Vacation rentals in Portland
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Top-rated vacation rentals in Portland
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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.
Private Garden Retreat on Munjoy Hill
This well-appointed, new space is located on first floor of a modern, new home on Munjoy Hill - Portland’s most charming neighborhood. This convenient suite has a separate, private entrance with a private outdoor seating area. The location is perfect for walking - just minutes to excellent restaurants, coffee shops, gourmet market, Eastern Promenade, St. Lawrence Arts Center and Washington Avenue. Portland’s Old Port and bustling harbor is just a 10 - 15 minute walk down the Hill.
The Maine Frame | Modern A-Frame Cabin in Freeport
• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!
Mary J. Eastburn House--Mountain View Suite
City of Portland Reg. No. : STHR-002888-2021 Perched on a quiet street corner on Portland's Western Promenade, this historic residence enjoys what Longfellow called the "rarefied air of this little town by the sea," spectacular sunsets, and commanding views of the White Mountains. Built in 1891, the Mary J. Eastburn House now offers 3 private and exclusive guest suites for those who enjoy the grandeur of the past, updated with the luxuries and technology of the present.
Adorable getaway on the Eastern Promenade
Lovely third-floor apartment on the East End just steps from the glorious Eastern Promenade. Cozy and cute, this adorable spot resides in the neighborhood which boasts the best restaurants, breweries, and coffee shops in the city all within walking distance. On a quiet residential street, there is plenty of on-street parking. This apartment is on the 3rd floor of the house . **Please note that the last 9 steps leading up to the apartment are quite steep.
Central Arts District Studio with Free Parking
2026 City of Portland registration STHR 000854 Enjoy the quieter end of Oak Street in the heart of Portland's Arts District. Abundant dining, shopping, galleries and museums are steps from this home-away-from-home studio apartment. This is a perfect space for couples, solo adventurers and business travelers. Easily walk to everything the peninsula has to offer from this centrally located studio apartment! Free off-street parking for one car available.
Garrison Cove Studio
Rare, Portland waterfront studio located in the heart of the historic Stroudwater neighborhood, awaits one or two guests looking for an urban hideaway. The studio occupies a 150 year old post and beam barn situated on the banks of the Stroudwater and Fore Rivers. Enjoy morning coffee on the river swing, meditate to the soothing sound of the nearby waterfall or linger over your favorite beverage in one of our comfy Adirondacks.
Charming 1 Bedroom Flat in the Heart of Portland
Welcome to our stunning 1-bedroom apartment located in the vibrant and historic West End neighborhood of Portland, Maine! Nestled in a charming and tree-lined street... As you enter, you'll be greeted by an inviting living area bathed in natural light, thanks to the large windows. Relax on the sofa, enjoying a cup of coffee from the nearby local roasters, and plan your day's adventures using the complimentary high-speed Wi-Fi.
Waterfront Two Master Suite Penthouse with Rooftop
CO2024-01785 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.
Beautiful West End studio, hot tub, free parking
Charming, comfortable, well-appointed studio, 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.
Fore River Suite
A rich and restful oasis for one or two traveling through or with Portland as destination. Our second story suite features views of a waterfall and the tidal river on Casco Bay. Unwind with a glass of wine and sketchbook or simply enjoy the birdlife while planning your stay in Maine. *Returning guests: this is the same suite you know and love, just reconfigured and updated for maximum enjoyment!*
Cityscape Loft. Central Location
Beautiful, spacious, 1 bedroom heart of the city urban apartment featuring 12 foot ceilings, high end kitchen and bath, refinished hardwood floors in a location that is absolutely terrific. Amazing City Scape Views! This is a second floor apartment. Expect stairs. Sleeps 3 : 1 Bedroom with queen bed and there is a Futon in small auxiliary room.
Popular amenities for Portland vacation rentals
Stay near Portland's top sights
Portland oceanfront vacation rentals
Alluring 1 Bedroom cabin just 50ft from beach no.6
Luxury Beach Front Condo! Prime Location!
Seaside Serenity: 4-BR Oceanfront Escape!
Oceanfront Condo with Awesome Views
Deja Blue~Guesthouse-Maine’s Best Oceanfront view!
Beautiful Kettle Cove Apt Steps to Beaches
Tiny Cottage Across The Street From Beach
LUX Designer Private Waterfront Hot Tub - Secluded
Private Portland vacation rentals
Portland + Cape Elizabeth + Beaches + luxurious!
Charming West End Studio Apartment
Sunshine Kitty Retreat - Private Suite
The Copper Fox Treehouse
Renovated Exchange St. Loft w/Free Parking
Cozy SoPo Condo
Port City Studio Loft
Cozy Rock Cabin #thewaylifeshouldbe
Portland house rentals
The LOTUS welcomes you, stay a while
East End Unit
Entire house w/king bed & parking near downtown!
Historic, pastoral home in charming Yarmouth, ME!
Adorable Beach House Across the Street From Beach!
comfy cozy house with yard and central location
East End Portland, Water Views
3 bedroom house in the heart of Portland
When is the best time to visit Portland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R 2,484 ZAR | R 2,452 ZAR | R 2,468 ZAR | R 2,779 ZAR | R 3,351 ZAR | R 3,956 ZAR | R 4,658 ZAR | R 4,740 ZAR | R 4,005 ZAR | R 3,743 ZAR | R 2,958 ZAR | R 2,762 ZAR |
| Avg. temp | -4°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 21°C | 16°C | 10°C | 4°C | -1°C |
Frequently Asked Questions
What are the best places to stay in Portland?
