Holiday Homes in Chesapeake Bay

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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Holiday Homes in Chesapeake Bay

Blufin Bungalows & Marina
Relax in a serene waterfront retreat with enclosed balconies and a tranquil atmosphere.

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (154)
"Excellent place to stay"
Blufin Bungalows & Marina
Charming Historic Townhouse Steps From USNA
Fridge, microwave, oven, stovetop

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (27)
"It was great!"
Charming Historic Townhouse Steps From USNA
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Enjoy a meal with a view at this oceanfront restaurant, overlooking the pier and beach.

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

9.0 out of 10, Wonderful, (65)
"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$743
includes taxes & fees
13 Aug - 14 Aug
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Next to the park and 2 blocks to the Beach and restaurants! RIGHT side of Duplex
Stroll up to the entrance of this charming two-story home, where a cozy porch invites relaxation.

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

9.8 out of 10, Exceptional, (87)
"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
Sweet home to share with the family
Kitchen features a spacious cabinet with two open shelves for storing a variety of dishes.

Sweet home to share with the family

8.8 out of 10, Excellent, (28)
"I stayed here for my birthday to hang out with friends and we loved it. The host was super sweet and very accommodating. Even let us stay later and check in early."
The price is NZ$775
includes taxes & fees
22 Aug - 23 Aug
Sweet home to share with the family
Your own private beach with this charming 3-bedroom beachfront house!
Enter a serene space with a view of the outdoors from the window, featuring a comfortable rocking chair and a small table with a plant.

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

9.6 out of 10, Exceptional, (15)
"We enjoyed 4 days and 3 nights at this cute home. The house was just perfect for our family and we throughly enjoyed the porch and back yard which is where we spent most of our time. The house had everything we needed and more. The walk down to the beach was beautiful and it felt like we had our own private beach. If you are looking to get away from the hustle and bustle this is a great place. Neighbors are close in proximity, but we never really saw anyone and it was all quiet. We did meet one...
Your own private beach with this charming 3-bedroom beachfront house!
Tiny House Near Beach & Naval Base - Privacy Fence
Walk along the pier to the Ocean View Fishing Pier building, offering stunning ocean views.

Tiny House Near Beach & Naval Base - Privacy Fence

9.8 out of 10, Exceptional, (25)
"Great little place! Clean, safe, & has everything you need for a weekend getaway! "
Tiny House Near Beach & Naval Base - Privacy Fence
☆ Beachfront Home w/ Stunning Views, Hot Tub, Luxury Kitchen & Private Beach!
Relax on the deck with ocean views and comfortable seating.

☆ Beachfront Home w/ Stunning Views, Hot Tub, Luxury Kitchen & Private Beach!

10.0 out of 10, Exceptional, (40)
"The owner is easily accessible and they maintain a fantastic property true to its listing. My teenagers loved the property and our stay."
☆ Beachfront Home w/ Stunning Views, Hot Tub, Luxury Kitchen & Private Beach!
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Walk along the Ocean View Fishing Pier, taking in the serene views of the surrounding waters.

Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

8.8 out of 10, Excellent, (58)
"Great stay "
The price is NZ$808
includes taxes & fees
3 Aug - 4 Aug
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Enjoy serene waterfront views and easy access to moorings and facilities.

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

10.0 out of 10, Exceptional, (227)
"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!
Capitol Hill Row Home: 1 Block to Metro and Groceries -- and has Garage!
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and gas stove, set against a clean and contemporary backdrop.

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

9.6 out of 10, Exceptional, (50)
"The location of the house was close to metro, grocery store and restaurants. Nice and quiet neighborhood. I would highly recommend this house. "
Capitol Hill Row Home: 1 Block to Metro and Groceries -- and has Garage!
Canton’s Finest Luxury Stay: Walk to Park, Bars!
Timekeeping and dining in a serene, stylish space with a dining area for two and a touch of greenery.

Canton’s Finest Luxury Stay: Walk to Park, Bars!

