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Results: 93 Rentals

  • Geary House at Fifield Point
    From $210 per night (USD)

    VRBO

    Geary House at Fifield Point

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Privately situated saltwater farmhouse on the narrow peninsula of Fifield Point, capturing both easterly and westerly vi ...

    From $210 per night (USD)

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    Details
  • Dorsey Cottage - On a quiet cove
    From $165 per night (USD)

    Expedia

    Dorsey Cottage - On a quiet cove

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Dorsey Cottage is situated on a quiet cove that is just off the popular sailing lanes of Eggemoggin Reach (a mile wide b ...

    From $165 per night (USD)

    Expedia

    Details
  • Sweet Grass Bay Cottage
    From $197 per night (USD)

    VRBO

    Sweet Grass Bay Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Sweet Grass Cottage is a cozy log cabin located right at the water's edge. With one bedroom on the main floor and anot ...

    From $197 per night (USD)

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    Details
  • Shangri-La Cottage - Designed with fun in mind
    From $225 per night (USD)

    Expedia

    Shangri-La Cottage - Designed with fun in mind

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Shangri-La sits on the waters edge, looking out onto Billings Cove and the Freese Islands. Offering upper and Lower Deck ...

    From $225 per night (USD)

    Expedia

    Details
  • Oak Point Cottage - Waterfront with a great beach
    From $285 per night (USD)

    VRBO

    Oak Point Cottage - Waterfront with a great beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Waterfront with a great beach! This 3-bedroom south-facing cottage on Deer Isle has deep water frontage and easy access ...

    From $285 per night (USD)

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    Details
  • Artists Retreat - Overlooking Northwest Harbor
    From $265 per night (USD)

    Expedia

    Artists Retreat - Overlooking Northwest Harbor

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Overlooking Northwest Harbor on Deer Isle, this oceanfront estate has 4 bedrooms and 2 full/split bathrooms. The setting ...

    From $265 per night (USD)

    Expedia

    Details
  • Sea Green Cottage - Delightful tidal oceanfront camp
    From $125 per night (USD)

    VRBO

    Sea Green Cottage - Delightful tidal oceanfront camp

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Sitting on the waters' edge of Greenlaw Cove in a peaceful, serene setting, this delightful, well-kept and immaculate ca ...

    From $125 per night (USD)

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  • Cottage On The Shore
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    Expedia

    Cottage On The Shore

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    6

    Cottage on the Shore rests in one of Deer Isle's most picturesque settings on family land owned for generations. The se ...

    Click For Pricing

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    Details
  • Premiere 4-season home in Deer Isle Maine
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    Premiere 4-season home in Deer Isle Maine

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Located in one of the most beautiful areas of Deer Isle, this 4-season, cedar post & beam house overlooks the bay and th ...

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    Details
  • Pat's Place - Peacefull & charming cottage
    From $175 per night (USD)

    Expedia

    Pat's Place - Peacefull & charming cottage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This peaceful and quiet cottage on Greenlaw Cove has an open floor plan and pine walls adding warmth and coziness to you ...

    From $175 per night (USD)

    Expedia

    Details
  • Gull Ledge, Stonington Harbour!
    From $390 per night (USD)

    VRBO

    Gull Ledge, Stonington Harbour!

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    One of the most unique properties in Stonington, Maine. Located within a 5 minute walk to downtown Stonington, this rec ...

    From $390 per night (USD)

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    Details
  • House At The Point - Rustic Cottage on Ocean's Edge
    From $165 per night (USD)

    Expedia

    House At The Point - Rustic Cottage on Ocean's Edge

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Enjoy this simple, rustic cabin that sits just 50 feet from the ocean between Burnt Cove and Crockett Cove. This priva ...

    From $165 per night (USD)

    Expedia

    Details
  • Poseidon Cottage - A Modern Chalet
    From $412 per night (USD)

    VRBO

    Poseidon Cottage - A Modern Chalet

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Poseidon is a new, chalet-style cottage with modern finishes and new appliances throughout, designed with large windows ...

