Cottage holiday rentals in Drakes Island

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Top-rated cottage rentals in Drakes Island

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Top Guest favourite
A vibrant blue cottage sits nestled among greenery, with a welcoming entrance and an American flag displayed. A dock with two kayaks rests at the water's edge, reflecting the serene lake. A patio area is visible on the upper deck, inviting relaxation.
Cottage in Northwood
4.94 out of 5 average rating, 133 reviews

Cottage on the lake! Includes kayaks & rowboat!

Super cozy, beautiful cottage right on the lake & dirt roads. Yard: sitting areas, propane fire pit, fenced in yard. Inside includes reading areas, dvds, wifi, books, coloring books, puzzles, games. Enjoy the rowboat & kayaks or bring your own boat. We are on Antique Ally and State Parks are nearby (2 miles away). Enjoy a day at Chucksters, Concord, Portsmouth or the lakes region. Enjoy the LAKE LIFE! No animals (Health concern for cleaner) 4 adults or 2 adults 3 kids. Life jackets provided

Top Guest favourite
Cottage in Buxton
4.97 out of 5 average rating, 163 reviews

Peaceful Cottage on Maine Flower Farm

Maine’s Peaceful Off-Season Escape Nestled next door to Ferris Farm, our family-run flower farm, this charming cottage offers a private place to rest and recharge. Enjoy slow, coffee-filled mornings, quiet walks, and cozy evenings by the fire pit. Use the cottage as your home base to explore nearby beaches (30 minutes) or head into Portland (35 minutes) for breweries, coffee shops, and great dining. Perfect for a couple retreat, solo escape, or remote work getaway, with dedicated workspace.

Guest favourite
Cottage in Lyman
4.82 out of 5 average rating, 111 reviews

RK North : All season Waterfront cottage with dock

Waterfront get away !You will love the cottage in any season - right on the pond! Enjoy a private dock, swimming and floating right at your door. Relax at the fireplace under twinkle lights , enjoy birdwatching, hiking and swimming during your stay. Lots of ATV and snowmobile trails near by. A close drive to Kennebunkport where your find beach’s , shops and restaurants galore. The cottage has 2 kayaks and a canoe for use during your stay. There are 2 Smart TVs for streaming. Shows and DVD

Top Guest favourite
The living room is bright and airy, featuring large windows that fill the space with natural light. Comfortable seating is provided on two white couches and a blue chair. A neutral area rug complements the wooden flooring, and a television is mounted on the wall.
Cottage in Ogunquit
4.95 out of 5 average rating, 115 reviews

Sunny Beach Cottage / Sleeps 7 + Walk to the beach

Your perfect getaway! Just a brief walk to the beach & steps away from the trolley! This adorable, super clean 2 bedroom/ 1 bath cottage (sleeps 7) is located on a private cul-de-sac within walking distance to (.25 miles) Footbridge Beach and local restaurants, and 1 mile from Ogunquit’s center. You'll love the cottage's charming appeal, with its fresh & inviting ambiance. Every inch of this beautiful space has been thoughtfully furnished ensuring a truly memorable experience inside and out!

Top Guest favourite
The exterior of a post and beam cottage is shown, featuring a light wood facade and a brown shingled upper section. Two black Adirondack chairs are placed on a wooden deck, accompanied by potted plants. Large windows offer a view of the forested surroundings under a partly cloudy sky.
Cottage in Pownal
4.99 out of 5 average rating, 451 reviews

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

Top Guest favourite
A modern two-story home is set amidst a wooded area, featuring a spacious outdoor seating arrangement with a picnic table and various chairs. A fire pit and grill are present, with the soft glow of twilight highlighting the inviting exterior.
Cottage in Acton
4.99 out of 5 average rating, 166 reviews

Eclectic Lakefront Cottage on Great East Lake

Welcome to a relaxing stay on the shores of Great East Lake! The fall and winter are the definition of peace and quiet. Often you'll be the only folks on the cove! Come back inside after your outdoor adventures and warm your feet on the radiant slate floors .You can also prepare a home cooked meal in the vintage, fully applianced kitchen. This home is the perfect base for all your winter excursions, or enjoy family time inside with plenty of games, puzzles, ping pong, or air hockey! Enjoy!

