Holiday houses in Kittery Foreside

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Top-rated holiday rentals in Kittery Foreside

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

An open living area features a comfortable gray sofa with decorative pillows, a wooden coffee table on a textured rug, and two light-colored armchairs. The space is illuminated by natural light from nearby windows, with a modern kitchen visible in the background.

Cottage in Kittery

4.93 out of 5 average rating, 276 reviews

Maine Harbor Escape | Porch&BBQ, Walk 2 Portsmouth

🌊🏡Welcome to Our Coastal Cottage!🦞☀️ The perfect home for a small family or couple💑looking to escape to the Maine Seacoast. Located in a quaint residential neighborhood within harbor view⚓, this cottage has a relaxing farmers porch🌿, a BBQ grill🍖, 2 full bathrooms🛁, and is within a 45-second walk🚶‍♀️to Kittery Foreside; a small downtown area with shops🛍️and restaurants🍽️. Our cottage was tastefully decorated by a professional interior designer🎨and comes with smart TVs📺 in every room.

LocationFamilyTV

Top Guest favourite

A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.

Treehouse in Sanford

4.91 out of 5 average rating, 596 reviews

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.

LocationFamilyRiver

Top Guest favourite

A deck overlooking the water features a round table surrounded by four chairs, each with turquoise cushions. An umbrella stands in the center of the table, providing shade. A decorative rug with an oceanic design is positioned underneath the table, complementing the serene water views.

Cottage in Eliot

4.99 out of 5 average rating, 205 reviews

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.

LocationFamilyHiking

Top Guest favourite

A relaxed living room features a spacious modular couch, a cozy accent chair, and a circular coffee table. A patterned rug lies beneath, while natural light floods from large windows. The kitchen is visible in the background, highlighting the open-concept layout.

Apartment in Portsmouth

4.98 out of 5 average rating, 120 reviews

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.

LocationValueAmenities

Guest favourite

A cozy sitting area features a dark leather sofa facing a wall-mounted television. A wooden coffee table occupies the center, with decorative items placed on its surface. The adjacent wall showcases a colorful patchwork of reclaimed wood, complemented by warm lighting and a mirror.

Apartment in Portsmouth

4.94 out of 5 average rating, 330 reviews

Studio Apt. in Historical Portsmouth NH

Second floor studio in an 1890's historical house with a queen pull down "Murphy" bed. Walking distance to downtown with many restaurants/shopping/nightlife/theaters/walking trails/liquor store/grocery/gas/pharmacy/pubs/coffee shop/ice skating/laundry. Close by are beaches/boat tours and golf to name a few. The seacoast has much to offer. 1 hr. from Boston, 1.5 hr from White Mountains. This is a very friendly neighborhood and you'll just love the charm that Portsmouth has to offer!

ValueFamilyIndoor spaces

Top Guest favourite

An aerial view captures the waterfront of Portsmouth, featuring several tugboats docked along the river. Historical buildings line the shore, showcasing brick facades and a bustling atmosphere. A vibrant marketplace is visible along the waterfront, with boats gently bobbing in the water.

Apartment in Portsmouth

4.98 out of 5 average rating, 353 reviews

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.

LocationValueAccuracy

Top Guest favourite

The kitchen features modern wooden cabinetry with glass-front doors, showcasing kitchen essentials. A stainless-steel refrigerator and microwave are visible, alongside a sleek stove and coffee maker. A wooden dining table with three chairs offers a cozy space for meals. Warm lighting enhances the inviting atmosphere.

Condo in Portsmouth

4.97 out of 5 average rating, 204 reviews

Unbeatable condo/host in the heart of Portsmouth

DM for availability. This hidden gem in the heart of Market Square is literally just a few steps away from everything Portsmouth has to offer. This spacious, top floor walk-up, 2 bedroom condo has direct views of North Church. It features a full, newly updated kitchen and appliances, Brentwood hypoallergenic mattresses. Generously supplied with extras. 14’ ceilings with exposed beams. Modern decor, super cozy, super clean, and quiet. This space is limited to NO more than 4 adults.

ValueLocationWalkability

Top Guest favourite

A charming cottage is adorned with warm outdoor lighting, creating a welcoming presence. The porch features festive decorations, while neatly trimmed bushes lined with lights add to the inviting atmosphere. Adjacent, another structure can be seen, surrounded by greenery and utility lines.

Cottage in Kittery

4.94 out of 5 average rating, 164 reviews

Badgers Island Cottage

You will fall in love with this cozy Maine cottage on Badgers Island! From its lovely views of the Piscataqua River, to its gardens, open-concept floor plan and tasteful style -- it is everything an island home should be. Features an updated kitchen with brand new appliances with granite counters, Brand new tub, toilet, and vanity, wood floors in every room, and full walk-out basement. Walk to Portsmouth or sit on the porch and watch the boats go by -- island living at its best!

LocationValueLaundry

Superhost

A light-filled living area features a spiral staircase ascending to the upper level. A cozy sofa is complemented by a white coffee table and a media console with a television. Large windows allow natural light to brighten the space, while indoor plants add a touch of nature.

Cottage in Portsmouth

4.84 out of 5 average rating, 136 reviews

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.

FamilyLocationSleep quality

Guest favourite

A bright living area is highlighted by high ceilings with exposed beams. A comfortable chair and a stylish table set are present, alongside a television. Colorful artwork decorates the space, while natural light filters through large windows, illuminating a woven area rug.

Apartment in Portsmouth

4.94 out of 5 average rating, 150 reviews

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!

LocationFamilyBeach

Top Guest favourite

A contemporary cabin retreat is nestled among tall trees, softly illuminated by warm outdoor lights. A wooden deck with steps leads to a welcoming entrance. A separate sauna structure is visible, surrounded by snow-covered ground, providing a serene atmosphere in a tranquil forest setting.

Home in South Berwick

5 out of 5 average rating, 141 reviews

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.

LocationValueOutdoor spaces

Top Guest favourite

Apartment in Kittery

4.98 out of 5 average rating, 299 reviews

Goose Point Getaway (a boutique AirBnB experience)

Our Goose Point Getaway is a one bedroom apartment located in the lower level of our home. Completely private with its own entrance and no shared space with the owners. You can see a peek of Spruce Creek (a tidal inlet) from the bedroom window and deck. The space has been designed to offer a relaxed, comfortable get away experience. Our home is located in a quiet neighborhood which loops around Spruce Creek.

ValueFamilyKitchen