
Cottage vacation rentals in Drakes Island Beach
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Top-rated cottage rentals in Drakes Island Beach
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Secluded Coastal Home & Cottage 3 Minutes to Beach
Escape to Thistle Pond Cottage, a peaceful coastal retreat in southern Maine. Nestled on 2 acres with pond views, lush gardens, and local wildlife, it’s minutes from beaches and Portland. Every stay begins with homemade bread from our kitchen and thoughtful, locally sourced welcome accompaniments. Weather and seasonal permitting, guests may occasionally savor a host-prepared wood-fired pizza made with fresh garden ingredients. Cozy, bright, and full of garden-to-table charm and seasonal delight.
5.0 out of 5 average rating, 107 reviews
The Relax Shack
The Relax Shack is filled with thoughtful details and designed for comfort, featuring soothing coastal colors throughout. Our Moody beach house is the ideal place to begin and end your sun-soaked, salty days on vacation, offering a serene escape. With ample space for larger groups, it's also perfect for two small families. We warmly invite you to our coastal Maine retreat and hope you, your loved ones, and friends will enjoy this beautiful area as much as we have over the years. Cheers & Relax
4.89 out of 5 average rating, 125 reviews
Wells Maine Home with a View
Our Contemporary Cottages, at Seagull, gracefully sits on a grassy 11 acre bluff with panoramic views of the Rachel Carson Refuge and the Atlantic Ocean. This tastefully decorated cottages offer air conditioning, heat, ceiling fans, fully equipped kitchen with dishwasher, gas grill, cable TV, skylights, and a large screened in porch with sliding glass doors opening into the livingroom and master bedroom. Cottage has a great pool/hot tub. WIth ocean view and comfortably accommodates six guests.
4.93 out of 5 average rating, 213 reviews
Salty Mermaid Cottage/Boat House
This 2br home is nestled at the end of a peninsula’s over the water, 5min drive to downtown Portsmouth. Spend the day on the on deck, grilling or enjoy your own authentic Maine lobster bake, swimming and treasure hunting the shore. Also explore Kittery or downtown Portsmouth, both just five minutes away. Enjoy this freshly renovated home, water views from every room and window, all bedrooms are equipped with a/c, free WiFi and smart TVs. Fully equipped kitchen has an amazing view of the water.
4.99 out of 5 average rating, 212 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!
4.95 out of 5 average rating, 134 reviews
Spacious Coastal Cottage
This 3 bedroom, 2 bath home is surrounded by tall pines and greenery and has a peaceful screened in front porch, with an outside space and fire pit, perfect for sitting back and relaxing with a glass of wine in hand or locally crafted beer. This space is located on a quiet street, just off the beaten path of Route 1 in Wells. About a mile from Wells Beach, walking distance to several restaurants; Mike's Clam Shack, Varano’s, The Steak House and Congdon's to name a few popular favorites.
4.95 out of 5 average rating, 292 reviews
4br2ba House+parking@PeacefulOasis on Munjoy Hill
This standalone 1500sf 3-story cottage is set in an ideal location, close to the Eastern Prom, cafes, award-winning restaurants, breweries and the Old Port. -Main floor: well-equipped kitchen + open concept living/dining room -Upper floor: 3BR (1 queen, 1 full, 1 twin) + bath -Garden level: 1BR/1 bath (queen) with private entrance - Off-street parking for 1 car This charming home @ A Peaceful Oasis offers plenty of space, privacy & comfort, making it the perfect home base for your stay.
4.97 out of 5 average rating, 305 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.
4.95 out of 5 average rating, 179 reviews
Charming Designer Cottage on Marsh
Cozy renovated Cottage w/ stunning marsh views is short walk to beautiful Goose Rocks Beach. No need to pack gear, cottage comes equipped w/ 2 kayaks, 2 bikes/helmets & beach buggy. Stroll to general store for morning coffee, walk on beach or head out and explore the Kennebunks & Cape Porpoise. Our community offers world class dinning, boutique shopping , entertainment and beautiful hiking trails all close by. At days end kick back & relax by the fire pit...”The way life should be”
4.98 out of 5 average rating, 123 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!
4.98 out of 5 average rating, 233 reviews
Fair Winds Cottage~1 mi to beach~
Our home, a renovated 1930’s Maine summer cottage, is located 1 mile from Kennebunk beaches and 1.5 miles from dining and shopping in Kennebunkport’s Dock Square. Close to golf, nature trails and only a 1/2 mile from the Mousam River for fishing and kayaking, it’s a great location to take in all southern coastal Maine has to offer. The cottage provides plenty of outdoor space, so come relax, dine on the back deck and take in the night sky with s'mores by the fire pit.
5.0 out of 5 average rating, 122 reviews
The Little Cottage - Under the Trees & By the Sea
It's been called Magical Maine and that it is. Located just 1.5 hours from Boston, Ogunquit is a quaint coastal town offering restaurants, shopping, wild-life & hiking at Mt Agamanticus and, best of all, the beach! Our little home is tucked away on a 1/2 acre of wooded land just down the way from a frog pond, but still within walking distance to town and the beach. Perfect for a family vacation, romantic weekend getaway, reunion amongst friends or even solo trip!
4.86 out of 5 average rating, 298 reviewsPopular amenities for Drakes Island Beach cottage rentals
Cottage rentals with a hot tub