    From $412 per night (USD)

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    Details
  • Blue House - Private Location
    From $128 per night (USD)

    Expedia

    Blue House - Private Location

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Blue House is located in a private setting on Dow Road just outside of Deer Isle village and close to Lily Pond, a favor ...

    From $128 per night (USD)

    Expedia

    Details
  • Point Field Cottage - A delightful little cape
    From $199 per night (USD)

    VRBO

    Point Field Cottage - A delightful little cape

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This delightful little cape sits on 7 acres of perhaps one of the areas most valuable and most admired parcels, with nea ...

    From $199 per night (USD)

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    Details
  • Sherwood Cottage - Panoramic views
    From $270 per night (USD)

    Expedia

    Sherwood Cottage - Panoramic views

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Meander down to the impressive 730 feet of shorefrontage on this beautifully situated cottage resting on 8.5 private, wo ...

    From $270 per night (USD)

    Expedia

    Details
  • White Birch Cottage - Webb Cove
    From $331 per night (USD)

    VRBO

    White Birch Cottage - Webb Cove

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    Stunning newly built contemporary on Web Cove, just a 5-10 minutes ride in to downtown Stonington. Beautiful, peaceful ...

    From $331 per night (USD)

    VRBO

    Details
  • A+ on Harbor w\/ 10 Kayaks, Dock, Deck, Patio, Beach, Walk To Town, Best Views
    Click For Pricing

    Expedia

    A+ on Harbor w\/ 10 Kayaks, Dock, Deck, Patio, Beach, Walk To Town, Best Views

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    9

    Harbor Heights Cottage has a premier setting right on Stonington Harbor in the quaint fishing village of Stonington, in ...

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    Details
  • Deer Isle Farmhouse - New!
    From $307 per night (USD)

    VRBO

    Deer Isle Farmhouse - New!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    The large farm house dining table is perfect for Maine-Lobster boils with friends and family. Enjoy a private screened p ...

    From $307 per night (USD)

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    Details
  • Cozy in-town cottage at harbor's edge w\/ garden, 4 kayaks, walk to downtown.
    From $195 per night (USD)

    Expedia

    Cozy in-town cottage at harbor's edge w\/ garden, 4 kayaks, walk to downtown.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Relax literally cove side in this adorable and cozy cottage with close up views of Stonington Harbor, distant islands, a ...

    From $195 per night (USD)

    Expedia

    Details
  • Apt 1 Studio apartments in downtown Stonington
    From $99 per night (USD)

    VRBO

    Apt 1 Studio apartments in downtown Stonington

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Apt 1 studio apartment in the fishing village of Stonington, Maine. Located in the heart of the village. Walk to all t ...

    From $99 per night (USD)

    VRBO

    Details
  • Secluded Rustic Cabin in the Woods with Distant Water View
    From $204 per night (USD)

    Expedia

    Secluded Rustic Cabin in the Woods with Distant Water View

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    A peaceful cabin in the woods for your family to get away from the cares of the world. The reviews from all of our gue ...

    From $204 per night (USD)

    Expedia

    Details
  • Shipshape, next door to Sand Beach in Stonington
    From $150 per night (USD)

    VRBO

    Shipshape, next door to Sand Beach in Stonington

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Shipshape is a one-level waterfront cottage located in one of the best locations in Stonington. Cozy, charming and unpr ...

    From $150 per night (USD)

    VRBO

    Details
  • Dow Road Waterfront - Privately situated
    From $148 per night (USD)

    Expedia

    Dow Road Waterfront - Privately situated

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Privately situated cottage on 3+ acres with steps leading down to the 300 feet of shore frontage and beach. Excellent v ...

    From $148 per night (USD)

    Expedia

    Details
  • New Secluded Deer Isle Cottage With Island Views - Quiet Woodland Retreat
    From $179 per night (USD)

    VRBO

    New Secluded Deer Isle Cottage With Island Views - Quiet Woodland Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beautiful quiet cottage in the woods. Great place to get away from the cares of the world. Comfortable family get-away ...

