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. 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...

  2. 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

  3. 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...

  4. 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
  5. 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

  6. 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

  7. 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

  8. 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 $457/night

  9. 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 $248/night

  10. 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

  11. 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

    $203 to $699/night

  12. 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 $563/night

  13. CONDOMINIUM
    8 Mcfarland Point Dr Condo Unit 31

    8 Mcfarland Point Dr Condo Unit 31

    Boothbay Harbor, ME

    Spread across three spacious floors, this 3BR/1.5BA condo in the Signal Point community offers a fantastic location just a few minutes' walk from downtown. With an idyllic spot between the harbor and Mill Cove, you’ll find all Boothbay Harbor has...

    FREE CANCELLATION

    $146 to $500/night

  14. COTTAGE
    18 Spring St Cottage

    18 Spring St Cottage

    East Boothbay, ME

    Property Overview  Located in the majestic Ocean Point Colony, this two-story 4BR/2BA home boasts incredible ocean views. Detailed with original patina pumpkin pine, natural hardwood floors, and a beach-stone fireplace, this inviting home affords...

    Pets OK
    FREE CANCELLATION

    $177 to $642/night

  15. 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 $421/night

  16. 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

    $179 to $635/night

  17. 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

  18. 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

  19. 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
  20. 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...

  21. 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
  22. 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

  23. COTTAGE
    South Bristol Cottage

    South Bristol Cottage

    South Bristol, ME

    A charming 1BR + Loft cottage in the fishing village of South Bristol. Here you're steps to the water, an easy stroll to cafes and the boat launch, and a short drive from Christmas Cove. Sleeps 4, though you can also rent the main house for larger...

    Pets OK
    FREE CANCELLATION

    $84 to $225/night

  24. 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

  25. 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

  26. 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

  27. 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 $509/night

  28. HOUSE
    19 Hill Home at South Bristol

    19 Hill Home at South Bristol

    South Bristol, ME

    Tucked in the fishing village of South Bristol, enjoy a quintessential Maine vacation at this quaint 1BR cottage and renovated 4BR farmhouse with charming wraparound porch. This property is perfect for multi-family getaways! Fire up the grill to...

    FREE CANCELLATION

    $219 to $556/night

  29. 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 $2,495/night

  30. 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