BEST VACATION RENTALS NEAR ANNAPOLIS

EXPERIENCE A TRUE VACATION

When you’re traveling, you shouldn’t have to sacrifice comfort or cleanliness. These two things can make or break your experience. B4K adheres to the highest standards of property management so that nothing interferes with your ability to enjoy your vacation. Our diverse inventory of vacation rentals near Annapolis has something for everyone. Find your dream getaway today!

VACATION RENTALS NEAR ANNAPOLIS

We specialize in vacation rentals near Annapolis, Maryland. Because we live and work in the area, you can benefit from local recommendations, knowledgeable advice, and quick responses to any question. We are (literally) here for you! Explore our growing list of amazing vacation rentals near Annapolis to find your next getaway!

Entrance and Deck
Comfortable Beds
Steps to Water

RENOVATED BUNGALOW

Stroll on the beach or walk to historic London Town & Gardens. This home mixes indoor charm with outdoor inspiration to provide you with the perfect getaway.

  • 2 BR / 2 Beds / Sleeps 4-6
  • Parking for 2 Vehicles
  • WiFi Included
  • Outdoor Seating with Fire Pit
  • Washer/Dryer
  • Beach Access
  • Keypad Entry
  • Dog-Friendly
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Waterfront Location
RV Exterior
Updated Interior
Comfortable Bed
Versatile Seating
Endless Fun

WATERFRONT UNIT - DOCK ACCESS

Waterfront fun at its finest! This camper is fully loaded with all the amenities you need for a comfortable and exciting stay near the water!
  • 1 BR / 4 Beds / Sleeps 6
  • 1 Bath
  • Parking for 1 Vehicle or Boat
  • WiFi Included
  • Washer/Dryer
  • River View, Boat Slip
  • Keypad Entry
  • Kayaks & SUPs Available
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Waterfront Location
Modern Exterior
Gorgeous Kitchen
Spacious Bedrooms
Stress-Free Vacation

SOUTH RIVER WATERFRONT

On the shores of the South River, this space  offers you a veritable sanctuary! Escape to this tranquil getaway, and experience the vacation you deserve!
  • 3 BR / Sleeps 8
  • 4.5 Bath
  • Parking for 2 Vehicles
  • Boat Slip
  • Gourmet Kitchen
  • Keypad Entry
  • Elevator
  • Hot Tub
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Pool & Yard Retreat

Located in the heart of South County, this tranquil retreat is perfect for families and groups. Relax, unwind, and gather for meals in the spacious eat-in kitchen.
  • 4 BR / Sleeps 12
  • 3 Baths
  • Rural surroundings
  • WiFi Included
  • Washer/Dryer
  • Private deck
  • Pool
  • Pets Allowed
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Waterfront Location
Equipped Kitchen
Endless Fun
Comfortable Beds
Family-Friendly Rooms

RIVERVIEW RETREAT ON WAREHOUSE CREEK

Your search for vacation rentals near Annapolis stops here! This space boasts privacy, comfortable beds, and a lovely spot on the water.

  • 2 BR / 3 Beds / Sleeps 6
  • 1 Bath
  • In-Law Suite with a View
  • Dock, Kayaks, Boat House Available
  • Washer/Dryer
  • Private Entrance
  • WiFi
  • Pets Allowed
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Waterfront Location
Versatile Gazebo
Outdoor Seating
Space for Groups
Area for Tents

SOUTH RIVER HANGOUT / EVENT SPACE

Take your camping trip to the next level or host a group event at this waterside location! Escape the daily grind and relax under the stars.
  • Waterfront Location
  • Charming Gazebo with Fan
  • Refrigerator on Premises
  • Ample Parking for Large Groups
  • Fits Groups Up to 40
  • Picnic Table & Outdoor Chairs
  • RV Parking Space Available
  • BBQ Grill
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Historic Annapolis Home Walk to Downtown 3BR

Stay in the heart of historic Annapolis in this beautifully restored home, just minutes from downtown, dining, the waterfront, and Navy events.
  • 3 BR / 3 Beds / Sleeps 6
  • 3 Full Bathrooms
  • Private Fenced Yard
  • Walk to Downtown & USNA
  • Fully Equipped Kitchen
  • Dedicated Workspace
  • Washer/Dryer
  • Dog-Friendly
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Welcoming Exterior
Cozy Gathering Space
Equipped Kitchen
Comfortable Beds
Classic Details

