Vacation Homes in Eastport, Annapolis: House Rentals & More

Discover a selection of 37 homes, 11 apartments, and other vacation rentals in Eastport that are perfect for your trip. Vacation homes provide the amenities you need and want for your family, friends, or furry companion, such as air conditioning and a pool. At the end of the day, you'll be able to choose a rental that has what everyone needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Eastport

Showing deals for:Aug 22 - Aug 29

Wonderful

(34 reviews)

Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis

Annapolis, MD

8% off

per night

All fees included

Exceptional

(7 reviews)

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

Annapolis, MD

9% off

per night

All fees included

Exceptional

(52 reviews)

Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA

Annapolis, MD

9% off

per night

All fees included

Front of the house, facing quiet and charming Prince George Street

Exceptional

(22 reviews)

Historic & sunny home w/ Fireplace steps from USNA & Downtown Annapolis

Annapolis, MD

17% off

per night

All fees included

Exceptional

(107 reviews)

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Annapolis, MD

9% off

per night

All fees included

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Eastport

Tastefully decorated fully-equipped Eastport Annapolis house with water views

Sleeps 6 · 3 bedrooms · 2+ bathrooms

Top rated rentals - Eastport

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Frequently asked questions

What is the most popular type of vacation rental accommodation in Eastport?

Condos are the most popular style of vacation rental in Eastport, according to our data. Even if you have something different in mind, Vrbo has vacation homes in a variety of sizes and shapes. Look over our options to find your ideal match.

How much does it cost to rent a vacation rental in Eastport?

Property type, length of stay and season are some factors that can affect the price of a vacation home. Simply click on your dates of travel to find your perfect escape. From homey country cottages to sprawling luxury villas, all Vrbo vacation rentals provide incredible value.

How much does it cost to rent a beach house in Eastport?

When you travel and the style and size of the property will determine the cost of your beachside stay. Enter your Eastport travel dates to view your options on Vrbo. Did someone just say “hot tub”? Use the filters to select the amenities and features you need.

Are there pet-friendly vacation rentals in Eastport?

Yes. You’ll have a choice of 50 vacation homes that allow pets in Eastport on Vrbo. Our furry best friends also need a break, so simply use our search function for pet-friendly vacation rentals to book a place where your doggie can join the fun.

Can I rent a house with a pool in Eastport?

Add a whole other level of fun to your adventure by booking your crew into one of the 13 houses with a private pool in Eastport. Use our search filter to find the kind of property you want on Vrbo, and then spend lazy days playing and splashing in a swimming pool that’s all yours.

What are popular rental amenities in Eastport?

When it comes to rental amenities that people are looking for in Eastport, a fireplace, a swimming pool and a barbecue grill rank highest. With Vrbo vacation rentals, you’ll discover options to match your style and taste, whether you’re vacationing with friends, family or even pets.

Are there large group vacation rentals in Eastport?

There are seven vacation homes in Eastport that can accommodate 10 or more people. Whether you’re organizing a vacation with extended family or some kind of special event, there’s plenty of room to get your group together under the same roof.

Are there vacation rentals in Eastport that welcome kids?

With 49 family-friendly vacation rentals available in Eastport, now is a great time to introduce the kiddos to the excitement of travel. Check our “Properties good for families” filter to search for stays packed with amenities ideal for vacationing families, like kitchens, pools, entertainment areas and bunk beds.

What are the top attractions for families in Eastport?

If you’re in the mood for something entertaining for the family close to the heart of Eastport, make your way to Annapolis Maritime Museum.

Are there one-bedroom vacation rentals in Eastport?

There are 15 one-bedroom properties in Eastport to select from. A one-bedroom vacation rental is an excellent option if it’s just you and your partner or if you’re traveling alone. Toss in more space, privacy and convenience than a standard hotel, and you’ll be sure to have a memorable trip.

Can I find two-bedroom vacation rentals in Eastport?

Eastport has 11 two-bedroom vacation properties for you to select from. Go for a vacation home with all the comfort and privacy you need at a price you’ll love on Vrbo.

Are there vacation rentals with WiFi in Eastport?

Whether you’d like to keep up to date with the news, look over emails or surf social networks, there are 24 vacation homes with WiFi in Eastport. Check the “WiFi” box when searching on Vrbo and stay connected on your getaway.

How can I find vacation rentals with air conditioning in Eastport?

Eastport has 49 vacation rentals where you can wind down in air-conditioned comfort. To find a stay on Vrbo that comes with this amenity, enter your dates of travel and use the handy filter tool to select the “air conditioning” box.

How old do you have to be to rent a vacation rental in Eastport?

The minimum age requirements can vary across properties on Vrbo, so double-check the rules of the vacation home in Eastport you’re considering. But normally, it’s 16, 18 or 21.

How long can I rent a vacation rental in Eastport for?

How long you can rent a vacation rental in Eastport varies according to the property. Just enter your chosen travel dates to see a list of options offering extended stays. With tons of features such as laundries and air conditioning, as well as some offering discounted weekly or monthly prices, you’re sure to get somewhere just right to call your home away from home in Eastport.

Does Vrbo offer discounts for vacation homes in Eastport?

Whether you’re after one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to find some great deals and discounts on Vrbo. From weekend trips to extended vacations, we’ve got the ideal space for your next Eastport escape.