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Brooksville Holiday Rentals

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50 rentals in Brooksville.
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Heated Cottage Perfect for Year Round Getaway, holiday rental in Brooksville

Heated Cottage Perfect for Year Round Getaway

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Come Relax on the Coast of Maine - Book your 7 night stay now!!!, holiday rental in Brooksville

Come Relax on the Coast of Maine - Book your 7 night stay now!!!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Peaceful location perfect for couples or small family, holiday rental in Brooksville

Peaceful location perfect for couples or small family

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Modern coastal Maine vacation home in a gorgeous setting, holiday rental in Brooksville

Modern coastal Maine vacation home in a gorgeous setting

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Hollyhock House, holiday rental in Brooksville

The Hollyhock House

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Farm Cabin at Tapley Farm's Waterfront, holiday rental in Brooksville

Farm Cabin at Tapley Farm's Waterfront

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Charming Maine Boathouse, Blue Hill Peninsula, Brooksville, Acadia, holiday rental in Brooksville

Charming Maine Boathouse, Blue Hill Peninsula, Brooksville, Acadia

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cape Rosier Maine 6 bedroom estate, holiday rental in Brooksville

Cape Rosier Maine 6 bedroom estate

6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Nautilus Island, Exclusive Private Island, holiday rental in Brooksville

Nautilus Island, Exclusive Private Island

9 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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Oceanfront Home Overlooking Penobscot Bay , Castine Maine. History abounds !, holiday rental in Brooksville

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

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New to VRBO! Private Beach, Beautiful Cottage, Minutes to Castine. Maine Heaven!, holiday rental in Brooksville

New to VRBO! Private Beach, Beautiful Cottage, Minutes to Castine. Maine Heaven!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Inchcliffe--Islesboro Island Waterfront Apartment, holiday rental in Brooksville

Inchcliffe--Islesboro Island Waterfront Apartment

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Charming, private cottage for two, holiday rental in Brooksville

Charming, private cottage for two

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tranquil Retreat on Woods Pond, holiday rental in Brooksville

Tranquil Retreat on Woods Pond

1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Peace and Tranquility on Private Pierces Pond, holiday rental in Brooksville

Peace and Tranquility on Private Pierces Pond

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded Saltwater Cabin 'Piney Home', holiday rental in Brooksville

Secluded Saltwater Cabin 'Piney Home'

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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In The Heart Of Castine, 3 blocks from docks, perfect for family reunions, holiday rental in Brooksville

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 Brooksville

Village Cottage with an Amazing Water View

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Water Front Heaven Little Deer Isle, 3 BR/2 Full BA, holiday rental in Brooksville

Water Front Heaven Little Deer Isle, 3 BR/2 Full BA

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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4 Bedroom/2.5 Bath Right On The Penobscot Bay And Close To Acadia.  Dog Friendly, holiday rental in Brooksville

4 Bedroom/2.5 Bath Right On The Penobscot Bay And Close To Acadia. Dog Friendly

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast..., holiday rental in Brooksville

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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Spacious Shore House Overlooking Penobscot Bay, holiday rental in Brooksville

Spacious Shore House Overlooking Penobscot Bay

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Maine. Lovely Cottage on Penobscot Bay, holiday rental in Brooksville

Maine. Lovely Cottage on Penobscot Bay

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Comfort & quiet on an island off the Maine Coast., holiday rental in Brooksville

Comfort & quiet on an island off the Maine Coast.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Remodeled farmhouse on 100 acres w/2 ponds - great spot to relax, holiday rental in Brooksville

Remodeled farmhouse on 100 acres w/2 ponds - great spot to relax

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Beach-Side Cottage: Windows By The Sea, holiday rental in Brooksville

Beach-Side Cottage: Windows By The Sea

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Comfy Downtown Getaway w/ Full Kitchen - Close to the Beach, holiday rental in Brooksville

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Parker House, National Register of Historic Places, holiday rental in Brooksville

Parker House, National Register of Historic Places

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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CANCELLED FOR 2020 Romantic Island Cabin for Two on the Ocean, holiday rental in Brooksville

CANCELLED FOR 2020 Romantic Island Cabin for Two on the Ocean

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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10 Acres on the Water and a Charming Home Large Enough for the Extended Family, holiday rental in Brooksville

10 Acres on the Water and a Charming Home Large Enough for the Extended Family

6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Eggemoggin Reach Oceanfront Contemporary Home With Mooring, holiday rental in Brooksville

Eggemoggin Reach Oceanfront Contemporary Home With Mooring

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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GASE COTTAGE - Deer Isle, holiday rental in Brooksville

GASE COTTAGE - Deer Isle

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Estabrooke Cottage, in the Heart of the Village of Castine, holiday rental in Brooksville

Estabrooke Cottage, in the Heart of the Village of Castine

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Great Deer Isle Property with Best Views of Pumpkin Island & Penobscot Bay, holiday rental in Brooksville

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

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Exquisitely Modern Maine Cottage, holiday rental in Brooksville

Exquisitely Modern Maine Cottage

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Totally Remodeled Vacation Home in Blue Hill, holiday rental in Brooksville

Totally Remodeled Vacation Home in Blue Hill

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Downtown Getaway w/ a Full Kitchen & Furnished Porch - Walk to the Beach/Harbor, holiday rental in Brooksville

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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Maine. Lovely Tiny House on Penobscot Bay, holiday rental in Brooksville

Maine. Lovely Tiny House on Penobscot Bay

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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New listing! Dog-friendly home w/ an enclosed yard, Ping-Pong, & air hockey, holiday rental in Brooksville

New listing! Dog-friendly home w/ an enclosed yard, Ping-Pong, & air hockey

4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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The Pickering House - an 1854 Harbor View Home, holiday rental in Brooksville

The Pickering House - an 1854 Harbor View Home

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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BECKS CAMP - Deer Isle, holiday rental in Brooksville

BECKS CAMP - Deer Isle

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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LEDGELAWN - Little Deer Isle, holiday rental in Brooksville

LEDGELAWN - Little Deer Isle

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Waterfront Cottage Just Steps from East Penobscot Bay, holiday rental in Brooksville

Charming Waterfront Cottage Just Steps from East Penobscot Bay

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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LITTLE DEER ISLE - Meadow Point Cottage, holiday rental in Brooksville

LITTLE DEER ISLE - Meadow Point Cottage

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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WEISS LOWER - Little Deer Isle, holiday rental in Brooksville

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 Brooksville

WEISS UPPER - Little Deer Isle

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Family Friendly, Waterfront Home near Castine, Maine, holiday rental in Brooksville

Family Friendly, Waterfront Home near Castine, Maine

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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This quintessential Maine Coast town is in the Center of Everything., holiday rental in Brooksville

This quintessential Maine Coast town is in the Center of Everything.

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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NICEST RENTAL IN CASTINE HANDS DOWN!! ON THE WATER!! FULLY REMODELED IN 2020!!, holiday rental in Brooksville

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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Waterfront home overlooking scenic blueberry fields!, holiday rental in Brooksville

Waterfront home overlooking scenic blueberry fields!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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