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  • Cozy apartment near the river:  walk to town & local attractions
    From $206 per night (USD)

    VRBO

    Cozy apartment near the river: walk to town & local attractions

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Finest Kind Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...

    From $206 per night (USD)

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    Details
  • The Gathering Place/Jefferson
    From $313 per night (USD)

    VRBO

    The Gathering Place/Jefferson

    Bedrooms:
    1
    Bathrooms:
    6
    Sleeps:
    13

    Ideal for Two Families or Large Groups – Lakefront Retreat on Damariscotta Lake This spacious and inviting lakefront co ...

    From $313 per night (USD)

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    Details
  • Best View | 3 Bedroom | Shared Dock
    From $507 per night (USD)

    VRBO

    Best View | 3 Bedroom | Shared Dock

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    THIS HOME RENTS WITH A 4-NIGHT MINIMUM WEEKLY SPECIAL AVAILABLE Escape to Serenity at Best View If your kind of luxur ...

    From $507 per night (USD)

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  • Osprey Oasis | Dog-Friendly | EV Charger | Nature Retreat
    From $610 per night (USD)

    Expedia

    Osprey Oasis | Dog-Friendly | EV Charger | Nature Retreat

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    THIS HOME RENTS WEEKLY, JUNE-SEPTEMBER 4 NIGHT MINIMUM IN FALL. STAY THE WEEK FOR A SPECIAL RATE! Osprey Oasis: Your C ...

    From $610 per night (USD)

    Expedia

    Details
  • Morning Sun | Spruce Point | 1 Bedroom | 1 Bathroom
    From $460 per night (USD)

    VRBO

    Morning Sun | Spruce Point | 1 Bedroom | 1 Bathroom

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    THIS HOME RENTS WEEKLY, JUNE-SEPTEMBER. 4 NIGHT MINIMUM IN FALL. WEEKLY SPECIAL AVAILABLE! Morning Sun: Your Cozy Carr ...

    From $460 per night (USD)

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  • Experience this stylish and unique stay just 8 minutes from Boothbay Harbor.
    From $247 per night (USD)

    VRBO

    Experience this stylish and unique stay just 8 minutes from Boothbay Harbor.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Escape to an enchanting 2-bedroom house in Boothbay. This marvelous retreat features 2 queen beds, 1 sofa bed, and a coz ...

    From $247 per night (USD)

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    Details
  • Deck w/ Water Views: Quiet East Boothbay Retreat!
    From $259 per night (USD)

    VRBO

    Deck w/ Water Views: Quiet East Boothbay Retreat!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Pets Welcome w/ Fee | Cookout Ready | Near Public Kayak & Canoe Launches Nestled between Damariscotta River and Linekin ...

    From $259 per night (USD)

    VRBO

    Details
  • 4 Mi to Boothbay Harbor: Quiet Retreat w/ Deck
    Click For Pricing

    Expedia

    4 Mi to Boothbay Harbor: Quiet Retreat w/ Deck

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Fire Pit | RV Parking | 3 Mi to the Coastal Maine Botanical Gardens Your next Midcoast adventure awaits at this Boothba ...

    Click For Pricing

    Expedia

    Details
  • Sea Drift Cottage/ New Harbor
    From $779 per night (USD)

    VRBO

    Sea Drift Cottage/ New Harbor

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Sea Drift – Oceanfront Comfort with Sweeping Views of John’s Bay Step into coastal serenity at Sea Drift, a ...

    From $779 per night (USD)

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    Details
  • Heron Oaks/Rutherford Island
    From $403 per night (USD)

    VRBO

    Heron Oaks/Rutherford Island

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Bright Coastal Cottage with Panoramic Ocean Views Escape to this contemporary seaside cottage perched above John's Bay ...

    From $403 per night (USD)

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  • Dog-Friendly Boothbay Getaway with New Dock & Walk to Country Store!
    From $471 per night (USD)

    VRBO

    Dog-Friendly Boothbay Getaway with New Dock & Walk to Country Store!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Cottage Connection Presents: Long Dock This home has a 4-night minimum. Stay the week (or longer!) for a special rate! ...

    From $471 per night (USD)

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  • Harbor House Cottage/ Bremen
    From $715 per night (USD)

    VRBO

    Harbor House Cottage/ Bremen

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Stunning Oceanfront Shingle-Style Cottage with Harbor Views This beautiful contemporary cottage offers an unforgettable ...

