Eastport holiday lettings
We found 180 holiday rentals — enter your dates for availability
Discover a selection of 36 homes, 11 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:14 Nov - 21 Nov
Image gallery for Secluded Cozy Cottage in Historic Downtown
9.49.4 out of 10 rating
Exceptional
(13 reviews)
Secluded Cozy Cottage in Historic Downtown
Annapolis, MD
24% off
Price is £2,151
£2,151
£307 per night
includes taxes & fees
Image gallery for Eastport Charmer Summ
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Eastport Charmer Summ
Annapolis, MD
6% off
Price is £2,084
£2,084
£298 per night
includes taxes & fees
Image gallery for 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
1010 out of 10 rating
Exceptional
(114 reviews)
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Annapolis, MD
8% off
Price is £2,767
£2,767
£395 per night
includes taxes & fees
Image gallery for "The Flat" Apartment in Colonial Historic District, Annapolis.
1010 out of 10 rating
Exceptional
(5 reviews)
"The Flat" Apartment in Colonial Historic District, Annapolis.
Annapolis, MD
8% off
Price is £2,500
£2,500
£357 per night
includes taxes & fees
Image gallery for Nautical Feel to This Beautiful Eastport Home
9.89.8 out of 10 rating
Exceptional
(54 reviews)
Nautical Feel to This Beautiful Eastport Home
Annapolis, MD
16% off
Price is £3,043
£3,043
£435 per night
includes taxes & fees
Image gallery for Downtown Pinkney House w/Parking
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Downtown Pinkney House w/Parking
Annapolis, MD
7% off
Price is £2,324
£2,324
£332 per night
includes taxes & fees
Image gallery for Beautifully Renovated Historic District Home
1010 out of 10 rating
Exceptional
(69 reviews)
Beautifully Renovated Historic District Home
Annapolis, MD
20% off
Price is £3,017
£3,017
£431 per night
includes taxes & fees
Image gallery for Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport
1010 out of 10 rating
Exceptional
(50 reviews)
Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport
Annapolis, MD
11% off
Price is £1,296
£1,296
£185 per night
includes taxes & fees
Image gallery for “Athens of America,” Annapolis Apartment One B
8.88.8 out of 10 rating
Excellent
(14 reviews)
“Athens of America,” Annapolis Apartment One B
Annapolis, MD
7% off
Price is £1,187
£1,187
£170 per night
includes taxes & fees
Image gallery for Large Luxury Apartment In Downtown Annapolis
9.89.8 out of 10 rating
Exceptional
(35 reviews)
Large Luxury Apartment In Downtown Annapolis
Annapolis, MD
7% off
Price is £2,704
£2,704
£386 per night
includes taxes & fees
Image gallery for Location Location Location!!!50 Steps from Main Street and all of the action
9.89.8 out of 10 rating
Exceptional
(66 reviews)
Location Location Location!!!50 Steps from Main Street and all of the action
Annapolis, MD
7% off
Price is £2,191
£2,191
£313 per night
includes taxes & fees
Image gallery for Bay View Studio Apartment
1010 out of 10 rating
Exceptional
(49 reviews)
Bay View Studio Apartment
Annapolis, MD
15% off
Price is £1,528
£1,528
£218 per night
includes taxes & fees
Image gallery for All-stop. Rental Midships.
1010 out of 10 rating
Exceptional
(27 reviews)
All-stop. Rental Midships.
Annapolis, MD
8% off
Price is £3,126
£3,126
£447 per night
includes taxes & fees
Image gallery for ★ Midcentury Modern Getaway ★ Prime Location ★
1010 out of 10 rating
Exceptional
(33 reviews)
★ Midcentury Modern Getaway ★ Prime Location ★
Annapolis, MD
7% off
Price is £4,313
£4,313
£616 per night
includes taxes & fees
Image gallery for Charm & Style in this Renovated Eastport Home
9.89.8 out of 10 rating
Exceptional
(30 reviews)
Charm & Style in this Renovated Eastport Home
Annapolis, MD
16% off
Price is £3,019
£3,019
£431 per night
includes taxes & fees
Image gallery for “Athens of America,” Annapolis Apartment Two B
8.08.0 out of 10 rating
Very good
(9 reviews)
“Athens of America,” Annapolis Apartment Two B
Annapolis, MD
7% off
Price is £1,063
£1,063
£152 per night
includes taxes & fees
Image gallery for Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
1010 out of 10 rating
Exceptional
(120 reviews)
Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
Annapolis, MD
7% off
Price is £1,154
£1,154
£165 per night
includes taxes & fees
Image gallery for Charming 239-year-old former tavern 1 block to water & shops
1010 out of 10 rating
Exceptional
(10 reviews)
Charming 239-year-old former tavern 1 block to water & shops
Annapolis, MD
7% off
Price is £4,546
£4,546
£649 per night
includes taxes & fees
Image gallery for Beautiful Condo - Water View Near City Dock
9.69.6 out of 10 rating
Exceptional
(145 reviews)
Beautiful Condo - Water View Near City Dock
Annapolis, MD
14% off
Price is £920
£920
£131 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Cottage
Villa
Chalet
Find the best place to stay - Eastport
Charming apt in the heart of Eastport & Annapolis
Sleeps 8 · 3 bedrooms · 1 bathroom
Walkable Eastport Home with Firepit, Porch & Fenced-in Yard
Sleeps 7 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
50 reviews(50 reviews)
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
56 reviews(56 reviews)
Eastport Historic Firehouse with Parking, Dogs OK
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
70 reviews(70 reviews)
Perfect Eastport Location, walk everywhere, Annapolis
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Top rated rentals - Eastport
Amazing
1010 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
Perfect
Steven H.
