We found 168 holiday rentals — enter your dates for availability
Discover a selection of 46 homes, 10 apartments and other holiday rentals in Eastport that are perfect for your trip. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as parking and air conditioning. No matter what you're looking for, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts – Eastport
Showing deals for:19 Feb - 26 Feb
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Find out more about Eastport
Why visit Eastport
Charming waterfront: Eastport boasts a picturesque marina and scenic waterfront perfect for leisurely strolls.
Historic architecture: Explore the area’s quaint streets lined with charming historic houses that reflect its rich past.
Outdoor spaces: Enjoy family-friendly parks and outdoor areas ideal for relaxation and recreation.
Culinary delights: Indulge in fresh local seafood at various eateries, showcasing the best of Maryland's cuisine.
Vibrant community spirit: Experience the friendly atmosphere and community events that highlight Eastport's unique charm.
Popular types of accommodation around Eastport
Planning a getaway to Eastport, Annapolis, Maryland? This charming neighbourhood offers a delightful array of houses, cottages, and apartments for your stay. Explore the scenic waterfront, indulge in local seafood, or stroll along the picturesque streets lined with historic architecture. With a vibrant arts scene and easy access to the Annapolis Harbour, Eastport promises an unforgettable experience. Discover the perfect Eastport vacation rental to immerse yourself in this captivating locale.
Houses: The top choice for holidaymakers in Eastport, offering spacious and comfortable living tailored for families or groups.
Cottages: Quaint and charming, these cosy retreats provide a perfect blend of rustic charm and modern amenities.
Apartments: Ideal for those seeking convenience, these self-contained units offer a city vibe with easy access to local attractions.
Condos: Stylish and contemporary, condos in Eastport provide a fantastic base with community facilities.
Villas: Luxurious and expansive, villas offer an upscale experience, perfect for a lavish getaway.**
Top attractions in and around Eastport
Eastport, Annapolis, Maryland, is a delightful neighbourhood perfect for outdoor and family-themed vacations. Visitors can explore scenic urban parks, enjoy the vibrant marina, and discover charming historic houses. With a range of cultural experiences and activities suitable for all ages, Eastport invites tourists to immerse themselves in its unique coastal atmosphere, making it an ideal destination for those seeking both relaxation and adventure.
Annapolis Maritime Museum: Nestled in Eastport, this museum showcases the rich maritime heritage of the region, offering engaging exhibits and programmes that celebrate local culture and the importance of the Chesapeake Bay.
Maryland State House: A short stroll from Eastport, this historic building is the oldest state capitol still in continuous legislative use, featuring stunning architecture and a fascinating history of Maryland's governance.
Sandy Point State Park: Located 8km from Eastport, this expansive park boasts beautiful beaches, scenic views, and opportunities for outdoor adventures like hiking, picnicking, and birdwatching.
Things to do recommended for couples
For a romantic getaway in Eastport, take a sunset sail on the Chesapeake Bay, relishing the stunning views. Enjoy a candlelit dinner at a waterfront restaurant, followed by a leisurely stroll along the charming streets filled with quaint boutiques and art galleries. It’s the perfect couple's retreat.
Things to do recommended for families
Families can explore the scenic waterfront at Eastport, enjoy a day at Sandy Point State Park with its sandy beaches and picnic areas, or take a delightful boat tour around the historic Annapolis harbour for a unique view of the city.
Things to do recommended for groups
Groups visiting Eastport can enjoy a delightful seafood tasting tour at local eateries, followed by a scenic sailing trip on the Chesapeake Bay. Don’t miss exploring the vibrant arts scene and historic sites that make this charming area truly unique.
*Distances are measured in a straight line; actual driving distances may vary depending on the route.
What do I need to keep in mind when booking a vacation around Eastport
If you're travelling with a group, as a family, bringing your pets along, or seeking longer stays, ensure you filter your options according to your key priorities. Here are some helpful booking tips for using Vrbo.
Traveling to Eastport with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily apply filters for all of these options, and more, on Vrbo.
Traveling to Eastport with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
Taking your pets with you to Eastport: For many, a family holiday isn’t truly complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
Planning for a long term stay visiting Eastport: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.
Where to stay near Eastport
Eastport, a charming neighbourhood in Annapolis, Maryland, offers a delightful blend of history and waterfront beauty. Visitors can stroll along the picturesque streets, enjoying the vibrant atmosphere filled with friendly locals. The area is perfect for family outings, with parks and outdoor spaces to explore. A short walk will take you to the bustling Downtown Annapolis, where you can experience local shops and eateries, all while soaking in Eastport's unique charm and community spirit.
Annapolis: Annapolis, the capital of Maryland, is a vibrant city that beautifully merges history with modern living. Eastport is nestled within its boundaries, providing easy access to an array of attractions. Visitors flock to Annapolis for its family-friendly atmosphere, outdoor activities, and bustling city life. You can explore educational institutions, indulge in shopping at local centres, or take a scenic stroll along the bay and beach areas. Key landmarks include the United States Naval Academy and the picturesque waterfront, offering a delightful blend of culture and recreation.