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks
4.97 out of 5 average rating, 238 reviews
The Loon Nest, Waterfront Lake House, Wood Hot Tub
4.97 out of 5 average rating, 125 reviews
Fully Renovated/4min to K-port/HotTub/Game Room
4.92 out of 5 average rating, 79 reviews
Paradise Found Minutes from Ogunquit | Heated Pool
5.0 out of 5 average rating, 94 reviews
Contemporary Cottage With Ocean View 13
4.81 out of 5 average rating, 27 reviews
Beautiful 2 bedrm cottage in Beach Dreams complex
4.94 out of 5 average rating, 48 reviews
Super cute one bedroom with hot tub and pool.
4.98 out of 5 average rating, 91 reviews
Foliage, Fairs and Family Fun
5.0 out of 5 average rating, 7 reviewsPet-friendly cottage rentals

Lovely cottage on Sunrise Lake, Middleton, NH.
4.98 out of 5 average rating, 122 reviews
Eclectic Lakefront Cottage on Great East Lake
4.99 out of 5 average rating, 186 reviews
Lake View Cottage / Fenced in Yard / Pet Friendly
4.93 out of 5 average rating, 228 reviews
Sweet cottage in quiet convenient coastal setting.
4.78 out of 5 average rating, 355 reviews
Bright & Cozy Beachside Cottage in Camp Ellis
4.91 out of 5 average rating, 187 reviews
RiverPine Retreat - Clean & Bright Waterfront Home
4.84 out of 5 average rating, 195 reviews
#3 Couples Cottage Minutes from the Beach
4.96 out of 5 average rating, 288 reviews
Maine Harbor Escape | Porch&BBQ, Walk 2 Portsmouth
4.93 out of 5 average rating, 283 reviewsPrivate cottage rentals

Cozy cottage
4.96 out of 5 average rating, 152 reviews
Dreamy Post&Beam Hideaway Near Portland & Freeport
4.99 out of 5 average rating, 483 reviews
Waterfront Cottage Private Dock | Kayaks | Rowboat
4.94 out of 5 average rating, 161 reviews
Adorable cottage, great location!
5.0 out of 5 average rating, 102 reviews
Peaceful Cottage on Maine Flower Farm
4.97 out of 5 average rating, 187 reviews
Cozy Wolfeboro Getaway | Lake, Ski & Fireplace
4.97 out of 5 average rating, 145 reviews
Cozy Cottage steps from Hampton Strip With Parking
4.84 out of 5 average rating, 331 reviews
Edgewater Retreat - Lakefront w/Sauna & EV Charger
4.81 out of 5 average rating, 120 reviewsDestinations to explore
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