Vacation rentals in Rollinsford

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Top-rated vacation rentals in Rollinsford

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Top guest favourite

A modern cabin with an A-frame shape is illuminated by warm lights, surrounded by tall trees. In front, a fire pit with wooden chairs invites gatherings, while a hot tub and sauna are visible nearby, contributing to the outdoor relaxation space.

Cabin in South Berwick

Romantic A-Frame cabin in the woods

Stay at Hidden Pines Cabins. Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

5.0 out of 5 average rating, 329 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

4.9 out of 5 average rating, 63 reviews

Top guest favourite

A serene view of the tranquil tidal Salmon Falls River is captured, with clear blue skies reflected on the water's surface. Lush greenery surrounds the riverbank, featuring a solitary tree in the foreground. The peaceful landscape is framed by dense foliage on both sides.

Home in Dover

Spacious 4-Bedrooms/ Two En Suite Bedrooms

We are sorry no animals are allowed. Maximum overnight guests: 8 Maximum number of people on property at one time: 15 (no events) 3,500+ sq. ft.; Sleeps 8 4 bedrooms (5 beds)-3 ½ baths 1st-king, en-suite (walk-in shower & jet tub), walk-in closet 2nd-1 king, en-suite (walk-in shower) 2nd-1 queen, shared hall bath 2nd-2 singles, shared hall bath All have TVs, floor fans, luggage racks, hangers & blankets. Maple hardwood floors. Movie/pool room above garage. Fireplace NOT usable.

5.0 out of 5 average rating, 68 reviews

Top guest favourite

Home in Durham

Newly Renovated | Farm Stay | Near Portsmouth!

Welcome to the Brown House at Emery Farm. This recently renovated charming cedar shake farmhouse is situated on 130 picturesque acres, on the oldest family farm in America. If you’re looking for a quintessential New England farm stay experience that offers a quiet peaceful stay, this is the place! • 3 bd | 3 bath | sleeps 6 • Private, quiet, picturesque • Located on a working farm • 2 min walk to Emery Farm Market & Café • 10 min to Portsmouth • Surrounded by nature • EV charger

4.94 out of 5 average rating, 200 reviews

Guest favourite

Home in Dover

Historic Downtown Cottage | Quiet patio | Parking

Stay in a charming 1870 home in the heart of downtown Dover. Walk to local cafés, restaurants, and the riverfront trail, then return to your private patio to relax. Original wide-plank floors, exposed beams, a quirky staircase, and historic woodwork pair with an updated kitchen and modern amenities. Sleeps up to 6 with two queen bedrooms, a cozy twin bedroom, a fold-out sofa, and two dedicated workspaces. The perfect home base for exploring the New Hampshire Seacoast in every season.

4.91 out of 5 average rating, 96 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.

5.0 out of 5 average rating, 65 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!

5.0 out of 5 average rating, 207 reviews

Superhost

Home in Milton

Magical Milton in Fall | Cozy | Bonfire | Hot Tub*

Welcome to Camp Lollywood at Milton Three Ponds—a modern luxury lakefront retreat for unforgettable fall getaways. This sleek 3-bedroom, 2-bath lakehouse sleeps 8 and blends sophisticated design with genuine warmth. Step inside to clean lines, soaring ceilings, and a fireplace perfect for cozy evenings. The chef's kitchen and open living spaces flow to your private dock and sandy beach. Firepit nights, s'mores, and stargazing define your stay. Hot Tub Coming Fall 2026!

5.0 out of 5 average rating, 3 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.

4.99 out of 5 average rating, 69 reviews

Guest favourite

Home in Dover

Waterfront Oasis~Pool Table~Deck~Dock~Garage

Welcome to our Peaceful Waterfront Oasis! This 3-bed, 3-bath retreat offers panoramic views from your private deck and dock. Unwind in style with a pool table, store your car in. the garage and enjoy the dock on the tidal river with water access. Bask in sunsets, relax by the electric fireplace or enjoy your favorite beverage in the sunroom. Perfect for families and friends seeking a luxurious escape. Book now for an unforgettable stay.

4.94 out of 5 average rating, 93 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!

4.98 out of 5 average rating, 41 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 !

4.88 out of 5 average rating, 144 reviews