Stayed Oct 2024
Fabulous! Loved our stay!
1010 out of 10
Exceptionalexceptional
114 reviews(114 reviews)
My husband, two boys and I stayed for nearly two weeks in August and had the BEST time. The house is super cute and very comfortable with all the things you need - including comfortable beds! Eastport is also super cute and has lots you can walk to. We loved Carrol's Creek restaurant, and we had one of the best meals/date nights ever at the Chart House with a stunning sunset and excellent food. The kids loved the pool (which is a nice big size!) and parasailing (we used Z Flight). Liz the owner is incredibly nice and helpful. Other stuff: towels for the pool are provided, there are two large TVs with Netflix, etc, cooking pans and stuff are all great. Take the water taxi into town at least once if you have kids, ours loved it. And if you have a car, go to Quiet Waters Park... there is a big playground and water activities there too. We totally recommend - 5 stars!
Audra W.
Stayed Aug 2023
Perfect Base
1010 out of 10
Exceptionalexceptional
43 reviews(43 reviews)
Well maintained clean property where everything has been provided that is required. Jenny and Patrick have good taste in this character property
and my thanks for an ideal base in pleasant area of Eastport.
maureen h.
Stayed Apr 2022
Comfortable and convenient house in Annapolis.
1010 out of 10
Exceptionalexceptional
160 reviews(160 reviews)
Spacious; well equipped; clean; walking distance to town, shops, bars, etc.
Paul G.
Stayed Oct 2019
Perfect home in charming neighborhood
1010 out of 10
Exceptionalexceptional
85 reviews(85 reviews)
This was the second time we have stayed at this delightful Eastport home, having also stayed here for a week this past summer. As before, my husband, toddler and I had a wonderful stay. The house so perfectly fits all of our needs. All of the appliances are top of the line and it is the perfect size for us. At one point we had all 3 grandparents spend the night in addition to us and it was still very comfortable. The house is half a block from a nice playground, where we spent a lot of time with our son - and he never tired of looking at the boats, which are right across the street (and the upstairs windows give a lovely view of the harbor). Eastport and downtown Annapolis were so beautifully decorated over the holiday season - it was a truly special time to be there. The house itself is lovely and the owners have done an exquisite job renovating it and decorating it with beautiful artwork throughout. Having expressed how much I liked the artwork, they even kindly sent through the details of some of their favorite local Annapolis galleries. The owners were extremely responsive and pleasant to deal with and even left us a bottle of prosecco in the refrigerator. There is no question that we will use this house again the next time we spend time in Annapolis. Truly perfect!
Jennifer B.
Stayed Dec 2017
Frequently asked questions
What is the most popular type of holiday rental in Eastport?
In Eastport, holiday houses are the most prevalent type of rental, with around 30 available in the area. These homes often provide spacious living environments, complete with multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation, making them ideal for families or groups. Additionally, there are several condos and apartments, which typically include modern amenities such as kitchen facilities and comfortable living areas, suiting those seeking a more compact stay. For a great experience, several cottages and houseboats can also be found, offering charming accommodations close to the waterfront and local attractions.
Are there any beach house rentals in Eastport?
In Eastport, Maryland, there are several beach house rentals available, providing a charming getaway near the waterfront. These properties are typically located in picturesque neighbourhoods, allowing guests easy access to the nearby Annapolis Harbour and the vibrant downtown area. Most beach houses come equipped with modern amenities such as fully stocked kitchens, spacious living areas, and outdoor decks or patios, superb for enjoying the pleasant Maryland weather. Many also feature multiple bedrooms, making them ideal for families or groups looking to spend quality time together while being close to local attractions like the Eastport Yacht Club and various waterfront dining options.
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?
July is the most popular month to visit Eastport, as it falls within the peak season that runs from May to July. During this lively period, visitors flock to the area to enjoy the warm summer temperatures, which typically hover around the mid-20s Celsius. This is an ideal time for those seeking outdoor activities, such as sailing, kayaking, or simply relaxing by the waterfront, all while soaking in the vibrant local culture.
The charming streets of Eastport come alive with festivals, art shows, and an array of dining options that cater to a variety of tastes. The bustling atmosphere is superb for travellers looking to mingle with fellow holidaymakers while enjoying the scenic beauty of the Chesapeake Bay.
For those seeking a more budget-friendly experience, consider planning your visit in December. While this month may be quieter, it offers a unique opportunity to explore Eastport's festive holiday events and enjoy the peaceful charm of the off-peak season. The winter scenery can be quite picturesque, creating a lovely backdrop for leisurely strolls and cosy evenings.
Are there any remote work holiday rentals in Eastport?
In Eastport, Maryland, there are plenty of remote work-friendly holiday rentals available, with around 42 options to choose from. This charming waterfront community, located near Annapolis, offers a range of properties that cater to those looking to combine work and leisure. Many of these rentals are equipped with essential amenities such as high-speed Wi-Fi, dedicated desks, and comfortable office chairs, providing an ideal environment for productivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
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?
In Eastport, Maryland, visitors can enjoy a variety of attractions that showcase the area's maritime charm and local culture. The Eastport Historic District is a delightful area to explore, featuring quaint streets lined with colourful homes and independent shops. The Annapolis Maritime Museum offers insights into the region's rich boating history and maritime heritage, making it a must-visit for those interested in local lore.
Nearby, the scenic waterfront at Eastport's Spa Creek provides beautiful views and opportunities for boating and kayaking. For a taste of local cuisine, the area is known for its seafood restaurants, many of which offer outdoor seating with views of the water. Additionally, the vibrant arts scene in Eastport is highlighted by galleries and studios showcasing local artists, making it a pleasant place for art enthusiasts to explore.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.