Holiday Homes in Chesapeake Bay

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Chesapeake Bay

Blufin Bungalows & Marina
Exterior

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (165)
"It was a very clean, comfortable place to stay in on vacation "
Blufin Bungalows & Marina
Next to the park and 2 blocks to the Beach and restaurants! RIGHT side of Duplex
Exterior detail

Next to the park and 2 blocks to the Beach and restaurants! RIGHT side of Duplex

9.8 out of 10, Exceptional, (89)
"This is a nice quiet location but still close to the park and the restaurants and shops. We enjoyed our stay here."
Next to the park and 2 blocks to the Beach and restaurants! RIGHT side of Duplex
3BDR, 2BA townhome at The Historic Powhatan Resort, Sleeps 8
Outdoor dining

3BDR, 2BA townhome at The Historic Powhatan Resort, Sleeps 8

10.0 out of 10, Exceptional, (5)
3BDR, 2BA townhome at The Historic Powhatan Resort, Sleeps 8
A MINI PARADISE-"THE FRISKY DOLPHIN"PRIVATE BEACH- 3BED, 2BATH!!
On the beach, sun-loungers, beach towels

A MINI PARADISE-"THE FRISKY DOLPHIN"PRIVATE BEACH- 3BED, 2BATH!!

9.6 out of 10, Exceptional, (167)
"Great location. Listing was accurate. "
A MINI PARADISE-"THE FRISKY DOLPHIN"PRIVATE BEACH- 3BED, 2BATH!!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (31)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Charming Home • Free Parking & Free Metro Shuttle
Fridge, microwave, oven, stovetop

Charming Home • Free Parking & Free Metro Shuttle

10.0 out of 10, Exceptional, (6)
"The house was clean and nicely maintained. The host was accommodating, helpful, and quick to respond. Overall, a very nice stay."
Charming Home • Free Parking & Free Metro Shuttle
Beachfront Bungalow w/ BEST Location in Ocean View!
Outdoor dining

Beachfront Bungalow w/ BEST Location in Ocean View!

10.0 out of 10, Exceptional, (1)
"This place was a great stay for my friends and I, right on the beach and a very quiet area. The house was clean and the beds were very comfortable. George was very responsive with any questions we had. Will be back!"
The price is NZ$590
includes taxes & fees
9 Sept - 10 Sept
Beachfront Bungalow w/ BEST Location in Ocean View!
Your own private beach with this charming 3-bedroom beachfront house!
Interior

Your own private beach with this charming 3-bedroom beachfront house!

9.8 out of 10, Exceptional, (16)
"We had a great time!! 55yr anniversary our daughter, son inlaw & 2 great grand kids joined us for a couple days!!!"
Your own private beach with this charming 3-bedroom beachfront house!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Marina

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (228)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Hidden Gem@Capitol Hill, 4BDR,2.5BA , 2 Blocks to Metro - DowntownDC, DCA, IAD
Fridge, microwave, oven, stovetop

Hidden Gem@Capitol Hill, 4BDR,2.5BA , 2 Blocks to Metro - DowntownDC, DCA, IAD

9.8 out of 10, Exceptional, (33)
"Accommodations as depicted, close to the Metro, nice neighborhood "
The price is NZ$1,060
includes taxes & fees
26 Aug - 27 Aug
Hidden Gem@Capitol Hill, 4BDR,2.5BA , 2 Blocks to Metro - DowntownDC, DCA, IAD
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!
Terrace/patio

Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

7.2 out of 10, Good, (7)
"Wonderful property!! My family and I had a great time. The location is very convenient to about everything. "
The price is NZ$949
includes taxes & fees
1 Sept - 2 Sept
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!
☆990ft² ☆Heart of Georgetown☆99 Walk Score☆<1 min→Shops☆Smart TV☆
Fridge, microwave, stovetop, coffee/tea maker

☆990ft² ☆Heart of Georgetown☆99 Walk Score☆<1 min→Shops☆Smart TV☆

10.0 out of 10, Exceptional, (9)
"Very nice place to return to after a full day!"
The price is NZ$613
includes taxes & fees
18 Aug - 19 Aug
☆990ft² ☆Heart of Georgetown☆99 Walk Score☆<1 min→Shops☆Smart TV☆
Waterfront with spectacular view, close to restaurants and bars
Interior

Waterfront with spectacular view, close to restaurants and bars

10.0 out of 10, Exceptional, (41)
"Everything was great. "
Waterfront with spectacular view, close to restaurants and bars
Spacious Home w/Free Parking-Close to Old-town Alexandria and DC!
Smart TV, fireplace, computer monitors

Spacious Home w/Free Parking-Close to Old-town Alexandria and DC!