    From $179 per night (USD)

    VRBO

    Details
  • Waterfront Getaway Near Acadia w\/ Spectacular View
    From $145 per night (USD)

    Expedia

    Waterfront Getaway Near Acadia w\/ Spectacular View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Retreat to this coastal Maine getaway just steps away from your own private ocean front while roasting marshmallows by t ...

    From $145 per night (USD)

    Expedia

    Details
  • Spacious family retreat on a quiet cove with dock access
    From $350 per night (USD)

    VRBO

    Spacious family retreat on a quiet cove with dock access

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Wine and cheese on the deck, take a swim or launch your kayak. Enjoy an evening in front of a grand stone fireplace in a ...

    From $350 per night (USD)

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    Details
  • Garden cottage w\/ 4 kayaks\/gear\/dock\/patio, parking on Stonington Harbor nearby
    From $175 per night (USD)

    Expedia

    Garden cottage w\/ 4 kayaks\/gear\/dock\/patio, parking on Stonington Harbor nearby

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    4

    Sweet Pea Cottage is an affordable and charming 3 bedroom cottage located just a few minutes walk to downtown Stoningto ...

    From $175 per night (USD)

    Expedia

    Details
  • Cozy Cottage on Cat Cove w\/ Wraparound Deck!
    From $260 per night (USD)

    VRBO

    Cozy Cottage on Cat Cove w\/ Wraparound Deck!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Leave your worries behind for the beauty of coastal Maine when you escape to this Stonington vacation rental! The 3-bedr ...

    From $260 per night (USD)

    VRBO

    Details
  • Renovated 1854 Sea Captain's House w\/Harbor Views in Deer Isle Village<br>
    From $421 per night (USD)

    Expedia

    Renovated 1854 Sea Captain's House w\/Harbor Views in Deer Isle Village<br>

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    The Pickering House is an old sea captain's house with over 3000 sq feet of relaxing Down East charm. This property off ...

    From $421 per night (USD)

    Expedia

    Details
  • 2 BR Shorefront Shingled Classic  Pristine Long Water
    From $250 per night (USD)

    VRBO

    2 BR Shorefront Shingled Classic Pristine Long Water

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    Wonderful getaway! An enchanted seaside classic with expansive views straight down secluded Crockett Cove. Sun fi ...

    From $250 per night (USD)

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    Details
  • Charming, well-appointed home, pond side, and easy walk  to Deer Isle Village
    From $325 per night (USD)

    VRBO

    Charming, well-appointed home, pond side, and easy walk to Deer Isle Village

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    A beautiful, recently restored home with exceptional amenities. Cozy atmosphere with kitchen and porch dining. Owner i ...

    From $325 per night (USD)

    VRBO

    Details
  • Cozy Apartment. Family Size!
    From $300 per night (USD)

    VRBO

    Cozy Apartment. Family Size!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Newly renovated and thoughtfully furnished Perfect for families or groups Three spacious bedrooms sleep up to 6 guests w ...

    From $300 per night (USD)

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    Details
  • Spectacular Salt Water Farm on Penobscot Bay
    From $2500 per night (USD)

    VRBO

    Spectacular Salt Water Farm on Penobscot Bay

    Bedrooms:
    8
    Bathrooms:
    7
    Sleeps:
    14

    Classic salt water farm situated on 85 acres with 1500' of spectacular Penobscot Bay shorefront. Includes dock, 18th cen ...

    From $2500 per night (USD)

    VRBO

    Details
  • Kate's House in Spruce Harbour
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    VRBO

    Kate's House in Spruce Harbour

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    Come explore Spruce Harbor, a captivating oceanfront retreat on Deer Isle, where retreating glaciers left behind a beaut ...

    Click For Pricing

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  • Boat house in Spruce Harbor
    From $160 per night (USD)

    VRBO

    Boat house in Spruce Harbor

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Come explore Spruce Harbor, a captivating oceanfront retreat on Deer Isle, where retreating glaciers left behind a beaut ...

