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
    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 $654/night

  2. 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

    $229 to $509/night

  3. 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

    $119 to $249/night

  4. 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

    $123 to $249/night

  5. 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

    $230 to $458/night

  6. 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

    $330 to $1,110/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. 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
  9. 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...

  10. 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
  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. 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
  15. HOUSE
    176 Samoset Drive Home

    176 Samoset Drive Home

    Boothbay Harbor, ME

    Savor gorgeous views of Boothbay Harbor from your 1BR/1.5BA waterside retreat. Custom woodwork and a charming post-and-beam structure give this home its unique character. You’ll feel like a true Mainer as you spend mornings sipping coffee down by...

    Hot Tub Pets OK
    FREE CANCELLATION

    $166 to $292/night

  16. COTTAGE
    17 Ranger Lane Cottage

    17 Ranger Lane Cottage

    Arundel, ME

    Escape to the beautiful Maine coast at this upscale 3BR/2BA cottage for six. Your Arundel rental is set within a gated community near beaches and Kennebunkport. Stroll the 200-acre nature preserve with scenic walking trails, and make use of the...

    Pool
    FREE CANCELLATION

    $161 to $332/night

  17. 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 $528/night

  18. HOUSE
    79 Middle Home at East Boothbay

    79 Middle Home at East Boothbay

    East Boothbay, ME

    Property Overview  This 3BR/2.5BA Cape Cod style getaway embodies quintessential midcoast Maine with incredible indoor/outdoor entertaining space. Affectionately named the Owl House, your two-story home features a screened porch, a deck with a...

    Pets OK
    FREE CANCELLATION

    $159 to $420/night

  19. 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

    $190 to $472/night

  20. HOUSE
    11 High Street House

    11 High Street House

    Bar Harbor, ME

    Property Overview  A classic period home in the historic village of Bar Harbor, this three-level 6BR/6BA home spans 3,691 square feet with hardwood floors, stained glass windows, and beautiful woodwork throughout. You’ll certainly appreciate the...

    FREE CANCELLATION

    $626 to $935/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

    $302 to $517/night

  22. COTTAGE
    306 Eddy Road Unit 603

    306 Eddy Road Unit 603

    Edgecomb, ME

    Escape to mid-coast Maine with a stay in this dreamy 3BR/3BA Edgecomb cottage just a short walk from Wiscasset and 15 minutes from Boothbay Harbor. The open-concept layout features inviting coastal décor and an abundance of natural light...

    Pets OK
    FREE CANCELLATION

    $262 to $596/night

  23. HOUSE
    7 Apple Hill Lane Home

    7 Apple Hill Lane Home

    Boothbay, ME

    This airy, light-filled home is steps from the Back River. With 2,900 square feet of tastefully decorated living space, a sunroom, and a spacious patio with river views, you’ll have everything you need for a perfect stay in Boothbay Harbor. The...

    Pets OK
    FREE CANCELLATION

    $252 to $591/night

  24. HOUSE
    306 Eddy Rd Home #604

    306 Eddy Rd Home #604

    Edgecomb, ME

    Your group will love this 3BR/3BA home within an Edgecomb resort community, featuring nearby access to a kayak launch on the pristine waterfront. Walk to the town of Wiscasset, or hop in the car and take a short drive to Boothbay Harbor. Featuring...

    Pets OK
    FREE CANCELLATION

    $262 to $483/night

  25. 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

    $330 to $579/night

  26. 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

    $358 to $760/night

  27. CABIN
    Saltaire Boothbay Harbor

    Saltaire Boothbay Harbor

    Boothbay Harbor, ME

    Saltaire Head down to the ocean from your front porch and enjoy your private dock and float right on linekin bay. Or, head to the end of your driveway and enjoy a shared sandy beach at the freshwater appalachee lake! Saltaire is the perfect location...

  28. 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
  29. 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

    $169 to $404/night

  30. COTTAGE
    American Pale Ale Cottage

    American Pale Ale Cottage

    Boothbay, ME

    Property Overview Experience the quintessential Maine vacation at this 2BR cottage on the grounds of the Boothbay Craft Brewery, less than 10 minutes from downtown Boothbay Harbor. Featuring beautiful hardwood floors, a well-equipped kitchen, and...

    Pets OK
    FREE CANCELLATION

    $131 to $241/night