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Chesapeake Bay Bridge, Annapolis, Maryland, United States of America
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Chesapeake Bay Bridge vacation rentals

We found 800 vacation rentals — enter your dates for availability

Discover a selection of 1,000 vacation rentals near Chesapeake Bay Bridge that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $120 per night, and houses and cottages are popular options for a stay near Chesapeake Bay Bridge. Either way, you'll find a rental for everyone's needs.
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Find spaces that suit your style

Houses

View 661 Houses

Cottages

View 52 Cottages

Cabins

View 53 Cabins

Bungalows

View 52 Bungalows

Condos/Apartments

View 104 Condos/Apartments

Townhouses

View 58 Townhouses

Studios

View 82 Studios

Find the best place to stay — Chesapeake Bay Bridge

Renovated Rowhome in the Heart of Downtown Annapolis Historic District!

Sleeps 4 · 2 Bedrooms · 1 Bathroom
$350 avg/night
(8)

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Sleeps 8 · 4 Bedrooms · 3 Bathrooms
$821 avg/night
(22)

Firefly Cottage at Cape St. Claire. Walk to private community beach.

1 Bedroom · 1 Bathroom
$270 avg/night
(17)

Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!

3 Bedrooms · 1 Bathroom
$214 avg/night
(13)

Little Magothy Riverfront Home With Pool

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
$394 avg/night
(36)

My Annapolis Studio

1 Bedroom · 1 Bathroom
$120 avg/night

Search 800 vacation rentals

Top rated rentals — Chesapeake Bay Bridge
Stayed Mar 2023

Great house in a great location

The house was great! We arrived to a very clean place and had a great level of communication with the owner. The house had everything we needed for a great stay. We were also happy to find out that the beds were very comfortable. Additionally, the ho...

Jocelyn K.
Jocelyn K.
Stayed Mar 2023

Quick getaway

If you're looking for a quick quite getaway this is a perfect cottage to use! They did a great job of fixing up the place to meet all your modern needs and comforts. I would check the weather and make sure the temps are above 50 but other than that i...

Mike T.
Mike T.
Stayed Mar 2023

Winter hideout

This home was perfect for our family. The location is convenient to necessities. The home is great for a large group with plenty of seating and gathering areas. We had several family members visit and there was plenty of room for several conversation...

Lauren C.
Lauren C.
Stayed Feb 2023

Even Better Than Expected

Pat and Ken’s cottage was amazing! We walked into a gift basket, wine, snacks, and even a toy for our dog Nala. The cottage was clean and well decorated. It had everything you could think of needing from a blender and mixer to coffee, water, and brea...

Alex C.
Alex C.

Norfolk, VA

Stayed Feb 2023

Peaceful oasis

Staying at the guesthouse is a wonderful experience. This is our second visit to celebrate a 30th birthday and girl’s weekend. The house is beautifully appointed and provides a pampered stay with many amenities. It’s also a convenient location to man...

Janice M.
Janice M.
Stayed Feb 2023

Beautiful!

A beautiful, roomy and clean space perfect for a weekend with our mid.It was an easy and quick drive to the yard. It's a lovely neighborhood, the walk and the visit to the beach was very nice even in February. Our host was very attentive but not intr...

Rhonda E.
Rhonda E.
Stayed Feb 2023

Beautiful

The pictures on the listing matched the condo perfect but the dining room table. The one in the condo was bigger and nicer. The decor was so nice and the beds were very comfortable. We didn't cook, but looked like there was plenty of pots and pans. T...

Ranelle R.
Ranelle R.
Stayed Jan 2023

Well-appointed Family Retreat

We stayed here for an extended time while our kitchen was renovated, and it was everything we needed and more. You can tell that every detail for a guest's comfort was considered. Our kids loved the children's dishes, cups, and utensils, and we loved...

Amy A.
Amy A.

Annapolis, MD USA

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How many vacation rentals are available around Chesapeake Bay Bridge?

Our 2023 property listings offer a large selection of 800 vacation rentals around Chesapeake Bay Bridge. From 661 house rentals to 52 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses near Chesapeake Bay Bridge?

Yes, of course. Vrbo has 661 Houses near Chesapeake Bay Bridge. Our other popular types of vacation rentals near Chesapeake Bay Bridge include:

  • Cottages: 52 rentals available
  • Cabins: 53 rentals available
  • Bungalows: 52 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool near Chesapeake Bay Bridge?

Yes, you can select your preferred vacation rental with pool among our 150 vacation rentals with pool available near Chesapeake Bay Bridge. Please use our search bar to access the selection of vacation rentals available.