
Holiday houses in Islesboro
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Top-rated holiday rentals in Islesboro
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Loon Lodge
Located on beautiful Damariscotta Lake, "Loon Lodge" is a rustic cabin from another era. Fall asleep to the sound of crickets and frogs and wake every morning to the call of the lake's many loons. The cabin is 30 minutes from Augusta and 15 minutes from Damariscotta. Hiking enthusiasts will enjoy climbing the Camden Hills-a quick 45 minute drive from the lake. You’ll love my place because of the views, the ambiance, the people, and the location. My place is good for couples and solo adventurers.

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!

Cozy Cottage on the Penobscot — Panoramic Luxury!
Escape to your private waterfront retreat where tranquility meets luxury. Our Coastal Maine Cottage style home rests on a granite ledge that disappears twice daily with the tide. Enjoy a sun-filled interior with cherry floors, a gourmet kitchen, and a private deck for sunrise coffee or evening wine. Wake to sweeping Penobscot River views & unwind by the fire pit at river’s edge. Just 10 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

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.

Lobstermen's ocean-front cottage
Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

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.

Belfast Harbor Loft | Downtown
Come and experience the peaceful, yet vibrant, atmosphere of Belfast! This downtown loft is a great place to stay, being just two blocks away from the beach. Enjoy the morning light in the two bedrooms, both facing the harbor, while the living room offers a stunning view of Main Street. The loft is full of character, with its refurbished floors, exposed brick and rafters, large windows, and newly renovated kitchen and bathroom. Make yourself at home in a calm and inviting atmosphere.

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!

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.
Popular amenities for Islesboro holiday rentals
Other great holiday rentals in Islesboro

Ocean Front Island Cottage

Keeper's House Apartment at the Lighthouse

Megunticook Retreat

Studio on Camden Harbor

Antique Coastal Maine Cape

SunnySide - Cottage w/ Pen Bay Views in Bayside

The Bell | Beach House | Northport Ocean View

Rockport Oceanfront Home
When is the best time to visit Islesboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $328 NZD | $335 NZD | $335 NZD | $368 NZD | $335 NZD | $446 NZD | $466 NZD | $461 NZD | $415 NZD | $387 NZD | $293 NZD | $335 NZD |
| 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 $100 NZD 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!
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- 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




