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Penobscot Vacation Rentals

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50 rentals in Penobscot.
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New to VRBO! Private Beach, Beautiful Cottage, Minutes to Castine. Maine Heaven!, vacation rental in Penobscot

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

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Peace and Tranquility on Private Pierces Pond, vacation rental in Penobscot

Peace and Tranquility on Private Pierces Pond

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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WATERFRONT home on pristine Maine Lake; FAMILY FRIENDLY!, vacation rental in Penobscot

WATERFRONT home on pristine Maine Lake; FAMILY FRIENDLY!

7 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Maine. Lovely Cottage on Penobscot Bay, vacation rental in Penobscot

Maine. Lovely Cottage on Penobscot Bay

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Maine. Lovely Tiny House on Penobscot Bay, vacation rental in Penobscot

Maine. Lovely Tiny House on Penobscot Bay

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Heated Cottage Perfect for Year Round Getaway, vacation rental in Penobscot

Heated Cottage Perfect for Year Round Getaway

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Oceanfront Home Overlooking Penobscot Bay , Castine Maine. History abounds !, vacation rental in Penobscot

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

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Come Relax on the Coast of Maine - Book your 7 night stay now!!!, vacation rental in Penobscot

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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Charming, private cottage for two, vacation rental in Penobscot

Charming, private cottage for two

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Awanadjo Shores on Toddy Pond, vacation rental in Penobscot

Awanadjo Shores on Toddy Pond

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Peaceful location perfect for couples or small family, vacation rental in Penobscot

Peaceful location perfect for couples or small family

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Tranquil Retreat on Woods Pond, vacation rental in Penobscot

Tranquil Retreat on Woods Pond

1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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In The Heart Of Castine, 3 blocks from docks, perfect for family reunions, vacation rental in Penobscot

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 Penobscot

Village Cottage with an Amazing Water View

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private Sandy Beach, Sleeps 24+ large family's, Retreats and Weddings   5 star, vacation rental in Penobscot

Private Sandy Beach, Sleeps 24+ large family's, Retreats and Weddings 5 star

7 bedrooms
3 bathrooms
Sleeps 21
Match: Sleeps
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Chic Farmhouse Cottage, ROW private beach, Wi-Fi unlimited streaming, A/C, 600sf, vacation rental in Penobscot

Chic Farmhouse Cottage, ROW private beach, Wi-Fi unlimited streaming, A/C, 600sf

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Water's Edge Setting With Spectacular Views Of Blue Hill Bay, vacation rental in Penobscot

Water's Edge Setting With Spectacular Views Of Blue Hill Bay

5 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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Charming Sandy Point Home, vacation rental in Penobscot

Charming Sandy Point Home

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Gorgeous Oceanfront On A Private Lane, vacation rental in Penobscot

Gorgeous Oceanfront On A Private Lane

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Modern coastal Maine vacation home in a gorgeous setting, vacation rental in Penobscot

Modern coastal Maine vacation home in a gorgeous setting

3 bedrooms
2 bathrooms
Sleeps 6
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 Penobscot

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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Lake-side Living at Its Best on Toddy Pond, vacation rental in Penobscot

Lake-side Living at Its Best on Toddy Pond

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Upscale Waterfront Cedar Log Cabin, vacation rental in Penobscot

Upscale Waterfront Cedar Log Cabin

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Seacroft, vacation rental in Penobscot

Seacroft

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Vacation in affordable luxury!  Scenic, private, quiet. May & June now open!, vacation rental in Penobscot

Vacation in affordable luxury! Scenic, private, quiet. May & June now open!

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

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

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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'Your Maine Retreat' is a unique, one of a kind experience., vacation rental in Penobscot

'Your Maine Retreat' is a unique, one of a kind experience.

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Farm Cabin at Tapley Farm's Waterfront, vacation rental in Penobscot

Farm Cabin at Tapley Farm's Waterfront

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Comfy Downtown Getaway w/ Full Kitchen - Close to the Beach, vacation rental in Penobscot

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private Bayside Retreat On Penobscot Bay:  Perfect Midcoast/DownEast Location!, vacation rental in Penobscot

Private Bayside Retreat On Penobscot Bay: Perfect Midcoast/DownEast Location!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Parker House, National Register of Historic Places, vacation rental in Penobscot

Parker House, National Register of Historic Places

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Tranquility on Penobscot Bay Private Retreat: Perfect Midcoast/DownEast Location, vacation rental in Penobscot

Tranquility on Penobscot Bay Private Retreat: Perfect Midcoast/DownEast Location

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Maine Boathouse, Blue Hill Peninsula, Brooksville, Acadia, vacation rental in Penobscot

Charming Maine Boathouse, Blue Hill Peninsula, Brooksville, Acadia

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Private 2-Story Cottage with Lake View on 7 Acres, vacation rental in Penobscot

Private 2-Story Cottage with Lake View on 7 Acres

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Steamboat Crossing Cabins: #2 Maple Cabin, vacation rental in Penobscot

Steamboat Crossing Cabins: #2 Maple Cabin

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront shingled cottage w/ shared boat dock - near Acadia!, vacation rental in Penobscot

Waterfront shingled cottage w/ shared boat dock - near Acadia!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Updated lakefront cottage w/ shared grill & boat dock - near Acadia, vacation rental in Penobscot

Updated lakefront cottage w/ shared grill & boat dock - near Acadia

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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A cozy cabin just 20 feet from the shore of Toddy Pond, vacation rental in Penobscot

A cozy cabin just 20 feet from the shore of Toddy Pond

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Hollyhock House, vacation rental in Penobscot

The Hollyhock House

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Sandy Point Getaway w/ Wraparound Deck!, vacation rental in Penobscot

Beautiful Sandy Point Getaway w/ Wraparound Deck!

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Estabrooke Cottage, in the Heart of the Village of Castine, vacation rental in Penobscot

Estabrooke Cottage, in the Heart of the Village of Castine

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Totally Remodeled Vacation Home in Blue Hill, vacation rental in Penobscot

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, vacation rental in Penobscot

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

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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Nautilus Island, Exclusive Private Island, vacation rental in Penobscot

Nautilus Island, Exclusive Private Island

9 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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Family Friendly, Waterfront Home near Castine, Maine, vacation rental in Penobscot

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 Penobscot

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 Penobscot

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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Sandy Point Brook side Coastal Cottage- Easy Shores, vacation rental in Penobscot

Sandy Point Brook side Coastal Cottage- Easy Shores

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Brand new farm cottage close to downtown Blue Hill and Acadia National Park, vacation rental in Penobscot

Brand new farm cottage close to downtown Blue Hill and Acadia National Park

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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