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

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.

ValueFamilyPets

4.92 out of 5 average rating, 132 reviews

Guest favourite

Guesthouse in Eliot

Skylights & Tides King Studio - Kittery/Portsmouth

Fall asleep under the stars. Wake up to birdsong and coffee on the deck. You’re 7 minutes from Kittery’s outlets and 10 from Portsmouth’s waterfront - but a world away in your skylit sanctuary. - King Bed - Queen sofa bed - Ample free parking - Serene atmosphere - 5 minutes to Downtown Kittery - 10 Minutes to Downtown Portsmouth - Loaded Kitchenette - Coffee and tea bar - Elevated private deck - Walking paths & Water views - Mini Split heating and cooling for the perfect temp - Elliot ME

LocationFamilyCheckout

4.9 out of 5 average rating, 63 reviews

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

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.

ValueFamilyAmenities

4.87 out of 5 average rating, 61 reviews

Guest favourite

A spacious bedroom features soft blue walls and a yellow quilted bedspread atop a large bed. Soft lighting from a lamp adds a gentle glow, while two doors lead to adjoining spaces. A closet is visible in the background, providing ample storage.

Apartment in South Berwick

Sleeps 6! Free Wine! Comfy 2-Bedroom In S. Berwick

OFF STREET PARKING ~ 2 BEDROOMS ~ QUIET PROPERTY ~ FULL KITCHEN ~ COFFEE & TEA ~ FREE WINE ~ HEAT/AC/WIFI ~ EXCELLENT SERVICE! Tucked away in a quiet neighborhood, just one block from South Berwick's quaint and beautiful Main Street. Step outside your door into an ancient New England town settled in 1631, and with a current population of only 7500. Then quickly escape to more popular New England getaways such as Boston, Portsmouth, Dover, Durham, Wells, Portland, Freeport, and Brunswick!

FamilyValueBathroom

4.79 out of 5 average rating, 87 reviews

Top Guest favourite

An open-concept kitchen features mint green retro appliances and a butcher block island with two bar stools. Light pours in through a window, highlighting the warm wood beams above. Shelves display a mix of dinnerware and kitchen essentials, creating an inviting space for cooking and dining.

Barn in Dover

The Barn on Broadway

The Barn on Broadway: A 1900's reno was brought back to life in 2025. This fresh space balances history with beautiful new finishes. It's a stand alone property with an open concept- loft-style one bedroom king, full kitchen, 3/4 bath and a cozy back patio. The space sits next to Body Mechanix Massage (don't forget to book your services ahead of time!) and is within walking distance to historic downtown Dover, just a short drive to many seacoast beaches and minutes from UNH.

ValueFamilyParks

5.0 out of 5 average rating, 65 reviews

Top Guest favourite

A spacious beachfront deck features two blue Adirondack chairs facing the expansive ocean view. The calm waters extend towards the horizon, with rocky formations visible in the distance. A sandy shore is seen below, framed by the deck's white railing.

Cottage in Ogunquit

Seaside Serenity 1 - Oceanfront

New in May 2025! Enjoy the amazing sunsets and sunrises from the huge beachfront deck overlooking expansive ocean views. This luxurious oceanfront condo has top of the line furnishings and is located in Ogunquit’s famous Perkin’s Cove. The magical location is a hidden gem within the serenity of your new condo with, in addition to 2 bedrooms, has a full bath, full modern kitchen, dining area, and living room, and has he most amazing large outside deck overlooking the ocean.

LocationFamilyNearby

4.96 out of 5 average rating, 23 reviews

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

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!

LocationValueCleanliness

5.0 out of 5 average rating, 207 reviews

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

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.

ValueFamilyOutdoor spaces

4.99 out of 5 average rating, 69 reviews

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

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.

LocationValueQuiet

5.0 out of 5 average rating, 149 reviews

Top Guest favourite

Apartment in South Berwick

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!

ValueLocationAmenities

4.98 out of 5 average rating, 41 reviews

Superhost

Tiny home in South Berwick

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.

LocationFamilyNearby

4.84 out of 5 average rating, 32 reviews

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

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 !

ValueFamilyBeach

4.88 out of 5 average rating, 144 reviews