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. 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...

  5. 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...

  6. 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
  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. 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

    $357 to $380/night

  9. 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

    $143 to $424/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

    $141 to $313/night

  11. 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

    $141 to $556/night

  12. 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

    $77 to $188/night

  13. 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

    $77 to $442/night

  14. 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

    $139 to $320/night

  15. 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

    $140 to $390/night

  16. 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

    $188 to $859/night

  17. 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

    $77 to $212/night

  18. 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

    $255 to $647/night

  19. 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

    $91 to $250/night

  20. COTTAGE
    48 Maquoit Cottage at Freeport

    48 Maquoit Cottage at Freeport

    Freeport, ME

    Stunning water views await at this 1BR cottage situated mere minutes from downtown Freeport shopping and dining. Launch a kayak from your backyard, dine al fresco on the oceanfront deck, and spend quiet evenings by the wood-burning fireplace....

    FREE CANCELLATION

    $202 to $317/night

  21. 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

    $93 to $329/night

  22. COTTAGE
    1976 Portland Road Cottage Unit 3 Porpus Place

    1976 Portland Road Cottage Unit 3 Porpus Place

    Kennebunkport, ME

    Your group of up to eight will love this brand-new 2BR/2BA cottage in a gated community near Kennebunkport. Here, you’ll find a pastoral setting and resort amenities, including a clubhouse with an outdoor pool, foosball and pool tables, tennis and...

    FREE CANCELLATION

    $102 to $302/night

  23. HOUSE
    7 Barter Home at Boothbay Harbor

    7 Barter Home at Boothbay Harbor

    Boothbay Harbor, ME

    This charming and immaculate 4BR/2.5BA Cape home has been redesigned with an addition to make it the perfect family spot for groups of six. Sleeping accommodations include a luxurious master suite on the first floor and three bedrooms on the second...

    FREE CANCELLATION

    $214 to $498/night

  24. 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 $155/night

  25. 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

    $155 to $325/night

  26. 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

    $100 to $265/night

  27. 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

    $207 to $751/night

  28. 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

    $100 to $253/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

    $244 to $776/night

  30. HOUSE
    22 Cottage Lane Home

    22 Cottage Lane Home

    Cape Elizabeth, ME

    Luxury amenities abound at this exquisite 6BR/4.5BA home in Cape Elizabeth, offering an idyllic oceanside setting and direct beach access. Spread across three spacious levels, this home boasts a private hot tub and multiple outdoor sitting areas. A...

    Hot Tub
    FREE CANCELLATION

    $760 to $2,451/night