Places to stay near Head Beach

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Top-rated vacation rentals near Head Beach

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Guest favorite

Condo in Kennebunk

4.89 out of 5 average rating, 204 reviews

Over 1000 Five Star Reviews! Walk to Dock Square !

Free onsite parking for 1 car. Beautiful coastal décor and modern amenities makes this a perfect choice for your vacation. Walking distance to EVERYTHING! Dock Square is a 1 minutes walk. Music, Art and Fine Dining surrounds you. Lots of windows and a slider to the deck make this location bright and airy 2 private decks for your enjoyment, two bedrooms, 2 full bathrooms. Perfect for couples or families. Parking for one car in lot, added public park across s NO PARTIES Pets considered

Guest favorite

A sandy pathway leads to the beach, bordered by green grass and wooden posts. Open water stretches out to the horizon, under a clear blue sky. Gentle waves can be seen lapping at the shore, inviting relaxation and leisure.

Condo in Old Orchard Beach

4.87 out of 5 average rating, 23 reviews

Desirable Location. Steps from the beach. Cozy

Location. Location. This vacation spot has everything you could want. Immaculate, newly renovated one bedroom condo, two parking spots, across the street from the beach and minutes from the boardwalk (great restaurants, gift shops and amusement rides). Fun for the whole family. Take your morning coffee and walk to the beach for sunrise or enjoy a glass of wine at sunset. We welcome you to enjoy the place we love! It's time to make your own memories. Three (3) Night Minimum. Ground Level.

Guest favorite

A sandy pathway is bordered by tall grasses, leading directly to a calm blue ocean. The serene waters meet a light sky, creating a tranquil scene that suggests easy access to the beach.

Condo in Old Orchard Beach

4.73 out of 5 average rating, 118 reviews

Attractive 1 bedroom cabin only 50 ft from beach#1

nestled in a restful pine grove just 50 feet from Maine’s finest beach. These 8 one & two bedroom charming Old Orchard Beach Cottages are decorated in a modern beach theme, providing guests with the modern conveniences of today. Conveniences include Smart TVs with Amazon Fire Sticks, Wi-Fi, individually controlled heat & air conditioning, fully equipped efficiency kitchenettes, & private baths. Ideal for group getaways! Enjoy the privacy of your own seaside cottage, oh, so close to the beach.

Top guest favorite

A wooden dock extends over vibrant green marshland, leading to a serene body of water. Lush trees and rolling grass create a peaceful backdrop, emphasizing the natural beauty of the surroundings.

Apartment in Arundel

4.98 out of 5 average rating, 330 reviews

Cape Arundel Cottage 1 mile to downtown KPT

Tastefully appointed 1 bedroom apartment one mile from desirable Dock Square, Kennebunkport. This apartment features Panoramic views of the famous Cape Arundel Golf Course and Goff's Brook Tidal River. Private, secluded back deck with dining and lounge areas, Cozy furnishings throughout, King sized bed with memory foam topper, Fully Equipped Kitchen, and more! At Cape Arundel Cottage, guest experience is our highest priority! *See “other things to note” for additional important information.*

Guest favorite

A charming house features a light-colored exterior with a sloped roof. Green accents are found on the front door and window trims. A small porch offers a welcoming entrance, while a well-maintained lawn with green grass surrounds the property. Clear blue skies serve as a backdrop.

Home in Old Orchard Beach

4.89 out of 5 average rating, 19 reviews

Cozy cottage, 1 mile from beach

Your family will be close to everything when you stay at this centrally-located place. Walking distance to several restaurants, Lee nails, agency liquor store and 24 hour convenience store. Two minute drive to 7 miles of Sandy Beach. Close to historic downtown Biddeford restaurants and shopping, Kennebunkport and Portland’s Old Port. Five minutes from Maine Turnpike, Palace Playland beachfront amusement park and a five minute drive to Funtown Splashtown. Several mini golf courses And 18 hole.

Top guest favorite

Home in Windham

4.94 out of 5 average rating, 126 reviews

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Top guest favorite

The modern retreat is nestled among trees, featuring a deck with outdoor seating and a picnic table. The structure showcases large windows, allowing natural light to fill the interior, with a welcoming red door standing out against the dark exterior.