9.8 out of 10, Exceptional, (32)
"Nurten's place was perfect for our family of all ages. Very spacious with comfortable beds, a well-equipped kitchen and nice furnishings. I'd highly recommend Nurten's house for a stay in the DC area!"
The price is NZ$586
includes taxes & fees
18 Aug - 19 Aug
Spacious Home w/Free Parking-Close to Old-town Alexandria and DC!
5BR/4BA HomeI Backyard in VA!
Fridge, microwave, oven, stovetop

5BR/4BA HomeI Backyard in VA!

9.4 out of 10, Exceptional, (10)
"The property was exactly like the listing. We had three families staying here all together for a quick trip to Washington DC. It was easy to get into the city to visit museums and the house was close to plenty of restaurants. "
5BR/4BA HomeI Backyard in VA!
Capitol Hill Row Home: 1 Block to Metro and Groceries -- and has Garage!
Fridge, microwave, oven, stovetop

Capitol Hill Row Home: 1 Block to Metro and Groceries -- and has Garage!

9.6 out of 10, Exceptional, (51)
"Metro so handy, Safeway even handier! So nice after a long day of walking to return to a comfortable, quiet neighborhood and enjoy sitting on the patio with beverage of choice and dinner snacks. The Pretzel Bakery and Eastern Market are a must! "
Capitol Hill Row Home: 1 Block to Metro and Groceries -- and has Garage!
1 Mi to Dtwn: Townhome w/ Patio in Baltimore!
Fridge, microwave, stovetop, dishwasher

1 Mi to Dtwn: Townhome w/ Patio in Baltimore!

8.8 out of 10, Excellent, (9)
"This place was very beautiful and I really enjoyed my stay. When they said first come, first serve for parking it was definitely true. For anyone who doesn’t know the area (like my family) there’s barely parking available as none of the cars moved the entire weekend. Once we found parking we spent a lot using the Lyft app to move around, if not we would not have found parking for blocks upon returning from some of the planned destinations of our trip. Other than that the stay really was...
1 Mi to Dtwn: Townhome w/ Patio in Baltimore!
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Fridge, microwave, oven, stovetop

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

10.0 out of 10, Exceptional, (114)
"My friends and I were looking for a relaxing place to have a long weekend - this place was great! The location was wonderful and the house had everything we needed. The host was a fabulous communicator and helped us with everything we needed! Can’t wait to stay here again! "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Affordable Furnished LuxuryTownhouse near Stadiums In Baltimore Pig Town.
Fridge, microwave, stovetop, dishwasher

Affordable Furnished LuxuryTownhouse near Stadiums In Baltimore Pig Town.

9.0 out of 10, Wonderful, (30)
"Nice place close to everything neighborhood decent for Baltimore. Would stay here with my family "
Affordable Furnished LuxuryTownhouse near Stadiums In Baltimore Pig Town.
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
On the beach, sun-loungers

Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

9.0 out of 10, Wonderful, (66)
"Like the fire pit outside and so close to the beach and the pier the only downside is 1 bedroom doesn’t have AC but other than that it’s perfect We’ll stay there again "
The price is NZ$540
includes taxes & fees
9 Sept - 10 Sept
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesapeake Bay Hotel Reviews

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

10/10 Excellent
"Our room was clean and the beds were comfortable. We had a nice, hot breakfast (sausage, eggs, waffles,) as well as traditional cold items. Everyone was kind and considerate. We would definitely stay again!"
Rhonda 2-night trip
Posted 18 hours ago
La Quinta Inn & Suites by Wyndham Baltimore BWI Airport