HISTORIC ANNAPOLIS HOME

Experience the charm of downtown Annapolis in this renovated, historic home. Access Main Street, shops, restaurants, and local attractions!
  • 3 BR / 5 Beds / Sleeps 9
  • 2 Baths
  • 2 Blocks to Main St.
  • Fenced Backyard
  • Contactless Check-in
  • WiFi
  • Private Entrance
  • Outdoor Seating
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GRANDMA'S SUMMER HOUSE

Recently renovated and filled with charm, this cottage has easy access to trails, boat launching, fishing, and so much more. Experience tranquility!
  • 3 BR / 5 Beds / Sleeps 6
  • 1 Baths
  • Parking for 4 Vehicles
  • WiFi
  • Outdoor seating
  • Access to trails
  • Contactless check in
  • Pets allowed
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STADIUM-SIDE ANNAPOLIS

Just minutes from Navy-Marine Corps Memorial Stadium, this space gives you a peaceful escape near serene parks, with access to local activities!
  • 3 BR / Sleeps 6
  • 3.5 Baths
  • Steps to stadium
  • WiFi
  • Chef's kitchen
  • Access to parks
  • Contactless check in
  • Pets allowed
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FAMILY HOME ON MAYO PENINSULA

Nicely situated in the Mayo Peninsula this is one of our latest vacation rentals. Perfectly mixing indoor and outdoor comfort, this is an ideal retreat.
  • 3 BR / 7 Beds / Sleeps 10
  • 2 Baths
  • Parking for 8
  • Contactless check in
  • Outdoor seating
  • Access to playground
  • Nearby beach
  • Pets Allowed
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LONDONTOWNE RANCHER

A charming and cozy 3-bedroom, 2-bathroom rancher perfect for your getaway! Bright living space, private yard, and minutes from local attractions.
  • 3 BR / Sleeps 8
  • 2 Baths
  • Parking on premises
  • WiFi Included
  • Washer/Dryer
  • Private yard
  • Walk to Main St.
  • Pet-friendly
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LONDONTOWNE HOME Near BEACH

With access to multiple beaches and a charming historic town, this home has it all!
  • 3 BR / Sleeps 7
  • 3 Baths
  • Free Parking
  • Spacious Master Suite
  • Access to 5 beaches
  • 2 min to London Town & Gardens
  • Laundry
  • Pets Allowed
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POOL LOFT SUITE

Where style meets privacy! Settle into a peaceful retreat with easy access to beaches, Annapolis charm, and high-end amenities.

  • BR / 1 Queen Bed
  • Extra Air Mattress
  • 1.5 Bath
  • 2 Parking Spots
  • Washer/Dryer
  • Shared Pool Access
  • Wheelchair Accessible
  • Bay Access & Beach Passes
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south river estate 4br sleeps 10

This magnificent waterfront estate on the South River combines luxurious interior spaciousness with outdoor tranquility!
  • 3 BR / Sleeps 10
  • 3 Baths
  • Washer/Dryer
  • Spa-like Master Suite
  • Expansive deck
  • Outdoor gazebo
  • Sunset views
  • Great for families
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Quiet Waters Family Home 4BR Sleeps 8

Charming space located in a highly desirable waterfront neighborhood! Enjoy the peace and tranquility of your outdoor space, with convenient access to downtown, Naval Academy, and the best of Chesapeake Bay activities!
  • 4 BR / 5 Beds / Sleeps 8
  • 3 Baths
  • Fully equipped kitchen
  • WiFi Included
  • Screened-in porch
  • Deck
  • Big backyard
  • Access to water
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Waterfront Retreat Private Pier and Sunset Views

Enjoy total serenity when you stay in this charming home on Cadle Creek! Sunset views, a pier and boat slip, and a sprawling lawn make this the perfect space for a quiet getaway!
  • 3 BR / 5 Beds
  • 4 Bathrooms
  • Beautiful Outdoor Space
  • Private Boat Slip
  • West-Facing Deck
  • Walking Distance to SERC
  • Easy Access to USNA
  • Pet Friendly
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EXPLORE MORE VACATIONS RENTALS

In addition to our gorgeous vacation rentals near Annapolis, B4K has expanded its service area to vacation rentals across the country. Explore our listings below, and be sure to check back often, as more will be added soon!