    From $160 per night (USD)

    VRBO

    Details
  • The Carriage House at Spruce Harbor
    From $175 per night (USD)

    VRBO

    The Carriage House at Spruce Harbor

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Come explore the captivating Spruce Harbor on Deer Isle, where retreating glaciers left behind a beautiful landscape of ...

    From $175 per night (USD)

    VRBO

    Details
  • LUXURIOUS OCEANFRONT WITH PRIVATE BEACH  - June 8 to June 22 still available
    From $875 per night (USD)

    VRBO

    LUXURIOUS OCEANFRONT WITH PRIVATE BEACH - June 8 to June 22 still available

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Stinson Point Retreat is a luxurious, oceanfront property with 300 feet of private beach. Stinson Point Retreat has ...

    From $875 per night (USD)

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    Details
  • 'Beautiful Secluded Coastal Maine  Island cottage Rental' Four Season
    From $189 per night (USD)

    VRBO

    'Beautiful Secluded Coastal Maine Island cottage Rental' Four Season

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Discover this uniquely located and beautifully furnished cottage nestled in the woods on an Island off the Coast Of Main ...

    From $189 per night (USD)

    VRBO

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

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

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Stunning westerly views of Penobscot Bay, Pumpkin Island Lighthouse, and Eggemoggin Cove. First floor bedroom with two ...

    Click For Pricing

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    Details
  • Eggemoggin Reach Oceanfront Contemporary Home With Mooring
    From $450 per night (USD)

    VRBO

    Eggemoggin Reach Oceanfront Contemporary Home With Mooring

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    9

    Contemporary shingle style cottage on Thompson Cove located on the world-class sailing lanes of Eggemoggin Reach. Grey L ...

    From $450 per night (USD)

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    Details
  • Secluded Cottage with Stunning Ocean Views
    From $250 per night (USD)

    VRBO

    Secluded Cottage with Stunning Ocean Views

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Privately situated at the end of a winding wooded lane, The Cottage is nestled at the edge of a 115 acre wooded setting, ...

    From $250 per night (USD)

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    Details
  •  Coastal Shorefront Home, Tidal Beach\/Views  Major Discount:1-2 person, Multiwk
    From $380 per night (USD)

    VRBO

    Coastal Shorefront Home, Tidal Beach\/Views Major Discount:1-2 person, Multiwk

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    5

    Waterfront tidal shore property. Cottage style post & beam 4 season year-round house with inviting wrap-around deck, sou ...

    From $380 per night (USD)

    VRBO

    Details
  • Secluded Oceanfront Home, with private beach and pier
    From $1363 per night (USD)

    Expedia

    Secluded Oceanfront Home, with private beach and pier

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    14

    Granite Shores is a spacious waterfront home set on over 10 secluded acres, and surrounded by many more acres of conserv ...

    From $1363 per night (USD)

    Expedia

    Details
  • Waterfront Home with Spacious 50ft x 10ft Deck Overlooking Water
    From $295 per night (USD)

    VRBO

    Waterfront Home with Spacious 50ft x 10ft Deck Overlooking Water

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Relax in a renovated, 3-bedroom, 2 bath home located on a 1.4-acre elevated waterfront lot in Deer Isle. A master bedroo ...

    From $295 per night (USD)

    VRBO

    Details
  • Historic Maine Summer Cottage with private beach, hot tub, 8BR, 3BA
    From $1500 per night (USD)

    VRBO

    Historic Maine Summer Cottage with private beach, hot tub, 8BR, 3BA

    Bedrooms:
    3
    Bathrooms:
    8
    Sleeps:
    12

    The Frederick Law Olmsted Summer Home, also known as Felsted, is a historic house located on the west side of Deer Isle, ...

    From $1500 per night (USD)

    VRBO

    Details
  • The Playhouse at Spruce Harbor
    From $285 per night (USD)

    VRBO

    The Playhouse at Spruce Harbor

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Come explore Spruce Harbor, a captivating oceanfront retreat on Deer Isle, where retreating glaciers left behind a beaut ...

