What is Maine famous for besides lobster? If you have to ask, then you have obviously never been graced by this majestic state littered with unique lighthouses and boasting more coastline than California itself! The natural parks of Maine can only be outdone by their delectable wild blueberries and of course, the stunning RedAwning properties available year-round.

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  1. CABIN
    Tarbox Cottage Westport Island

    Tarbox Cottage Westport Island

    Wiscasset, ME

    Built in the 1800's, this classic Greek Revival farmhouse on Westport Island is ready for you to settle in for a memorable Maine Vacation. Enjoy the ambience of this gem perched on a hillside overlooking an historic stone wharf and granite-clad...

    Pets OK
  2. CABIN
    Oh What A View Westport Island Maine

    Oh What A View Westport Island Maine

    Wiscasset, ME

    A beautiful, contemporary waterfront property sitting among the salty pines is ready for you to settle in for a memorable Maine Vacation. This three bedroom, three bath home is equipped with all modern amenities and is comfortably furnished...

    $634 to $668/night

  3. HOUSE
    Atlantic Sunset Boothbay Harbor

    Atlantic Sunset Boothbay Harbor

    Boothbay Harbor, ME

    A classic seaside family home on the Atlantic Ocean is ready for you to settle in for a memorable Maine Vacation. This four bedroom, three bath cottage is well equipped and comfortably furnished throughout. Its spacious floor plan and large windows...

    Pets OK
  4. COTTAGE
    Pine Cliff Dweller Southport

    Pine Cliff Dweller Southport

    Southport, ME

    Pine Cliff Dweller Pine cliff dweller is perched on the edge of a cliff overlooking burnt and squirrel islands and the entrance to boothbay harbor and the open atlantic! The owners of this magnificent property have maximized the view with tons of...

  5. CABIN
    Thankfulnest East Boothbay

    Thankfulnest East Boothbay

    East Boothbay, ME

    A treasured family home nestled at the end of Grimes Cove is waiting for you to settle in for a Memorable Maine Vacation! This Ocean Point Cottage is ideal for sunset watchers and communing with nature. Begin your day with the sunrise out on the...

    Pets OK
  6. CABIN
    Merwick Cottage Georgetown

    Merwick Cottage Georgetown

    Georgetown, ME

    Merwick Cottage Due to allergies, this is a non pet friendly home with no exceptions.  Merwick Cottage is perched atop a rise overlooking the Sheepscot Bay.  Enjoy panoramic views and ocean breezes from the deck and its generously windowed...

  7. CABIN
    The Villa East Boothbay

    The Villa East Boothbay

    East Boothbay, ME

    The Villa Views, views and more views are what make this summer home so popular and memorable.  Everywhere you look you can see the ocean, islands and big blue sky.  This quintessential maine summer home is classic, timeless, and a vacationer's...

    Pets OK
  8. CABIN
    286 Back River Road Cabin

    286 Back River Road Cabin

    Boothbay, ME

    Six guests can have a quintessential lakefront vacation at this 3-bed, 1-bath cabin on two lush acres, including 350 ft. of private lake frontage (2 kayaks provided!). Newly renovated but with a classic Maine cabin vibe, you can tuck in here for...

    FREE CANCELLATION

    $150 to $326/night

  9. HOUSE
    1800s South Bristol Farmhouse

    1800s South Bristol Farmhouse

    South Bristol, ME

    This is a gorgeously renovated 4BR 1800s Victorian (sleeps 7) in the fishing village of South Bristol. Located on a quiet street by the harbor, you can spend the morning on a blissful wraparound porch or stroll to town for coffee and the paper. A...

    Pets OK
    FREE CANCELLATION

    $124 to $487/night

  10. HOUSE
    Storybook New England's Sheepscot Village

    Storybook New England's Sheepscot Village

    Alna, ME

    A storybook stay in New England's Sheepscot Village awaits at our serene 3BR farmhouse. A quiet waterside retreat with rolling hills, you're less than 30 minutes to Boothbay Harbor and 7 minutes to Wiscasset. Newly remodeled and tastefully furnished...

