
Holiday houses in Portland
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Top-rated holiday rentals in Portland
Guests agree: these stays are highly rated for location, cleanliness and more.

Large Loft—Walk to Breweries— Coffee Bar—King Bed
Located on outer Forest Avenue in Portland, Maine, Forest Loft is an impressive, custom built, 1 bedroom / 2 bathroom apartment with vaulted ceilings and plenty of space. Due to its close proximity to the breweries on Industrial Way, Forest Loft commonly welcomes craft beer fans from all over the world. Enjoy the proximity to popular amenities while only a short ride from downtown Portland. MAINE'S TOP HOST OF 2022 https://news.airbnb.com/celebrating-our-top-new-hosts-in-each-us-state-for-2022

Cozy SoPo Condo
Welcome to this cozy one-bedroom apartment in Ferry Village, South Portland, Maine. This charming neighborhood is located just across the Casco Bay from Portland, and it's the perfect place to relax and admire the natural beauty of Maine. Enjoy a tour of our gardens and relax on the string light lit patio. The apartment is located on a quiet street, less than a mile walk from Willard Beach. Take a walk on the Greenway to Bug Light park or towards Knightville for some food and drink options.

RETRO BnB in the Heart of East End Portland
Retro BnB in The Heart of Portland's East End offers a combination of 70's mod charm with a vibrant comfortable style. Sunny, first floor back apartment with private entrance, one hybrid coil/thermarest queen bed overlooking yard with lovely perennial garden, bathroom with central, well appointed kitchen/dining room. This space is perfect for one couples looking for a cozy home base hideaway. A short walk to gourmet restaurants, cafes, East End beach and all Portland peninsula has to offer!

Old Port Penthouse Suite - Amazing Harbor Views
2023 City of Portland Registration #20182242-ST 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.

Luxury One Bedroom Loft in Portland’s Old Port
Immerse yourself in the culture of the Old Port at your luxury loft. A top choice for travelers, The Docent's Collection was most recently awarded Condé Nast Readers' Choice (2025) and Tripadvisor Travelers' Choice (2025). Enjoy this spacious open-concept floor plan featuring a full-sized kitchen and bedrooms with soft luxurious linens and cozy pillows for your comfort. Admire the tapestry of a curated collection of local artists and enjoy five-star service from our local hospitality team.

First Floor Portland Condo 3 Bed 2 Bath + Parking
A cozy getaway nestled in the Portland's Deering neighborhood. Enjoy the retreat that this beautiful light-filled condo has to offer, whilst being less than three miles from the Old Port! The space is bright, and open--filled with luxurious touches and local Maine art. With three bedrooms and two full bathrooms, there is plenty of space for a large group to stay. Also, enjoy three free parking spots during your stay. We can't wait to have you! 3.5 miles to Airport 3 miles to bus station

Higgins Beach *New* Beach Home & Private Offices
Custom designed contemporary at the beach. Perfect for a relaxing getaway, visiting family and friends or working remotely. Chef's kitchen w/ high end appliances, granite countertops, enclosed porch grill area. 3 bedrooms and 2 private offices Huge windows and amazing views from all of the rooms highlight the natural beauty of high tides, sun rises and sun sets. Wonderful beachfront walks and beautiful surroundings inside and out. Easy proximity to Portland's Old Port.

Winter Sale Now! 2 Bedroom in City w/ Laundry
Our annual winter sale happening now! Book before it ends! At our Airbnb we leave lots of towels for each guest. We do not ask our guests to clean the apartment. Organic coffee and high quality toiletries. We strive to provide a quality experience in our fully equipped two bedroom apartment within walking distance to restaurants, bars, Longfellow Square, the State Theater, the Portland Museum of Art and the Western Promenade. Washer and dryer in the apartment and Pack n play.

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!

Boutique 1BR Suite * East End* Bay View
Beautifully appointed boutique 1 BR suite with Maine-sourced wide-plank pine floors, luxury bathroom, and a serene view of Casco Bay. Bright, modern furnishings, local artwork, quality linens and towels, and local coffee. Shared patio with grill and firepit. A short walk to Eastern Prom and Old Port restaurants. Quiet owner-occupied building. Non-smoking, non-cooking space. Not suitable for infants/children. High-speed internet. No TV.

Downtown Historical Victorian 2 BR APT
The West End is one of Portland's most historical districts. The house is within walking distance of Long Fellow Square, and the Western Promenade. It is a great home base while exploring. From its rich history rooted in the Victorian era, to its parks and restaurants, Portland's West End is consistently ranked as a favorite local hotspot. New reno located on a popular street in a neighborhood filled with historic homes.

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.
Popular amenities for Portland holiday rentals
Stay near Portland's top sights
Other great holiday rentals in Portland

The Maine Frame | Modern A-Frame Cabin in Freeport

Bright & Sunny Apartment with Patio

Ocean Paradise Sunrise/Sunset Peaks Portland

Lovely studio in downtown Portland

Sweet Home Near Food & Old Port

Amazing Views! Perfect Location. Loft style feel.

"Periwinkle" ~ a Charming Oceanfront Cottage

Bright and Minimalist Home!
When is the best time to visit Portland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $249 NZD | $241 NZD | $249 NZD | $283 NZD | $341 NZD | $402 NZD | $474 NZD | $482 NZD | $407 NZD | $381 NZD | $301 NZD | $281 NZD |
| 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.
Quick stats about holiday rentals in Portland

Total holiday rentals
Explore 1,600 holiday rentals in Portland

Nightly prices starting at
Portland holiday rentals start at $50 NZD per night before taxes and fees

Verified guest reviews
Over 194,630 verified reviews to help you choose

Family-friendly holiday rentals
860 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 460 rentals that welcome pets

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
820 properties have a dedicated workspace

Wi-Fi availability
1,570 of Portland holiday 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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