    From $285 per night (USD)

    VRBO

    Details
  • 4 Bedroom Oceanville Home w\/ Breathtaking Views- Steps from Ocean
    From $400 per night (USD)

    VRBO

    4 Bedroom Oceanville Home w\/ Breathtaking Views- Steps from Ocean

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Does the vacation you are envisioning include waking up to breathtaking views of schooners passing by as you sip your ho ...

    From $400 per night (USD)

    VRBO

    Details
  • Contemporary Shorefront Home on Quiet Cove
    From $300 per night (USD)

    VRBO

    Contemporary Shorefront Home on Quiet Cove

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    This is a stunning house with beautiful views of the Deer Isle Thoroughfare. The main living area is a true great room w ...

    From $300 per night (USD)

    VRBO

    Details
  • Cottage for Six on the Waters of Eggemoggin Reach
    From $350 per night (USD)

    VRBO

    Cottage for Six on the Waters of Eggemoggin Reach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Classic all-season shingle cottage with three bedrooms, 18 acres of woods (spruce, pine, oak, birch, ash, etc.), large p ...

    From $350 per night (USD)

    VRBO

    Details
  • Oceanfront  apartment with private beach!
    From $125 per night (USD)

    VRBO

    Oceanfront apartment with private beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Eggemoggin Reach is home to some of the most ardent sailors around. From the front yard, you can watch the yatchs as wel ...

    From $125 per night (USD)

    VRBO

    Details
  • Custom-designed waterfront vacation home on 18+ acres of pristine natural beauty
    From $289 per night (USD)

    VRBO

    Custom-designed waterfront vacation home on 18+ acres of pristine natural beauty

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    7

    With 1000 feet of shoreline, Blue Arches is a beautiful contemporary 4 bedroom 2264 sq ft home on a private cove with sp ...

    From $289 per night (USD)

    VRBO

    Details
  • J & E Riggins - Stunning Stonington History w\/ king (Inn on the Harbor)
    From $74 per night (USD)

    VRBO

    J & E Riggins - Stunning Stonington History w\/ king (Inn on the Harbor)

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    4

    Welcome to Inn on the Harbor - Stonington: The J & E Riggins is a gorgeous 2nd-floor village street-side room perfect f ...

    From $74 per night (USD)

    VRBO

    Details
  • The Isaac Evans - Stunning Stonington History (Inn on the Harbor)
    From $70 per night (USD)

    Expedia

    The Isaac Evans - Stunning Stonington History (Inn on the Harbor)

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    4

    Welcome to Inn on the Harbor - Stonington: The Issac Evans is a lovely 1st-floor room on the village side of the inn wit ...

    From $70 per night (USD)

    Expedia

    Details
  • The Roseway - Stunning Harbor Views (Inn on the Harbor)
    From $121 per night (USD)

    VRBO

    The Roseway - Stunning Harbor Views (Inn on the Harbor)

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    Welcome to Inn on the Harbor - Stonington: The Roseway is a cozy 2nd-floor room perfect for two with a queen bed, full ...

    From $121 per night (USD)

    VRBO

    Details
  • The Angelique - Stunning Harbor Views (Inn on the Harbor)
    From $96 per night (USD)

    Expedia

    The Angelique - Stunning Harbor Views (Inn on the Harbor)

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    Welcome to Inn on the Harbor - Stonington: The Angelique is a lovely 1st-floor room perfect for two with a king bed, fu ...

    From $96 per night (USD)

    Expedia

    Details
  • The Stephen Taber - Stunning Harbor Views w\/ king bed (Inn on the Harbor)
    From $116 per night (USD)

    VRBO

    The Stephen Taber - Stunning Harbor Views w\/ king bed (Inn on the Harbor)

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    Welcome to Inn on the Harbor - Stonington: The Stephen Taber is a stunning 1st-floor room converted from what was once ...

    From $116 per night (USD)

    VRBO

    Details
  • The Victory Chimes - Stunning Harbor Views w\/ king bed (Inn on the Harbor)
    From $120 per night (USD)

    Expedia

    The Victory Chimes - Stunning Harbor Views w\/ king bed (Inn on the Harbor)

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    Welcome to Inn on the Harbor - Stonington: The Victory Chimes is an adorable 1st-floor room perfect for two with a king ...

