
Vacation rentals in Portland
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Top-rated vacation rentals in Portland
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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.

Lobstermen's ocean-front cottage
Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

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.

Oceanfront w/ Stunning views and Private Deck☀️🏖
Welcome to the Beach House on the Rocks, your very own oceanfront retreat! This beautiful, 1350 sq ft house is nestled right next to the ocean. With panoramic views and the ocean just steps away, you won’t forget this one of a kind experience. Tucked away in the hidden gem of Camp Ellis, you’ll enjoy a lively beach scene in the summer and a tranquil retreat in the off season. Just a short trip away to Old Orchard Beach and 30 min to Portland you’ll never be in need of fun activities.

Cedar Sauna+Near Beach/Hiking+Pond+FirePit
Come relax and unwind at Pine Cabin! * Cedar Barrel Sauna w/Glass Front * Minutes Reid State Park Beach & 5 Island🦞 * Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat & Automatic Kohler Generator * SmartTV & Record Player w/Vinyl *Pine Cabin is one of two cabins on our 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart and separated by a privacy screen and natural landscaping.

Harborview - Curated East End Escape w/ Parking
Harborview is a newly renovated, top-floor apartment perched on the edge of Munjoy Hill in Portland's East End. This home is a short stroll to the Eastern Promenade and the East End Beach, the Casco Bay Islands Ferry Terminal, and the historic Old Port. The apartment features a spacious open kitchen, dining, and living room floor plan adjoined by a large private deck. It's the perfect spot to gather, relax, and dine while enjoying the breathtaking views of Casco Bay!

Waterfront Two Master Suite Penthouse with Rooftop
2023 City of Portland Registration #20185280-ST Penthouse suite w/modern amenities, exposed beams and brick, poplar walls. Rooftop deck w/views of harbor and city. Separate master suites with custom showers and one with soaking tub. Gas-fired Jotul stove in living room. Washer/dryer in unit. Easy elevator access. Spacious kitchen with granite countertops and wine cooler. Please note: animals (including assistance animals) not allowed due to owner's health.

Sunny West End Guest Suite w/Harbor Views and Pool
Enjoy views of the working harbor from this bright, two floor guest suite in the historic West End. The space features a garden oasis and seasonal, heated saltwater pool—just a short walk from the Old Port and Arts District. The suite is attached to our home but fully private, with its own entrance. (Portland City Permit: 20185360-ST) Note: Guests agree to indemnify and hold the property owners harmless from any liability for injury or property damage.

Beautiful West End studio, hot tub, free parking
Charming, comfortable, well-appointed studio apartment, in an historic building, just steps away from everything downtown Portland has to offer: restaurants, museums, shopping, galleries, parks, Congress Street, and the Old Port. Close to Maine Medical and Mercy Hospital, the Portland Expo, Sea Dogs stadium, and Deering Oaks Park. The studio rental includes free parking for one car and exclusive use of a hot tub.

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."

Sunset Suite 42
Breathtaking views, privacy, and convenient location make Sunset Suite a great place to be while visiting ME! The great room with a cathedral ceiling and skylights offers the best of natural light... day and night! The Portland skyline is all yours from your private and expansive deck as you put your feet up and reminisce about your day and plan for the next.

Cozy Rock Cabin #thewaylifeshouldbe
*As seen on Magnolia Network's 'The Cabin Chronicles'* Cozy Rock Cabin is an 800 sq ft cabin on three acres of wooded land. Carefully designed for couples and digital nomads, it has everything you'll need to explore southern Maine (#thewaylifeshouldbe) or just stay cozy in front of a fire. Follow the journey on IG at @cozyrockcabin!
Popular amenities for Portland vacation rentals
Stay near Portland's top sights
Private Portland vacation rentals

Cape Elizabeth Garden Apt+Beach+Close to Portland!

Cozy * Awesome Location * With Parking

Beautiful large studio on the ocean.

3 bedroom house in the heart of Portland

Cottage Under a Crabapple Tree

Sunflower Retreat in North Back Cove

Apt in Victorian Mansion w/ Hot Tub, Pool, Parking

Bright Guest Studio Near Lighthouses and Beach
Pet-friendly vacation rentals in Portland

Luxury Year-round Treehouse with private hot tub

62 Views

On the water Boathouse!

Gorgeous Studio on the Kennebec

Tiny A-Frame Romantic Getaway

East End Unit

Waterfront Private Apartment only 5 min to LLBean!

Stunning Ocean Views From This Peaks Island Home
Portland home rentals

Reno Barn w/ a lot of Charm! Breweries & Airport

Bay View Craftsman with Easy Old Port Access

Distinctive Home & Garden

An Airy Private Suite steps off Washington Ave

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Beautiful Coastal Maine Getaway

