Portland vacation rentals
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Top-rated vacation rentals in Portland
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Apartment in Portland
4.82 out of 5 average rating, 348 reviewsSpacious and Comfortable Private Apartment
Third floor (i.e. a few stairs) spacious apartment with a private entrance. Walking distance to Thompson’s Point, Maine Med and many other trails and attractions. The Old Port is a 5 minute drive (1.5 mi.). There is plenty of free street parking available. Space heaters warm the space in the winter, and a/c is provided in the summer. The house is shared by first floor tenants while our family occupies the second floor. Again, several stairs to navigate, but quite comfortable once you settle in!
Mar 14 – 21
Guesthouse in Portland
4.95 out of 5 average rating, 278 reviewsBeautiful large studio on the ocean.
Our large, light, 2nd floor studio is airy and modern with a deck overlooking the garden, ocean and sunrise. We love to welcome guests to share our beautiful property so if you'd like to book please introduce yourselves and let us know about who is coming and some hopes for your trip. We are caring, unobtrusive hosts who value getting to know our guests a little beforehand. We think we have the best of both worlds here - the peace and beauty of Casco Bay, yet 5 minutes to the center of town.
Apr 25 – 30
Apartment in Portland
4.97 out of 5 average rating, 352 reviewsMunjoy Hill, East End 1 BR Portland, ME
The Portland Observatory marks your way home to this apartment atop Munjoy Hill. Furnished for guests, private entrance, 1st floor unit of our 2 unit home of twenty years. BEST LOCATION! Skip the car. WALK to restaurants, music, shops, breweries, beach, parks, & historic Old Port. Stones throw to fresh produce, bakeries, wine & spirits. Furnished with LOCAL ART (made by your host in adjacent studio) the cozy apartment offers humble elegance. Just arrive, fun awaits. All are welcome here.
Apr 6 – 13
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Portland vacation rentals
Portland beach vacation rentals
Apartment in Portland
4.97 out of 5 average rating, 219 reviews"Percival" Penthouse Suite - Amazing Harbor Views
Feb 18 – 25
Apartment in Portland
4.9 out of 5 average rating, 342 reviewsHip & Cozy, high end Modern Design
Dec 15 – 22
Apartment in Portland
4.81 out of 5 average rating, 189 reviewsClean East Bayside Apartment- Amazing Location!!
May 3 – 10
Apartment in Portland
4.88 out of 5 average rating, 374 reviewsModern East End studio, perfect Portland home base
Oct 31 – Nov 7
Cottage in Scarborough
4.97 out of 5 average rating, 161 reviewsBright, clean, private cottage near Higgins Beach!
Feb 20 – 27
Apartment in South Portland
4.91 out of 5 average rating, 148 reviewsSunny and beautiful brick house apartment
Apr 27 – May 4
Apartment in Portland
4.9 out of 5 average rating, 378 reviewsPrivate Hill Top Apartment Two/On Street Parking
Apr 8 – 15
Apartment in Portland
4.88 out of 5 average rating, 377 reviewsUpdated stylish 1 BR Downtown Apt
Nov 3 – 10
Guesthouse in South Bristol
4.98 out of 5 average rating, 342 reviewsWaterfront Guest House on the Maine Coast
Dec 15 – 22
Guest suite in South Portland
5.0 out of 5 average rating, 675 reviewsOceanfront with amazing views and private entrance
Sep 15 – 22
Apartment in Portland
4.98 out of 5 average rating, 292 reviewsLight-Filled Spacious Apartment in Ideal Location
May 2 – 9
Apartment in Portland
4.85 out of 5 average rating, 157 reviewsLovely studio in downtown Portland
Dec 5 – 12
Private Portland vacation rentals
Guest suite in Freeport
4.96 out of 5 average rating, 114 reviewsSolar Suite surrounded by Nature
Oct 27 – Nov 3
Cabin in Lovell
4.98 out of 5 average rating, 246 reviewsSecluded, cozy cabin nestled in the Maine woods
Sep 14 – 21
Apartment in Gorham
4.96 out of 5 average rating, 194 reviewsCozy Private 1 Bedroom Apartment - Gorham Village
Apr 17 – 24
Apartment in Arundel
4.91 out of 5 average rating, 125 reviewsGinger Hilltop
Nov 3 – 10
Guesthouse in Windham
5.0 out of 5 average rating, 214 reviewsCottage on Black Brook Preserve
May 30 – Jun 6
Cottage in Scarborough
4.85 out of 5 average rating, 279 reviewsCharming beach cottage
Apr 11 – 18
Apartment in Westbrook
4.79 out of 5 average rating, 121 reviewsStudio Apt In Walkable Distance to Restaurants
Apr 19 – 26
Guest suite in Scarborough
4.98 out of 5 average rating, 138 reviewsBeautiful, private apartment!! Great location!