    From $715 per night (USD)

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  • Fox Lane located in Bremen
    From $448 per night (USD)

    VRBO

    Fox Lane located in Bremen

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy lakeside serenity on Pemaquid Lake! Tucked away on a beautifully wooded and private lot along the shores of Pemaq ...

    From $448 per night (USD)

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    Details
  • The Cottage | Bristol
    From $344 per night (USD)

    VRBO

    The Cottage | Bristol

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Tranquil Maine Getaway on Biscay Pond Tucked away in the heart of Miane's stunning wilderness, this charming cottage of ...

    From $344 per night (USD)

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  • The Cottage | Nobleboro
    From $329 per night (USD)

    VRBO

    The Cottage | Nobleboro

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    10

    This house is designed as a modern retreat in the woods, full of windows and light to highlight the beauty of vaulted ce ...

    From $329 per night (USD)

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    Details
  • Pemaquid Loop Cottage/Pemaquid Point
    From $497 per night (USD)

    VRBO

    Pemaquid Loop Cottage/Pemaquid Point

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Stylish Coastal Cape with Ocean Views on Pemaquid Loop Welcome to your perfect Maine getaway — a beautifully renovated ...

    From $497 per night (USD)

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  • Houseboat ROAM on Lake Pemaquid
    From $320 per night (USD)

    VRBO

    Houseboat ROAM on Lake Pemaquid

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    - A Little Closer To Nowhere - A one-of-a-kind eco-travel experience, ROAM is a simple - but comfortably equipped - hou ...

    From $320 per night (USD)

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  • West Camp Stay - Cabins 5 + 6
    From $673 per night (USD)

    Expedia

    West Camp Stay - Cabins 5 + 6

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    10

    The Ultimate Maine Escape! Stay at two of Otyokwa's Exclusive Lakeside Cabins in Bremen, Maine. Nestled along the shore ...

    From $673 per night (USD)

    Expedia

    Details
  • East Camp Stay - Cabin 1 + 3 + 4
    From $687 per night (USD)

    VRBO

    East Camp Stay - Cabin 1 + 3 + 4

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    10

    The Ultimate Maine Escape! Stay in three of Otyokwa's Exclusive Lakeside Cabins in Bremen, Maine. Nestled along the sho ...

    From $687 per night (USD)

    VRBO

    Details
  • Houseboat NOMAD on Lake Pemaquid
    From $410 per night (USD)

    Expedia

    Houseboat NOMAD on Lake Pemaquid

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    - A Little Closer to Nowhere - A one-of-a-kind eco-travel experience, NOMAD is a simple - but comfortably equipped - ho ...

    From $410 per night (USD)

    Expedia

    Details
  • Ambleside- a beautifully renovated home in Boothbay Harbor Maine!
    From $880 per night (USD)

    VRBO

    Ambleside- a beautifully renovated home in Boothbay Harbor Maine!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Situated on the Eastside of the quintessential Maine harbor town of Boothbay Harbor, this home is just a short walk acro ...

    From $880 per night (USD)

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  • The Farmhouse at Otyokwa
    From $285 per night (USD)

    Expedia

    The Farmhouse at Otyokwa

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    A summer getaway or winter respite, our four-season Farmhouse at Otyokwa is the 'Top House' of the original boys camp op ...

    From $285 per night (USD)

    Expedia

    Details
  • Enchanting apartment with WiFi in charming Jefferson
    From $113 per night (USD)

    VRBO

    Enchanting apartment with WiFi in charming Jefferson

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover the beauty of Damariscotta from this welcoming 1-bedroom apartment in the quiet of Jefferson at the north end o ...

    From $113 per night (USD)

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    Details
  • Ship's Wheel - Charming Ocean View in Ocean Point!
    From $389 per night (USD)

    VRBO

    Ship's Wheel - Charming Ocean View in Ocean Point!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Ship's Wheel, an awesome place to chill! Combine an authentic Maine camp with great amenities and linens, in ...

    From $389 per night (USD)

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    Details
  • Upscale Oceanfront with Panoramic Views!
    From $448 per night (USD)

    VRBO

    Upscale Oceanfront with Panoramic Views!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Seaside Cottage in East Boothbay! This is a gorgeous, recently renovated cottage perched on the edge of the D ...

