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Vacation Homes in Chesapeake Bay

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (153)
"Excellent place to stay"
Blufin Bungalows & Marina

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!

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 SAR 747
SAR 1,331 total
includes taxes & fees
24 Jul - 25 Jul
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

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

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 SAR 844
SAR 1,759 total
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!

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

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!

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

8.8 out of 10, Excellent, (58)
"Great stay "
The price is SAR 1,122
SAR 1,823 total
includes taxes & fees
27 Jul - 28 Jul
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!

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!

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!

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 SAR 466
SAR 1,146 total
includes taxes & fees
28 Jul - 29 Jul
Canton’s Finest Luxury Stay: Walk to Park, Bars!

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

2.0 star property
8.8 out of 10, Excellent, (5)
The price is SAR 882
SAR 1,901 total
includes taxes & fees
21 Aug - 22 Aug
Charming 4-bedroom house with WiFi and AC in fabulous Norfolk

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 SAR 656
SAR 1,736 total
includes taxes & fees
12 Aug - 13 Aug
Arlington Home, Minutes to DC!, Secure Parking, King Bed, Firepit, Pet Friendly

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

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

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

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!

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