Feb 11 – 18
Apartment in Portland
4.93 out of 5 average rating, 596 reviewsExtraordinary Architectural Masterpiece Downtown
Mar 16 – 23
Apartment in Portland
4.99 out of 5 average rating, 300 reviewsQuiet West End Retreat - parking - 100% Non Smoker
Oct 24 – 31
Home in Portland
4.95 out of 5 average rating, 291 reviewsExplore Portland from a 18th-Century Victorian
Mar 22 – 29
Apartment in Portland
4.78 out of 5 average rating, 317 reviewsThe Royal Exotic Portland Downtown
Dec 12 – 19
Portland house rentals
Home in Falmouth
4.86 out of 5 average rating, 173 reviewsAmazing Bay View Home with Hot Tub
Dec 3 – 10
Home in Lebanon
4.96 out of 5 average rating, 158 reviewsTranquility, Relaxation, Family, Romance
Oct 22 – 29
Home in Portland
4.96 out of 5 average rating, 128 reviewsQuiet Comfy Victorian Escape
Nov 23 – 30
Home in Hollis
4.98 out of 5 average rating, 353 reviewsBirch Ledge Guesthouse--Four Season Maine Getaway
Sep 16 – 23
Home in Edgecomb
4.99 out of 5 average rating, 117 reviewsCozy Lodge Meets Mid Century Hideaway
Apr 22 – 29
Home in Lewiston
4.98 out of 5 average rating, 133 reviewsClean and comfortable home
Apr 30 – May 7
Home in Portland
4.98 out of 5 average rating, 308 reviews3 bedroom house in the heart of Portland
Nov 3 – 10
Home in Acton
4.98 out of 5 average rating, 117 reviewsThe ZEN welcomes you, your home away from home.
Aug 22 – 29
Home in Gorham
4.99 out of 5 average rating, 138 reviewsBeautiful Home In Gorham Maine
Jul 15 – 22
Home in Oxford
5.0 out of 5 average rating, 178 reviewsThe Modern Lakehouse
Nov 2 – 9
Home in Westbrook
4.88 out of 5 average rating, 439 reviewsReno Barn w/ a lot of Charm! Breweries & Airport
Mar 6 – 13
Home in Freeport
4.85 out of 5 average rating, 249 reviewsHome On Pond in Woods - Guest Suite
Sep 15 – 22
Quick stats about vacation rentals in Portland
Total rentals | 1.5K properties |
---|---|
Rentals with dedicated workspaces | 770 properties have a dedicated workspace |
Rentals with a pool | 50 properties have a pool |
Pet-friendly rentals | 390 properties allow pets |
Family-friendly rentals | 780 properties are a good fit for families |
Total number of reviews | 151K reviews |
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 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.
Where should I stay in Portland?
Make yourself at home in Portland by choosing from our most frequently booked neighborhoods. We have over 1,410 vacation rentals in Downtown Portland, over 1,410 vacation rentals in Waterfront District, and over 1,040 vacation rentals in Peaks Island.
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 120 condo rentals to over 370 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Are there vacation rentals with a dedicated workspace in Portland?
Yes! Work meets play with ease at over 770 vacation rentals in Portland featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Portland?
Four-legged friends are welcome in Portland. Choose from more than 390 vacation rentals for guests traveling with pets.
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