    From $448 per night (USD)

    VRBO

    Details
  • LobsterCliff by Chill Vacation Rentals!
    From $372 per night (USD)

    Expedia

    LobsterCliff by Chill Vacation Rentals!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to LobsterCliff Cottage in East Boothbay! Our beautiful oceanfront cottage offers great amenities and some of th ...

    From $372 per night (USD)

    Expedia

    Details
  • Rosewater Cottage - Oceanfront on Linekin Bay!
    From $433 per night (USD)

    VRBO

    Rosewater Cottage - Oceanfront on Linekin Bay!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Rosewater Seaside Cottage! If you're looking for a special waterfront escape that has all the comforts of hom ...

    From $433 per night (USD)

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    Details
  • Atlantic Edge - Oceanfront with Stunning Views!
    From $431 per night (USD)

    VRBO

    Atlantic Edge - Oceanfront with Stunning Views!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Atlantic Edge Cottage in beautiful East Boothbay Maine! This beautiful 2 bedroom, 1 bath cottage sits directl ...

    From $431 per night (USD)

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    Details
  • Cabin in the woods/Bristol
    From $214 per night (USD)

    VRBO

    Cabin in the woods/Bristol

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to a warm and peaceful mid-century modern style cottage overlooking tranquil Biscay Pond in Bristol. It features ...

    From $214 per night (USD)

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    Details
  • THE NOOK Apartment
    From $251 per night (USD)

    Expedia

    THE NOOK Apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Enjoy the simplicity of Cabin Life in THE NOOK, our cozy corner apartment at Camp Otyokwa in MidCoast Maine. Nestled on ...

    From $251 per night (USD)

    Expedia

    Details
  • Lakeside Cabin Stay
    From $1634 per night (USD)

    VRBO

    Lakeside Cabin Stay

    Bedrooms:
    2
    Bathrooms:
    6
    Sleeps:
    27

    Gather with your family and friends at Camp! **SUMMER GETAWAY RATE August 17th through 28th** 10% Discount on our nigh ...

    From $1634 per night (USD)

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    Details
  • SeaGlass Cottage: Incredible waterfront Retreat!
    From $353 per night (USD)

    VRBO

    SeaGlass Cottage: Incredible waterfront Retreat!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to SeaGlass Cottage, an absolutely magical waterfront cottage in East Boothbay! SeaGlass is perched right next t ...

    From $353 per night (USD)

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    Details
  • Mainelandia! Stunning New Waterfront Home!
    From $449 per night (USD)

    VRBO

    Mainelandia! Stunning New Waterfront Home!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Mainelandia, a stunning new home nestled on the edge of Pleasant Cove. This stylish cottage beautifully blend ...

    From $449 per night (USD)

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    Details
  • Sail Loft - Upscale Oceanfront on a Pier near BBH!
    From $242 per night (USD)

    VRBO

    Sail Loft - Upscale Oceanfront on a Pier near BBH!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Sail Loft, a one-of-a-kind vacation destination in Boothbay Harbor! You can't get any closer to the water tha ...

    From $242 per night (USD)

    VRBO

    Details
  • Owl's Nest by Sea Maine
    From $480 per night (USD)

    VRBO

    Owl's Nest by Sea Maine

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Escape to the serene beauty of Owl's Nest by Sea Maine, a charming single-family home nestled along the picturesque King ...

    From $480 per night (USD)

    VRBO

    Details
  • Serene 4-bedroom house with WiFi in South Bristol
    From $316 per night (USD)

    Expedia

    Serene 4-bedroom house with WiFi in South Bristol

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    Discover this fully furnished 4-bedroom gem in South Bristol with saltwater frontage on Clarks Cove. This beautiful, ful ...

    From $316 per night (USD)

    Expedia

    Details
  • Ocean views, private beach, garden patio, red clay tennis, dock access, WiFi
    From $356 per night (USD)

    VRBO

    Ocean views, private beach, garden patio, red clay tennis, dock access, WiFi

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Discover this brilliant 2-bedroom cottage in Boothbay Harbor. This fifth generation cottage features a cozy king bed and ...

    From $356 per night (USD)

    VRBO

    Details
  • Enjoyable 1-bedroom rustic cottage in Southport.
    From $235 per night (USD)

    Expedia

    Enjoyable 1-bedroom rustic cottage in Southport.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Get ready to relax in this welcoming 1-bedroom rustic cottage in Southport. This gorgeous retreat features a cozy queen ...

