Photo by Ronanne Vinson

Search Chesapeake Beach Villa Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Browse Select Chesapeake Beach Villas

We don't have any properties that match your exact search

Recommended hotels in Chesapeake Beach

SureStay by Best Western Prince Frederick
Exterior

SureStay by Best Western Prince Frederick

2.5 star property
7.6 out of 10, Good, (165)
"Clean rooms and comfortable beds. "
The price is CA $109
CA $121 total
includes taxes & fees
Aug 21 - Aug 22
SureStay by Best Western Prince Frederick
St Michaels Inn
View from property

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1001)
"Very nice stay"
The price is CA $134
CA $148 total
includes taxes & fees
Sep 14 - Sep 15
St Michaels Inn
Springhill Suites by Marriott Prince Frederick
Exterior

Springhill Suites by Marriott Prince Frederick

3.0 star property
8.6 out of 10, Excellent, (902)
"Everything was nice "
The price is CA $127
CA $141 total
includes taxes & fees
Aug 31 - Sep 1
Springhill Suites by Marriott Prince Frederick
Rod 'N' Reel Resort
Superior Studio Suite | Balcony

Rod 'N' Reel Resort

4.0 star property
8.2 out of 10, Very good, (1000)
"Great place to stay."
The price is CA $184
CA $232 total
includes taxes & fees
Aug 17 - Aug 18
Rod 'N' Reel Resort
Family Beach House: Spacious Deck, Grill & Views
Outdoor dining

Family Beach House: Spacious Deck, Grill & Views

9.2 out of 10, Wonderful, (5)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is CA $313
CA $707 total
includes taxes & fees
Aug 19 - Aug 20
Family Beach House: Spacious Deck, Grill & Views
SpringHill Suites by Marriott Annapolis
Exterior

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Great place"
The price is CA $139
CA $159 total
includes taxes & fees
Aug 20 - Aug 21
SpringHill Suites by Marriott Annapolis
Wylder Tilghman Island
Seasonal outdoor pool

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (59)
"Good service and good options to enjoy the stays. "
The price is CA $235
CA $319 total
includes taxes & fees
Aug 24 - Aug 25
Wylder Tilghman Island
Holiday Inn Express Prince Frederick by IHG
Exterior

Holiday Inn Express Prince Frederick by IHG

2.5 star property
8.8 out of 10, Excellent, (661)
"The staff was very welcoming and nice. "
The price is CA $153
CA $185 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Express Prince Frederick by IHG
Candlewood Suites Annapolis by IHG
Exterior

Candlewood Suites Annapolis by IHG

2.5 star property
8.8 out of 10, Excellent, (99)
"Great stay"
The price is CA $129
CA $147 total
includes taxes & fees
Aug 19 - Aug 20
Candlewood Suites Annapolis by IHG
Anchored Inn at Hidden Harbour Marina
Marina

Anchored Inn at Hidden Harbour Marina

2.5 star property
9.4 out of 10, Exceptional, (442)
"The staff specifically Victoria was impeccable! "
The price is CA $246
CA $281 total
includes taxes & fees
Sep 1 - Sep 2
Anchored Inn at Hidden Harbour Marina
Hilton Garden Inn Solomons
Exterior

Hilton Garden Inn Solomons

3.0 star property
8.6 out of 10, Excellent, (611)
"Convenient location and next to a good restaurant and brewery."
The price is CA $175
CA $194 total
includes taxes & fees
Aug 24 - Aug 25
Hilton Garden Inn Solomons
The Wildset
Front of property

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (356)
"This is where we stay everytime we come to St. Michaels - Top Knotch!"
The price is CA $296
CA $356 total
includes taxes & fees
Aug 18 - Aug 19
The Wildset
Sonesta ES Suites Annapolis
Exterior

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (855)
"Great room for a great price... Very friendly staff, too."
The price is CA $131
CA $149 total
includes taxes & fees
Sep 2 - Sep 3
Sonesta ES Suites Annapolis
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (130)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
The price is CA $315
CA $346 total
includes taxes & fees
Aug 17 - Aug 18
Parsonage Inn
Laurel Grove Inn on the South
Land view from property

Laurel Grove Inn on the South

3.5 star property
9.0 out of 10, Wonderful, (519)
"Beautiful property and lovely hosts."
The price is CA $248
CA $282 total
includes taxes & fees
Aug 17 - Aug 18
Laurel Grove Inn on the South
Cozy centrally located studio with WiFi and AC in delightful Port Republic, MD
Fridge, microwave, stovetop, coffee/tea maker

Cozy centrally located studio with WiFi and AC in delightful Port Republic, MD

10.0 out of 10, Exceptional, (3)
"Very friendly and convenient!"
The price is CA $99
CA $231 total
includes taxes & fees
Aug 26 - Aug 27
Cozy centrally located studio with WiFi and AC in delightful Port Republic, MD
The Tilghman Island Inn
Outdoor banquet area

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (101)
"Beautiful location on the water. The staff are super nice and helpful. The restaurant is very good. We had an excellent house smoked pulled pork sandwich and a shrimp po boy."
The price is CA $282
CA $310 total
includes taxes & fees
Aug 24 - Aug 25
The Tilghman Island Inn
Executive Inn And Suites
Exterior

Executive Inn And Suites

2.0 star property
7.2 out of 10, Good, (540)
"Clean and friendly staff"
The price is CA $131
CA $149 total
includes taxes & fees
Aug 27 - Aug 28
Executive Inn And Suites
Sleep Inn & Suites Near Joint Base Andrews - Washington Area
Exterior

Sleep Inn & Suites Near Joint Base Andrews - Washington Area

2.5 star property
7.4 out of 10, Good, (803)
"Hotel was nice but limited restaurants to choose from. "
The price is CA $104
CA $255 total
includes taxes & fees
Sep 1 - Sep 2
Sleep Inn & Suites Near Joint Base Andrews - Washington Area
Holiday Inn Express Waldorf by IHG
Exterior

Holiday Inn Express Waldorf by IHG

2.5 star property
8.2 out of 10, Very good, (975)
"Great place to stay "
The price is CA $146
CA $162 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express Waldorf by IHG
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesapeake Beach Hotel Reviews

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Very nice stay"
Anthony 1-night trip
Posted 19 hours ago
St Michaels Inn