Top Guest favourite
A bright kitchen area features modern white cabinetry and a spacious countertop. Barstools with woven seats are positioned at the counter. Natural light floods in through a nearby door, illuminating the polished wooden floor and light blue walls.
Cottage in Wells
4.95 out of 5 average rating, 166 reviews

Cozy Cottage with Ocean Views, Wells Maine

Ocean breezes, panoramic views of the Atlantic, comfortable cottage to relax & enjoy your time in Maine, what more could you ask for on a getaway?! This cozy cottage for 6 boasts near panoramic views of the Rachel Carlson preserve and the Atlantic Ocean. Tastefully decorated and newly updated, our cottage offers AC/heat, ceiling fans, fully equipped kitchen with dishwasher, outdoor gas grill, cable TV in all rooms, WiFi, cabled phone, skylights, in unit W/D & a large screened in porch.

Top Guest favourite
Tall trees frame a serene view of the lake, with calm waters reflecting the surrounding nature. A wooden deck offers a vantage point, inviting peaceful moments in the outdoors. A dock is visible at the water's edge, enhancing the tranquil lakeside setting.
Cottage in Middleton
4.97 out of 5 average rating, 169 reviews

Beautiful Lakeside Cottage

Beautiful, quiet and secluded lakeside cottage. Enjoy amazing sunsets on our pristine lake. Swim, kayak, fish or just relax and take in the natural beauty. COVID UPDATE: We know everyone has different levels of concern regarding the virus. Please know that while we feel our sanitation and cleanliness of the Cottage is exceptional, we have doubled our efforts providing multiple cleanings between guests. This is a NON-SMOKING property. We are sorry, but we cannot accommodate pets.

Top Guest favourite
Cottage in Kennebunkport
4.98 out of 5 average rating, 215 reviews

Sunrise at 15 Mills Road. Fully renovated Cottage.

In the beautiful and quaint village of Cape Porpoise, Kennebunkport, you’ll find our cottage, just two doors down from Nunans Lobster Hut and a 3-minute walk to Cape Porpoise Kitchen and Bradbury’s Market. Built in 1880, and after a complete renovation, we’d love to have you as our guests! We added many windows, to bring the outdoors in. Lots of light! The two added balconies make for a wonderful place to sit and talk or just stare into space. Lots of stars! Air conditioning!

Top Guest favourite
A beverage sits on a small table beside a glass bottle filled with sticks. The view through a window reveals the sandy beach and calming ocean waves, with a colorful sunset casting soft hues in the sky. An American flag is partially visible in the background.
Cottage in Saco
4.94 out of 5 average rating, 494 reviews

Deja Blue~Guesthouse-Maine’s Best Oceanfront view!

Our year round beach guest house is an oceanfront dream for a single or couple's retreat. Come relax by the sea. Listen to the waves crashing right outside your door. Disconnect or work while here we have fast WiFi for you. Enjoy this gem of a place on the coast of Maine as a year round escape. Come make some memories to cherish for a lifetime. Pro tip: Wake up early and observe the beautiful sunrise over the ocean. It is totally worth getting up early and will not disappoint.

Guest favourite
A charming cottage exterior showcases a covered porch with two white rocking chairs, surrounded by lush green grass. Tall trees provide shade, while the cottage is accented by a mix of shingle siding and light-colored trim. A clear blue sky complements the serene setting.
Cottage in Kennebunk
4.85 out of 5 average rating, 102 reviews

Adorable Cottage Steps From Dock Square

This bright and cozy cottage is perfect for a romantic getaway or a family vacation on the coast. The cottage is very well maintained and newly furnished - the bedroom features a plush king size bed, while the queen size sleeper sofa in the living room allows for 4 guests. A short stroll to many amazing restaurants, or grab your groceries nearby and use kitchen, including stove/oven, microwave, keurig coffee maker and lobster pot! Walk, bike or drive to the beach (1.3 miles).

Top Guest favourite
A serene lakeside view is presented, featuring a well-maintained garden with colorful flowers and lush greenery. Smooth stones create a path leading towards the calm waters of Sunrise Lake. The dock and surrounding trees are visible under a bright blue sky with scattered clouds.
Cottage in Middleton
4.96 out of 5 average rating, 225 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. The sunsets can be unbelievable!

Popular amenities for Drakes Island cottage rentals

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  4. York County
  5. Wells
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