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
    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...

  2. 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
  3. 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...

  4. 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...

  5. 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

  6. 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...

  7. 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
  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. 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
  10. 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
  11. HOUSE
    Willow Cottage Prospect Harbor

    Willow Cottage Prospect Harbor

    Prospect Harbor, ME

    Enjoy the beauty of DownEast Maine in this charming home overlooking Prospect Harbor. Built in the 1800's this home has all the feel of 'yesterday' yet has been completely renovated. Just steps from the village of Prospect Harbor and minutes from...

    FREE CANCELLATION

    $13 to $392/night

  12. 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 Steuben,...

    FREE CANCELLATION

    $13 to $457/night

  13. APARTMENT
    Downtown Boothbay Harbor Apartment

    Downtown Boothbay Harbor Apartment

    Boothbay Harbor, ME

    Get the authentic New England experience at this bright 1BR, 1BA Captains Quarters apartment (sleeps 4) in downtown Boothbay Harbor near shopping and bars. Enjoy steamed clams, whale-watching boat trips, & Monhegan Island, a nature lover’s...

    FREE CANCELLATION

    $225 to $236/night

  14. 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 $317/night

  15. 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

    $99 to $365/night

  16. HOUSE
    4 Briarwood Drive Home

    4 Briarwood Drive Home

    Kennebunkport, ME

    Located just one mile from Kennebunkport's Dock Square, this 3BR home offers storybook gambrel charm near a hub of activity. Walk or bike to nearby restaurants and shops. Fitted with beautiful hardwood floors throughout, this spacious home has a...

    FREE CANCELLATION

    $246 to $770/night

  17. 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

    $82 to $218/night

  18. 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 $519/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

    $194 to $666/night

  20. 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 $641/night

  21. 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

    $222 to $837/night

  22. 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

    $269 to $789/night

  23. 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

    $88 to $323/night

  24. HOUSE
    73 Standish Way Home

    73 Standish Way Home

    West Yarmouth, MA

    This 3BR, 2BA West Yarmouth house is ideal for families with young children. Nearby Colonial Acres Beach and local shops and eateries are kid-friendly options for how to spend time. Relax in the private yard with the sound of gulls and ocean...

    FREE CANCELLATION

    $135 to $518/night

  25. 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

    $183 to $563/night

  26. 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 $946/night

  27. 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

    $155 to $482/night

  28. 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

    $134 to $435/night

  29. 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

    $148 to $401/night

  30. COTTAGE
    27 Ranger Lane Cottage

    27 Ranger Lane Cottage

    Arundel, ME

    This brand-new 2B/ 2BA cottage in Arundel is located in a quiet, gated community set inside of a 200-acre nature preserve. In this nature-surrounded setting, you can head out on a winding trail for long strolls amid pastoral scenes and woodlands. If...

    FREE CANCELLATION

    $206 to $330/night