State Park, Colonial Gables Oceanfront Village Belfast villa is boasting a sunbathing terrace, a shuffleboard court, and playground for guests' enjoyment. Located 4.9 km from the superb Penobscot Marine Museum, this property provides Wi-Fi and parking.
Volleyball and fisheries are available.
Colonial Gables Oceanfront Village
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Sun terrace
Colonial Gables Oceanfront Village
Nestled around a 25-minute walk from Moose Point State Park, Colonial Gables Oceanfront Village Belfast villa is boasting a sunbathing terrace, a shuffleboard court, and playground for guests' enjoyment. Located 4.9 km from the superb Penobscot Marine Museum, this property provides Wi-Fi and parking.
Volleyball and fisheries are available.
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 Historic New England Nickels-Sortwell House, the 1-bedroom Lovely Studio W/Full Kitchen/Free Wifi- Next To River/Antique Shops/Restaurants Wiscasset villa offers opportunities for hiking, mini golf, and cycling in the area. With a maximum capacity of 2 guests, the Wiscasset holiday home offers private car parking.
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 Historic New England Nickels-Sortwell House, the 1-bedroom Lovely Studio W/Full Kitchen/Free Wifi- Next To River/Antique Shops/Restaurants Wiscasset villa offers opportunities for hiking, mini golf, and cycling in the area. With a maximum capacity of 2 guests, the Wiscasset holiday home offers private car parking.
Cheap Vacation Rentals in Islesboro Maine
Bar Harbor Cottages & Suites
- BBQ facilities
- Free parking
- Tours/Ticket assistance
- Air conditioning
- Flat-screen TV
- Garden area
Situated nearly 5 minutes' walk from Eden Baptist Church, Bar Harbor Cottages & Suites entices guests to explore various tourist attractions in the area.
Bar Harbor Cottages & Suites
- BBQ facilities
- Free parking
- Tours/Ticket assistance
- Air conditioning
- Flat-screen TV
- Garden area
Bar Harbor Cottages & Suites
Situated nearly 5 minutes' walk from Eden Baptist Church, Bar Harbor Cottages & Suites entices guests to explore various tourist attractions in the area.
Pond Memories - National Parks Suite - Paddling Included!
- Shared kitchen
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Sun terrace
Pond Memories - National Parks Suite - Paddling Included! Surry provides guests with Wi-Fi, as well as a private garden with a sun terrace.
Other facilities at this accommodation include a sunbathing terrace and a picnic area.
Pond Memories - National Parks Suite - Paddling Included!
- Shared kitchen
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Sun terrace
Pond Memories - National Parks Suite - Paddling Included!
Pond Memories - National Parks Suite - Paddling Included! Surry provides guests with Wi-Fi, as well as a private garden with a sun terrace.
Other facilities at this accommodation include a sunbathing terrace and a picnic area.
The Sovereign Suite - Cozy And Convenient With Home Theater
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Heating
- Patio
Situated approximately a 10-minute ride from Hirundo Wildlife Refuge, the spacious 74 m² The Sovereign Suite - Cozy And Convenient With Home Theater Old Town provides guests with Wi-Fi for either business or leisure.
The Sovereign Suite - Cozy And Convenient With Home Theater
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Heating
- Patio
The Sovereign Suite - Cozy And Convenient With Home Theater
Situated approximately a 10-minute ride from Hirundo Wildlife Refuge, the spacious 74 m² The Sovereign Suite - Cozy And Convenient With Home Theater Old Town provides guests with Wi-Fi for either business or leisure.
Pet Friendly Vacation Rentals Islesboro Maine
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
The 1-bedroom Brand New Guest Apartment With Furnished Deck, Fast Wifi, Dock, & Water Views Boothbay Harbor villa can host up to 4 guests, boasting a convenient location 3.8 km from iconic cultural attractions such as Boothbay Railway Village Museum. Located within a 10-minute drive of Boothbay Region Land Trust, the holiday home comes with a patio and a golf course for added enjoyment.
The outdoor activities include canyoning, snow skiing, and cycling.
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
The 1-bedroom Brand New Guest Apartment With Furnished Deck, Fast Wifi, Dock, & Water Views Boothbay Harbor villa can host up to 4 guests, boasting a convenient location 3.8 km from iconic cultural attractions such as Boothbay Railway Village Museum. Located within a 10-minute drive of Boothbay Region Land Trust, the holiday home comes with a patio and a golf course for added enjoyment.
The outdoor activities include canyoning, snow skiing, and cycling.
Vana Kuti-Cabin In The Woods
- BBQ facilities
- Free parking
- Tea and coffee facilities
- Heating
- Golf centre
- Terrace
Situated around 20 minutes' walk from Bald Mountain Preserve, Vana Kuti-Cabin In The Woods Camden entices guests to explore various tourist attractions in the area.
