Islesboro Island Rentals
From $315 per night (USD)VRBO
Beautiful and cozy sanctuary in Islesboro
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Located on the gorgeous and relaxing island of Islesboro, enjoy what this 2-bedroom house has to offer. This delightful ...
From $315 per night (USD)VRBO
From $325 per night (USD)Expedia
Comfort & quiet on an island off the Maine Coast.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Red House was a farmhouse for a working farm from the late 1800s until the mid-1900s. Miss Grace, the daughter of th ...
From $325 per night (USD)Expedia
From $393 per night (USD)VRBO
Beach-Side Cottage: Windows By The Sea
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 9
Secluded down a dead-end dirt road, our beach-side cottage sits in the lap of a beautiful sand and pebble beach, so clos ...
From $393 per night (USD)VRBO
From $177 per night (USD)Expedia
Island log home in Maine with ocean views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Modern 2 bedroom log home on Islesboro, an island off the coast of Maine with daily ferry access. Secluded lot. One qu ...
From $177 per night (USD)Expedia
From $232 per night (USD)VRBO
Inchcliffe--Islesboro Island Waterfront Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
If you are a small family of two or three looking for a quiet and beautiful place in which to spend a vacation, please ...
From $232 per night (USD)VRBO
From $372 per night (USD)Expedia
Historic Seaside Cottage with its own beaches overlooking Penobscot Bay..
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
The Gables is a historic cottage built in the mid to late 1800's and has always been family owned. The 2 plus acre prop ...
From $372 per night (USD)Expedia
From $249 per night (USD)VRBO
Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This 16' x 24' cabin sits on eleven acres of ocean frontage at 105 feet above sea level (one of the highest points on Is ...
From $249 per night (USD)VRBO
From $568 per night (USD)Expedia
MASSIVE Oceanfront Dark Harbor Home on ISLESBORO
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
This elegant 5+ bedroom Victorian Cottage has been carefully restored and renovated to highlight the natural charm and c ...
From $568 per night (USD)Expedia
From $372 per night (USD)VRBO
\"The Dory\" on Penobscot Bay, Mid-Coast Maine
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Looking over Penobscot Bay, "The Dory" is a perfect place to relax and enjoy island life. Set on a dead end street in a ...
From $372 per night (USD)VRBO
From $196 per night (USD)Expedia
~ Peaceful And Quaint Family Cottage On An Island In Maine ~
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This summer cottage on an island in Maine overlooks the beautiful Penobscot Bay. This rustic cottage has a moderate livi ...
From $196 per night (USD)Expedia
From $490 per night (USD)VRBO
Charming Waterfront Cottage Just Steps from East Penobscot Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
2 WEEK MINIMUM RENTAL. Stay in a charming oceanfront cottage on 4 wooded acres just feet from the beach. Enjoy morni ...
From $490 per night (USD)VRBO
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Blue Moon Cottage, Islesboro
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Centrally located three bedroom rustic cottage. Bordered by golf course and nature trail. Large deck, ramp to front door ...
Click For PricingExpedia
From $327 per night (USD)VRBO
Islesboro Island Maine Oceanfront Home on 12 Private Acres
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
PLEASE NOTE: The house is booked or I am in it myself through the summer and into mid-October, 2024. Generally I know ...
From $327 per night (USD)VRBO
From $401 per night (USD)Expedia
Take a Ferry to the Island of Your Dreams.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your vacation home - a barn style summer home on Broad Cove near the ferry. Imagine yourself relaxing on the ...
From $401 per night (USD)Expedia
From $193 per night (USD)VRBO
Penobscot Island Cabin, Waterfront Privacy
- Bedrooms:
- 0
- Bathrooms:
- 1
- Sleeps:
- 3
Privacy, magic, loon calls and your own beach. Wake to a sparkling sun on the water, sleep to a glittering Milky Way abo ...
From $193 per night (USD)VRBO
From $112 per night (USD)Expedia
~ Cozy Cabin in the woods On Penobscot Bay Right Near the water ~
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a 300 square foot, one room, efficiency cabin. That Is Perfect For A Couple's Getaway On An Island In Maine! Se ...
From $112 per night (USD)Expedia
From $305 per night (USD)VRBO
Charming 2-bedroom house with WiFi on marvelous Islesboro
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This Islesboro house boasts 2 inviting bedrooms, including 1 queen bed and 2 twin beds. With amenities like a hair dryer ...
From $305 per night (USD)VRBO
From $360 per night (USD)Expedia
Sweet three bedroom Cape on peaceful cove
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This three bedroom, two bath cape was built by an islander in the 1970s. This well-built house is an easy house to live ...
From $360 per night (USD)Expedia
From $342 per night (USD)VRBO
Surrounded by Water . . . A Very Special Place
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 10
***2023 July/August availability will be released mid-Oct 2022*** Many people have told us that our home is one of the ...
From $342 per night (USD)VRBO