    From $235 per night (USD)

    Expedia

    Details
  • Gather in Comfort at The Flying Cloud
    From $1208 per night (USD)

    VRBO

    Gather in Comfort at The Flying Cloud

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    14

    Visiting for an event or getaway? The Flying Cloud offers space for your group—where everyone gets their own bedroom and ...

    From $1208 per night (USD)

    VRBO

    Details
  • New! Pemaquid Escape | Curated Comfort + Hot Tub
    From $498 per night (USD)

    Expedia

    New! Pemaquid Escape | Curated Comfort + Hot Tub

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    This fully stocked 4-bedroom retreat blends relaxation and recreation with a hot tub, screened porch, lounge for kids (o ...

    From $498 per night (USD)

    Expedia

    Details
  • Cozy Dog-Friendly Retreat on Westport Island: Enjoy Serene Nature & Walk to Waterfront!
    From $320 per night (USD)

    VRBO

    Cozy Dog-Friendly Retreat on Westport Island: Enjoy Serene Nature & Walk to Waterfront!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Tranquil Retreat on Westport Island Escape to the serene beauty of Westport Island, where this cozy single-story home a ...

    From $320 per night (USD)

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    Details
  • Charming, private, waterfront 3-bedroom cottage on Westport Island ME on 1 acre
    Click For Pricing

    Expedia

    Charming, private, waterfront 3-bedroom cottage on Westport Island ME on 1 acre

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Want a one-of-a-kind, traditional Maine coast getaway? Look no further… This meticulous Westport Island private waterf ...

    Click For Pricing

    Expedia

    Details
  • Keene`s Cottage/Damariscotta Lake
    From $404 per night (USD)

    VRBO

    Keene`s Cottage/Damariscotta Lake

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Charming Lakeside Retreat with Private Dock and Stunning Sunset Views Welcome to Keene’s Cottage, a beautifully renovat ...

    From $404 per night (USD)

    VRBO

    Details
  • More Boathouse than Lakehouse
    From $469 per night (USD)

    Expedia

    More Boathouse than Lakehouse

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    Escape to this serene lakefront retreat in the heart of Mid-Coast Maine, in the heart of coastal charm, culinary gems an ...

    From $469 per night (USD)

    Expedia

    Details
  • Charming Lakefront Cottage ~ Private Dock w/ Stunning Lake Views
    From $340 per night (USD)

    VRBO

    Charming Lakefront Cottage ~ Private Dock w/ Stunning Lake Views

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to our charming lakefront retreat in the heart of scenic Maine! Nestled on the shores of Biscay Pond, only feet ...

    From $340 per night (USD)

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    Details
  • Gorgeous Waterfront& Yard on Damariscotta Lake with an Amazing Home
    From $561 per night (USD)

    VRBO

    Gorgeous Waterfront& Yard on Damariscotta Lake with an Amazing Home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Serenity Point – A Waterfront Retreat on Damariscotta Lake Discover the magic of Serenity Point, a stunning waterfront e ...

    From $561 per night (USD)

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    Details
  • A Garden with a Cottage in Waldoboro
    From $221 per night (USD)

    VRBO

    A Garden with a Cottage in Waldoboro

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    Welcome to this enchanting cottage in Waldoboro. This fairytale property features a cozy attic bedroom featuring two bed ...

    From $221 per night (USD)

    VRBO

    Details
  • Elegant home with a cozy living area, Wifi, backyard, and washer/dryer
    From $326 per night (USD)

    Expedia

    Elegant home with a cozy living area, Wifi, backyard, and washer/dryer

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    Wiscasset Woodland Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...

    From $326 per night (USD)

    Expedia

    Details
  • Charming Oceanfront Home with Stunning Water Views and Wifi
    From $317 per night (USD)

    VRBO

    Charming Oceanfront Home with Stunning Water Views and Wifi

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Ocean's Edge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...

    From $317 per night (USD)

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  • Clark’s Cove Retreat on Damariscotta River
    From $288 per night (USD)

    VRBO

    Clark’s Cove Retreat on Damariscotta River

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Our house sits directly on the Damariscotta River and is tucked up in beautiful Clarks Cove . This location has a commer ...