Vana Kuti-Cabin In The Woods
- BBQ facilities
- Free parking
- Tea and coffee facilities
- Heating
- Golf centre
- Terrace
Vana Kuti-Cabin In The Woods
Situated around 20 minutes' walk from Bald Mountain Preserve, Vana Kuti-Cabin In The Woods Camden entices guests to explore various tourist attractions in the area.
-
Top location
Spacious Cabin W/ Full Kitchen & Fireplace -Enjoy A No Wifi Unplugged Experience
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Flat-screen TV
- Tea and coffee facilities
- Fitness centre
Offering a location approximately 10 minutes by car from Warren Island State Park, the 2-bedroom Spacious Cabin W/ Full Kitchen & Fireplace -Enjoy A No Wifi Unplugged Experience Northport gives access to various tourist spots in the area. Guests can enjoy snow skiing, horseback riding, and mini golf at this accommodation, located 4.3 km from Grindle Point Sailor's Museum and Lighthouse.
Spacious Cabin W/ Full Kitchen & Fireplace -Enjoy A No Wifi Unplugged Experience
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Flat-screen TV
- Tea and coffee facilities
- Fitness centre
Spacious Cabin W/ Full Kitchen & Fireplace -Enjoy A No Wifi Unplugged Experience
Offering a location approximately 10 minutes by car from Warren Island State Park, the 2-bedroom Spacious Cabin W/ Full Kitchen & Fireplace -Enjoy A No Wifi Unplugged Experience Northport gives access to various tourist spots in the area. Guests can enjoy snow skiing, horseback riding, and mini golf at this accommodation, located 4.3 km from Grindle Point Sailor's Museum and Lighthouse.
Islesboro Vacation Rentals Oceanfront
Charming Studio ~ 20 Mi To Acadia Nat'L Park!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Heating
- Sun loungers
Situated about 7 km from Contemporary Functional Craft, the 93 m² Charming Studio ~ 20 Mi To Acadia Nat'L Park! Ellsworth provides convenient access to numerous nearby attractions. Wi-Fi and private car parking are also available at this 1-bedroom apartment.
Charming Studio ~ 20 Mi To Acadia Nat'L Park!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Heating
- Sun loungers
Charming Studio ~ 20 Mi To Acadia Nat'L Park!
Situated about 7 km from Contemporary Functional Craft, the 93 m² Charming Studio ~ 20 Mi To Acadia Nat'L Park! Ellsworth provides convenient access to numerous nearby attractions. Wi-Fi and private car parking are also available at this 1-bedroom apartment.
Howard House Lodge
- On-site car park
- Flat-screen TV
- Tea and coffee facilities
- Patio
Situated around a 25-minute walk from Coastal Maine Botanical Gardens, Howard House Lodge Boothbay Harbor entices guests to explore various tourist attractions in the area.
Hiking can be enjoyed in the area.
Howard House Lodge
- On-site car park
- Flat-screen TV
- Tea and coffee facilities
- Patio
Howard House Lodge
Situated around a 25-minute walk from Coastal Maine Botanical Gardens, Howard House Lodge Boothbay Harbor entices guests to explore various tourist attractions in the area.
Hiking can be enjoyed in the area.
Pet-Friendly Maine Cottage By Northern Bay
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Ironing facilities
Pet-Friendly Maine Cottage By Northern Bay Penobscot is located within a 10-minute drive of Wight Pond, giving access to various tourist spots nearby. The 1-bedroom welcoming villa hosts up to 3 guests and provides them with private parking.
Pet-Friendly Maine Cottage By Northern Bay
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Ironing facilities
Pet-Friendly Maine Cottage By Northern Bay
Pet-Friendly Maine Cottage By Northern Bay Penobscot is located within a 10-minute drive of Wight Pond, giving access to various tourist spots nearby. The 1-bedroom welcoming villa hosts up to 3 guests and provides them with private parking.
Islesboro Vacation Rentals with Private Pool
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 is situated only 5 minutes' walk from Sea Pier Aquarium, featuring such comforts as Wi-Fi and private car parking. Suitable for 6 guests, this holiday home offers snorkelling, diving, and cycling to diversify guests' leisure.
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 is situated only 5 minutes' walk from Sea Pier Aquarium, featuring such comforts as Wi-Fi and private car parking. Suitable for 6 guests, this holiday home offers snorkelling, diving, and cycling to diversify guests' leisure.