Explore the Old Port for historic brick streets and harbor views, or look to the West End for charming architecture and tree-lined avenues. Munjoy Hill is often recommended for its relaxed vibe and proximity to cafes and green spaces.
What are the best things to do in Portland with kids?
Families often explore the Children's Museum and Theatre of Maine, enjoy hands-on marine exhibits at the local science center, or picnic in one of the city’s waterfront parks. Lighthouse visits and ferry rides are also frequently suggested for all ages.
What are some of the best things to do in Portland?
Wander the Old Port’s cobblestone streets, explore art at the Portland Museum of Art, and sample locally rooted seafood at the city’s markets. The Eastern Promenade draws many for bay views and walking paths.
How is the weather in Portland?
Portland has chilly winters near 16–32°F (-9–0°C) with frequent snowfall, while summers are mild with highs around 80°F (26°C) and comfortable evenings. Spring and autumn are often cool and can bring rain, so packing layers is recommended.
What are the best places to visit in Portland?
Explore the Portland Head Light, wander the Old Port district, and take in displays at the Portland Museum of Art. The Eastern Promenade is also frequently suggested for its scenic bay views.
What are some hiking trails in Portland?
The Eastern Promenade has popular walking and biking trails overlooking Casco Bay, while Evergreen Cemetery’s woodland paths blend history and nature. Baxter Woods is also frequented for its shaded trails and birdwatching spots.
What are some family activities we can do in Portland?
Families often visit the Children's Museum and Theatre of Maine, explore hands-on science exhibits, or enjoy boat rides around the harbor. Public parks and seasonal outdoor concerts are also welcoming for all ages.
What are some of the best day trip ideas from Portland?
Consider exploring nearby islands in Casco Bay, relaxing on local beaches, or visiting state parks just outside the city. Lighthouses and small coastal towns around Portland frequently draw visitors seeking New England charm.
Are there any pet friendly accommodations available in Portland?
Pet-friendly vacation rentals can be found in many neighborhoods such as Munjoy Hill, West End, and areas near the waterfront. Parks and walking trails nearby make it convenient to explore with your pet.
What are some local tips for visiting Portland?
Dressing in layers is helpful due to changing coastal weather, and comfortable shoes are useful for walking the city’s brick streets. Weekdays or early mornings in the Old Port can feel quieter compared to weekends.
What is Portland known for?
Portland is known for its vibrant food scene, working waterfront, and historic architecture. The city’s lighthouses, arts community, and scenic harbor are also well recognized.
What are the best hidden gems to explore in Portland?
Discover Fort Gorges on an island in Casco Bay, browse artisan studios in the East End, or explore the quiet trails of Baxter Woods. Small galleries and local coffee shops around Munjoy Hill add to the city’s creative spirit.
What are the best foods to try in Portland?
Portland is known for fresh lobster rolls, clam chowder, and baked goods from local bakeries. Many enjoy tasting locally made cheeses, craft beers, and seasonal seafood at neighborhood markets and restaurants.
What should I bring for a trip to Portland?
Pack layers for shifting coastal weather, a rain jacket, and comfortable shoes for city walks. A warm hat and gloves are helpful from autumn through early spring, especially along the waterfront.
What is the nightlife in Portland like?
Portland has lively breweries, live music venues, and bars clustered in the Old Port and Arts District. Locally owned restaurants and performance spaces often set a welcoming evening scene.
What are the most popular events or festivals in Portland?
Portland has several well-known events, including local seafood celebrations, arts festivals in neighborhoods like the Old Port, and summer concerts on the waterfront. Holiday markets and music gatherings are frequently suggested, especially in warmer months. Community spaces often host seasonal programming.
Are there family friendly vacation rentals in Portland?
Many vacation rentals around Portland are suitable for families, with options in neighborhoods such as Munjoy Hill, the West End, and areas near local parks. Some homes feature multiple bedrooms and easy access to family attractions.
When is the best time to visit Portland?
Late spring through early fall is often recommended, with milder temperatures and active waterfront events. Fall foliage draws many visitors, while winter brings a quieter city atmosphere and seasonal festivities.
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.
What are the 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.
Quick stats about vacation rentals in Portland
Total vacation rentals
Explore 1,510 vacation rentals in Portland
Nightly prices starting at
Portland vacation rentals start at R 490 ZAR per night before taxes and fees
Verified guest reviews
Over 194,270 verified reviews to help you choose
Family-friendly vacation rentals
820 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 460 rentals that welcome pets
Vacation rentals with a pool
60 properties feature pools
Rentals with dedicated workspaces
720 properties have a dedicated workspace
Wi-Fi availability
1,480 of Portland vacation rentals include wi-fi access
Popular amenities for guests
Guests love Self check-in, Gym, and BBQ grill across Portland rentals
4.9 Average rating
Portland stays are highly rated by guests—averaging 4.9 out of 5!
Nearby attractions
Portland's top spots, include Peaks Island, Portland Museum of Art, and Crescent Beach State Park
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- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- York Harbor Beach
- Scarborough Beach
- Willard Beach
- Pemaquid Beach
- Short Sands Beach
- Popham Beach State Park
- East End Beach
- Pemaquid Point Lighthouse
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- King Pine Ski Area
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- Footbridge Beach
- Wolfe's Neck Woods State Park
- Conway Scenic Railroad
- Coastal Maine Botanical Gardens
- Crescent Beach State Park
- Funtown Splashtown USA
- Pleasant Mountain Ski Area
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