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Islesboro Holiday Rentals

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50 rentals in Islesboro.
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Inchcliffe--Islesboro Island Waterfront Apartment, holiday rental in Islesboro

Inchcliffe--Islesboro Island Waterfront Apartment

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast..., holiday rental in Islesboro

Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming Waterfront Cottage Just Steps from East Penobscot Bay, holiday rental in Islesboro

Charming Waterfront Cottage Just Steps from East Penobscot Bay

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beach-Side Cottage: Windows By The Sea, holiday rental in Islesboro

Beach-Side Cottage: Windows By The Sea

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Comfort & quiet on an island off the Maine Coast., holiday rental in Islesboro

Comfort & quiet on an island off the Maine Coast.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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CANCELLED FOR 2020 Romantic Island Cabin for Two on the Ocean, holiday rental in Islesboro

CANCELLED FOR 2020 Romantic Island Cabin for Two on the Ocean

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Charming Cottage a Stroll to Camden Harbor- Come for fall foliage!, holiday rental in Islesboro

Charming Cottage a Stroll to Camden Harbor- Come for fall foliage!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Heated Cottage Perfect for Year Round Getaway, holiday rental in Islesboro

Heated Cottage Perfect for Year Round Getaway

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Oceanfront home with breathtaking panoramic views of Penobscot Bay, near Camden, holiday rental in Islesboro

Oceanfront home with breathtaking panoramic views of Penobscot Bay, near Camden

5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Oceanfront Home Overlooking Penobscot Bay , Castine Maine. History abounds !, holiday rental in Islesboro

Oceanfront Home Overlooking Penobscot Bay , Castine Maine. History abounds !

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Ashgrove--Farm and Gardens on the Ocean, holiday rental in Islesboro

Ashgrove--Farm and Gardens on the Ocean

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Custom Built Penobscot Bay Retreat, holiday rental in Islesboro

Custom Built Penobscot Bay Retreat

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Walking Distance to Camden Harbor - First Floor, 3 Bed Apt, holiday rental in Islesboro

Walking Distance to Camden Harbor - First Floor, 3 Bed Apt

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Near Camden,  serene setting in the Maine woods, excellent reviews., holiday rental in Islesboro

Near Camden, serene setting in the Maine woods, excellent reviews.

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Oceanfront Cottage Near Camden, Islands And Lakes!, holiday rental in Islesboro

Oceanfront Cottage Near Camden, Islands And Lakes!

2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious lakefront home - 4 seasons/high speed WiFi/remote work/MSAD28, holiday rental in Islesboro

Luxurious lakefront home - 4 seasons/high speed WiFi/remote work/MSAD28

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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In The Heart Of Castine, 3 blocks from docks, perfect for family reunions, holiday rental in Islesboro

In The Heart Of Castine, 3 blocks from docks, perfect for family reunions

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Village Cottage with an Amazing Water View, holiday rental in Islesboro

Village Cottage with an Amazing Water View

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Handsome Maine Cottage at Water's Edge--panoramic ocean views & private beach!, holiday rental in Islesboro

Handsome Maine Cottage at Water's Edge--panoramic ocean views & private beach!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Harbor's Nest Apartment ~Over Looking Beautiful Camden Harbor!, holiday rental in Islesboro

Harbor's Nest Apartment ~Over Looking Beautiful Camden Harbor!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Lighthouses - Lobster - Moose, holiday rental in Islesboro

Lighthouses - Lobster - Moose

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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New listing! Cozy and unique abode on 200 acres with sweeping views, holiday rental in Islesboro

New listing! Cozy and unique abode on 200 acres with sweeping views

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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In the Heart of Maine, Nestled in Camden Village, holiday rental in Islesboro

In the Heart of Maine, Nestled in Camden Village

2 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
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QUINTESSENTIAL MAINE LOG CABIN SET ON GORGEOUS LAKE, holiday rental in Islesboro

QUINTESSENTIAL MAINE LOG CABIN SET ON GORGEOUS LAKE

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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OCEAN COTTAGE - Beachfront property w/ water views - 2 private decks & beach, holiday rental in Islesboro

