Holiday rentals in Little Boars Head

Rye Coastal Cottage |2BR| Dog-Friendly | Patio

Welcome to the Rye Coastal Cottage! This cozy 2BR beach ranch sits on a quiet, wooded street just a 9-min walk to Jenness Beach. The single-level home offers comfort, privacy, and all the essentials for a laid-back Seacoast stay for four, plus a dog! Unwind after the beach, explore nearby Portsmouth and Kittery, or relax in the large yard or patio. Professionally cleaned and dog-friendly, this is ideal for couples, families, or friends looking for a classic coastal escape optimized for guests.

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.

Relax at Rye Beach & Portsmouth

Kick back and relax in this calm, stylish, quiet space w easy parking. Walk/bike to the beach. Enjoy your private space with dining area, sofa, queen bed and private bath & kitchenette. The space is over 600 sq ft (about twice the size of a hotel room) with plenty of sunshine -- and room to relax on the couch, rest in bed or dine/work at the table. Visit the shops & cafes of Portsmouth. Two bikes & beach chairs. We are close to the beach (we walk there most days) and an easy drive Maine sites.

Seacoast Solo

A New England stopover 10+ min from the Atlantic Coast, restaurants, arts, shops, historical sites, and outdoor explores. Easily en route to MA, ME, VT +. One very small guest room for a solo traveller, separate entrance, private bath, forest facing yard, semi private deck, off road close-by parking, and trails to meander steps from your door. This weathered lived loved home has been in the family since built in 1908. No relation to a hotel room, but clean, comfy, and convenient location.

Luxury on Rye Harbor w/ 360 Degree Views

This fun and charming Rye Harbor home offers views that only a few properties on the Seacoast provide. Watch the lobster boats and harbor cruises depart and return throughout the day while enjoying all that this three level, single family home has to offer. The two bedrooms are on the entry level, while the kitchen and living area are on the second level to provide a serene view of Rye Harbor. The outdoor deck on the top level of the home showcases a 360 degree view of Rye's natural beauty.

Beach Retreat with 3 bedrooms and hot tub

This unique place has a style all its own. Perfect getaway with all the comforts! Completely remodeled with new furniture, new beds and new hot tub. Fully equipped kitchen with dining room, fireplace in living room & lots of decks to relax outdoor. New Smart TVs in all bedrooms, Ping pong room. We have all the comforts of luxury hotel with tons of activities at your doorstep. Half mile to ocean , 5 min drive to Nth Hampton & Rye beach, Fuller Gardens. Close to Portsmouth & Kittery.

*Beachfront* Vintage Coastal Cottage - Relaxation

It's always about the view and this place will leave you feeling energized and calm. Situated on premium beachfront property, this single family home has luxurious amenities like super plush towels, organic cotton bedding and touches to make your getaway feel that much Take a virtual tour here once you book I can send you a link (per Airbnb’s rules) I’ve outfitted it with an extra monitor & a setup o WFH. Google home and Sonos systems bring this 100 year old beauty into this century.

Portsmouth Waterfront Cottage

Our waterfront cottage is a unique property offering style, tranquility, and walking access to Portsmouth’s Market Square. The theme is a blend of New England charm and Scandinavian modern. We offer an amazing view, two decks, a modern kitchen, laundry, and free parking for one vehicle. This premium property sleeps four, counting children. It offers a quiet romantic escape for the discerning traveler, and yet is just a ten minute walk to Market Square.

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.

Ocean & Marsh Views | Rooftop Deck | Private Yard

Welcome to "The Surf", Rye's ultimate private vacation home. You'll love the views from your bedroom and rooftop deck being directly across the street from the ocean. Lots of back-yard fun to be had or simply enjoy relaxing on the first-level deck while looking out at the marsh. Centrally located to Jenness Beach, Wallis Sands State Beach and Rye Harbor, this single-level property makes for the perfect coastal getaway.

Seacoast Escape with a View

Enjoy the peace and tranquility of staying in Kittery Maine’s exclusive waterfront area. • Walk to downtown Portsmouth • 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! See our other home and awesome reviews: airbnb.com/h/pepperrellparadise