
Holiday houses in Islesboro
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Islesboro
Guests agree: these stays are highly rated for location, cleanliness and more.

Cozy cottage in Orland Village-Penobscot Bay area
Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 800 Mbs fiber internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. We’re very pet friendly!

Flower Farm Loft
When you arrive at the Flower Farm Loft you're greeted by our dogs, who will likely jump on you with muddy paws and request fetch and pets. You're immediately surrounded by flowers in our gardens and flower studio. The loft has big east facing windows that look over our farm and surrounding fields. You'll open the curtains in the morning to incredible sunrises over Kilkenny Cove, and end your nights at your private fire pit with immaculate star filled skies that will make it hard to go inside.

Bright, new apt near coastal villages!
Enjoy this country setting on Hatchet Mountain in Hope near the Maine coast, about 8 miles from Camden. Hobbs Pond (2 miles long!) is just a mile away with public access for swimming, boating, and kayaking. Loads of hiking trails surround us, too. Beaver Lodge, a favorite spot for weddings and other family events, is also nearby. The Camden Snow Bowl, a year-round recreation area offers hiking, mountain biking, skiing (with ocean views), and more! This listing has an exemption for all animals.

Eco-friendly studio - ocean views, close to beach
Sunny eco-friendly cottage on Route 1, steps from the beach! A cozy studio with a Murphy bed, a full bath, and kitchenette - stovetop, fridge, toaster, & microwave. Beautiful views of Penobscot Bay – don't worry, the blinds will keep the sunshine at bay when you need a nap! You're within easy walking distance of sandy beaches, restaurants, shops, a coffee roaster, and a market. Explore nearby hiking trails, Mount Battie, and the charming towns of Belfast, Camden, Rockport, and Rockland.

"The Lair" Guesthouse
"The Lair" is a just recently renovated small 200 square foot cabin with vaulted ceilings and plenty of natural sunlight. The building is located close to Green Tree Coffee and Tea, a coffee roaster, so the aroma of coffee will be in the air. We located about 400 yards South of the Islesboro Ferry and Lincolnville Beach and 2.4 milres North of Camden Hills State Park and Mount Battie. Free coffee and tea everyday, all day! We are closed for Winter, will re-open Mid-April. Thank you.

5 Laurel Studio private entrance STR20-69
Open concept small studio, private patio and entrance, full kitchen. *SHARED wall between studio and main house, therefore some shared noise. 2 minute walk to the ocean , Lobster and Blues Festivals. A small swimming beach is a 5 minute walK, 5-10 minutes to the Farnsworth and CMCA museums, Strand Theater, restaurants, antiques shops & galleries. ALSO NOTE we do not have television. We have wifi but you must bring your own device . EXEMPT FROM ACCEPTING SERVICE DOG

Spectacular Cottage on Penobscot bay in Belfast
Spectacular cottage on Penobscot bay in Belfast. The cottage is focused on the views from the great room and screened porch. You’ll love the spacious, clean, open cottage with a complete kitchen and propane fireplace. Sit on the porch with a book/glass of wine and watch for seals and schooners. Easy access to the shore along a gradual path and short boardwalk. Great amenities and comfort for vacationers both young and old. Perfect for couples and families (with kids).

Birch Hill Cabin w/Hot Tub
Birch Hill Cabin is set on the side of a hill, surrounded by almost 8 acres of woods. The cabin is 288 square feet, and the bathroom is detached and located approximately 20 feet from the cabin. A hot tub is conveniently located off the deck for ultimate relaxation! This cabin is tucked away, surrounded by nature! But also conveniently located to so many wonderful spots in the Midcoast! Come enjoy the peace and quiet, where you can rest and recharge!

Peaceful Guesthouse in Rockport
This peaceful studio guesthouse has everything you need for your Rockport/Camden trip. The unit comes with Wi-Fi, free parking, and laptop-friendly workspace. During your stay, you can enjoy your private studio with kitchenette. Within close proximity to Camden (3 Miles) and Rockland (6 Miles.) Rockport Harbor (1 mile walk) features several popular restaurants, coffee shops, and beaches. An ideal base to explore Rockport.

Modern Cabin in the Pines • Hot Tub + Near Acadia
Enjoy our cozy home-away-from-home amid towering pines and granite boulders — the perfect respite after exploring Acadia. Our newly built cabin has rustic Maine charm and modern comforts: AC, waterfall shower, memory foam mattresses, indoor gas fireplace, outdoor gas fire pit, gas grill, hot tub, 4KTV, high-speed internet, modern kitchen, filtered water, gas range, high-end appliances, and front-loading washer/dryer.

