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Vacation rentals in Portland

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Top-rated vacation rentals in Portland

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

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Guest favorite
A private hot tub is surrounded by trees displaying vibrant autumn leaves, with a gentle stream flowing nearby. A fire pit sits beside the hot tub, offering a cozy gathering space. The cabin's exterior features wooden siding and large windows that invite natural light.
Tiny home in Norway
4.94 out of 5 average rating, 252 reviews

Glass Wall Waterfront Hot Tub Fireplace Tiny Home

Wake up to rushing waterfalls right outside your glass wall in this romantic waterfront tiny home in Norway, Maine! Private hot tub with river views, see-through gas fireplace, cozy raised queen bed overlooking the water, outdoor shower, hammocks, and direct access to hiking trails. Total privacy—no neighbors in sight. Modern kitchen, heated floors, fast WiFi, and thoughtful touches for couples or solo escapes. Romantic getaway near Sunday River skiing, golf & Maine adventures. Nature's oasis

Top guest favorite
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, 457 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 favorite
A spacious room is highlighted by large windows allowing natural light to fill the space. A bed with neutral bedding is positioned in the center, accompanied by a cozy armchair. A decorative rug adds warmth, while a small dining table is set beside an additional seating area.
Apartment in Downtown Portland
4.94 out of 5 average rating, 678 reviews

Historic Home in the West End. Private Parking.

With the Portland Museum of Art and the State Theater a 5 minute walk away, the Old Port just 15, this stunning apartment is just steps from the best eateries, arts & shopping the city has to offer. When you arrive, park your car in the private parking space and forget about it for a while! Built in 1835, this sunny and spacious second-floor apartment features 14-foot ceilings and original hardwood floors. A his and her bathroom is linked with a walk-through stone tiled shower.

Top guest favorite
The exterior of the A-frame cabin is showcased, featuring a unique wooden facade and metal roof. Sunlight streams through tall triangular windows, illuminating the surrounding wooded area. A gravel path leads to the entryway, enhancing the cabin's connection to nature.
Cabin in Freeport
5 out of 5 average rating, 128 reviews

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!

Guest favorite
The kitchen features modern stainless steel appliances and a spacious countertop with a light wood finish. Bright bay windows allow natural light to illuminate the area. A classic mantle adds a touch of historic charm, while overhead lighting enhances the contemporary design.
Apartment in Portland
4.94 out of 5 average rating, 144 reviews

The Margaret at Hawley Marie w/ Parking

Work + play in this modern retreat featuring original architecture with updated amenities. The sunny bay windows flood the living room with light, while the rest of the space benefits from lofty ceilings and an open floor plan. The en suite bathroom has new tiled floor and backsplash, while the kitchen features a beautiful white quartz countertop with stainless appliances. The convenient location and free, private parking is really the cherry on top of this beautiful space!

Guest favorite
Home in West End
4.89 out of 5 average rating, 111 reviews

Mary J. Eastburn House - Eastburn 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.

Top guest favorite
A modern lounge area is highlighted by large skylights, allowing abundant natural light to fill the space. A sleek, white sectional is complemented by colorful accent pillows and a patterned area rug. Exposed brick walls add an element of rustic charm, with scenic views of the harbor visible through the glass.
Apartment in Downtown Portland
4.96 out of 5 average rating, 312 reviews

Old Port Penthouse Suite - Amazing Harbor Views

CO2024-01992 Private Old Port Penthouse w/Breathtaking Views + Your Own Cupola. Quiet + Secure. Gorgeous contemporary suite full of light located right across from the working waterfront. Lobster and seafood off the boat is 100 meters from your front door. Watch the ferries to the islands from the cupola. Smell the salt air from your private deck. Welcome to Portland! Please note: animals (including assistance animals) not allowed due to owner's health.

Top guest favorite
Apartment in West End
4.97 out of 5 average rating, 468 reviews

Large Sunny Apartment Near Downtown/Arts District

(License Number: STHR-007574-2026) Quiet neighborhood, quick walk to downtown Portland. Short drive to beautiful sandy beaches. Newly furnished one bedroom on *3RD FLOOR*. Spacious rooms with mansard roof ceilings. Washer and dryer. Off street parking for one car. Clean and well maintained. We happily welcome guests, but if you or someone in your group has difficulty with stairs this *3rd floor* apartment may not be the best fit for you or your group.

Top guest favorite
An urban scene in Portland's Arts District features historic brick buildings with large windows. Colorful banners showcasing art design hang from lamp posts, while greenery from nearby trees adds a vibrant touch. The image captures the local atmosphere, highlighting the blend of culture and community.
Loft in Downtown Portland
4.94 out of 5 average rating, 745 reviews

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.

Top guest favorite
A charming exterior of a black post and beam barn is displayed featuring a natural wood door with metal hardware. A decorative star adorns the upper section of the barn, while a small metal bench sits on a gravel pathway beside the structure.
Barn in Portland
5 out of 5 average rating, 471 reviews

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.

Top guest favorite
An open space features a vaulted wooden ceiling with beams and skylights. A cozy seating area includes a brown sofa and a modern coffee table. A wood stove adds warmth, while a well-equipped kitchen with dark green cabinets is visible in the background.
Tiny home in Freeport
4.99 out of 5 average rating, 371 reviews

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!

Guest favorite
An open concept living space is presented, featuring a comfortable seating area with a gray sofa adorned with colorful cushions. A round coffee table is positioned at the center, while a small dining table is set with greenery. Plants are placed decoratively along the walls.
Condo in Downtown Portland
4.91 out of 5 average rating, 165 reviews

Modern Condo Portland's Historic Old Port District

Enjoy a stylish experience at this centrally-located loft. A converted factory building has been transformed into this chic and modern condo. Cobblestone streets, endless incredible dining and nightlife, boutiques, shops and historic architecture. A quintessential New England seacoast town and working waterfront.

Popular amenities for Portland vacation rentals

When is the best time to visit Portland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$31,797 GYDG$31,379 GYDG$31,588 GYDG$35,563 GYDG$42,885 GYDG$50,625 GYDG$59,620 GYDG$60,666 GYDG$51,252 GYDG$47,905 GYDG$37,864 GYDG$35,354 GYD
Avg. temp-4°C-3°C1°C7°C13°C18°C21°C21°C16°C10°C4°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 G$6,276 GYD 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, Crescent Beach State Park, and Portland Museum of Art

Destinations to explore

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