Vacation rentals in Rollinsford

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

Luxury Year-round Treehouse with private hot tub

The Canopy 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.

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.

New, private, clean and comfy 1 bedroom apartment!

Welcome to our new 1 bedroom, 1 bath apartment in a beautiful, tranquil setting. We are minutes away from the Kittery Outlets, Seapoint Beach, Fort Foster, Fort McClary, Pepperell Cove, Portsmouth, York beaches and Ogunquit Beach. When you arrive, you will feel at peace in our truly tranquil oasis, surrounded by nature. We abutt 87 acres of conservation land. Turkeys, deer and birds visit us daily! We are secluded, yet close to everything. Welcome to our little slice of paradise!

Beautiful studio, pasture view - 20 min to beach.

This special place offers peace and quiet with lovely views of a local farm, and is only a short walk to the bustling Main Street of South Berwick, with restaurants, cafe, a neighborhood market and more. The Red Barn wedding venue at Overlook is five minutes away, as is the beautiful eighteen hole golf course. Explore the many hiking trails and beaches, twenty or so minutes away by car. Enjoy the lovely city of Portsmouth, offering restaurants, brew pubs, local shops and bookstores.

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.

Lovely Waterfront Seacoast Suite

Cozy waterfront suite , king size bedroom perfect for a relaxing escape. Just minutes from Portsmouth and Durham, it’s ideal for a romantic getaway, attending a local event, or visiting the University of New Hampshire. Enjoy a private patio and waterfront deck featuring a seasonally heated dome and a year-round fire pit. A duraflame log for winter use in the living room fireplace. You’ll find many nice extras here. Peaceful coastal charm near the New Hampshire–Maine border.

Peaceful Studio Farmstay with Pasture Views

Welcome to our charming studio apartment overlooking a picturesque dairy farm and flower gardens. Nestled in the peaceful countryside of Eliot, this spacious yet affordable retreat offers rustic elegance without compromising comfort. Our farm is home to chickens, ducks, and geese, adding to your authentic rural experience. Guests are welcome to feed the animals, watch the cows graze, and unwind in the beauty of nature—all just 20 minutes from the beach.

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.

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!

The Silver Fox Den

The Silver Fox Den is a cozy one-bedroom retreat at historic Silver Fox Farm, just minutes from Portsmouth and New Hampshire's beautiful Seacoast. Inspired by curiosity and the joy of slowing down, it's the perfect home base for beach days, local shops, and scenic trails. Return to peaceful evenings, thoughtful comforts, and quiet mornings with coffee, we hope you'll feel right at home.

✨Charming Stay-Downtown Dover🍷FreeWine🍷Portsmouth

FULL KITCHEN ~ WASHER/DRYER ~ COFFEE & TEA ~ FREE WINE ~ HEAT/AC/WIFI ~ DOWNTOWN PROPERTY NEAR SHOPS, RESTAURANTS, & PUBLIC TRANSPORTATION ~ EXCELLENT SERVICE! You are now on 1st Street, smack-dab in the center of Downtown Dover – an aged and gorgeous mill town and colonial seaport tucked between two New Hampshire hot spots, Durham and Portsmouth.