Belfast Ocean Front Cottage
This quaint ocean front cottage is surrounded by lovely flower gardens and a panoramic view of Belfast Harbor. You're 20 feet from the beach ,and a 10 min walk to town.We have recreational kayaks you can use to paddle about the bay and up the river. With a shabby-chic decor, lots of windows & light, the cottage will steal your heart & give you a Maine experience to remember!

Sunny In-Town Camden Studio, 10% weekly discount
Make this cozy, contemporary studio apartment your home-away-from-home. Located just two blocks from downtown Camden, it's a five minute walk to downtown in one direction, or to one of the many trailheads in Camden Hills State Park in the other. In any season, our central location gives you access to the best of the Midcoast. License Number: STR-00030
Popular amenities for Islesboro holiday rentals
Other great holiday rentals in Islesboro

Camp Tranquility @ Rock Cove

Antique Barn Apartment at Salt Water Farm

Coastal Retreat • Spa Bath • Forest Privacy

Seaside Cottage - Steps to the Bay

Keeper's House Apartment at the Lighthouse

Megunticook Retreat

Studio on Camden Harbor

SunnySide - Cottage w/ Pen Bay Views in Bayside
When is the best time to visit Islesboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $278 AUD | $284 AUD | $284 AUD | $312 AUD | $284 AUD | $378 AUD | $395 AUD | $390 AUD | $352 AUD | $328 AUD | $248 AUD | $284 AUD |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 13°C | 18°C | 21°C | 20°C | 16°C | 9°C | 3°C | -3°C |
Frequently Asked Questions
Do cottage rentals in Islesboro have a bbq area?
Absolutely! We offer over 10 cottage rentals with a bbq area in Islesboro. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Islesboro have wifi?
Absolutely! We offer over 30 cottage rentals with wifi in Islesboro. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly cottage rentals in Islesboro?
Islesboro has more than 20 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do cottage rentals in Islesboro have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Islesboro. Enjoy a tailored experience with all the comforts you desire.
Are there cabin rentals with a dedicated workspace in Islesboro?
Yes! Work meets play with ease at over 40 cabin rentals in Islesboro featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly cottage rentals in Islesboro?
Four-legged friends are welcome in Islesboro. Choose from more than 10 cottage rentals for guests traveling with pets.
Do cabin rentals in Islesboro have a gym?
Absolutely! We offer over 30 cabin rentals with a gym in Islesboro. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Islesboro?
Experience the best of Islesboro with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Quick stats about holiday rentals in Islesboro

Total holiday rentals
Explore 220 holiday rentals in Islesboro

Nightly prices starting at
Islesboro holiday rentals start at $85 AUD per night before taxes and fees

Verified guest reviews
Over 7,380 verified reviews to help you choose

Family-friendly holiday rentals
150 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 100 rentals that welcome pets

Rentals with dedicated workspaces
120 properties have a dedicated workspace

Wi-Fi availability
210 of Islesboro holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Islesboro rentals

4.8 Average rating
Islesboro stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Boston Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Island of Montreal Holiday rentals
- Quebec City Area Holiday rentals
- Halifax Holiday rentals
- Laval Holiday rentals
- Québec Holiday rentals
- Lanaudière Holiday rentals
- Portland Holiday rentals
- Cambridge Holiday rentals
- Rentals with beach access Islesboro
- Beachfront rentals Islesboro
- Rentals with a fireplace Islesboro
- Rentals with outdoor seating Islesboro
- Rentals with a washing machine and dryer Islesboro
- Rentals with a patio Islesboro
- House rentals Islesboro
- Waterfront rentals Islesboro
- Cabin rentals Islesboro
- Family-friendly rentals Islesboro
- Cottage rentals Islesboro
- Fitness-friendly rentals Islesboro
- Pet-friendly rentals Islesboro
- Rentals with a fire pit Islesboro
- Apartment rentals Islesboro
- Acadia National Park
- Acadia National Park Pond
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- The Camden Snow Bowl
- Sand Beach
- Farnsworth Art Museum
- University of Maine
- Rockland Breakwater Light
- Schoodic Peninsula
- Bass Harbor Head Light Station
- Hollywood Slots Hotel & Raceway
- Maine Discovery Museum
- Maine Lighthouse Museum
- Cellardoor Winery
- Moose Point State Park
- Camden Hills State Park