    From $120 per night (USD)

    Expedia

    Details
  • The Mary Day - Stunning Harbor Views w\/ king bed (Inn on the Harbor)
    From $88 per night (USD)

    VRBO

    The Mary Day - Stunning Harbor Views w\/ king bed (Inn on the Harbor)

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    Welcome to Inn on the Harbor - Stonington: The Mary Day is a 1st-floor room perfectly suited for two with a king bed, f ...

    From $88 per night (USD)

    VRBO

    Details
  • The Nathaniel Bowditch w\/ queen bed (Inn on the Harbor)
    From $73 per night (USD)

    Expedia

    The Nathaniel Bowditch w\/ queen bed (Inn on the Harbor)

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    Welcome to Inn on the Harbor - Stonington: The Nathaniel Bowditch is a gorgeous 2nd-floor corner room with a queen bed, ...

    From $73 per night (USD)

    Expedia

    Details
  • The American Eagle - Stunning Harbor Views w\/ 2 bedroom (Inn on the Harbor)
    From $542 per night (USD)

    VRBO

    The American Eagle - Stunning Harbor Views w\/ 2 bedroom (Inn on the Harbor)

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    4

    The American Eagle is a gorgeous unit with 2 bedrooms: one with twin beds and a master bedroom room furnished with one q ...

    From $542 per night (USD)

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  • The Heritage - Stunning Harbor Views w\/ king bed (Inn on the Harbor)
    From $115 per night (USD)

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    The Heritage - Stunning Harbor Views w\/ king bed (Inn on the Harbor)

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    Welcome to Inn on the Harbor - Stonington: The Heritage is a lovely 2nd-floor room perfect for two with a king bed, ful ...

    From $115 per night (USD)

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    Details
  • Enjoy Gorgeous Views all around this Eggemoggin Reach Waterfront Home
    From $295 per night (USD)

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    Enjoy Gorgeous Views all around this Eggemoggin Reach Waterfront Home

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Locals say the summer shoulder months (June and September) are the best months of the year! In addition to both sunrise ...

    From $295 per night (USD)

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  • Cozy Harbor View Apartment
    From $255 per night (USD)

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    Cozy Harbor View Apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Watch the lobsterman haul in their catch from your scenic bay windows overlooking the charming Stonington Harbor and sur ...

    From $255 per night (USD)

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  • Stunning private oceanfront home
    From $749 per night (USD)

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    Stunning private oceanfront home

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    10

    Take in the glistening ocean view of the Penobscot Bay as you drink your coffee from the deck, and watch distant lobster ...

    From $749 per night (USD)

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    Details
  • A Victorian Gem on Deer Isle - Walkable to beaches and local shops
    From $216 per night (USD)

    Expedia

    A Victorian Gem on Deer Isle - Walkable to beaches and local shops

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Come and stay in the heart of Deer Isle. This victorian gem will embrace you with the charm and warmth only a home built ...

    From $216 per night (USD)

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  • Quiet, family friendly cottage
    From $200 per night (USD)

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    Quiet, family friendly cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Wanting to be close to the coast, but the quietness of the forest? This cottage is for you! This quiet cottage is sited ...

    From $200 per night (USD)

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  • Waterfront Deer Isle Retreat w\/ Fire Pit!
    From $239 per night (USD)

    Expedia

    Waterfront Deer Isle Retreat w\/ Fire Pit!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    The beauty of coastal Maine awaits you at this charming 2-bedroom, 2.5-bathroom vacation rental in Deer Isle! This home ...

    From $239 per night (USD)

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  • Wolfhound Cottage - Dogs welcome!
    From $285 per night (USD)

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    Wolfhound Cottage - Dogs welcome!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Wolfhound Cottage, a beautifully built post & beam cottage, sits at the end of a dirt road surrounded by moss-covered bo ...