    From $288 per night (USD)

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    Details
  • Tiny A-Frame Romantic Getaway
    From $400 per night (USD)

    VRBO

    Tiny A-Frame Romantic Getaway

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Camp Lupine is a brand new Luxury 400 sq ft Tiny A-Frame tucked away on a private wooded lot with a small stream just a ...

    From $400 per night (USD)

    VRBO

    Details
  • Hillside Cottage- Bristol
    From $278 per night (USD)

    VRBO

    Hillside Cottage- Bristol

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Tranquil Wooded Cabin Retreat Near Biscay Pond & Pemaquid River Nestled in the woods and thoughtfully built in 2005, th ...

    From $278 per night (USD)

    VRBO

    Details
  • Cozy 1-bedroom apartment in charming Damariscotta with AC, WiFi
    From $210 per night (USD)

    VRBO

    Cozy 1-bedroom apartment in charming Damariscotta with AC, WiFi

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Downtown neighborhood in Damariscotta: This delightful apartment offers a brilliant stay for guests. With one bedroom f ...

    From $210 per night (USD)

    VRBO

    Details
  • 4BR, 2 BA Traditional Cottage with Ocean Views on Pemaquid Point
    From $215 per night (USD)

    VRBO

    4BR, 2 BA Traditional Cottage with Ocean Views on Pemaquid Point

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    This traditional cottage is spacious and beautifully updated, offering water views from the front porch, two bedrooms, a ...

    From $215 per night (USD)

    VRBO

    Details
  • Enchantingly beautiful with views of Five Islands Harbor and Ocean
    From $471 per night (USD)

    VRBO

    Enchantingly beautiful with views of Five Islands Harbor and Ocean

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Beautiful new home nestled in Five Islands with views of the harbor and ocean. Open concept kitchen/living room with a s ...

    From $471 per night (USD)

    VRBO

    Details
  • Charming Cottage with Ocean Views, Wifi, and Washer and Dryer
    From $269 per night (USD)

    Expedia

    Charming Cottage with Ocean Views, Wifi, and Washer and Dryer

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    Sea Breeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...

    From $269 per night (USD)

    Expedia

    Details
  • Fully Remodeled Coastal Retreat with Spacious Deck and Dog-Friendly Comfort
    From $504 per night (USD)

    VRBO

    Fully Remodeled Coastal Retreat with Spacious Deck and Dog-Friendly Comfort

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    Pine Ledge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...

    From $504 per night (USD)

    VRBO

    Details
  • SHEEPSCOT LOOKOUT - Town of Westport Island - Sheepscot River
    From $740 per night (USD)

    Expedia

    SHEEPSCOT LOOKOUT - Town of Westport Island - Sheepscot River

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    THIS PROPERTY ONLY RENTS ON A SATURDAY TO SATURDAY SCHEDULE - 7 NIGHT MINIMUM REQUIRED **New for 2025- New Deck and sta ...

    From $740 per night (USD)

    Expedia

    Details
  • JONES COTTAGE - Town of Boothbay Harbor
    From $643 per night (USD)

    VRBO

    JONES COTTAGE - Town of Boothbay Harbor

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    THIS PROPERTY ONLY RENTS ON A SATURDAY TO SATURDAY SCHEDULE - 7 NIGHT MINIMUM REQUIRED ROOM LAYOUT: 1st Floor: Kitchen ...

    From $643 per night (USD)

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    Details
  • Charming Restaurant/Venue in amazing Boothbay Harbor on the water!
    From $1090 per night (USD)

    Expedia

    Charming Restaurant/Venue in amazing Boothbay Harbor on the water!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    1

    Your getaway becomes complete when you visit Brady's Restaurant in Boothbay Harbor. This amazing venue is perfect for yo ...

    From $1090 per night (USD)

    Expedia

    Details
  • Serene Seaside Retreat on Monhegan Island - NEW to being rented in 2025
    From $536 per night (USD)

    VRBO

    Serene Seaside Retreat on Monhegan Island - NEW to being rented in 2025

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    4

    A Serene Seaside Retreat on Monhegan Island Escape to our private 4-bedroom, 2-bathroom cottage nestled on the tranquil ...

    From $536 per night (USD)

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  • Gracious 4-bedroom house in Southport on Townsend Gut with a private pond.
    From $578 per night (USD)

    VRBO

    Gracious 4-bedroom house in Southport on Townsend Gut with a private pond.

