Top Vacation Rentals in Chesapeake Bay ᐅ Instant booking

Vacation apartment for 7 people, with balcony - 1

Mariners Cove Waterfront - Private Dock, Pet Friendly, Wi-Fi, Off-Street Parking

0.7 mi to the beach

Sleeps 12 pers.3 bedrooms3,498 ft²

BalconyYardParkingInternet

Buckroe Bungalow · #Buckroe Bungalow ~Escape to the Beach 2mins Away!

5 mi to the beach

Sleeps 8 pers.3 bedrooms13,455 ft²

BalconyYardParkingKitchen

Cozy 2br home w/ parking in downtown Annapolis

1.3 mi to the beach

Sleeps 6 pers.2 bedrooms904 ft²

YardTerraceParkingInternet

Sweet Bamboo Beach Cottage

Sleeps 6 pers.3 bedrooms958 ft²

YardTerraceParkingInternet

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

2.2 mi to the beach

Sleeps 7 pers.4 bedrooms

YardTerraceParkingInternet

Now available for Usna Commissioning Week! 16-22 May. Easy walk to Stadium. <br>Your Annapolis Wat...

1.8 mi to the beach

Sleeps 4 pers.1 bedroom700 ft²

Your Annapolis Adventure Starts Here!!

0.7 mi to the beach

Sleeps 6 pers.3 bedrooms1,593 ft²

YardTerraceParkingInternet

Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger

3.5 mi to the beach

Sleeps 8 pers.3 bedrooms

BalconyYardParkingInternet

Across from the park and 2 blocks from beach & restaurants- Left side of duplex

5.4 mi to the beach

Sleeps 6 pers.3 bedrooms

YardTerraceParkingInternet

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

3 mi to the beach

Sleeps 3 pers.1 bedroom484 ft²

BalconyParkingInternet

Charming garden row home, easy 4 block walk to the heart of Annapolis.

0.9 mi to the beach

Sleeps 6 pers.3 bedrooms

Cozy home w/fenced in yard-Dog Friendly with Pet fee. 2 block walk to downtown!

6.7 mi to the beach

Sleeps 3 pers.2 bedrooms1,098 ft²

YardTerraceParkingInternet

Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

9 mi to the beach

Sleeps 6 pers.3 bedrooms1,098 ft²

YardTerraceParkingInternet

Secluded Waterfront Cottage on 200 acre farm near Queenstown

3.9 mi to the beach

Sleeps 8 pers.4 bedrooms

TerraceParkingInternet

Blocks to the Boardwalk!

Sleeps 2 pers.1 bedroom441 ft²

TerraceParkingInternet

Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis

600 yd to the beach

Sleeps 4 pers.2 bedrooms

Annapolis Condominium in the heart of the historic center

1.2 mi to the beach

Sleeps 6 pers.3 bedrooms1,399 ft²

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Sleeps 6 pers.3 bedrooms2,099 ft²

TerraceParkingInternet

Sophisticated Charmer with Parking & Views of the Usna Chapel Dome

0.9 mi to the beach

Sleeps 6 pers.3 bedrooms1,798 ft²

YardTerraceParkingInternet

Eastport Cottage .5 mi from Downtown Annapolis

1.1 mi to the beach

Sleeps 3 pers.2 bedrooms

YardTerraceParkingInternet

Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!

2.9 mi to the beach

Sleeps 4 pers.2 bedrooms1,292 ft²

YardTerraceParkingInternet

Beachfront Getaway, Mermaid Suite, 🐶 💙

0.6 mi to the beach

Sleeps 6 pers.3 bedrooms2,067 ft²

YardTerraceParkingInternet

One more unit available

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

6.3 mi to the beach

Sleeps 8 pers.4 bedrooms2,486 ft²

YardTerraceParkingInternet

Quaint fishing retreat on the lower Potomac Piney Pt

1.4 mi to the beach

Sleeps 3 pers.2 bedrooms1,195 ft²

BalconyYardParkingInternet

200 steps to the beach!

6 mi to the beach

Sleeps 4 pers.2 bedrooms1,195 ft²

YardTerraceParkingInternet

2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free

1 mi to the beach

Sleeps 8 pers.2 bedrooms2,390 ft²

BalconyParkingInternet

Park Place - Comfy Condo Close to Beach

Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Spacious Home < 1 Mi to Kiptopeke State Park!

Mariners Cove Waterfront - Private Dock, Pet Friendly, Wi-Fi, Off-Street Parking

Buckroe Bungalow · #Buckroe Bungalow ~Escape to the Beach 2mins Away!

Cozy 2br home w/ parking in downtown Annapolis

Sweet Bamboo Beach Cottage

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Now available for Usna Commissioning Week! 16-22 May. Easy walk to Stadium. <br>Your Annapolis Wat...

Your Annapolis Adventure Starts Here!!

Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger

Across from the park and 2 blocks from beach & restaurants- Left side of duplex

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Cozy home w/fenced in yard-Dog Friendly with Pet fee. 2 block walk to downtown!

Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

Secluded Waterfront Cottage on 200 acre farm near Queenstown

Blocks to the Boardwalk!

Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis

Annapolis Condominium in the heart of the historic center

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Sophisticated Charmer with Parking & Views of the Usna Chapel Dome

Eastport Cottage .5 mi from Downtown Annapolis

Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!

Beachfront Getaway, Mermaid Suite, 🐶 💙

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Quaint fishing retreat on the lower Potomac Piney Pt

200 steps to the beach!

2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free