OCEAN COTTAGE - Beachfront property w/ water views - 2 private decks & beach

3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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New listing! Secluded, modern farmhouse w/ gas fireplace, full kitchen & balcony, holiday rental in Islesboro

New listing! Secluded, modern farmhouse w/ gas fireplace, full kitchen & balcony

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Exquisite Carriage House in Beautiful Coastal Maine, holiday rental in Islesboro

Exquisite Carriage House in Beautiful Coastal Maine

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Moose Tracks, holiday rental in Islesboro

Moose Tracks

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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3 BR Lake Front Cottage - On Pitcher Pond, holiday rental in Islesboro

3 BR Lake Front Cottage - On Pitcher Pond

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful cottage in the heart of Mid-Coast Maine!, holiday rental in Islesboro

Beautiful cottage in the heart of Mid-Coast Maine!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Maine Midcoast Vacation at Lincolnville Beach, holiday rental in Islesboro

Maine Midcoast Vacation at Lincolnville Beach

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Comfy Downtown Getaway w/ Full Kitchen - Close to the Beach, holiday rental in Islesboro

Comfy Downtown Getaway w/ Full Kitchen - Close to the Beach

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Maine Ocean Front - Near Camden - Family Friendly, holiday rental in Islesboro

Maine Ocean Front - Near Camden - Family Friendly

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Contemporary Loft apartment with ocean views, hot tub & private beach!, holiday rental in Islesboro

Contemporary Loft apartment with ocean views, hot tub & private beach!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Ocean Frontage at the Mouth of The Ducktrap River, holiday rental in Islesboro

Ocean Frontage at the Mouth of The Ducktrap River

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Great Deer Isle Property with Best Views of Pumpkin Island & Penobscot Bay, holiday rental in Islesboro

Great Deer Isle Property with Best Views of Pumpkin Island & Penobscot Bay

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Downtown Getaway w/ a Full Kitchen & Furnished Porch - Walk to the Beach/Harbor, holiday rental in Islesboro

Downtown Getaway w/ a Full Kitchen & Furnished Porch - Walk to the Beach/Harbor

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Starry Nights Cottage- Bayside Village, Northport, holiday rental in Islesboro

Starry Nights Cottage- Bayside Village, Northport

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Breezeway Cottage, holiday rental in Islesboro

Breezeway Cottage

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Camden Harborfront Loft, holiday rental in Islesboro

Camden Harborfront Loft

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Windy Corner in Bayside, Maine, holiday rental in Islesboro

Windy Corner in Bayside, Maine

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Forge, holiday rental in Islesboro

The Forge

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Lakeside camp on Pitcher Pond, holiday rental in Islesboro

Lakeside camp on Pitcher Pond

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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LEDGELAWN - Little Deer Isle, holiday rental in Islesboro

LEDGELAWN - Little Deer Isle

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Full service Inn, B$B ,Bar, Restaurant, close to Camden & Winery, holiday rental in Islesboro

Full service Inn, B$B ,Bar, Restaurant, close to Camden & Winery

6 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
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WEISS LOWER - Little Deer Isle, holiday rental in Islesboro

WEISS LOWER - Little Deer Isle

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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WEISS UPPER - Little Deer Isle, holiday rental in Islesboro

WEISS UPPER - Little Deer Isle

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NICEST RENTAL IN CASTINE HANDS DOWN!! ON THE WATER!! FULLY REMODELED IN 2020!!, holiday rental in Islesboro

NICEST RENTAL IN CASTINE HANDS DOWN!! ON THE WATER!! FULLY REMODELED IN 2020!!

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Tentrr State Park Site - Maine Camden Hills State Park - Site 2 - Single Camp, holiday rental in Islesboro

Tentrr State Park Site - Maine Camden Hills State Park - Site 2 - Single Camp

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr State Park Site - Maine Camden Hills State Park - Site 1 - Single Camp, holiday rental in Islesboro

Tentrr State Park Site - Maine Camden Hills State Park - Site 1 - Single Camp

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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