Holiday houses in Kittery Foreside

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Top-rated holiday rentals in Kittery Foreside

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Top Guest favourite
An outdoor deck is shown, offering views of the harbor and bustling waterfront activities. The spacious living room features comfortable seating and large windows. The bright bedroom includes a king-sized bed. A well-lit layout highlights the inviting ambiance throughout.
Home in Kittery
4.97 out of 5 average rating, 259 reviews

#1 Home in Kittery Foreside - PVT Harbor View Deck

Escape to Kittery, Maine for a peaceful getaway! Our 3-bedroom, 3-bathroom home sleeps up to 10 and is just a short walk from the popular Kittery Foreside, offering a range of shopping and dining options. Perfect for those seeking a quiet vacation, our home is equipped with modern amenities and comfortable furnishings. Enjoy a fully stocked kitchen, comfortable living room, and 3rd floor deck for relaxation. Book now for a stress-free vacation filled with delicious dining and retail therapy!

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, 302 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.

Top Guest favourite
A modern living area features a light-colored sectional sofa adorned with green accent pillows. A sleek coffee table with a reflective surface is centered on the wood flooring. Natural light filters through a nearby window, illuminating the space and a botanical print hangs on the wall.
Apartment in Kittery
4.97 out of 5 average rating, 246 reviews

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

Top Guest favourite
A cozy living room features a white-brick fireplace, with a functional gas flame. Stylish furniture includes a patterned armchair and a soft couch, complemented by a light-colored striped wooden floor. Large windows allow natural light and offer views of the surrounding area.
Home in Rye
4.98 out of 5 average rating, 342 reviews

*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: https://bit.ly/3vK5F0G We've outfitted it with an extra screen and a setup to get you up and running. Google home and Sonos systems bring this 100 year old beauty into this century.

Top Guest favourite
A welcoming living area showcases a large screen displaying Netflix. Two brown armchairs with throw pillows are positioned beside a modern coffee table. A cozy fireplace adds warmth, while soft gray and blue tones create a relaxing atmosphere. Natural light filters through the windows.
Home in Kittery Point
5 out of 5 average rating, 165 reviews

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!

Guest favourite
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
4.88 out of 5 average rating, 104 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.

Guest favourite
A cozy living room is featured, furnished with a green couch and a wooden coffee table. Natural light is provided by two large windows, framed with gray curtains. A flat-screen TV is positioned on a contemporary media console, complemented by a leather ottoman.
Apartment in Kittery
4.98 out of 5 average rating, 108 reviews

Charming retreat in Kittery

Welcome to our Airbnb. Less than 10 min drive to downtown Kittery and Portsmouth - easy access to the shops and restaurants in Market Square and the Kittery Foreside. Take a drive along the seacoast, explore Fort Foster, or sit back and relax on Long Sands beach. Enjoy the 43" 4K TV with all the apps. The kitchen is stocked with all the essentials including a Keurig machine & K-Cups. Plus, off-street parking, air conditioner, FAST WiFi, & a comfy bed!

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, 105 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.

Guest favourite
A classic Cape Cod-style home is presented, featuring crisp white siding and a welcoming American flag displayed on the front porch. Lush green grass surrounds the house, complemented by mature trees and vibrant shrubbery, creating a serene outdoor setting.
Home in Kittery
4.97 out of 5 average rating, 314 reviews

Family Friendly 2BR 1 BA Coastal Kittery Home

Welcome to our cozy family guest home in beautiful Kittery, just 2 miles from downtown Portsmouth. Nearby are beaches, great restaurants, historic sites, boutique shopping, shopping outlets and Portsmouth Naval Shipyard. This home has 2 bedrooms, 1 bathroom, a fenced in yard for up to 4 adults with their children. This house is set up nicely for families of all ages. Dogs welcomed with permission from the owner. STR License #ABNB-25-52

Top Guest favourite
An open layout features a kitchen area and dining space with a wood table and two chairs. The cozy sleeping area includes a spacious bed against a wooden accent wall. Pendant lights hang above, while natural light from the windows highlights the wood flooring.
Apartment in Kittery
4.98 out of 5 average rating, 265 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.

Top Guest favourite
The living area features exposed brick walls and wooden beams, giving it a historic charm. A neutral-colored sofa is positioned beside a small wooden coffee table. A round dining table with black chairs is visible, providing a cozy space for meals.
Condo in Portsmouth
4.99 out of 5 average rating, 108 reviews

Lovely 1-bdr condo in historic downtown Portsmouth

Awesome historic 1 bedroom condo in downtown Portsmouth close to everything. Sleeps up to 4 with bedroom, and queen sleeper sofa in living room. Newly renovated. Enjoy relaxing in this unique and charming space with exposed brick and beams. Full kitchen, eat in or go out! Shops and restaurants at your doorstep. Walking distance to everything downtown Portsmouth has to offer.

Top Guest favourite
A cozy living area features a light-colored sofa with decorative pillows, paired with a comfortable armchair. A flat-screen TV is mounted above a gas fireplace, while natural light illuminates the space through a nearby window. A round coffee table sits in the center, enhancing the inviting atmosphere.
Guesthouse in Kittery
5 out of 5 average rating, 363 reviews

Newly built, private deck with 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.

Popular amenities for Kittery Foreside holiday rentals

  1. Airbnb
  2. United States
  3. Maine
  4. York County
  5. Kittery
  6. Kittery Foreside