Holiday houses in South Berwick

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Top-rated holiday rentals in South Berwick

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

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Top Guest favourite

A hobbit house is nestled among lush green trees, with a sloping earth-covered roof adorned with grass and ferns. The rounded front features a large window framed in white, complemented by a natural stone border, emphasizing the home's connection with its woodland surroundings.

Earthen home in Sanford

4.92 out of 5 average rating, 130 reviews

Luxury Year-round Hobbit House w/ private hot tub

Fern Hollow 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.

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Guest favourite

A contemporary kitchen is presented with white cabinetry and a large island featuring a marble countertop. A dining area with wooden chairs is visible in the background, complemented by pendant lighting. Natural light enters through windows, enhancing the open layout.

Home in North Berwick

4.87 out of 5 average rating, 61 reviews

Bullseye Modern Farm House

Forget your worries in this spacious and serene space. Come stay at the newly renovated Bullseye Farm house "in the center of it all". 9.3 miles from Ogunquit Beach 9 miles to Wells Beach 9.2 miles to Footbridge Beach 15 miles to York Beach Go golfing at Links at Outlook golf course 6 miles away or Old Marsh golf course, just 11 miles . Kick back and relax in the rocking chairs on the spacious front porch. Enjoy the best southern Maine! July 18-Aug 31, Sat-Sat check-in checkout.

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Top Guest favourite

The living area features a blend of comfortable seating, including a dark brown recliner and a soft sofa. A wooden coffee table is centrally placed, adorned with decorative items. Natural light illuminates the space, complemented by neutral walls and subtle décor.

Home in Lebanon

4.95 out of 5 average rating, 376 reviews

Tranquility, Relaxation, Family, Romance

Bring your family or have a romantic getaway in this beautiful 2 bedroom, 2 private baths located in this quiet country setting. Pet friendly. Big fenced in wooded back yard for your pets to roam. Big back yard deck w/ seating, grill. Minutes away to boat launching area to rent party boats, kayaks, paddle boats, Swimming, winter sports on Milton 3 ponds. Seasonal blueberry, peach, apple picking in town. Park your boat or snowmobile trailors. Skydive New England right in town. Fall leaves.

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Top Guest favourite

A welcoming living area showcases a large screen displaying Netflix. Two brown armchairs with throw pillows are positioned beside a modern coffee table. A cozy fireplace adds warmth, while soft gray and blue tones create a relaxing atmosphere. Natural light filters through the windows.

Home in Kittery Point

5.0 out of 5 average rating, 204 reviews

A water view slice of heaven at Pepperrell Cove

Enjoy the peace and tranquility of staying in Kittery Point Maine’s exclusive Pepperrell Cove area. • Walk three minutes to dinner at one of three amazing waterfront restaurants • Enjoy a private chartered boat ride from across the street • Rent kayaks • Visit Fort McClary • Hike Cutts Island Trail • Visit Crescent and Seapoint beaches • Shop and dine in Kittery’s Wallingford Square, downtown Portsmouth, and the Kittery Outlets. Everything is within fifteen minutes away!

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Top Guest favourite

A lakeside view of a spacious house features large windows and a multi-level deck, surrounded by tall trees with autumn foliage. A dock extends into the water, accommodating a small boat, while the tranquil lake reflects the natural scenery.

Home in North Berwick

4.91 out of 5 average rating, 90 reviews

The Lake House

We would love to welcome you to The Lake House. As its name implies it sits directly on the water, and boasts a stunning view of gorgeous Bauneg Beg Lake in the lovely little town of North Berwick. If you are looking for a few days of relaxation, beautiful nature and quality time, you have found the right spot. Best of all it's only 1.5 Hrs from Boston, and within 30 minutes from Maine’s most popular beaches and destinations. Maine: The Way Life Should Be!

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Top Guest favourite

A spacious kitchen features wooden cabinetry and stainless steel appliances, providing a blend of modern and rustic elements. A large wooden dining table with an inviting centerpiece is illuminated by natural light from the windows, enhancing the warm tones of the hardwood flooring.