PLANO HOME WITH POOL & BACKYARD OASIS

Available now for a long summer stay, between May 22-August 10th, 2026. Enjoy the sparkling pool and dedicated music room! Inquire for bookings beyond August.

  • 4 BR
  • 4 Baths
  • Washer/Dryer
  • Equipped kitchen
  • Dedicated music room
  • Close to parks
  • Great for families
  • Sparkling pool
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Welcoming Exterior
Kitchen
Bedroom
Exterior

CHIC COUNTRY HOME

One of our newest vacation rentals! Visit this beautifully updated farmhouse in Portage, WI. Your charming getaway sits on 80 acres of sprawling land.
  • 3 BR / 4 Beds / Sleeps 10
  • 2 Baths
  • 80 acres of picturesque land!
  • Ideal for large gatherings
  • Contactless Check-in
  • WiFi
  • Kitchen/dining seating for 26
  • Pets Allowed
LEARN MORE AND BOOK

GUEST REVIEWS

When you trust B4K with your vacation rentals, you’ll put your guests in great hands. We strive to create a welcoming, comfortable, stress-free experience for every guest. See what they have to say about us!
Hannah

Beautiful place and exactly what we needed for a girls’ weekend! Pros: Everything looked like the pictures, the hot tub was great, and we had cozy breakfasts in the sunroom next to the fireplace! Historic Annapolis Main Street was a 20 minute drive, and the host sent a helpful welcome brochure with a list of local spots.

Erika

Carolyn and her team were great. They were super responsive and very accommodating. We had a small snafu with the hot tub when we first checked in, but they had someone out there within a day to work on it. The house was exactly what we hoped for and the peace and quiet of the neighborhood was just the icing on the cake. My husband and I are already talking about planning for a family trip back!

Scott

Everything was exceptional and we appreciate a welcoming home away from home. The space was clean, comfortable, and had all the necessities for an accommodating stay. The neighborhood is quiet, peaceful, and safe. Carolyn’s offering is 5 stars across the board and we had 100% satisfaction. Thank you for a wonderful stay.

Anna

My family stayed in this camper and it was so nice! Better than a hotel! It was peaceful, calm, the view of the water was great. The camper is so clean and love that it has wifi, so I was able to work on my laptop. The main bedroom and bed was so comfortable and loved that it had a mini washer/dryer. Shower was nice as well... Definitely recommend …

John

We have lived in MD for a long time but had never spent time in Mayo. We were blown away by the pace, the people, the waterways, the restaurants and bars - all of it. Definitely coming back. The accommodations were perfect for four of us and we were completely comfortable. Great vacation! Thanks Carolyn!

Lisa

My husband and I boated up to this wonderful place - a rare find for boaters, especially with a dog. The RV is fully loaded with top of the line appliances, comfortable beds, a peaceful porch area, full bathroom. Carolyn and her husband JP are gracious hosts; they are there when you need them and offer complete privacy otherwise. We will definitely return.

Mike

Carolyn was amazing and super communicative. The house itself was AMAZING - super views, hot tub, amazingly clean. Really great place to stay for a time away from reality.

Juliet

We loved this retreat along the river. The space was beautifully decorated, modern and comfortable. The views were stunning and we had great sunrises and sunsets along the water. My kids loved the dock and walking to the water as well as playing games and doing the puzzles in the space. We have family in the area and plan to return again. I highly recommend this space.

Nicole

We had a lovely stay at Carolyn’s place. The apartment was very clean and spacious, had a super comfy couch and beds, and a well equipped kitchen. The view of the river was beautiful and the hosts were very responsive and accommodating. Would love to come back in warmer weather and use the kayaks!

Rob

We stayed at the Fisher House with our kids for the St. Patrick’s day fun and parade. The house is charming and in a wonderful location. It was a pleasure dealing with the folks at B4K. Definitely hope to return!

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