    Pets OK
    FREE CANCELLATION

    $152 to $321/night

  11. HOUSE
    The Coal Shack: Harborfront Studio

    The Coal Shack: Harborfront Studio

    Boothbay Harbor, ME

    Situated in the heart downtown of Boothbay Harbor, our 1-bed studio harborfront apartment - The Coal Shack - is walking distance to independent shops, restaurants and boat cruise tours. Stroll outside your front door to Pier 1 and Pier 8 to book...

    Pets OK
    FREE CANCELLATION

    $102 to $450/night

  12. CONDOMINIUM
    306 Eddy Rd Condo Unit 702B

    306 Eddy Rd Condo Unit 702B

    Edgecomb, ME

    This newly constructed 1BR condo in Sheepscot Harbour Resort is a perfect home away from home on the Edgecomb waterfront. With a well-stocked kitchen, a water-view deck, and an open-concept living and dining area, there’s plenty of space for four...

    FREE CANCELLATION

    $82 to $216/night

  13. HOUSE
    60 Middle House at South Bristol

    60 Middle House at South Bristol

    South Bristol, ME

    Tall pines, perennial gardens, and the Damariscotta River make up the scenery around this picturesque Christmas Cove retreat. Located on Rutherford Island’s highest hill, Middlepoint is the ideal setting for a private multigenerational gathering....

    Pets OK
    FREE CANCELLATION

    $279 to $663/night

  14. HOUSE
    Lobstermen’s Cottage

    Lobstermen’s Cottage

    Boothbay Harbor, ME

    Named Lobstermen’s Cottage in honor of the original inhabitants, this 3BR/2BA home sits off the road in tranquil East Boothbay Harbor and features a large back deck with a BBQ. Beautiful hardwood floors, an open-concept main living area, and a...

    FREE CANCELLATION

    $153 to $568/night

  15. HOUSE
    7 Spyglass Hill Rd Home

    7 Spyglass Hill Rd Home

    East Boothbay, ME

    Spread out between multiple sitting areas, a spacious kitchen, and three floors at this expansive 4BR/3.5BA East Boothbay home. Outdoors, a sprawling deck, gazebo, and gorgeous perennial garden offers an outdoor haven for al fresco dining and...

    Pets OK
    FREE CANCELLATION

    $190 to $799/night

  16. CONDOMINIUM
    Willard Beach Condo #2

    Willard Beach Condo #2

    South Portland, ME

    Life is better with an ocean view! There are wonderful OCEAN VIEWS! VERY close to the beach! Right here in the quiet beachfront community of Willard Beach in South Portland, there are lots of things to do and see VERY CLOSE BY, and many are within...

    FREE CANCELLATION

    $69 to $170/night

  17. COTTAGE
    301 Adams Pond Rd Cottage

    301 Adams Pond Rd Cottage

    Boothbay, ME

    Property Overview  Built on the Boothbay Craft Brewery property, this 2BR brewer’s cottage is named “Ken Brown Ale” after one of the brewery’s craft beers. Wake up in the morning and enjoy coffee on the patio with covered seating, then take...

    Pets OK
    FREE CANCELLATION

    $108 to $258/night

  18. HOUSE
    Boothbay Harbor Home

    Boothbay Harbor Home

    East Boothbay, ME

    3BR, 2BA Boothbay Harbor Home w/Water Views—Near Dining & Whale Watching Set back on a grassy knoll overlooking the water, this 3BR, 2BA Boothbay Harbor home offers a truly tranquil vacation retreat. Drive minutes to restaurants, hiking trails,...

    FREE CANCELLATION

    $155 to $434/night

  19. CABIN
    226 Shore Cabin at East Boothbay

    226 Shore Cabin at East Boothbay

    East Boothbay, ME

    A haven of serenity, this historic 1BR Ocean Point log cabin sits right on the water’s edge. This two-story getaway features vaulted wood ceilings, an A-frame loft, sunroom, and wood-burning fireplace. Dine al fresco at the picnic table...

    Pets OK
    FREE CANCELLATION

    $168 to $443/night

  20. CONDOMINIUM
    306 Eddy Rd Condo #D

    306 Eddy Rd Condo #D

    Edgecomb, ME

    Newly built and lovingly furnished, your 1BR condo has coastal touches and a relaxing vibe. Located in a quiet spot overlooking the river, the place is perfect for a couple or small family. The Resort is across the bridge from Wiscasset and within...

