Holiday Homes in Northern Chesapeake Bay

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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Northern Chesapeake Bay and around

Adorable two-bedroom retreat close to Easton, Denton, Centreville
Property grounds

Adorable two-bedroom retreat close to Easton, Denton, Centreville

10.0 out of 10, Exceptional, (26)
"This home was perfect for a quiet getaway. Relaxing to come back to after a busy day out."
The price is €314
includes taxes & fees
22 Aug - 23 Aug
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is €368
includes taxes & fees
21 Aug - 22 Aug
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Waterfront Getaway with Dock
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (49)
"Fit all of our needs. Clean,well furnished, nice kitchen. Stayed there twice and will probably go back."
The price is €245
includes taxes & fees
21 Aug - 22 Aug
Waterfront Getaway with Dock
Private top floor at 2067 Park Road, Nw Dc. P.sCheck out 2nd listing too- bigger
Property grounds

Private top floor at 2067 Park Road, Nw Dc. P.sCheck out 2nd listing too- bigger

10.0 out of 10, Exceptional, (13)
"Beautiful location . Close to all the things. Very convenient.. Felt like home!"
The price is €280
includes taxes & fees
21 Aug - 22 Aug
Private top floor at 2067 Park Road, Nw Dc. P.sCheck out 2nd listing too- bigger
Living in Luxury ..... Where Sophistication meets Elegance
Microwave, oven, stovetop, dishwasher

Living in Luxury ..... Where Sophistication meets Elegance

2.0 star property
The price is €389
includes taxes & fees
25 Aug - 26 Aug
Living in Luxury ..... Where Sophistication meets Elegance
Tranquil 3BR/2.5ba house with 4 beds for 7/Patio/BBQ & Gaming Room/15 mins to DC
Terrace/patio

Tranquil 3BR/2.5ba house with 4 beds for 7/Patio/BBQ & Gaming Room/15 mins to DC

2.0 star property
9.4 out of 10, Exceptional, (20)
"Overall a very nice stay."
The price is €433
includes taxes & fees
21 Aug - 22 Aug
Tranquil 3BR/2.5ba house with 4 beds for 7/Patio/BBQ & Gaming Room/15 mins to DC
Lux 4BR House-Mins to DC-Free Parking
Terrace/patio

Lux 4BR House-Mins to DC-Free Parking

8.8 out of 10, Excellent, (17)
"The place was clean and had what we needed. Plenty of bedrooms and bathrooms, and near a bus line. The beds could be a little uncomfortable. And we hoped they had a blender."
The price is €376
includes taxes & fees
2 Sept - 3 Sept
Lux 4BR House-Mins to DC-Free Parking
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (39)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is €280
includes taxes & fees
27 Aug - 28 Aug
Relax on Kent Island in 3 Bedroom Home w/Waterview
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Marina

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

9.6 out of 10, Exceptional, (28)
"Nice and peaceful stay for a quick local getaway. "
The price is €257
includes taxes & fees
24 Aug - 25 Aug
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Charm and Comfort in Capitol Hill
Property grounds

Charm and Comfort in Capitol Hill

2.0 star property
10.0 out of 10, Exceptional, (3)
"Communication with host was great. Place was clean and exactly as pictured. "
The price is €208
includes taxes & fees
21 Aug - 22 Aug
Charm and Comfort in Capitol Hill
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.8 out of 10, Exceptional, (11)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is €352
includes taxes & fees
21 Aug - 22 Aug
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Beautiful 2 Bedroom with Loft in Heart of Old Town—sleeps 6
Exterior

Beautiful 2 Bedroom with Loft in Heart of Old Town—sleeps 6

9.8 out of 10, Exceptional, (48)
"Great Location! Really cool town."
The price is €353
includes taxes & fees
21 Aug - 22 Aug
Beautiful 2 Bedroom with Loft in Heart of Old Town—sleeps 6
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
Beach nearby

Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

10.0 out of 10, Exceptional, (28)
"Absolutely beautiful and spacious home perfectly located in North Beach. Very peaceful area and close to the beach, restaurants and shopping. We really enjoyed our stay and hope to visit again in the future. "
The price is €544
includes taxes & fees
24 Aug - 25 Aug
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
Charming 3-bedroom house in peaceful Kensington with parking near DC
Property grounds

Charming 3-bedroom house in peaceful Kensington with parking near DC

2.0 star property
9.8 out of 10, Exceptional, (13)
"Owners were very communicative and helpful. House is delightful. "
The price is €447
includes taxes & fees
26 Aug - 27 Aug
Charming 3-bedroom house in peaceful Kensington with parking near DC
Canton’s Finest Luxury Stay: Walk to Park, Bars!
Interior

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

9.8 out of 10, Exceptional, (18)
"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 €225
includes taxes & fees
24 Aug - 25 Aug
Canton’s Finest Luxury Stay: Walk to Park, Bars!
Cozy Home in Beautiful Annapolis
Exterior

Cozy Home in Beautiful Annapolis

10.0 out of 10, Exceptional, (13)
"Great property and very clean!"
The price is €253
includes taxes & fees
25 Aug - 26 Aug
Cozy Home in Beautiful Annapolis
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier
Terrace/patio

Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is €418
includes taxes & fees
25 Aug - 26 Aug
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier
Large 2 bedroom house with private parking in a nice neighborhood
Smart TV, books

Large 2 bedroom house with private parking in a nice neighborhood

9.6 out of 10, Exceptional, (26)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
The price is €334
includes taxes & fees
21 Aug - 22 Aug
Large 2 bedroom house with private parking in a nice neighborhood
BAYSIDE BUNGALOW
Outdoor dining

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (46)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is €266
includes taxes & fees
21 Aug - 22 Aug
BAYSIDE BUNGALOW
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Exterior

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

10.0 out of 10, Exceptional, (2)
"The property is newly renovated and very comfortable. Property owner is responsive to any questions, and we enjoyed our stay here. Would recommend it for anyone staying in Shady Side."
The price is €444
includes taxes & fees
21 Aug - 22 Aug
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
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 Northern Chesapeake Bay Hotel Reviews

Washington Plaza Hotel

Washington Plaza Hotel

10/10 Excellent
"Everyone we encountered were very accommodating. The room was clean and comfortable. We enjoyed the pool and bar. Nice restaurant with good food too. All at a very reasonable price. "
Dennis 1-night trip
Posted 21 hours ago
Washington Plaza Hotel