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. 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

    $219 to $751/night

  2. 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

    $83 to $265/night

  3. 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

    $83 to $253/night

  4. 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

    $62 to $188/night

  5. 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 $325/night

  6. 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

    $74 to $250/night

  7. CABIN
    La Cabinita Boothbay Harbor

    La Cabinita Boothbay Harbor

    Boothbay Harbor, ME

    La Cabinita, or "Little Cabin,"  is nestled among the spruces, pines and hardwood trees in a picturesque setting that is often the image evoked when dreaming of a Maine vacation. The open floor plan living/dining/kitchen allows for everyone to...

  8. CABIN
    Sprucerock Southport Island

    Sprucerock Southport Island

    Southport, ME

    A classic log cabin nestled among the pines is ready for you to settle in for a memorable Maine Vacation. This three bedroom, two bath cottage on Southport Island is well equipped and comfortably furnished throughout. Enjoy the rustic feel with...

    Pets OK
  9. CABIN
    Bay Street Cottage Boothbay Harbor

    Bay Street Cottage Boothbay Harbor

    Boothbay Harbor, ME

    The owners of Bay Street Cottage wanted a quiet get-a-way spot that would still be close to local activities. They found it in this adorable two bedroom, one bath cottage, with a fenced yard and nice size deck on a quiet side street in boothbay...

    Pets OK
  10. COTTAGE
    Ebb And Flow East Boothbay

    Ebb And Flow East Boothbay

    East Boothbay, ME

    Looking for a great spot for a family get together but have some space?  These two cozy cottages provide the together time, but the private space as well.  Take a short walk to the water and enjoy the dock and float and views of the Damariscotta...

  11. CABIN
    Ledge The Southport

    Ledge The Southport

    Southport, ME

    The Ledge Listen to the gulls keen. Watch the cormorants and osprey dive. Smell the salty tang in the air. Feel the pounding of the surf come up through the ledge on which you stand taking it all. Imagine the taste of the yummy lobster dinner...

  12. CABIN
    Linekin Log Cabin East Boothbay

    Linekin Log Cabin East Boothbay

    East Boothbay, ME

    A treasured family cabin on Linekin Bay is ready for you to settle in for a memorable Maine Vacation. This four bedroom,  one bath cottage is quaint and rustic, yet comfortably furnished throughout. The classic log construction built among the...

    Pets OK

    $547 to $601/night

  13. CABIN
    Spruce Point Estate Boothbay Harbor

    Spruce Point Estate Boothbay Harbor

    Boothbay Harbor, ME

    Spruce Point Estate Wow! This house has it all! The perfect location, right on the ocean, beautiful gardens surrounding the newly renovated estate.  Professional kitchen, master bed & en suite bath on the main level along with another bedroom with...

    Pets OK
  14. HOUSE
    A Lucky Cast Westport Island

    A Lucky Cast Westport Island

    Wiscasset, ME

    A modern family home on the Sheepscot River is ready for you to settle in for a memorable Maine Vacation. This pet-friendly, four bedroom, three bath cottage is well equipped and thoughtfully furnished. Its airy and open floor plan offers plenty of...

    Pets OK
  15. CABIN
    Lazy Days Boothbay Harbor

    Lazy Days Boothbay Harbor

    Boothbay Harbor, ME

    Lazy Days Great place for kayakers! Lazy days is the perfect spot to watch the ‘commuters’ (I.E. Boat traffic) come and go into boothbay harbor and out to the atlantic. From your private water-side deck, you have one of the best views around....

    Pets OK
  16. CABIN
    Chic Boothbay Harbor Studio Cabin

    Chic Boothbay Harbor Studio Cabin

    Boothbay Harbor, ME

    Tucked among the pines with views towards the ocean, this chic 1BD cabin (sleeps 2) in Boothbay Harbor is newly renovated and includes access to the Sprucewold Beach. Relax on your woodland surrounded deck or take a walk to Boothbay Harbor. INSIDE...

    FREE CANCELLATION

    $62 to $309/night

  17. CABIN
    Mavooshen Retreat at Sprucewold

    Mavooshen Retreat at Sprucewold

    Boothbay Harbor, ME

    This newly renovated 2-bedroom log cabin has exclusive access to a private beach club and dock and is minutes to downtown Boothbay Harbor, by car or by foot. Find peace in this secluded, historic location. Vintage meets sophistication in the...

    FREE CANCELLATION

    $94 to $376/night

  18. APARTMENT
    Boothbay Harbor Apartment w/ Deck

    Boothbay Harbor Apartment w/ Deck

    Boothbay Harbor, ME

    The perfect retreat for couples—and full of New England charm—this crow’s nest hideaway has just enough room for 2, plus a private, romantic deck with lush treetop vistas in summer and ocean views in winter. Easily walk to downtown Boothbay...

