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Walk Everywhere From New Eastport Cape Cod with High-End finishes and Gourmet Kitchen

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Step inside the brand new renovated home with it's open floor plan and high-end finishes.
Welcome to Chesapeake Charmer, located in the popular Annapolis neighborhood of Eastport.
Overflow conversation from the kitchen and dining room can easily extend into the family room.
The main floor King suite is convenient for extended family members traveling together.
Once you've parked on the driveway behind the home, enter into the new chef's kitchen.

Reviews

10 out of 10
Exceptional
4 bedrooms2+ bathroomsSleeps 81980 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
  • Air conditioning

Rooms & beds

4 bedrooms (sleeps 8)

2nd Floor Front Queen

1 Queen Bed

2nd Floor Garden View

1 Queen Bed

2nd Floor King EnSuite

1 King Bed

Main Level King Suite

1 King Bed

2 bathrooms, 1 half bathroom

2nd Floor Ensuite/Hall

Toilet · Shower only

Main Level EnSuite

Toilet · Shower only

Main Level Powder Room

Toilet

Spaces

Kitchen

About this property

Walk Everywhere From New Eastport Cape Cod with High-End finishes and Gourmet Kitchen

Experience the Difference: Professionally Managed by iTrip Annapolis

Eastport Cape Cod – Walk to Downtown Annapolis



Welcome to your Annapolis retreat! This all-new Cape Cod in the heart of Eastport offers modern comfort with a touch of coastal charm. With 4 bedrooms and 2.5 baths, there’s plenty of room for families, couples, or friends traveling together.



The bright, open floor plan makes it easy to gather. Cook in the chef’s kitchen with sleek quartz counters and high-end stainless appliances, then share meals at the dining table for six or breakfast bar for four. After a day exploring historic Annapolis, relax in the cozy living area with the flatscreen TV and streaming apps.



The main floor King suite provides ultimate convenience, while upstairs you’ll find another King en-suite plus two Queen bedrooms that share the same spacious bath (double entrance from the King Suite and the hall).



Step outside and you’re in the middle of it all. Stroll across the street to Bakers & Co for morning pastries, wander to the waterfront for sunset cocktails, or explore downtown’s shops, restaurants, and cobblestone streets. The Naval Academy is just a mile away, and day trips to Washington, DC or Baltimore are under an hour away.



Sleeping Arrangements (Sleeps 8):

Main Floor King Suite – ensuite bath w/ stand-up shower and heated floor tiles

2nd Floor King En-Suite – private bath + hall access

2 Queen Bedrooms – shared large hall bath



What You’ll Love:

Chef’s kitchen + seating for 10

High-speed WiFi + streaming TV

Luxury linens + boutique touches

Washer/dryer

Keyless entry

Parking pad for 2 cars

Dogs permitted with a $150 non-refundable fee due prior to checkin



Distances:

Downtown Annapolis – .5 mile

U.S. Naval Academy – .9 mile

Washington, DC – 33 miles

Baltimore – 32 miles



House Rules: No smoking or parties. Primary renter must be 25+. Security camera at front door + noise monitor (law compliant).

Check-in: 4 PM | Check-out: 11 AM

Whether you’re here for a weekend escape, a family gathering, or a Naval Academy visit, this Eastport gem is the perfect home base.
Our prices include all fees. No hidden fees.

Add dates for prices

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Enjoy Eastport Easy's private backyard patio with a fire pit and fenced-in yard.
2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
10.0 out of 10, Exceptional, (42 reviews)
2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property

We should mention

This property does not have elevators

About the neighborhood

Annapolis

Eastport, a neighborhood in Annapolis, is home to this vacation home. Jonas Green State Park and Sandy Point State Park reflect the area's natural beauty and area attractions include Annapolis Maritime Museum and French Soldiers Monument. Looking to enjoy an event or a game while in town? See what's happening at Tose Family Tennis Center or Alumni Hall.
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Map
Annapolis, MD

What's nearby

  • Annapolis Harbor - 5 min walk - 0.4 km
  • Annapolis Maritime Museum - 8 min walk - 0.7 km
  • U.S. Naval Academy - 12 min walk - 1.1 km
  • Annapolis City Dock - 14 min walk - 1.2 km
  • Maryland State House - 17 min walk - 1.5 km

Getting around

  • Odenton Station - 23 min drive
  • Fort Meade, MD (FME-Tipton) - 35 min drive

Restaurants

  • ‪The Choptank - ‬13 min walk
  • ‪Carrol's Creek Cafe - ‬6 min walk
  • ‪Boatyard Bar & Grill - ‬6 min walk
  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬14 min walk
  • ‪Sammy's Italian Pizza Kitchen - ‬8 min walk

Frequently asked questions

Is 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Walk Everywhere From New Eastport Cape Cod with High-End finishes and Gourmet Kitchen?

As of Mar 26, 2026, prices found for a 1-night stay for 2 adults at Walk Everywhere From New Eastport Cape Cod with High-End finishes and Gourmet Kitchen on May 10, 2026 start from $729, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?

Check-in begins at 4:00 PM.

What time is check-out at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?

Check-out is at 11:00 AM.

Where is 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free located?

Located in Eastport, this vacation home is within 1 mi (2 km) of Spa Creek and U.S. Naval Academy. Annapolis Harbor and Annapolis Maritime Museum are also within 15 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Stacia T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This beautiful property was close to downtown Annapolis with an amazing bakery across the street. Everything was new and clean and fully stocked. Would definitely stay here again.
Stayed 2 nights in Dec 2025
Verified

10/10 Excellent

Audrey W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our stay in this home was absolutely lovely. All communication concerning check-in, house amenities, etc was handled quickly and efficiently. The house itself is absolutely immaculate and beautiful. We were there for Thanksgiving and had everything we needed to cook an entire traditional meal - from a very high end gas stove and oven to a large refrigerator and every cooking utensil you can think of. The house is near everything in Annapolis. A ten minute walk over the bridge to all the shops and restaurants although there are many great places without going over the bridge. Right across the street from the house is an incredible bakery with pastries and coffee. We will definitely stay here again
Stayed 8 nights in Nov 2025
Verified

10/10 Excellent

Kristin P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful accommodations! Great design/decor, good sized rooms, well appointed kitchen. My only suggestion is more furniture in the living room. Currently sits 4 comfortably. The location is great and a short (and beautiful) walk to downtown. Great place!
Stayed 3 nights in Mar 2026

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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