    FREE CANCELLATION

    $82 to $192/night

  21. HOUSE
    18 Bens Landing Rd Home

    18 Bens Landing Rd Home

    Boothbay, ME

    Tranquility and relaxation await at this brand-new 5BR/2.5BA home. Surrounded by trees on a private lot, spend leisurely afternoons on the wraparound porch with seating for six and views of a small pond on the property. This spacious home offers...

    FREE CANCELLATION

    $227 to $766/night

  22. COTTAGE
    180 King Phillips Cabin

    180 King Phillips Cabin

    East Boothbay, ME

    This classic 2BR cottage-On the Rocks- has been recently updated and offers a traditional American vacation. You will descend a set of wooded stairs to reach your rental, which sits on the rocky shoreline—so close you’ll hear the lapping of the...

    FREE CANCELLATION

    $111 to $337/night

  23. COTTAGE
    Boothbay Brewer's Cottage

    Boothbay Brewer's Cottage

    Boothbay, ME

    Property Overview  Enjoy a unique getaway experience at this 2BR brewer’s cottage conveniently located on the same property as Boothbay Craft Brewery and Watershed Tavern. Your updated cottage features hardwood floors and a patio with a grill as...

    Pets OK
    FREE CANCELLATION

    $108 to $271/night

  24. HOUSE
    1 Tupper House at Boothbay Harbor

    1 Tupper House at Boothbay Harbor

    Boothbay Harbor, ME

    There's room for up to 10 guests at this lovingly restored historic Boothbay Harbor home. Your 3BR/2BA abode is a 1-minute walk from downtown, but you're still far enough away from the bustle for peace and quiet. Enjoy water views and a tasteful...

    FREE CANCELLATION

    $200 to $875/night

  25. HOUSE
    200 South Sea Ave House

    200 South Sea Ave House

    West Yarmouth, MA

    A beach-centric stay is yours at this historic 4BR/2.5BA West Yarmouth home. A large, private backyard is ideal for the kids to explore, and a large swimming pool invites you to cool off June through Labor Day. Mealtime is a family affair in the...

    Pool
    FREE CANCELLATION

    $256 to $1,168/night

  26. APARTMENT
    4 Commercial St Admirals Quarters Apts

    4 Commercial St Admirals Quarters Apts

    Boothbay Harbor, ME

    Introducing "Admiral Quarters"- Located in the heart of downtown Boothbay Harbor, this sunlit top-floor 2BR/2BA penthouse (sleeps 6) is walking distance to everything, including restaurants, nightlife, and whale watching tours. Inside the House...

    FREE CANCELLATION

    $375 to $382/night

  27. CONDOMINIUM
    15C Atlantic Ave Condo

    15C Atlantic Ave Condo

    Boothbay Harbor, ME

    Property Overview  Set on the idyllic shores of Boothbay Harbor, this brand-new, all-suite 2BR condo promises a quintessential Coastal Maine getaway. Perched above Maine’s prettiest harbor, this third-floor penthouse offers a unique bird’s-eye...

    FREE CANCELLATION

    $162 to $331/night

  28. HOUSE
    49 Murray Hill House

    49 Murray Hill House

    East Boothbay, ME

    Plan a relaxing seaside escape to this 3BR/2BA waterfront home in East Boothbay. With three comfortable bedrooms plus a futon, there’s room for eight guests. Go swimming or kayaking right in your backyard, or launch a boat directly across the...

    Pets OK
    FREE CANCELLATION

    $158 to $399/night

  29. HOUSE
    Maine Waterfront Cottage

    Maine Waterfront Cottage

    Boothbay, ME

    A new deepwater dock, shared only with owner's other home next door, was recently installed and has been a highlight for guests of Little Dipper Cottage. A mooring is also available. Explore the stunning islands and wildlife that inhabit the tidal...

    FREE CANCELLATION

    $257 to $806/night

  30. CONDOMINIUM
    Resort Condominium Unit C

    Resort Condominium Unit C

    Edgecomb, ME

    Your 2BR chic condo offers stunning views of the Sheepscot River. The woodsy setting offers the perfect place to relax in peace and quiet. The culinary-minded guests in your party will love the open-concept kitchen with new stainless steel...

    FREE CANCELLATION

    $98 to $262/night