Guesthouse in Newcastle

4.98 out of 5 average rating, 103 reviews

Modern Hillside 1 BR near Damariscotta/Newcastle

Experience the best of mid-coast Maine at our cozy modern hillside retreat. Perfect for couples exploring the area for the first time or returning for another getaway, our 1 BR place has vaulted ceilings and a full wall of windows along the large kitchen and living space opening up to a peaceful deck and hillside forest. Minutes to historic downtown Damariscotta and Newcastle make our place your base camp for food, wine, shops, antiques, history, coastal activities, and oyster tastings!

Top guest favorite

A wooden dock extends into a calm lake, leading to a small boat anchored at the end. The water reflects a clear blue sky, with gentle ripples across the surface, and green hills visible in the distance.

Home in Harrison

5 out of 5 average rating, 6 reviews

2BR Lake House on Private Beach w/hot tub & sauna

Romantic getaway or peaceful family vacation, this lake house is right on a private beach, and perfect all year round!The beach is literally your back yard! Experience beautiful views while enjoying a cozy outdoor fire. Relax and take amazing sunset pics in the covered hot tub, or unwind indoor w/the sauna and fire place. Cook up a delicious meal in the fully stacked kitchen. Centrally located near hiking trails, and 45min from North Conway outlets. Book now and make memories! ✨

Guest favorite

A sandy beach scene is captured, featuring colorful kayaks arranged neatly in the foreground. Sunbathers and beachgoers enjoy the sunny weather, with umbrellas dotting the shoreline. A smooth ocean extends to the horizon, framed by a clear blue sky.

Townhouse in Kennebunkport

4.94 out of 5 average rating, 167 reviews

Great get away spot,historic home in Kennebunkport

Located 1.8 mi-dock square, 2.6 mi- Colony Beach, .7 mi -Cape Arundel Golf Course. Plenty of onsite parking, beach pass provided for Kbunk Beaches, a large back yard for fun and relaxation. Just on the outside of town in a country setting. Comfortable setting for relaxation. This is a daily reservation from Oct.1st-June. I love to make sure my guests have as much fun as they can while they are visiting and will help out in anyway possible. No dogs of any kind are allowed

Top guest favorite

A well-lit path made of gravel leads to a deck that connects to the cottage, surrounded by tall trees. The warm glow of lights enhances the evening atmosphere, while a small gathering area with chairs is visible nearby.

Cottage in Boothbay

5 out of 5 average rating, 116 reviews

Cottage in the woods on Ocean Point

Secluded getaway in the woods close enough to see and hear the ocean and catch amazing sunsets. Charming 1BR + Loft, 1BA cottage situated among an acre of Ocean Point fir trees providing privacy and a quiet get away. Less than 100yd walk to the shore, beach and path at Grimes Cove, Ocean Point Inn Restaurant & Bar, and daily activities at the community "casino" with playground, tennis, pickle ball, basketball, and Sunday softball. Harbor is 20 mins away for exploring.

Superhost

A wooden dining table is surrounded by six matching chairs on a spacious deck. A small vase filled with colorful flowers sits at the center of the table. Beyond the deck, trees provide a lush backdrop, with green views extending toward the distant golf course.

Apartment in Kennebunkport

4.93 out of 5 average rating, 29 reviews

Charming Kennebunkport

This gorgeous one bedroom apartment features floor-to-ceiling windows overlooking the prestigious Cape Arundel Golf Course and Kennebunk River. With hardwood floors throughout, updated stainless appliances, a private deck with teak furnishings, and views in all directions, this apartment is even more spectacular than the pictures show. If traveling with a larger group, consider booking the downstairs 2 bedroom apartment as well.

Guest favorite

A colorful Welcome to Kennebunkport sign stands prominently at the bridge entrance. Below, a charming red building on stilts is seen, featuring a conical rooftop. Surrounding structures showcase classic New England architecture, enhancing the coastal charm of the area.

Home in Kennebunk

4.95 out of 5 average rating, 151 reviews

Quiet cozy cottage close to restaurants, beach

Winter-wonderland, close to skiing and a walk from great dining. In the summer, enjoy the quiet backyard or walk to the beach! No need to find parking, my place is 3/10 of a mile from downtown Kennebunkport and 7/10 of a mile to Gooch's Beach. You will love my place because of the kitchen, the coziness, and the location. My place is good for couples. It has a tempurpedic king-sized bed and a queen sized pull out bed in the living room.