210 Main St
- Free parking
- Express check-in/ -out
- Air conditioning
- Flat-screen TV
The 7-room 210 Main St Apartment Ellsworth offers proximity to a number of tourist attractions, such as the non - denominational Connection Church, located nearly a 25-minute walk away. Wi-Fi and private parking are also available at the apartment.
210 Main St
- Free parking
- Express check-in/ -out
- Air conditioning
- Flat-screen TV
210 Main St
The 7-room 210 Main St Apartment Ellsworth offers proximity to a number of tourist attractions, such as the non - denominational Connection Church, located nearly a 25-minute walk away. Wi-Fi and private parking are also available at the apartment.
Dog-Friendly, Bayfront Home - Gorgeous Ocean Views, Private Balcony & Fireplace
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Garden area
The 4-bedroom Dog-Friendly, Bayfront Home - Gorgeous Ocean Views, Private Balcony & Fireplace East Boothbay is located approximately a 10-minute ride from the privately owned Squirrel Island and welcomes its guests to enjoy hiking, mini golf, and fisheries. The East Boothbay holiday home is suitable for up to 10 guests and features private car parking.
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
The 4-bedroom Dog-Friendly, Bayfront Home - Gorgeous Ocean Views, Private Balcony & Fireplace East Boothbay is located approximately a 10-minute ride from the privately owned Squirrel Island and welcomes its guests to enjoy hiking, mini golf, and fisheries. The East Boothbay holiday home is suitable for up to 10 guests and features private car parking.
Are you in a hurry?
Here is a quick list of Vacation Rentals in Islesboro, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Colonial Gables Oceanfront Village |
9.2 / 10 (803 Reviews) |
From 180$ | |
| Lovely Studio W/Full Kitchen/Free Wifi- Next To River/Antique Shops/Restaurants |
9.3 / 10 (18 Reviews) |
From 49$ | |
| Bar Harbor Cottages & Suites |
9.2 / 10 (363 Reviews) |
From 328$ | |
| Pond Memories - National Parks Suite - Paddling Included! |
9.7 / 10 (29 Reviews) |
From 170$ | |
| The Sovereign Suite - Cozy And Convenient With Home Theater |
9.8 / 10 (10 Reviews) |
From 87$ |
Frequently Asked Questions
What vacation rentals offer ocean views?
Pet-Friendly Maine Cottage By Northern Bay and Dog-Friendly, Bayfront Home both offer stunning ocean views. Enjoy your morning coffee while taking in the beautiful scenery.
Book a second-floor unit for the best panoramic views of the bay at sunrise.
Which vacation rentals are located near beaches?
Colonial Gables Oceanfront Village and Howard House Lodge are situated close to beautiful beaches. These rentals allow you to easily walk to the shore anytime.
Visit the beach early in the morning to find the best spots and enjoy quieter surroundings.
Where can I find vacation rentals with two bedrooms?
Coastal Bungalow and Pond Memories offer spacious two-bedroom accommodations ideal for families. Count on extra room for relaxation and fun.
Look for rentals that have family-friendly kitchens to make meal prep easier during your stay.
Which rentals have private balconies?
The Brand New Guest Apartment and Dog-Friendly, Bayfront Home each feature private balconies. These spaces provide perfect spots for evening relaxation.
Choose a west-facing balcony to enjoy captivating sunset views every night.
Are there vacation rentals with kitchens for families?
Lovely Studio and Spacious Cabin both come with full kitchens. This setup is perfect for families looking to prepare their meals.
Plan grocery shopping at the local market on Main St for fresh ingredients and better deals.
Which vacation rentals are dog-friendly?
Dog-Friendly, Bayfront Home and Pet-Friendly Maine Cottage allow you to bring your furry friends along. Enjoy family time together by the ocean.
Check nearby parks where dogs are welcome, like Bayfront Park, for great outdoor adventures.
What is the best vacation rental for a romantic getaway?
Howard House Lodge offers cozy settings perfect for couples. Enjoy intimate moments and stunning views of the surrounding landscape.
Consider booking a package that includes a romantic dinner at a nearby restaurant for a full experience.
How can I find the best time to visit Islesboro?
The best time to visit is during late spring and early fall when the weather is pleasantly warm and outdoor activities are plentiful. Check local calendars for events like the Islesboro Summer Festival in July.
Book accommodations well in advance for popular events, as they tend to fill up quickly during peak seasons.
What unique activities should I try while on Islesboro?
You should try kayaking and visiting the beautiful nature trails. Hiking trails near the coastline offer stunning views and are perfect for exploring.
Rent kayaks at Coastal Watersports for guided tours that showcase the best local sights.
How do I get around Islesboro?
Car rentals or bicycles are recommended for getting around. The island is small, making these options convenient for accessing different areas.
Use local bike rental services located near the ferry terminal to explore the island efficiently.