Holiday rentals in Kittery

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Top-rated holiday rentals in Kittery

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

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Top guest favourite
A modern cabin with an A-frame shape is illuminated by warm lights, surrounded by tall trees. In front, a fire pit with wooden chairs invites gatherings, while a hot tub and sauna are visible nearby, contributing to the outdoor relaxation space.
Cabin in South Berwick
5 out of 5 average rating, 254 reviews

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.

Top guest favourite
A spacious sleeping area features a large bed with decorative pillows and a textured blanket. Nightstands are positioned on both sides, each with a lamp and small items. Soft light filters through sheer curtains, complementing the pleasant wall art above the bed.
Guest suite in Kittery Point
4.97 out of 5 average rating, 160 reviews

Seacoast Suite

Welcome to our traditional Maine Gambrel where you will have a private entrance, bedroom, bathroom and sitting area. The 250 sq ft suite has a queen bed, tv, Wi-Fi, hot drinks, mini fridge, microwave, and private space. We are located just over an hour from Boston or Portland, 5 min to Kittery shopping outlets, half mile to a boat launch & 5-15 min drive to a number of beaches. We are located in a quiet residential neighborhood. We ask for no animals since there's a cat that lives here too.

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.
Flat 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.
Flat in Kittery
4.97 out of 5 average rating, 245 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 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.
Flat 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 dynamic scene showcases a gas fire pit, with flames dancing above dark stones. Two glasses are positioned on the edge, one filled with ice, the other with a warm beverage. The horizon displays a soft sunset over the water, adding a serene backdrop.
Guest suite in Dover
4.89 out of 5 average rating, 250 reviews

Lovely Waterfront Suite, New Hampshire Seacoast

Great location to enjoy the New Hampshire Seacoast. Just a few minutes to Portsmouth and Durham, perfect romantic getaway, or convenient spot to visit your student at the University of New Hampshire. Wonderful one bedroom suite, private patio. Enjoy the waterfront deck, complete with a heated dome for winter. This is place is truly magical. You will enjoy how special it is. Close and convenient spot on the New Hampshire - Maine boarder.

Top guest favourite
The cottage, featuring rustic cedar shingles, is set among lush greenery. A screened porch with large windows invites fresh air and natural light. The spacious yard is accented by varied plant life, contributing to a serene and private outdoor environment.
Cottage in Kittery
4.96 out of 5 average rating, 320 reviews

Charming Coastal Maine Cottage

Charming Coastal cottage on private way. Two bedrooms w 1 bath upstairs. Additional pullout futon in separate room downstairs. Sleeps up to 5. Surrounded by Rachel Carson National Wildlife Refuge, walk to Seapoint Beach, beautiful and peaceful. Large screened porch to relax in. Bird watchers paradise. Eclectic restaurants, galleries, museums, local food purveyors, breweries and more all 10-15 minutes away in Kittery/Portsmouth .

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.
Flat 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 cabin is illuminated warmly at dusk, featuring a hot tub in the backyard. Outdoor seating arrangements with four chairs are positioned around a fire pit, set against a backdrop of trees, creating a serene and inviting atmosphere.
Cabin in Kennebunk
4.98 out of 5 average rating, 182 reviews

HotTub/5min to K-port, Pet friendly, @anchorunwind

Follow us on IG @anchorunwind. Escape to a hidden gem nestled in the heart of the Kennebunkport area, where modern comfort meets nature's serenity. Our cabin offers an unforgettable vacation experience. ✭"...A must stay location. The host’s were very helpful and genuine..." ✭"...We’ve travelled all around the world and this is in our top 3 Airbnbs we’ve stayed in."

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.
Guest house 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 holiday rentals

When is the best time to visit Kittery?

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Frequently Asked Questions

  • Where should I stay in Kittery?

    Make yourself at home in Kittery by choosing from our most frequently booked neighborhoods. We have over 280 vacation rentals in New Castle Island, over 280 vacation rentals in Kittery Point, and over 120 vacation rentals in Elwyn Park.

  • Are there vacation rentals with a dedicated workspace in Kittery?

    Yes! Work meets play with ease at over 210 vacation rentals in Kittery featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Kittery?

    Four-legged friends are welcome in Kittery. Choose from more than 90 vacation rentals for guests traveling with pets.

  • Are there Kittery vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Kittery, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in guesthouse rentals in Kittery?

    Experience the best of Kittery with our guesthouse rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do hotel rentals in Kittery have wifi?

    Absolutely! We offer over 10 hotel rentals with wifi in Kittery. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Kittery have a gym?

    Absolutely! We offer over 20 house rentals with a gym in Kittery. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Kittery have a bbq area?

    Absolutely! We offer over 10 cottage rentals with a bbq area in Kittery. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Kittery have self check-in?

    Absolutely! We offer over 10 condo rentals with self check-in in Kittery. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Kittery?

    Kittery has more than 260 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about holiday rentals in Kittery

  • Total holiday rentals

    Explore 450 holiday rentals in Kittery

  • Nightly prices starting at

    Kittery holiday rentals start at £7 per night before taxes and fees

  • Verified guest reviews

    Over 32,590 verified reviews to help you choose

  • Family-friendly holiday rentals

    260 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 90 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

  • Wifi availability

    440 of Kittery holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Kittery rentals

  • 4.9 Average rating

    Kittery stays are highly rated by guests – averaging 4.9 out of 5!

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