Holiday rentals in Rollinsford

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.

Suite at Blackwater Farm

Come and enjoy a relaxing stay in a three room suite at Blackwater Farm. You will have a private entrance to a portion of the house built in the 16oos. The site has an entryway, living room with kitchenette, bathroom and bedroom all separate and private from the main house. Spend time exploring the 13 acres of the property which includes trails through woods, fields and along our own beaver pond. We're located just 10 minutes from WWD hospital /downtown and 20 minutes from Portsmouth /Durham.

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.

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.

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.

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.

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.

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!

✨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.

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.

Southern Maine Guest Suite

Welcome to our Southern Maine Guest Suite. Enjoy a private entrance, bedroom/sitting area, and bathroom. The 300 sq ft suite has a queen bed, tv, Wi-Fi, hot drinks, mini-fridge, microwave, and full-sized sofa bed. We are located 8 miles from Portsmouth, NH, and 20 minutes to several Maine beaches.