Unplug at a Beachy Bolthole with Classic New England Style

Explore Portland from a 18th-Century Victorian
Quick stats about vacation rentals in Portland
Total rentals
1.6K properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
188K reviews
Family-friendly rentals
870 properties are a good fit for families
Pet-friendly rentals
460 properties allow pets
Rentals with a pool
70 properties have a pool
Your guide to Portland
All About Portland
Perched along the dramatic slate-gray waters of the Atlantic Ocean, where gulls wheel and whitecaps dot the surf, Portland is quintessential Maine combined with the allures of a metropolis. Established as a booming port town by traders and fishermen, Portland is now the state’s biggest city. Here you can tread cobblestone streets, visit historic lighthouses, and dine on lobsters hauled from the nearby waters. But you’ll also find top-notch museums and galleries, boutique shopping, and a celebrated foodie scene that boasts award-winning restaurants and a thriving microbrew culture. New and old Maine commingle comfortably here, where you can enjoy the best of both worlds.
The best time to stay in a vacation rental in Portland
Summers are brief and mild in Portland, where June through September bring average temperatures in the 70s Fahrenheit. October and November cool down, with temperatures in the 40s and 50s, and December through February are chilly, with temperatures in the 30s. Things grow steadily warmer starting in March, ushering in 40-degree weather and climbing into the low 60s by May. You’re likely to encounter rainfall year-round, and snow December through March. Pack lots of warm layers, hats, and scarves.
Top things to do in Portland
Portland Head Light
The Portland area is home to several historic lighthouses, but the Portland Head lighthouse is the undisputed heavyweight. Construction began in 1790, making it the oldest in the state. Visitors can tour the quaint lighthouse and its grounds, which include the former keepers’ house, now repurposed as a museum. Take in the sweeping vista, which includes views of four more lighthouses and the possibility of watching lobstermen pulling their traps from the bay, before taking a scenic stroll through Fort Williams, the 90-acre park in which the lighthouse resides.
Casco Bay and the Calendar Islands
Hop on a ferry (or charter a water taxi) to tour the photogenic Calendar Islands, clustered in grand Casco Bay. You can experience small-town Maine life here. Teensy Cliff Island has fewer than 60 year-round residents and a small schoolhouse. Peaks Island offers four miles of uninterrupted coastline and historical sites such as a World War II artillery bunker. Tonier Great Diamond Island, where a private community has been installed within the refurbished military buildings of historic Fort McKinley, boasts upscale dining. Don’t have time to set ashore? Casco Bay Lines, the island ferry service, offers speciality cruises that will afford you a sailor’s-eye view of the islands and dazzling bay.
Old Port District
Travel back in time in this quaint maritime neighborhood that still looks very much the way it did in the early 19th century. Narrow cobblestone streets and historic brick warehouses lend the enclave its cozy feel, but that’s where the frozen-in-time vibe ends. The restored Old Port District, which is on the National Register of Historic Places, is home to quirky boutiques, inventive eateries, and brewpubs. You’ll find many of these offerings on buzzy Exchange Street.
Frequently Asked Questions
How is the weather in Portland?
Portland experiences a humid continental climate. Summers are typically warm, averaging 79°F (26°C), while winters, known for their snowfall, can drop to 12°F (-11°C). Autumn is colorful with fall foliage, and spring brings mild and refreshing weather.
What are some of the best things to do in Portland?
There's a wealth of activities to enjoy in Portland. Visitors often explore the historic Old Port district, sample local produce at the Portland Farmers' Market, or take a Casco Bay Lines Ferry to the nearby islands. Visiting the Portland Museum of Art is also frequently recommended.
What is the best time of year to visit Portland?
The most popular time to visit Portland is during the summer, from June to August. This period features warm weather and several local events, including the Old Port Festival in June and the Maine Lobster Festival in nearby Rockland in August.
What are the best places to stay in Portland?
Portland, Maine, has numerous charming neighborhoods, each with a unique character. The Arts District is known for its creative buzz and art galleries, while the Old Port area boasts cobblestone streets and waterfront views. Peaks Island, just a 20-minute ferry ride from downtown, provides a serene, coastal stay.
What are the best places to visit in Portland?
Visitors to Portland often find delight in exploring the Portland Museum of Art, the historic Victoria Mansion, and the Eastern Promenade park. A trip to the iconic Portland Head Light, one of the oldest functioning lighthouses in the US, is also frequently suggested.
What are some hiking trails in Portland?
For nature enthusiasts, Portland has several hiking trails. The Fore River Sanctuary Trail provides picturesque views and a chance to spot local wildlife, while the Back Cove Trail offers an easy urban hike around a tidal basin. The Peaks Island Loop is another scenic coastal trail.
What are some family activities to do in Portland?
Families visiting Portland can enjoy a fun-filled day at the Children's Museum and Theatre of Maine, explore the fascinating sea life at the Maine State Aquarium, or take a scenic ferry ride to Peaks Island. A stroll in the Eastern Promenade park is also a popular choice.
What are some of the best day trip ideas in Portland?
From Portland, visitors often take day trips to the coastal town of Kennebunkport, the scenic Peaks Island, or Freeport for shopping at the famed L.L. Bean flagship store. The stunning Acadia National Park, though a bit farther at 160 km, is a popular choice for a longer day trip.
What types of vacation rentals are available in Portland?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Portland. From over 100 condo rentals to over 430 house rentals, we've got you covered.
Are there vacation rentals with a dedicated workspace in Portland?
Yes! Work meets play with ease at over 830 vacation rentals in Portland featuring dedicated workspaces. Stay connected and productive in your home away from home.
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Long Sands Beach
- Popham Beach State Park
- Popham Beach, Phippsburg
- Pemaquid Beach
- Dunegrass Golf Club
- East End Beach
- Pemaquid Point Lighthouse
- Short Sands Beach
- Funtown Splashtown USA
- Willard Beach
- Coastal Maine Botanical Gardens
- Parsons Beach
- Crescent Beach State Park
- Wolfe's Neck Woods State Park
- Wentworth by the Sea Country Club
- Laudholm Beach
- Ferry Beach
- Cliff House Beach
- King Pine Ski Area
- Things to do Portland
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- Food and drink Portland
- Art and culture Portland
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- Things to do Maine
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