Holiday rentals in Portsmouth

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Top-rated holiday rentals in Portsmouth

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, 273 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
An outdoor deck is shown, illuminated with string lights and featuring two large umbrellas. Comfortable seating includes a dark sectional with colorful accent pillows and a rustic wooden stool. Lush greenery and views of surrounding buildings create a cozy and inviting atmosphere.
Loft in Portsmouth
4.96 out of 5 average rating, 266 reviews

Downtown Market St Loft—Style & Cozy, Above it All

Live local in the heart of Portsmouth! Relax in our bright, two-level loft above Historic Market Street—steps from cafés, boutique shops & more. Stay in PORTSMOUTH'S BEST VACATION HOME! 🏆 Editors Choice, Condé Nast Traveler. Why you’ll love it ➝ Full kitchen ➝ Eclectic & full of personality ➝ Sunny deck with skyline view ➝ Comfy queen bed ➝ Fast WiFi, dedicated workspace ➝ Walk 2min to "the decks", restaurants & Prescott Park. TREAT YOURSELF to a cozy downtown stay—reserve your dates today!

Top guest favourite
Guest suite in Kittery Point
4.97 out of 5 average rating, 162 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
A kitchenette features a granite countertop with a sink and a drying rack. Walls are decorated with stained wood panels in various colors. A doorway leads to a cozy living area, visible through the window, with two chairs and light provided by wall-mounted fixtures.
Flat in Portsmouth
4.96 out of 5 average rating, 295 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!

Top guest favourite
Flat in Portsmouth
4.98 out of 5 average rating, 313 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, 258 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-25-43

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, 350 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, 173 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 serene view of the water is framed by a white railing in the foreground, with a comfortable lounge chair suggesting a space for relaxation. The calm surface of the water reflects the surrounding greenery and distant buildings, creating a peaceful atmosphere.
Cottage in Portsmouth
4.86 out of 5 average rating, 113 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
Flat in Kittery
4.96 out of 5 average rating, 112 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
Flat in Kittery
4.98 out of 5 average rating, 272 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
A modern kitchen with white cabinetry and gray granite countertops is featured. A combination washer and dryer is present beside the stainless steel refrigerator. The space highlights exposed wooden beams and a glimpse of the living area with a sofa in the background.
Apartment in Portsmouth
4.99 out of 5 average rating, 111 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.

Popular amenities for Portsmouth holiday rentals

When is the best time to visit Portsmouth?

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Avg. price$227 SGD$236 SGD$235 SGD$255 SGD$285 SGD$322 SGD$351 SGD$381 SGD$314 SGD$303 SGD$265 SGD$265 SGD
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Frequently Asked Questions

  • What are the best places to stay in Portsmouth?

    Portsmouth has historic downtown stays, homes set along tree-lined streets, and properties near the waterfront. Many travelers look for stays in the Market Square area to be close to local dining and galleries.

  • What are the best things to do in Portsmouth with kids?

    Explore hands-on exhibits at the Children's Museum of New Hampshire, stroll Prescott Park’s gardens, or tour the historic Strawbery Banke Museum. Ice cream shops and short harbor cruises are frequently suggested family favorites.

  • What are some of the best things to do in Portsmouth?

    Discover historic homes at Strawbery Banke Museum, explore the waterfront near Prescott Park, and wander lively Market Square with shops and cafes. Many visitors enjoy local theater performances as well.

  • How is the weather in Portsmouth?

    Portsmouth’s winters are cold, often ranging from 14–33°F (-10–0°C), while summers are mild and pleasant near 58–81°F (15–27°C). Snow is common in winter, and spring brings increasing rain with warming temperatures.

  • When is the best time to visit Portsmouth?

    Late spring through early fall is often recommended for milder temperatures, blooming gardens, and local festivals. Winters are quieter, with snow and festive lights around downtown.

  • What are the best places to visit in Portsmouth?

    Strawbery Banke Museum, the historic waterfront around Prescott Park, and Market Square’s shops are frequently suggested places to explore. The Portsmouth Athenaeum has local history collections.

  • What are some hiking trails in Portsmouth?

    Explore walking trails at the Urban Forestry Center or loop paths through the Great Bay National Wildlife Refuge near Portsmouth. Many enjoy easy waterfront strolls in Prescott Park.

  • What are some family activities we can do in Portsmouth?

    Families often explore the Children's Museum of New Hampshire, picnic in Prescott Park, or join guided tours at Strawbery Banke Museum. Seasonal harbor cruises and ice cream stops are popular choices.

  • What are some of the best day trip ideas from Portsmouth?

    Around Portsmouth, many explore sandy beaches, local wineries, and historic towns in coastal New England. Outdoor lovers often visit nature reserves or take boat tours for a change of scenery.

  • Are there any pet friendly accommodations available in Portsmouth?

    Portsmouth has a range of pet-friendly homes and apartments, particularly near Market Square and the waterfront. Many hosts welcome pets and offer nearby parks for walks.

  • What are some local tips for visiting Portsmouth?

    Portsmouth’s downtown is very walkable, so comfortable shoes are helpful. Locals suggest exploring early to enjoy quieter mornings and sampling regional seafood at area restaurants.

  • What is Portsmouth known for?

    Portsmouth is known for its colonial-era architecture, thriving arts scene, and rich maritime heritage. The downtown area has historic homes, public gardens, and diverse dining.

  • What are the best hidden gems to explore in Portsmouth?

    The Portsmouth Athenaeum is often considered a quiet spot for history, and small galleries tucked off Market Square showcase local artists. Peaceful paths at the Urban Forestry Center invite relaxed walks.

  • What are the best foods to try in Portsmouth?

    Portsmouth’s cuisine highlights fresh seafood such as lobster rolls, clam chowder, and oysters. Many local bakeries serve maple-infused treats and New England-style pies.

  • What should I bring for a trip to Portsmouth?

    Pack layers for shifting coastal weather, walking shoes for downtown exploring, and a rain jacket during wet months. In winter, include warmer coats, gloves, and a hat.

  • What is the nightlife in Portsmouth like?

    Portsmouth has lively pubs, craft breweries, and venues hosting local bands or theater performances. The downtown area and waterfront bars are often suggested for evening outings.

  • What are the most popular events or festivals in Portsmouth?

    Portsmouth's Market Square Day in early summer celebrates local culture, and Prescott Park Arts Festival hosts outdoor performances and concerts in warmer months. Holiday tree lightings and fairs draw crowds in winter.

  • Are there family friendly vacation rentals in Portsmouth?

    Portsmouth has family-friendly rentals in neighborhoods near downtown, with homes suited for varying group sizes. Many listings include amenities such as kitchen facilities or outdoor spaces.

Quick stats about holiday rentals in Portsmouth

  • Total holiday rentals

    Explore 240 holiday rentals in Portsmouth

  • Nightly prices starting at

    Portsmouth holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 21,800 verified reviews to help you choose

  • Family-friendly holiday rentals

    120 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wifi availability

    240 of Portsmouth holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Beachfront, Self check-in and Gym across Portsmouth rentals

  • 4.9 Average rating

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