Home in South Berwick

4.98 out of 5 average rating, 66 reviews

Beautiful Maine home overlooking pasture

Kick back and relax in this calm, stylish space. This beautiful home is just 20 min to local beaches, walking distance to town and a short drive to the Red Barn wedding venue and golf course. If you are in town for a wedding during the summer months and need more space- we also have a beautiful large studio apartment over the garage available for rent. The rentals are very private- great for families wanting to gather but also have their own space.

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Top Guest favourite

A contemporary cabin retreat is nestled among tall trees, softly illuminated by warm outdoor lights. A wooden deck with steps leads to a welcoming entrance. A separate sauna structure is visible, surrounded by snow-covered ground, providing a serene atmosphere in a tranquil forest setting.

Home in South Berwick

5.0 out of 5 average rating, 146 reviews

Romantic Mirror cabin in the woods

Stay at Hidden Pines Cabins. The Mirror cabin is Maines only 3 sided floor to ceiling mirrored glass cabin. Unwind in the hot tub while looking up at the sky full of stars. Take a sauna while surrounded by nature all around. Located in the majestic forest of mount Agamenticus, the extensive trail system is off of our road. Short drive to the Ogunquit/York beaches, Outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

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Top Guest favourite

Apartment in South Berwick

4.97 out of 5 average rating, 38 reviews

Hikes and History Cozy Stay

Cozy 1-bedroom apartment across from beautiful Vaughan Woods State Park and Historic New England's Hamilton House. Perfect for hikers, history buffs, and anyone needing a peaceful escape. Enjoy morning coffee with park views, explore nearby trails, or relax in a space full of charm and quirky touches. Whether you're here to unwind or adventure, this fun little spot is your ideal home base. Come for the nature, stay for the vibes!

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Superhost

Tiny home in South Berwick

4.82 out of 5 average rating, 28 reviews

Cozy Cabin in the Woods

Enjoy your stay in this cozy cottage in the woods. This charming one-bedroom, one-bath home offers 468 Square feet of well-designed space. An additional 200 sq ft deck allows you to extend the living area and embrace the wooded, serene lot. This home is 7 miles to Mount Agamenticus, and 5 miles to Ogunquit beach. Queen Bed; pull out couch and pack and play available for kids. Strong WiFi for streaming and work.

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Guest favourite

A sandy beach stretches into the distance, visible from a coastal property. The exterior features a light-colored shingle design, with a covered porch offering seating. Green shrubbery lines the foreground, creating a natural border against the ocean backdrop and clear blue sky.

Home in Wells

4.88 out of 5 average rating, 142 reviews

Drakes Island Beach Front Breathtaking Property !

Ocean views from Kennebunkport to Cape Neddick and a gorgeous half mile sandy beach right outside your door! Watch the sunrise and the sunset over the sandy Drakes Island shores. Enjoy daily walks on the beach or take a walk on the peaceful trails nearby alongside the Rachel Carson Wildlife Refuge & Laudholm Farm, and go to town for restaurants, arcades and more fun. It doesn’t get better than this !

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Top Guest favourite

An aerial view captures the modern cabin surrounded by lush greenery, featuring warm string lights illuminating the outdoor area. A hot tub is positioned near a cozy seating arrangement, with a gravel path visible leading away from the cabin.

Cabin in Kennebunk

4.96 out of 5 average rating, 223 reviews

HotTub+Firepit/5 min to DockSquare, Dining, Beach

Follow us on IG @anchorunwind. Escape to a hidden gem nestled in the heart of the Kennebunkport area, where modern comfort meets nature's serenity. Our cabin offers an unforgettable vacation experience. ✭"...A must stay location. The host’s were very helpful and genuine..." ✭"...We’ve travelled all around the world and this is in our top 3 Airbnbs we’ve stayed in."

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Guest favourite

An open-concept living area showcases a modern kitchen with dark countertops and white cabinetry. A dining table with chairs is visible, alongside a spacious sofa. Natural light fills the space through large windows, with plants adding a touch of greenery.

Home in Dover

4.95 out of 5 average rating, 61 reviews

Cool New Dover Home

Welcome to our cozy 3 bedroom, 2.5 bathroom newly constructed home in Dover! We are conveniently located near Portsmouth, Downtown Dover, and Durham (UNH). Whether you are here for vacation, work, or to visit family, we'll be delighted to make your stay as comfortable as possible. We are able to comfortably accommodate 6 guests.

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