Holiday rentals in Jamaica Island

Charming Riverfront Cottage in Portsmouth-SouthEnd

This super comfortable, newly renovated (Nov 2022) and charming little cottage on the river couldn't be more convenient to all that the city and surrounding area has to offer. Enjoy true walking access yet be in a quiet 18th century neighorhood. Across the street from the historic Portsmouth waterfront and around the corner from Pierce Island, Prescott Park, Strawbery Banke and Point of Graves, 112 Mechanic is an incredibly charming home. No pets please. Street park with ease.

Coastal home on the water

A nautical look and feel is what this coastal home away from home offers. A detached from the main house in-law apartment is the perfect get away. Located directly on the water, on an estuary called Spinney Creek, part of the Piscataqua River. Bring your kayak, fishing rod, or sit back enjoy a cold beverage and watch the sunsets by the fire pit. Best water views ever. It is 1.5 miles to downtown Portsmouth, NH and less then 1 mile to the beautiful rejuvenated downtown Kittery.

Fresh + Modern Garden Level Kittery Studio

This stylish garden level modern apartment is well located in Kittery and provides local recommendations from the hosts that live in the upper unit. The kitchen is fully stocked with all your cooking and coffee needs, and includes an under-counter fridge, under-counter freezer, and microwave. The house is less than a mile to downtown Kittery and the shipyard gates, and less than two miles to Portsmouth. (All very walkable with sidewalks) Kittery STR License Number: ABNB-24-67

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!

Romantic A-Frame cabin in the woods

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.

Peaceful Studio Farmstay with Scenic 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.

The Rafters

The Rafters is a finished studio space above our late 1800s barn. It has beautiful light and feels like a getaway as soon as you open the door. With the proximity to Portsmouth, NH and local attractions in Maine, you can escape to the Rafters, but with the ease of being so close to everything. Our neighborhood is beautiful and you can walk down to many spots that overlook the Piscataqua River. Or Uber home from a fun night in Portsmouth!

Studio w Parking in Portsmouth Historic District

Sunny private studio in historic townhouse, with private entrance, kitchenette, and PARKING INCLUDED in the heart of the Historic Downtown District. Perfect for a couple's getaway, week+ work stay, or local family 'guest room'. One block from Market Square, amidst restaurants and shopping. 2 blocks to Prescott Park, Strawbery Banke, Portsmouth Harbor, and public parks. *Site of Daniel Webster's home. Operator license #100004

Cozy West End House

Enjoy the privacy of a 2 bedroom house, recently remodeled with new appliances, located in the heart of the West End, walking distance to everything, and just around the corner from a couple of the best breweries and restaurants in Portsmouth. This house is perfect for small groups or couples visiting Portsmouth, easy to find off the highway and close to everything. It has all of the amenities, including laundry on premise.