    From $285 per night (USD)

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  • Eastman's Seaside Cottage with Private Beach
    From $519 per night (USD)

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    Eastman's Seaside Cottage with Private Beach

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    10

    With panoramic ocean views on a 4 acre property, this historic beachfront Deer Isle, Maine cottage -- renovated in 2021 ...

    From $519 per night (USD)

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  • Historic Cottage on Secluded Cove, with kayak, canoe and private ocean access.
    From $300 per night (USD)

    VRBO

    Historic Cottage on Secluded Cove, with kayak, canoe and private ocean access.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Relax at my secluded oceanfront home! Surrounded by 18 acres, you will have complete privacy and peace here! 4 bedrooms, ...

    From $300 per night (USD)

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  • Cozy quiet Cottage
    From $150 per night (USD)

    Expedia

    Cozy quiet Cottage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Beautiful rental, in a quiet neighborhood. Sited off a side road, near the Deer Isle village. Take a morning walk, enjoy ...

    From $150 per night (USD)

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    Details
  • Ocean Bluff - Private Beach!
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    Ocean Bluff - Private Beach!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Ocean Bluff, lovely new listing available in Deer Isle, Maine! This spacious home sits on the ocean's edge and offers lo ...

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  • Beautiful cottage on a tidal cove in Stonington, ME
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    Beautiful cottage on a tidal cove in Stonington, ME

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Just a short drive down scenic Oceanville Road and only 2 1/2 miles from the beautiful fishing village of Stonington sit ...

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  • Secluded Stonington, Maine cottage gem with Rockefeller view of Penobscot Bay
    From $257 per night (USD)

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    Secluded Stonington, Maine cottage gem with Rockefeller view of Penobscot Bay

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    3

    ********* COTTAGE IS BOOKED FOR 2024 SEASON AS OF 12-12-23. I WILL UPDATE THIS SPACE TO POST ANY VACANCI ...

    From $257 per night (USD)

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  • Waterfront Deer Isle Apartment w\/ Fire Pit
    From $283 per night (USD)

    Expedia

    Waterfront Deer Isle Apartment w\/ Fire Pit

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Escape to Deer Isle, Maine, for an unforgettable coastal retreat! This vacation rental offers 2 bedrooms, 1 bathroom, a ...

    From $283 per night (USD)

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    Details
  • Ledgelawn - Amazing Views!
    From $330 per night (USD)

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    Ledgelawn - Amazing Views!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    Welcome to Ledgelawn! NEW offering for 2023. Sitting on the ocean's edge of Eggemoggin Reach in LDI, this lovely 4 bedr ...

    From $330 per night (USD)

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    Details
  • Secluded house just minutes away from Deer Isle\/Stonington villages and beaches!
    From $190 per night (USD)

    Expedia

    Secluded house just minutes away from Deer Isle\/Stonington villages and beaches!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    A Stone's Throw house is situated 3/4 mile from the main road on a small peninsula. Enjoy the peacefulness, the sunny ya ...

    From $190 per night (USD)

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    Details
  • Charming meticulously restored 1830s cape Deer Isle
    From $242 per night (USD)

    VRBO

    Charming meticulously restored 1830s cape Deer Isle

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Full of light with thoughtful touches throughout this sunny 200 year old home is perfect for your quintessential Maine g ...

    From $242 per night (USD)

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    Details
  • The Lewis R. French- Stunning Stonington History (Inn on the Harbor)
    From $76 per night (USD)

    Expedia

    The Lewis R. French- Stunning Stonington History (Inn on the Harbor)

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    4

    Welcome to Inn on the Harbor - Stonington: The Lewis R. French is a lovely room on the 1st-floor village side of the inn ...

    From $76 per night (USD)

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  • Tranquility By The Ocean
    From $275 per night (USD)

    VRBO

    Tranquility By The Ocean

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Our home was brought over from Denmark in the 1980's. It has been meticulously maintained. The kitchen is a cook's deli ...

    From $275 per night (USD)

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    Details
  • Charming Stonington Studio w\/ Ocean Views!
    From $288 per night (USD)

    Expedia

    Charming Stonington Studio w\/ Ocean Views!