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    This Southport Island house boasts 4 inviting bedrooms with 2 queen beds, 1 full bed, and 1 twin (convertible to king) i ...

    From $578 per night (USD)

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  • Charming Oceanfront House with Deck, Cozy Loft, and Direct Beach Access
    From $296 per night (USD)

    VRBO

    Charming Oceanfront House with Deck, Cozy Loft, and Direct Beach Access

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Five Islands Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...

    From $296 per night (USD)

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  • Charming Two-Bedroom Ocean-View Cottage in Quiet Southport
    From $202 per night (USD)

    Expedia

    Charming Two-Bedroom Ocean-View Cottage in Quiet Southport

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Located on Southport Island, this cottage is a dream for travelers looking to enjoy the slower pace of life. Sip your mo ...

    From $202 per night (USD)

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  • Friendship, Maine 4-bedroom house on the water with dock, tennis court and sauna
    From $779 per night (USD)

    VRBO

    Friendship, Maine 4-bedroom house on the water with dock, tennis court and sauna

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Welcome to this charming, roomy four bedroom waterfront house on Martin Point in Friendship overlooking Muscongus Bay. T ...

    From $779 per night (USD)

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  • Gordon's Getaway | AMAZING WATER VIEWS
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    Expedia

    Gordon's Getaway | AMAZING WATER VIEWS

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Waterfront Home on the Sheepscot River – Sunset Views & Modern Comfort! Enjoy the best of coastal Maine in this newly c ...

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  • Spacious 5-bedrooms on dead end street. WiFi, AC. Walk to charming Damariscotta.
    From $550 per night (USD)

    VRBO

    Spacious 5-bedrooms on dead end street. WiFi, AC. Walk to charming Damariscotta.

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Large Brick house in Downtown Damariscotta Our spacious and sunny historic home was built in the 1850s. It is located ...

    From $550 per night (USD)

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  • Appalachee Getaway - Pond Access and Water Views!
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    Expedia

    Appalachee Getaway - Pond Access and Water Views!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Modern Retreat with Pond Views – Walk to the Beach & Linekin Bay Dock! Relax and recharge at this contemporary coastal ...

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  • Cedarbush Cabin - Waterfront Cottage - walk to Robinson's Wharf!
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    Cedarbush Cabin - Waterfront Cottage - walk to Robinson's Wharf!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Mid-Century Modern Charm on the Waterfront! Discover the charm of coastal Maine at Cedarbush Cabin, a classic mid-centu ...

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  • Hove To - Whole Home - Close to Downtown Boothbay Harbor!
    From $383 per night (USD)

    Expedia

    Hove To - Whole Home - Close to Downtown Boothbay Harbor!

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    Coastal Retreat with Water Views – Two Apartments in Boothbay Harbor! Enjoy the best of Boothbay Harbor with this charm ...

    From $383 per night (USD)

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  • McFarland's Pond Cottage - Waterfront - West Harbor Pond!
    From $313 per night (USD)

    VRBO

    McFarland's Pond Cottage - Waterfront - West Harbor Pond!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Waterfront Cottage on West Harbor Pond – Peaceful Retreat with Dock & Float! Escape to this charming waterfront cottage ...

    From $313 per night (USD)

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  • Hove To - Upstairs - Close to Downtown Boothbay Harbor!
    From $231 per night (USD)

    Expedia

    Hove To - Upstairs - Close to Downtown Boothbay Harbor!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Harborview Getaway – Classic Maine Apartment with Wraparound Deck! Perched on the east side of Boothbay Harbor, this se ...

    From $231 per night (USD)

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  • Mill Cove Cottage - \On Top of The Water\ at Mill Cove
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    Mill Cove Cottage - \"On Top of The Water\" at Mill Cove

    Bedrooms:
    0
    Bathrooms:
    1
    Sleeps:
    2

    Mill Cove Cottage – Cozy Waterfront Retreat in Boothbay Harbor! Nestled on the shores of Mill Cove in Boothbay Harbor, ...

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  • Green Pastures - Classic Maine Cottage!
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    Green Pastures - Classic Maine Cottage!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    Charming & Classic Maine Cottage Getaway on Sawyer’s Island – Peaceful Retreat Close to Downtown Escape to this quaint, ...

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  • Crow's Nest -  Oceanfront Home!
    From $628 per night (USD)

    VRBO

    Crow's Nest - Oceanfront Home!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Coastal Escape with Panoramic Ocean Views! Welcome to your perfect coastal getaway! Perched right at the mouth of the D ...