    FREE CANCELLATION

    $62 to $224/night

  19. HOUSE
    116 East Boothbay Home

    116 East Boothbay Home

    East Boothbay, ME

    Private Oceanfront 4BR on 10 Acres w/ 2 Fireplaces, 4 Decks & Grill Enjoy magnificent ocean views at this 4BR/4BA home in East Boothbay. Architecturally stunning, the home features open living spaces, high ceilings, and four decks overlooking 10...

    Pets OK
    FREE CANCELLATION

    $179 to $686/night

  20. COTTAGE
    Hilltop Harbor Cottage

    Hilltop Harbor Cottage

    Edgecomb, ME

    Property Overview  Perched on a hilltop overlooking the Sheepscot River sits this 3BR Davis Island cottage. The two-story home features a gourmet kitchen, gas fireplace, radiant heat, as well as a balcony and large deck. Enjoy expansive bay views,...

    FREE CANCELLATION

    $148 to $497/night

  21. CONDOMINIUM
    14 Maddocks Rd Condo

    14 Maddocks Rd Condo

    Boothbay Harbor, ME

    Property Overview  Gordon’s Waterfront Retreat is an expansive 4BR/4BA lakefront getaway. This romantic and spacious haven is perfect for a couple seeking extra room, three couples traveling together, or a family of up to eight. Perched on a...

    FREE CANCELLATION

    $137 to $551/night

  22. HOUSE
    Big Sandy Pond Home

    Big Sandy Pond Home

    West Yarmouth, MA

    Set down the road from the private neighborhood beach on Big Sandy Pond, this newly remodeled 3BR home promises a memorable stay for the whole family. The shoreline has a nice spot for the kids to play in the clear shallow water. And further out,...

    Pets OK
    FREE CANCELLATION

    $134 to $423/night

  23. HOUSE
    85 North Street Home

    85 North Street Home

    Kennebunkport, ME

    This newly renovated 4BR/3BA property is set amid beautifully landscaped grounds surrounded by a charming picket fence, flowers, and trees. Providing ample space and privacy, your rental includes two floors of living space in the main New England...

    Hot Tub
    FREE CANCELLATION

    $170 to $620/night

  24. HOUSE
    8 Roberts Avenue Home

    8 Roberts Avenue Home

    Bar Harbor, ME

    This dreamy 2BR/2BA Victorian duplex offers charming decor, elegant gardens, and views of downtown. Rooms brightened by skylights put you in vacation mode the moment you arrive. Enjoy a movie night curled up in front of the wood-burning fireplace,...

    Pets OK
    FREE CANCELLATION

    $193 to $555/night

  25. HOUSE
    46 Maquoit Drive Home

    46 Maquoit Drive Home

    Freeport, ME

    This 3BR/3BA, coastal-inspired waterfront home features an open-concept living area with a wood-burning fireplace and a modern kitchen with midcentury modern-inspired appliances. An upper-level patio offers views of the water, and the lower-level...

    FREE CANCELLATION

    $211 to $773/night

  26. HOUSE
    East Boothbay Oceanfront Home

    East Boothbay Oceanfront Home

    East Boothbay, ME

    Close to town and 10 minutes to Boothbay Harbor, this historic 4BR, 3.5BA Maine home sleeps 10 and boasts an oceanfront location with deepwater dock. Close by East Boothbay General Store and Lobsterman's Wharf. Named the Green Landing Lodge, this...

    FREE CANCELLATION

    $190 to $863/night

  27. CABIN
    43 Crooked Pine Cabin

    43 Crooked Pine Cabin

    Boothbay Harbor, ME

    Located 5 minutes from downtown Boothbay Harbor, this classic 5BR/2BA cabin in the pines has a cozy feel and stunning water views. Relax on the upstairs and downstairs decks, or kick back in the airy great room. The two downstairs bedrooms have...

    FREE CANCELLATION

    $257 to $802/night

  28. HOUSE
    Picturesque Island Cottage

    Picturesque Island Cottage

    Milbridge, ME

    If you are looking to get away from it all, this island is the spot for you. The most remote cottage we have, our beautiful home on the shores of Pigeon Hill Bay is a great retreat for couples, families and friends. Close to the villages of...

    FREE CANCELLATION

    $13 to $457/night

  29. COTTAGE
    Bar Harbor Cottage

    Bar Harbor Cottage

    Bar Harbor, ME

    Escape to the woodlands at this 2BR cottage, a quintessential Maine getaway with charming interior detail including tall ceilings, plantation shutters, and antique furnishings sprinkled throughout. Take in views of the magical forested surroundings...

    FREE CANCELLATION

    $130 to $370/night

  30. HOUSE
    32B McKown Street Home

    32B McKown Street Home

    Boothbay Harbor, ME

    Tasteful coastal decor, dreamy harbor views, and a fabulous downtown location—this 3BR/2.5BA house in Boothbay Harbor has it all. Walk 5 minutes to arrange trips with Cap'n Fish's Whale Watch, or take a boat tour out to Monhegan Island on the...

    Pets OK
    FREE CANCELLATION

    $293 to $1,262/night