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    Escape to the coast and indulge in the island life when you stay at this 1-bath vacation rental studio! Spend your morni ...

    From $288 per night (USD)

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    Details
  • Cozy Deer Isle Farmhouse Retreat
    From $193 per night (USD)

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    Cozy Deer Isle Farmhouse Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Cozy two-bedroom farmhouse located in the heart of Deer Isle Village. This inviting retreat exudes a peaceful atmosphere ...

    From $193 per night (USD)

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  • Seabreeze on the Harbor 2 - Stunning Island Retreat perched on Stonington Harbor
    From $240 per night (USD)

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    Seabreeze on the Harbor 2 - Stunning Island Retreat perched on Stonington Harbor

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Experience the enchantment of seaside living at Seabreeze on the Harbor, located in beautiful downtown Stonington, Maine ...

    From $240 per night (USD)

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  • Seabreeze on the Harbor 1 - Stunning Island Retreat perched on Stonington Harbor
    From $272 per night (USD)

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    Seabreeze on the Harbor 1 - Stunning Island Retreat perched on Stonington Harbor

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Experience the enchantment of seaside living at Seabreeze on the Harbor, located in beautiful downtown Stonington, Maine ...

    From $272 per night (USD)

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    Details
  • The Pines, a Deer Isle cottage
    From $294 per night (USD)

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    The Pines, a Deer Isle cottage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    The Pines is a classic Maine cottage that combines the charm of a 90 year old home with updated, modern amenities. Th ...

    From $294 per night (USD)

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    Details
  • Charming home on the harbor w\/ ocean views, nestled on the shore w\/ a large deck
    From $394 per night (USD)

    VRBO

    Charming home on the harbor w\/ ocean views, nestled on the shore w\/ a large deck

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Do you crave balmy summer evenings or frosty winter days that make you feel like you've been transported back to a simpl ...

    From $394 per night (USD)

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    Details
  • Eboleth House - lovingly restored
    From $360 per night (USD)

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    Eboleth House - lovingly restored

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    New listing! Eboleth House, located in Sargentville, is named after the original family that lived there during the tur ...

    From $360 per night (USD)

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    Details
  • Heron Watch - Quintessential Oceanfront Home Sited at the Head of a Cove
    From $329 per night (USD)

    VRBO

    Heron Watch - Quintessential Oceanfront Home Sited at the Head of a Cove

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Heron Watch is a gorgeous privately sited oceanfront home positioned at the head of a tidal cove featuring expansive vie ...

    From $329 per night (USD)

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    Details
  • Apartment 3 in Merchants Row Building in downtown Stonington.
    From $250 per night (USD)

    VRBO

    Apartment 3 in Merchants Row Building in downtown Stonington.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Apartment 3 one-bedroom apartment in the fishing village of Stonington, Maine. Located in the heart of the village. W ...

    From $250 per night (USD)

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    Details
  • The Timberwind - Stunning Harbor Views (Inn on the Harbor)
    From $89 per night (USD)

    VRBO

    The Timberwind - Stunning Harbor Views (Inn on the Harbor)

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    Welcome to Inn on the Harbor - Stonington: The Timberwind is a lovely 2nd-floor room perfect for two with a queen bed, ...

    From $89 per night (USD)

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    Details
  • The Grace Bailey - Stunning Harbor Views w\/ twins (Inn on the Harbor)
    From $70 per night (USD)

    Expedia

    The Grace Bailey - Stunning Harbor Views w\/ twins (Inn on the Harbor)

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    Welcome to Inn on the Harbor - Stonington: The Grace Bailey is a cozy 1st-floor room with two twin beds, a full bath, a ...

    From $70 per night (USD)

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    Details
  • Sunlit Cottage on Crockett Cove
    From $306 per night (USD)

    VRBO

    Sunlit Cottage on Crockett Cove

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Open, airy and light filled cottage at the head of Crockett Cove’s tidal estuary. It is a very private and serene settin ...

    From $306 per night (USD)

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    Details