Drakes Island vacation rentals

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Top-rated vacation rentals in Drakes Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Lebanon

4.99 out of 5 average rating, 134 reviews

Rustic Rose Cottage of Historic West Lebanon

Rustic guest suite on serene four acres. Abutting colonial cape style house and West Lebanon Historic District date back to early 18th Century. Private parking & entrance, queen memory foam mattress, steam sauna, kitchen and laundry supplies, and desk and high speed wifi for telework. Minutes from Skydive New England, Prospect Hill Winery or McDougal Orchard. 30min to Portsmouth NH, Maine beaches, and Lake Winnipesaukee. Just over an hour to the White Mountains, Portland ME or the Boston area.

Guest favorite

Rental unit in Kennebunk

4.99 out of 5 average rating, 139 reviews

Birch Sea

This new, very private apartment attached to our home is in a quiet and picturesque environment minutes away from Dock Square. It's great for couples, solo adventurers and families with one child. If you are seeking to spend the day at one of the beautiful Kennebunk beaches they are just minutes away. We are committed to environmental sustainability and the apartment is powered by solar energy. A new outdoor hot tub was recently installed in February, 2024! We look forward to your visit!

Guest favorite

Loft in Kennebunk

4.95 out of 5 average rating, 170 reviews

Private Modern Loft featured in Maine Home+Design

Experience the tranquility of staying in a PRIVATE STUDIO LOFT IN SEPARATE BLDG. overlooking 13 acres of private land abutting 600 acres of Alewive Brook Preserve while being 20 minutes to several area beaches and swimming lakes. The land is full of walking trails, fishing pond, biking trails and is conveniently only 7 minutes from the highway. Immaculate with wood floors, comfy queen size bed with Tempur-pedic mattress , 400 thread count soft 100 % cotton sateen sheets and high speed Internet.

Guest favorite

Home in Arundel

4.99 out of 5 average rating, 149 reviews

NewBuilt/HotTub/Great Location-4 min Kennebunkport

Follow us on IG @anchorunwind. Welcome to Mama Bear's House! Perfect girlfriends' getaway or to celebrate a special someone. Sit back and relax in our brand new and fully equipped stylish home just 5 minutes away from Kennebunkport's Dock Square. Spend time reading and sipping a fresh grounded coffee on our cozy egg chair, looking in our peaceful backyard while the sunset closes another memorable chapter of your vacation. Enjoy the firepit with hot cocoa and s'mores or fall for a cornhole game!

Guest favorite

Rental unit in Wells

4.92 out of 5 average rating, 133 reviews

Wells Beach - Baywatch North

North Side 2 story apartment on 2nd and 3rd floors. Large deck with Weber gas grill and patio table and chairs. Large deck off of master bedroom with king size bed. There are 1 1/2 baths with a washer and dryer. Both decks overlook the bay with amazing sunsets. The bay has striped bass, seals, Egrets, Great Blue Herons and many other birds. Mitsubishi heat pumps for heat and air conditioning. Kayaks are available for use in the bay. Enjoy a short walk across the street to the beach (100 yards)

Superhost

Treehouse in Sanford

4.93 out of 5 average rating, 208 reviews

Luxury Year-round Treehouse with private hot tub

Skyframe is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Guest favorite

Guest suite in Cape Neddick

4.97 out of 5 average rating, 357 reviews

Peaceful Coastal Retreat

Tucked away in the woods along a stretch of rocky coastline, this hidden retreat is the perfect place to truly get away. Located midway between Ogunquit and York, guests can enjoy all the amenities of the towns, yet return to the quiet and peaceful seclusion of the Peaceful Coastal Retreat. Listen to the wind blow and the birds chirp as you gaze into the surrounding forrest or the star speckled sky; there is no place more perfect to relax and experience the magnificent Maine coastline.

Guest favorite

Home in Wells

4.97 out of 5 average rating, 108 reviews

Family Beach House, Wells Beach, Maine

Family Beach House on the Harbor/River of Wells Beach. House Sleeps 8 adults, plus 3 - 4 children. Full kitchen, 4 bedrooms plus Sleeping Loft, 3 baths, Dining Room, large deck, patio, laundry, outdoor shower, fire pit. Private access back beach. Bring your kayaks, paddle boards, surf boards, or boat. Water behind house at High Tide. Approx. 100 yard walk across Atlantic Ave to beach. Parking for 5 cars Max. Optional in-law apartment available, sleeps 5, for $115 per night/$800 per week

Guest favorite

Home in Wells

4.92 out of 5 average rating, 145 reviews

Three Beds | Hot Tub | Close To Beach

If you've never stayed in Wells before, make your first stay at the oldest established property in Wells, dating back to 1604, but updated for today's modern needs with wifi, streaming, hot tub, grill, outdoor furniture, and hammock all within a short drive to Wells beach in a peaceful neighborhood on a dead end street. Let the Webhannet Falls and Webhannet River lull you to sleep as they flow through the backyard and see the foundation of the historic gristmill and sawmill.

Guest favorite

Cabin in South Berwick

5 out of 5 average rating, 126 reviews

Romantic A-Frame cabin in the woods

Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

Guest favorite

Cottage in Middleton

4.96 out of 5 average rating, 164 reviews

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting!

Guest favorite

Guesthouse in Kennebunk

4.93 out of 5 average rating, 243 reviews

Intimate Ocean View Cottage Near the Mousam River

A newly renovated 700+ sqft one-bedroom, two story cottage, with a beautiful ocean view, is less than one mile from Parson’s Beach. The Mousam River access is less than ¼ of a mile away. A cozy Maine living space with a private backyard and fire pit for your enjoyment. Interested in biking or walking trails? We are less than 500' to the bridal path that can take you to nearby Mother’s Beach or into downtown Kennebunk.