Discover Your Perfect East Bayside Vacation Homes

East Bayside Luxury Rentals

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9.2 (5 Reviews)
Apartment
Back Cove Views
  • Air Conditioner
  • Security/Safety
  • Fireplace/Heating
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Why Choose Rent By Owner for your East Bayside Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for East Bayside Vacation Rentals

Where are the best neighborhoods to stay in East Bayside?

Discover the vibrant atmosphere of East Bayside in Portland, Maine, where your choice of neighborhood can greatly enhance your stay. This area offers a lively community feel combined with convenient access to local amenities, making it an ideal location for your vacation rental. Whether you're seeking a trendy, arts-oriented vibe or a peaceful retreat close to the waterfront, East Bayside provides a diverse range of options to suit your travel preferences. Choosing this neighborhood ensures you experience the authentic charm of Portland while enjoying the comfort and reliability of trusted accommodations.

Downtown Portland

Located just a short distance from East Bayside, this central neighborhood offers convenient access to the city's vibrant business and cultural scenes, making it an ideal base for exploring Portland.

View 143+ Rentals in Downtown Portland

Old Port

Famous for its historic charm and lively waterfront, this area provides a scenic setting for discovering Portland’s rich maritime heritage and enjoying culinary delights nearby.

View 57+ Rentals in Old Port

West Bayside

This emerging neighborhood offers a mix of modern amenities and local character, perfect for those seeking a trendy yet comfortable stay close to East Bayside.

View 589+ Rentals in West Bayside

Munjoy Hill

Perched atop a hill with panoramic views of the city and harbor, this neighborhood provides a peaceful retreat while still being near the lively attractions here.

View 70+ Rentals in Munjoy Hill

East End

Known for its historic architecture and scenic vistas, this district offers a charming environment to experience the region’s natural beauty and cultural sites.

View 70+ Rentals in East End

Oakdale

This residential neighborhood features tree-lined streets and parks, providing a quiet atmosphere that’s well-suited for relaxing stays within reach of downtown activities.

View 607+ Rentals in Oakdale

Back Cove

Surrounding a picturesque inlet, this neighborhood allows you to enjoy outdoor recreation and serene views while remaining conveniently close to the city’s core.

View 563+ Rentals in Back Cove

Best Times to Visit East Bayside

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here allows you to enjoy the region’s vibrant atmosphere and scenic beauty at its best, ensuring a memorable stay in your ideal vacation rental.

Peak Season Highlights

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Summer (June to August)

During the summer months, you can enjoy warm weather and longer daylight hours, perfect for exploring this vibrant coastal region. It's the peak time for visitors seeking outdoor activities and the lively atmosphere in Portland.

Average Temperature Daytime: around 75-85°F - Nighttime: approximately 60-65°F
autumn
Early Fall (September to October)

This is a popular season for experiencing the region's stunning fall foliage, attracting travelers looking for scenic drives and outdoor adventures amidst colorful landscapes. The area's mild climate makes it ideal for enjoying all it has to offer.

Average Temperature Daytime: about 65-75°F - Nighttime: around 50-55°F

Off-Season Highlights

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Late Fall to Early Winter (November to December)

As the region transitions into winter, fewer visitors find their way here, offering a quieter experience while still being close to holiday festivities. It's the perfect time to enjoy cozy accommodations and peaceful sightseeing.

Average Temperature Daytime: roughly 40-50°F - Nighttime: about 30-40°F
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Winter (January to February)

The cold winter months see the fewest tourists, providing an opportunity for serene exploration and intimate experiences in the area. If you prefer a tranquil escape, this season offers a calm retreat with less competition for vacation rentals.

Average Temperature Daytime: around 30-40°F - Nighttime: near 20-30°F

Weekly Weather Forecast for East Bayside

How to Book Your East Bayside Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in East Bayside

More Top-Rated Vacation Rentals in East Bayside Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor patio or deck perfect for relaxing after exploring the area.
  • Take advantage of beautifully landscaped gardens or yard spaces to unwind outdoors.
  • Make the most of shared or private outdoor dining areas for meals al fresco.
  • Utilize convenient parking areas, often available on-site for easy access during your stay.
  • Access nearby walking trails or scenic viewpoints that showcase the region’s natural beauty.
  • Have use of outdoor grills or barbecue stations to enjoy cookouts in the fresh air.
  • Benefit from proximity to waterfronts or harbor views that are common in this destination.

Top Attractions Around East Bayside

What attractions are nearby?

In this vibrant part of Portland, Maine, you can enjoy a variety of outdoor activities, explore local markets, or indulge in the region’s renowned culinary scene, all conveniently close to your East Bayside vacation rental.

