Vacation rentals in Kittery Foreside

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.

Location · Value · Outdoor spaces

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.

Location · Value · Shared spaces

Heart of Kittery Foreside, Waterfront Apartment

28 Wallingford Square is in the heart of Kittery Foreside, with a slice of industrial waterfront, and views towards the Portsmouth Naval Yard. Enjoy watching the lobster boats, the lights of the Naval Yard, or witness the wildlife passing by on the waterfront. This unit is only a 15 minute walk to downtown Portsmouth, and a mere 50 paces to the best that Kittery Foreside has to offer. This building is off Government St, on the lobster docks, tucked in behind the Corner Pub and across from Anju.

Family · Value · Nearby

The Perch on Penhallow, Downtown Portsmouth

Nestled in the heart of Downtown Portsmouth, this modern 2 bed, 2.5 bath unit is quintessential downtown city living. Featuring a fully loaded kitchen, mini spits, plush king beds, a sleeper sofa, and direct access to State street, this unit can't you any closer it all. The dining, shopping, and walkable venue access makes this location sought after by locals and travelers alike! Make this your home base for the night or the month and enjoy all of what Portsmouth offers all year round.

Family · Value · Getting around

The Tugboat - KingBed, Waterfront! Parking!

Location Location! Welcome to the Tugboat! A Tastefully decorated 1 Bedroom w/King Bd located on the Historic Waterfront of Portsmouth. All the shops, restaurants, rich history, festivities, and nightlife are right here a few steps away! Enjoy the sunsets over the river while sipping a glass of wine on the front steps before going out. Open the Dutch Door to watch the Tugboats and get all the smells from the restaurants surrounding you. It will be hard not to eat out every night.

Location · Value · View

Cozy Kittery Foreside escape

Stay in the heart of Kittery’s beloved Foreside neighborhood - known for its charming streets, great food, and local shops. Step outside and stroll to some of Kittery’s best restaurants, cafés, and boutiques. If you’re up for a scenic walk, downtown Portsmouth, New Hampshire is just a 20 minute walk away—perfect for a day of waterfront wandering, shopping, or grabbing a drink. Come make yourself at home in this peaceful, centrally located retreat—your Kittery adventure starts here

Value · Location · Condition

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-25-43

Location · Value · Sleep quality

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.

Value · Location · Beach

Chic Loft-Style Condo in Downtown Portsmouth

This contemporary loft-style condo in Portsmouth , is located directly on the Piscataqua River, offers two bedrooms, a comfortable living room, vibrant dining space, and galley kitchen. It's a short walk to all of the shops and restaurants in downtown Portsmouth, and just 8 miles to New Hampshire's most popular beaches. Come relax, dine, shop and play. It's all here for your enjoyment, and you just know it's time to book yourself getaway!

Location · Value · Indoor spaces

Small newly renovated 2 bedroom apartment

Newly refurbished 700 sq ft apartment with 2 bedroom, 1 bath, and open concept kitchen/living room in a residential neighborhood. 5-10 walk to brewery and restaurant. 20 min walk to downtown Kittery. 5-10 minute drive to downtown Portsmouth, NH. Easy walk to Portsmouth Naval Shipyard. 20 minutes to beaches.

Value · Family · Laundry

Guesthouse w/ EV charger, deck, & fire pit.

Kittery Cottage is a private, newly built property located 1.5 miles from the charming city of Portsmouth and minutes from many of the seacoast beaches. With a ten minute walk to Kittery Foreside you have access to many restaurants and shops. The Kittery outlets are less than 2 miles away.

Family · Location · EV charging

Seacoast 4BR | Mins 2 Portsmouth | Beach, Outlets

🌊 Welcome to the Seacoast! This 4-bedroom hideaway is privately nestled in Kittery Foreside while still keeping you close to the action. Decorated in a charming seacoast farmhouse style, this home is perfect for 2–3 couples, a family (or two), or an extended work-cation 💻🏡.

Family · Value · Outdoor spaces