Cottage holiday rentals in Kittery

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Top-rated cottage rentals in Kittery

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

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Guest favourite
A spacious living area features a comfortable sectional sofa with patterned upholstery, situated alongside large windows offering expansive views of the waterfront. Natural light floods the room, complemented by warm wooden accents on the ceiling and floor. A dining table for four is placed near the windows.
Cottage in Plum Island
4.92 out of 5 average rating, 132 reviews

Sunset Waterfront Retreat | Private Beach, Pool &

Waterfront retreat with private beach access, panoramic marsh views, and unforgettable sunsets. Designed for families and groups looking to relax, reconnect, and enjoy the best of Plum Island living. Enjoy the private pool (open seasonally), expansive outdoor living spaces, firepit lounge, and peaceful wildlife views directly from the property. Spend your days walking the island, to local beaches and restaurants, or simply unwinding by the water. Inside, the home features a modern kitchen, was

Top 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
4.94 out of 5 average rating, 271 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.

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
4.98 out of 5 average rating, 196 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.

Top guest favourite
A vibrant blue cottage sits nestled among greenery, with a welcoming entrance and an American flag displayed. A dock with two kayaks rests at the water's edge, reflecting the serene lake. A patio area is visible on the upper deck, inviting relaxation.
Cottage in Northwood
4.94 out of 5 average rating, 136 reviews

Cottage on the lake! Includes kayaks & rowboat!

Super cozy, beautiful cottage right on the lake & dirt roads. Yard: sitting areas, propane fire pit, fenced in yard. Inside includes reading areas, dvds, wifi, books, coloring books, puzzles, games. Enjoy the rowboat & kayaks or bring your own boat. We are on Antique Ally and State Parks are nearby (2 miles away). Enjoy a day at Chucksters, Concord, Portsmouth or the lakes region. Enjoy the LAKE LIFE! No animals (Health concern for cleaner) 4 adults or 2 adults 3 kids. Life jackets provided

Superhost
A charming cottage exterior is showcased, featuring a sloped roof and wooden steps leading to the entrance. Lush greenery and well-maintained shrubs surround the home, while a patio umbrella provides shade on the deck. A spacious yard with mature trees adds to the serene setting.
Cottage in Cape Neddick
4.78 out of 5 average rating, 338 reviews

Sweet cottage in quiet convenient coastal setting.

Our cottage is featured i n Terry John Woods "Summer House" as a quintessential cottage of Maine. Relax in our private, romantic Cape Neddick cottage, overlooking a 2 acre meadow and woodland, close by foot, bike, to the amenities of York, Ogunquit, Kennebunk, Kittery, and Portsmouth and within a ten minute ride to five beautiful beaches. Cape Neddick Beach being the closest one, a five minute ride. Our cottage is off the beaten path on a quiet private way, near the Cape Neddick River .

Top guest favourite
The exterior of a post and beam cottage is shown, featuring a light wood facade and a brown shingled upper section. Two black Adirondack chairs are placed on a wooden deck, accompanied by potted plants. Large windows offer a view of the forested surroundings under a partly cloudy sky.
Cottage in Pownal
4.99 out of 5 average rating, 456 reviews

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

Top guest favourite
A modern two-story home is set amidst a wooded area, featuring a spacious outdoor seating arrangement with a picnic table and various chairs. A fire pit and grill are present, with the soft glow of twilight highlighting the inviting exterior.
Cottage in Acton
4.99 out of 5 average rating, 170 reviews

Eclectic Lakefront Cottage on Great East Lake

Welcome to a relaxing stay on the shores of Great East Lake! The fall and winter are the definition of peace and quiet. Often you'll be the only folks on the cove! Come back inside after your outdoor adventures and warm your feet on the radiant slate floors .You can also prepare a home cooked meal in the vintage, fully applianced kitchen. This home is the perfect base for all your winter excursions, or enjoy family time inside with plenty of games, puzzles, ping pong, or air hockey! Enjoy!

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 Badger's Island
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!

Top guest favourite
A garden path winds through a colorful array of blooming flowers, including pink peonies and purple alliums. Green shrubs and neatly trimmed plants line the gravel walkway, which leads towards a decorative archway amidst a backdrop of lush trees.
Cottage in Essex
4.95 out of 5 average rating, 291 reviews

French Flair "Pied a Terre" Cottage on the Marsh

Sunny cottage with marsh views, under 5 minute walk to town. Eat on the water in one of the many village restaurants, rent a kayak or paddle board. Go "down river" like a local! Shop the world renowned antique stores or enjoy the local beaches. There are many unique places to visit in Gloucester, Manchester, Rockport, Ipswich, Salem and of course Boston. There is a Visitor Manual for your convenience and we would be happy to answer questions that you might have.

Guest favourite
A spacious living area on the second floor features two skylights and multiple windows that provide natural light and water views. A light-colored sofa and a coffee table are positioned on a soft carpet, alongside a television and decorative plants, creating a cozy yet modern atmosphere.
Cottage in Portsmouth
4.86 out of 5 average rating, 125 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.

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, 323 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
Cottage in Gloucester
4.97 out of 5 average rating, 149 reviews

Sunny & private cottage in Lanesville Village

Sunny private 2 bedroom cottage with large garden, deck,and great Lanesville location near the ocean. Living room with large flat screen smart TV with Roku, fast internet, and lounge with pull out couch and pocket door for privacy. Now with mini-split A/C throughout and new windows in the bedrooms! Dogs under 55 lbs allowed (no more than 2 ) no cats. Yard is not fenced in.

Popular amenities for cottage rentals in Kittery

Quick stats about cottage rentals in Kittery

  • Total holiday rentals

    Explore 20 holiday rentals in Kittery

  • Nightly prices starting at

    Kittery holiday rentals start at £112 per night before taxes and fees

  • Verified guest reviews

    Over 1,710 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Wifi availability

    10 of Kittery holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Kittery rentals

  • 4.9 Average rating

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

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