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Family Activities

  • Portland Observatory Tour: Discover the historic Portland Observatory, offering panoramic views of the waterfront that provide an engaging experience for families exploring this part of Maine.
  • Children’s Museum & Theatre of Maine: Engage your kids with interactive exhibits and live performances designed to entertain and educate during your stay in the region.
  • Eastern Promenade Trail: Enjoy a family-friendly walk or bike ride along this scenic trail that offers breathtaking views of Casco Bay and connects outdoor activities with natural beauty.
  • Casco Bay Ferry Rides: Take a relaxing boat tour around Casco Bay to explore nearby islands and marine wildlife, making unforgettable memories here for all ages.
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Adult Activities

  • Portland Museum of Art: Explore a diverse collection of American, European, and contemporary artworks to immerse yourself in local culture and creativity.
  • Bayside Trail: Enjoy scenic walking or biking along this picturesque trail that offers stunning views of the waterfront and access to the vibrant neighborhood.
  • Casco Bay Cruises: Embark on a boat cruise to experience the region’s beautiful islands and coastline from a unique perspective on the water.
  • Eastern Promenade Park: Relax or take part in outdoor activities at this popular park with panoramic views of Casco Bay and nearby islands.

Other Places to Stay in East Bayside, ME

Eastern Cemetery
Eastern Cemetery Vacation Rentals
Maine Jewish Museum
Maine Jewish Museum Vacation Rentals
Cathedral of the Immaculate Conception
Cathedral of the Immaculate Conception Vacation Rentals
More Places to Stay Near East Bayside

East Bayside Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the Local Food Scene: Take advantage of the area's renowned culinary offerings by visiting local eateries and markets to experience authentic flavors unique to here.
  • Discover Neighborhood Gems: Wander through the vibrant streets to find hidden spots and community hotspots that capture the true essence of this destination.
  • Plan Outdoor Adventures: Make the most of the region's scenic parks, waterfronts, or trails that showcase the natural beauty surrounding here’s vacation rentals.
  • Utilize Local Transportation: Use convenient transit options or bike rentals to explore the area efficiently and immerse yourself in the local vibe without hassle.

Transportation Options

  • Public Transit (METRO Bus): You can easily navigate the area using the METRO bus system, which offers convenient routes connecting to key destinations throughout Portland.
  • Bike Rentals: Biking is a popular way to explore here, with bike rental shops providing accessible options for enjoying the scenic streets and waterfront views.
  • Taxi Services: Reliable taxi services are available to get you around comfortably and efficiently as you explore this vibrant neighborhood.
  • Car Rental Agencies: Renting a car provides flexibility to visit nearby attractions and venture further into the region at your own pace.

Local Customs Options

  • Traditional Lobster Boil: Participating in a local lobster boil is a cherished custom here, offering a taste of authentic regional cuisine right at your vacation rental.
  • Summer Music Festivals: The area's vibrant summer music festivals celebrate Maine's rich musical heritage and are a popular way to enjoy community spirit during your stay.
  • Fishing Culture: Engaging in or observing the region’s fishing traditions provides insight into the maritime roots that define this destination's identity.
  • Local Artisan Markets: Visiting artisan markets offers an opportunity to experience the craftsmanship and creative spirit that thrive in this area.

East Bayside Vacation Rental Frequently Asked Questions

1. What are the top vacation rentals in East Bayside?

There are a lot of options in East Bayside. If you plan on staying in the East Bayside area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in East Bayside:

2. Which vacation homes in East Bayside are best for families?

If you are looking for a family-friendly vacation home in East Bayside, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in East Bayside:

3. How many Rentbyowner vacation rentals are available in East Bayside?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 36 in the East Bayside area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in East Bayside. 

4. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary by property. To ensure you understand the specific terms, please review the cancellation details listed with each property or contact the owner directly before booking.

5. How do I find the most suitable vacation rental in East Bayside, Portland, Maine?

You can filter your search based on amenities, price range, and guest capacity to find a vacation rental that best meets your needs. Reading detailed descriptions and reviews will also help you make an informed decision.

6. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning, service charges, or taxes are typically outlined in the listing details. Be sure to review these charges before confirming your reservation to avoid surprises.

7. Can I communicate directly with the property owner or manager before booking?

Yes, most listings allow you to message the owner or property manager to ask questions about the property, availability, or other concerns prior to finalizing your reservation.

8. What should I do if I need to modify or cancel my booking at the last minute?

To modify or cancel your reservation, consult the specific property's cancellation policy and contact the owner or management team promptly. Details are usually available in your booking confirmation or the listing description.