9.8 out of 10, Exceptional, (16)
"The host was great, the place was adorable and perfect for our stay. Very clean, had everything we needed and was close to everything. I highly recommend!"
The price is NZ$521
includes taxes & fees
28 July - 29 July
Canton’s Finest Luxury Stay: Walk to Park, Bars!
At the Water's Edge - is there anywhere you'd rather be?!
Enjoy a peaceful retreat with a balcony overlooking a serene lake or river, featuring a seating area with a table and chairs.

At the Water's Edge - is there anywhere you'd rather be?!

10.0 out of 10, Exceptional, (48)
"Great property! Very clean"
At the Water's Edge - is there anywhere you'd rather be?!
Charming 4-bedroom house with WiFi and AC in fabulous Norfolk
Relax on the deck with comfortable wicker furniture and enjoy the serene surroundings.

Charming 4-bedroom house with WiFi and AC in fabulous Norfolk

2.0 star property
8.8 out of 10, Excellent, (5)
The price is NZ$771
includes taxes & fees
13 Aug - 14 Aug
Charming 4-bedroom house with WiFi and AC in fabulous Norfolk
Arlington Home, Minutes to DC!, Secure Parking, King Bed, Firepit, Pet Friendly
Stunning two-story home with a charming bay window and beautifully manicured lawn.

Arlington Home, Minutes to DC!, Secure Parking, King Bed, Firepit, Pet Friendly

10.0 out of 10, Exceptional, (17)
"Great place, amenities, and location "
The price is NZ$763
includes taxes & fees
24 Aug - 25 Aug
Arlington Home, Minutes to DC!, Secure Parking, King Bed, Firepit, Pet Friendly
Affordable Luxury Town Home in Federal Hill Baltimore.
Enjoy cooking in this well-equipped kitchen with a granite countertop, wooden cabinets, and modern appliances.

Affordable Luxury Town Home in Federal Hill Baltimore.

9.4 out of 10, Exceptional, (51)
"Our third stay at this property. Very clean and comfortable. Everything that you need is walking distance. House is well appointed and as pictured. "
Affordable Luxury Town Home in Federal Hill Baltimore.
Cozy & Clean Norfolk Cottage- Fenced Yard for Dogs
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel stove, and microwave.

Cozy & Clean Norfolk Cottage- Fenced Yard for Dogs

10.0 out of 10, Exceptional, (23)
"Great location, clean & everything we needed was here. We would definately come back"
Cozy & Clean Norfolk Cottage- Fenced Yard for Dogs
Family-Friendly 3-Bedroom Hideaway Near Fort DuPont Park
Equipped with a double oven, microwave, and gas stove, this kitchen offers ample cooking space.

Family-Friendly 3-Bedroom Hideaway Near Fort DuPont Park

9.6 out of 10, Exceptional, (71)
"Plenty of room for our family of five and all the amenities we needed for a week in DC."
Family-Friendly 3-Bedroom Hideaway Near Fort DuPont Park
Quiet Relaxing Waterfront Suisse Chalet
Guests gather at the ceremony site, surrounded by lush greenery and a serene water view.

Quiet Relaxing Waterfront Suisse Chalet

9.6 out of 10, Exceptional, (76)
"Overall this was the most amazing experience from the location and the house itself to the property manager. The property manager was so amazing and made sure that if you needed anything in your stay they would make it happen. They were also very good about communication and responding quickly. On top of all of this the house itself is amazing and in the perfect location. Whether you want to have a chill getaway or explore Annapolis and the other amazing locations around it is the perfect house."
Quiet Relaxing Waterfront Suisse Chalet
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Enjoy cooking in this well-lit kitchen with a central island, wooden cabinetry, and stainless steel appliances.

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

10.0 out of 10, Exceptional, (112)
"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!
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

citizenM Washington DC NoMa

citizenM Washington DC NoMa

10/10 Excellent
"I have stayed at the CitizenM multiple times and it never fails to impress. Since I’m usually in town for business, I don’t need frills, just a clean, comfortable room. It’s super convenient, with multiple eateries right across the street and a CVS barely a block away. "
Kathleen 2-night trip
Posted 9 hours ago
citizenM Washington DC NoMa