    From $628 per night (USD)

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  • Lange Cottage - Waterfront Cottage!
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    Lange Cottage - Waterfront Cottage!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Lange Cottage – A Peaceful Family Escape on the Maine Coast! Welcome to Lange Cottage, your private coastal retreat ove ...

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  • Hove To - Downstairs - Close to Downtown Boothbay Harbor!
    From $195 per night (USD)

    VRBO

    Hove To - Downstairs - Close to Downtown Boothbay Harbor!

    Bedrooms:
    0
    Bathrooms:
    2
    Sleeps:
    4

    Classic Harborview Apartment – Walk to Downtown Boothbay Harbor! Enjoy a relaxing stay in this first-floor apartment l ...

    From $195 per night (USD)

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  • Historic charm, Modern amenities, Walk downtown
    From $206 per night (USD)

    VRBO

    Historic charm, Modern amenities, Walk downtown

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Newcastle historic district charm, modern amenities, walking distance to restaurants. Fast Wi-Fi, A/C, great bathroom, f ...

    From $206 per night (USD)

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  • Spacious, modern Maine house in New Harbor near beach, walk to harbor.
    From $445 per night (USD)

    VRBO

    Spacious, modern Maine house in New Harbor near beach, walk to harbor.

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Discover the beauty of the Pemaquid Peninsula at the Huddle House, a newly renovated bright and spacious 4 bedroom house ...

    From $445 per night (USD)

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  • Samoset House - Large Family Cottage - Water Views!
    From $435 per night (USD)

    Expedia

    Samoset House - Large Family Cottage - Water Views!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Spacious Family Retreat with Stunning Water Views – Sheepscot Bay & River! Bring the whole family to this large, comfo ...

    From $435 per night (USD)

    Expedia

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  • White Pines Cottage - Classic Maine Cottage - Waterfront on Linekin Bay!
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    White Pines Cottage - Classic Maine Cottage - Waterfront on Linekin Bay!

    Bedrooms:
    1
    Bathrooms:
    5
    Sleeps:
    8

    Classic 1890s Waterfront Cottage on Linekin Bay Step back in time and soak in the timeless beauty of the Maine coast at ...

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  • Osprey Perch Cottage - Water Views
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    Expedia

    Osprey Perch Cottage - Water Views

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Cozy Getaway with Water Views - Southport! Nestled in a peaceful spot with beautiful water views, Osprey Perch Cottage ...

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  • Osprey Perch - Large Family Cottage - Waterfront
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    Osprey Perch - Large Family Cottage - Waterfront

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    11

    Stunning Cliffside Cottage with Harbor Views! Perched on a 50-foot cliff with breathtaking views of the harbor, Mouse I ...

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  • Colburn Cottage - Whole Home
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    Expedia

    Colburn Cottage - Whole Home

    Bedrooms:
    1
    Bathrooms:
    7
    Sleeps:
    12

    Perfect Family Vacation Spot on Capitol Island – Spacious Waterfront Retreat! Gather your loved ones and escape to this ...

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  • Colburn Cottage - Downstairs - Waterfront + Beach!!
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    Colburn Cottage - Downstairs - Waterfront + Beach!!

    Bedrooms:
    0
    Bathrooms:
    2
    Sleeps:
    4

    Perfect Family Vacation Spot – Beachfront Bliss! This charming seaside retreat offers everything you need for a relaxin ...

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  • Cove Point House - Water Views of Decker's Cove!
    From $506 per night (USD)

    Expedia

    Cove Point House - Water Views of Decker's Cove!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Waterfront Retreat with Stunning Views of Decker's Cove - Southport! Relax and unwind at Cove Point House, a beautiful ...

    From $506 per night (USD)

    Expedia

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  • Colburn Cottage - Upstairs
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    Colburn Cottage - Upstairs

    Bedrooms:
    0
    Bathrooms:
    5
    Sleeps:
    7

    Perfect Family Vacation Spot – Coastal Comfort Awaits! Looking for the perfect place to unwind with the family? Welcome ...

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  • Charming 3-bedroom cottage in Southport with water views and close to Boothbay.
    From $348 per night (USD)

    VRBO

    Charming 3-bedroom cottage in Southport with water views and close to Boothbay.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Escape to a fabulous 3-bedroom cottage in Southport. This welcoming retreat features a queen bed, bunk bed, twin bed, an ...

