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Brooksville Vacation Rentals

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

Peaceful location perfect for couples or small family

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Lovely Cape Rosier Waterfront Cottage, vacation rental in Brooksville

Lovely Cape Rosier Waterfront Cottage

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Modern coastal Maine vacation home in a gorgeous setting, vacation rental in Brooksville

Modern coastal Maine vacation home in a gorgeous setting

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

Charming Maine Boathouse, Blue Hill Peninsula, Brooksville, Acadia

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Hollyhock House, vacation rental in Brooksville

The Hollyhock House

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cape Rosier Maine 6 bedroom estate, vacation 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, vacation 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 !, vacation rental in Brooksville

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

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Tranquil Retreat on Woods Pond, vacation rental in Brooksville

Tranquil Retreat on Woods Pond

1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Charming, private cottage for two, vacation rental in Brooksville

Charming, private cottage for two

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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New to VRBO! Private Beach, Beautiful Cottage, Minutes to Castine. Maine Heaven!, vacation 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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In The Heart Of Castine, 3 blocks from docks, perfect for family reunions, vacation 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, vacation rental in Brooksville

Village Cottage with an Amazing Water View

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Islesboro Contemporary !, vacation rental in Brooksville

Beautiful Islesboro Contemporary !

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Water Front Heaven Little Deer Isle, 3 BR/2 Full BA, vacation 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, vacation 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..., vacation 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, vacation 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, vacation rental in Brooksville

Maine. Lovely Cottage on Penobscot Bay

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Remodeled farmhouse on 100 acres w/2 ponds - great spot to relax, vacation 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, vacation rental in Brooksville

Beach-Side Cottage: Windows By The Sea

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

Cozy Downtown Getaway w/ a 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, vacation 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, vacation 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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Eggemoggin Reach Oceanfront Contemporary Home With Mooring, vacation 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, vacation 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, vacation 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, vacation 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, vacation rental in Brooksville

Exquisitely Modern Maine Cottage

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Downtown apartment w/ full kitchen - walk to beach/harbor, 2 dogs OK!, vacation rental in Brooksville

Downtown apartment w/ full kitchen - walk to beach/harbor, 2 dogs OK!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Maine. Lovely Tiny House on Penobscot Bay, vacation 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, vacation rental in Brooksville

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

4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Cozy Downtown Getaway w/ a Full Kitchen - Close to the Beach, vacation rental in Brooksville

Cozy Downtown Getaway w/ a Full Kitchen - Close to the Beach

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cozy Getaway for Two w/ a Kitchenette - Right in the Heart of Downtown, vacation rental in Brooksville

Cozy Getaway for Two w/ a Kitchenette - Right in the Heart of Downtown

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Downtown Studio w/ a Full Kitchen & Shared Porch - Walk Everywhere in Town, vacation rental in Brooksville

Downtown Studio w/ a Full Kitchen & Shared Porch - Walk Everywhere in Town

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Dog-friendly home w/ four separate apartments in heart of downtown!, vacation rental in Brooksville

Dog-friendly home w/ four separate apartments in heart of downtown!

7 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Downtown Getaway w/ a Full Kitchen & Furnished Porch - Walk to the Beach/Harbor, vacation 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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Comfortable Castine getaway w/ a full kitchen - walk to the waterfront, vacation rental in Brooksville

Comfortable Castine getaway w/ a full kitchen - walk to the waterfront

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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New listing! Dog-friendly home w/ an enclosed yard, Ping-Pong, & air hockey, vacation rental in Brooksville

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

4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Charming Waterfront Cottage Just Steps from East Penobscot Bay, vacation 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, vacation 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, vacation 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, vacation 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, vacation 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., vacation 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!!, vacation 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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Renovated 19th-century farmhouse w/ 270 feet of waterfront & sunset views!, vacation rental in Brooksville

Renovated 19th-century farmhouse w/ 270 feet of waterfront & sunset views!

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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