Historic District: The Historic District, located a mere 1km from Eastport, is a neighbourhood steeped in charm and heritage. It draws families and outdoor enthusiasts alike, thanks to its rich history and lively city vibe. Visitors can enjoy various educational opportunities and shop in quaint areas and centres. The district is home to notable landmarks, including the historic academy and the bustling tourist precinct. Enjoy the scenic views at the dock port, where you can watch boats glide along the water, making it a perfect spot for relaxation.
Murray Hill: Murray Hill, situated 2km from Eastport, is a picturesque neighbourhood that offers stunning scenery and a welcoming atmosphere. Ideal for families and outdoor lovers, this area boasts beautiful parks and green spaces, perfect for leisurely strolls and picnics. The local educational facilities and shopping options provide convenience for visitors. Notable attractions include the academy and the scenic bay, along with the nearby tourist precinct, where you can immerse yourself in the local culture and enjoy a variety of dining experiences.
Best time to go to Eastport
If you're planning a trip to Eastport, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like February and November to December tend to have fewer bookings and better deals.
Calendar Month
Temperature
Precipitation
Cloudiness
Occupancy
Pricing
January
35.6°F (2.0°C)
Light Rain
Mostly Sunny
Average
Slightly Low
February
37.9°F (3.3°C)
Light Rain
Mostly Sunny
Slightly Low
Slightly Low
March
44.6°F (7.0°C)
Light Rain
Mostly Sunny
Average
Slightly Low
April
55.0°F (12.8°C)
Light Rain
Mostly Sunny
Slightly High
Average
May
64.2°F (17.9°C)
Light Rain
Mostly Sunny
Average
Average
June
73.0°F (22.8°C)
Light Rain
Mostly Sunny
Slightly High
Slightly High
July
78.4°F (25.8°C)
Light Rain
Mostly Sunny
Slightly High
Slightly High
August
76.8°F (24.9°C)
Light Rain
Mostly Sunny
Average
Slightly High
September
70.7°F (21.5°C)
Light Rain
Mostly Sunny
Average
Average
October
60.4°F (15.8°C)
Light Rain
Mostly Sunny
Average
Average
November
48.7°F (9.3°C)
Light Rain
Mostly Sunny
Slightly Low
Average
December
41.5°F (5.3°C)
Light Rain
Mostly Sunny
Slightly Low
Average
Booking with Vrbo is a breeze
Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.
Vrbo Trips: Effortless planning
Vrbo's innovative Trip Board offers you a convenient platform to plan new journeys, pick up where you last stopped, or manage and arrange your travel plans. You can easily access your previously saved and booked properties under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.
**Based on Vrbo properties bookings.
Frequently Asked Questions
How much does it cost to rent a holiday home in Eastport?
Prices for holiday rentals in Eastport vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Eastport to more spacious homes. To get the best value, book early and take advantage of Vrbo’s free rewards program.
Are there any discounts for Eastport holiday house rentals?
You can find great discounts on house rentals in Eastport on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Eastport holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Eastport with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the “Parking available” filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in Eastport?
A long-stay holiday rental in Eastport is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Eastport for a holiday rental?
The peak travel season in Eastport typically runs from May to July, with July being the most popular month for visitors. This lively period attracts those eager to enjoy the vibrant waterfront, indulge in fresh seafood, and explore the charming streets filled with unique shops and galleries. The warm temperatures, often reaching the mid-20s Celsius, create a friendly space for outdoor activities, making it superb for sailing, kayaking, or simply relaxing by the bay.
If you prefer a more tranquil experience, consider visiting in December. This month, while quieter, offers a unique charm, especially with the festive atmosphere as Eastport adorns itself in holiday decorations. You can enjoy peaceful strolls by the water and perhaps catch some local holiday events without the hustle and bustle of peak season.
Ultimately, the best time to visit Eastport for a holiday rental depends on your preferences.
How early should I book a Eastport holiday rental?
Book your Eastport holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.
*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Eastport, Maryland, United States of America?
In Eastport, Maryland, visitors can enjoy a charming waterfront atmosphere with a variety of attractions. The Eastport Historic District is renowned for its picturesque streets lined with colourful houses and boutique shops, providing a delightful environment for a leisurely stroll. Nearby, the Annapolis Maritime Museum offers insights into the region's rich maritime heritage and features exhibits focused on the Chesapeake Bay.
For those who appreciate outdoor activities, the area boasts beautiful parks such as Broadneck Park, which offers walking trails and sports facilities. Additionally, the scenic waterfront along Spa Creek provides opportunities for kayaking and paddleboarding, allowing visitors to immerse themselves in the natural beauty of the surroundings.
Can I change or cancel my Eastport home rental booking on Vrbo?
To find Eastport holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.
Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Eastport holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo’s mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you’re protected and that if something goes wrong, we will do our best to make it right as applicable.
If a significant issue arises that your host can’t resolve, we’ll help you address it, find a similar property, or get your reservation refunded if applicable. That’s our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.
Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.