    From $348 per night (USD)

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  • 5 BR, 2 BA  Spacious Farmhouse Walking Distance to Golf Course
    From $585 per night (USD)

    VRBO

    5 BR, 2 BA Spacious Farmhouse Walking Distance to Golf Course

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    12

    This charming five-bedroom, two-bath farmhouse sits on just over three acres of open grass and fields along Route 129, o ...

    From $585 per night (USD)

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  • Whale's Tail by Rocky Coast Rentals
    From $465 per night (USD)

    Expedia

    Whale's Tail by Rocky Coast Rentals

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to your perfect getaway in Boothbay, Maine—a newly renovated, stunning vacation rental that offers the ideal ble ...

    From $465 per night (USD)

    Expedia

    Details
  • Charming Sheepscot Overlook Cottage
    From $1061 per night (USD)

    VRBO

    Charming Sheepscot Overlook Cottage

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Experience luxury and convenience in this 4-bed, 4-bath house with stunning Sheepscot River views. Complete privacy, mo ...

    From $1061 per night (USD)

    VRBO

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  • Elegant riverside retreat with breathtaking views and modern comforts
    From $207 per night (USD)

    Expedia

    Elegant riverside retreat with breathtaking views and modern comforts

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The Rice Andrews House circa 1762 Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...

    From $207 per night (USD)

    Expedia

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  • Spruce Ledge by Sea Maine
    From $639 per night (USD)

    VRBO

    Spruce Ledge by Sea Maine

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Nestled amidst the quaint charm of Boothbay Harbor, Maine, sits a picturesque house that exudes timeless elegance and mo ...

    From $639 per night (USD)

    VRBO

    Details
  • WATERFRONT Retreat venue for up to 60 guests!…\nWeddings, Reunions, Meetings!……
    From $2530 per night (USD)

    Expedia

    WATERFRONT Retreat venue for up to 60 guests!…\nWeddings, Reunions, Meetings!……

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    12

    WESTPORT ISLAND in mid coast Maine! Step back in time …for your small wedding, corporate meeting, retreat or family reu ...

    From $2530 per night (USD)

    Expedia

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  • Relax and recharge at Cold Comfort Farm on the coast of Maine
    From $386 per night (USD)

    VRBO

    Relax and recharge at Cold Comfort Farm on the coast of Maine

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Located in Waldoboro, our beautiful farmhouse offers 3 bedrooms - 2 with full beds and 1 with two twin beds. Blending ru ...

    From $386 per night (USD)

    VRBO

    Details
  • New Listing: Five Islands Waterfront Retreat
    From $553 per night (USD)

    Expedia

    New Listing: Five Islands Waterfront Retreat

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy this quintessential Maine, newly renovated home in Five Islands! The home is equipped with a custom kitchen, spaci ...

    From $553 per night (USD)

    Expedia

    Details
  • Bright and Beautiful Farmhouse at Wanderwood
    From $812 per night (USD)

    VRBO

    Bright and Beautiful Farmhouse at Wanderwood

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    This five-bedroom Farmhouse is the perfect location to spend quality time with friends and family. Located on an organic ...

    From $812 per night (USD)

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    Details
  • Oceanfront 2Q Rm | Coastal Vibe | No Hidden Fees
    From $528 per night (USD)

    Expedia

    Oceanfront 2Q Rm | Coastal Vibe | No Hidden Fees

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Seabreeze 1 offers serene ocean views and upscale comfort in a split-level layout designed for relaxation. With two quee ...

    From $528 per night (USD)

    Expedia

    Details
  • Oceanfront King Rm | Sunset View | No Hidden Fees
    From $689 per night (USD)

    VRBO

    Oceanfront King Rm | Sunset View | No Hidden Fees

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Set along the ocean’s edge, Sunset A delivers timeless Boothbay elegance with panoramic water views. This cottage-style ...

    From $689 per night (USD)

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  • King Rm | Fireplace + Water View | No Hidden Fees
    From $517 per night (USD)

    Expedia

    King Rm | Fireplace + Water View | No Hidden Fees

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Seabreeze 2 welcomes you with a tranquil, upscale layout that captures Boothbay's nautical charm. From its king bed and ...

    From $517 per night (USD)

    Expedia

    Details