Search and Rent Chesapeake Beach Condos

Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6
No exact matches found, but these alternatives could be just right

Recommended hotels in Chesapeake Beach

Outdoor wedding area

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,008 reviews)
"Great place to stay with lovely views"
United States
David
$162 nightly
The price is $177
May 18 - May 19
Total with taxes and fees
Rod 'N' Reel Resort
Pool

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
$470 nightly
The price is $493
May 19 - May 20
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views
Free daily continental breakfast

SureStay by Best Western Prince Frederick

SureStay by Best Western Prince Frederick
2.5 star property
Prince Frederick
7.6 out of 10, Good, (244 reviews)
"Great staff and Room was very clean. Me and my wife enjoyed it. We will definitely be back."
United States
James
$78 nightly
The price is $86
May 18 - May 19
Total with taxes and fees
SureStay by Best Western Prince Frederick
Terrace/patio

Hilton Garden Inn Solomons

Hilton Garden Inn Solomons
3.0 star property
Solomons
8.6 out of 10, Excellent, (663 reviews)
"The hotel was nice and clean in a great location. The breakfast was different i came down and they had fruit pastries and cereal didnt see eggs sausage and potatoes like other hilton hotel i have visited. But over all i will be going back to stay again."
United States
Kenya
$122 nightly
The price is $136
May 24 - May 25
Total with taxes and fees
Hilton Garden Inn Solomons
Reception

Spark by Hilton Waldorf

Spark by Hilton Waldorf
3.0 star property
Waldorf
8.2 out of 10, Very Good, (131 reviews)
"Staff was top notch, they are what made the stay extremely enjoyable "
United States
Joshua
$84 nightly
The price is $93
Jun 2 - Jun 3
Total with taxes and fees
Spark by Hilton Waldorf
Front of property

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1,002 reviews)
"We had a lovely stay and would go back again! Pleasant staff and a short ride to everything."
United States
JoAnn
$120 nightly
The price is $132
Jun 1 - Jun 2
Total with taxes and fees
St Michaels Inn
Exterior

Holiday Inn Express Prince Frederick by IHG

Holiday Inn Express Prince Frederick by IHG
2.5 star property
Prince Frederick
8.8 out of 10, Excellent, (716 reviews)
"This hotel is currently (5/7/26) being renovated. This is probably the first hotel I stayed at that I didn’t feel like I needed to check for cleanliness. I wouldn’t have felt weird walking barefoot if I had needed to. The room was spacious and clean. Full, large bottles of shampoo, conditioner, body wash, lotion and hand soap were on board. The staff was amazing! Friendly, with great personalities and made you feel very welcome! And the continental breakfast was very good. They even provided...
United States
Corey
$128 nightly
The price is $142
May 24 - May 25
Total with taxes and fees
Holiday Inn Express Prince Frederick by IHG
Reception

Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick
3.0 star property
Prince Frederick
8.6 out of 10, Excellent, (954 reviews)
$127 nightly
The price is $141
May 17 - May 18
Total with taxes and fees
Springhill Suites by Marriott Prince Frederick
Lobby

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
8.8 out of 10, Excellent, (243 reviews)
"Rooms were clean staff very welcoming."
United States
Maurice
$105 nightly
The price is $120
May 24 - May 25
Total with taxes and fees
Candlewood Suites Annapolis by IHG
Property grounds

Sandaway Suites & Beach

Sandaway Suites & Beach
3.0 star property
Oxford
9.4 out of 10, Exceptional, (160 reviews)
"The rooms were so thoughtfully laid out. Coffee and a breakfast goodie bag was delivered in a thermos each morning. Great view of the water. Looking forward to staying here again!"
United States
Caitlin
$191 nightly
The price is $210
May 14 - May 15
Total with taxes and fees
Sandaway Suites & Beach
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (20 reviews)
"Although the house itself could use some maintenance, our stay was very comfortable. The rooms were spacious and it had all the amenities we needed. "
United States
Donovan B.
$280 nightly
The price is $309
May 14 - May 15
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes
Front of property

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (441 reviews)
"Wonderful rooms and many amenities."
United States
Gene
$249 nightly
The price is $274
May 26 - May 27
Total with taxes and fees
The Wildset
Exterior

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (44 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
$321 nightly
The price is $340
May 14 - May 15
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Front of property

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (485 reviews)
"absolutely perfect for this traveler!"
United States
BENNY
$263 nightly
The price is $300
May 27 - May 28
Total with taxes and fees
Anchored Inn at Hidden Harbour Marina
Property grounds

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (8 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
$241 nightly
The price is $266
May 12 - May 13
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Outdoor banquet area

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (132 reviews)
"Spotless room! Well kept grounds. Would definitely stay here again."
United States
Bethany
$250 nightly
The price is $275
May 17 - May 18
Total with taxes and fees
The Tilghman Island Inn
Porch

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (134 reviews)
"We really enjoyed our stay at The Parsonage. The property and room were kept well. The staff were sweet and attentive. Very good location as far as walking distance to shops, restaurants and the waterfront area. I would certainly return and certainly recommend to anyone visiting St. Michael’s. "
United States
Katie
$250 nightly
The price is $275
May 12 - May 13
Total with taxes and fees
Parsonage Inn
Free daily self-serve breakfast

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,005 reviews)
"Very friendly and helpful staff. Room was very comfortable and well laid out. Would definitely stay again! "
United States
Cristi
$124 nightly
The price is $141
May 24 - May 25
Total with taxes and fees
SpringHill Suites by Marriott Annapolis
Free daily buffet breakfast

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (1,009 reviews)
"Wonderful place to stay!"
United States
Michele
$106 nightly
The price is $121
May 26 - May 27
Total with taxes and fees
Sonesta ES Suites Annapolis
Basic Single Room | Desk, laptop workspace, blackout drapes, free WiFi

Rips Country Inn

Rips Country Inn
2.5 star property
Bowie
6.6 out of 10, (67 reviews)
"Room was extremely outdated. Carpets are disgustingly filthy, unclean scent."
United States
heidi
$76 nightly
The price is $86
May 13 - May 14
Total with taxes and fees
Rips Country Inn
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 Beach Hotel Reviews

St Michaels Inn

St Michaels Inn

6/10 Okay
"I was surprised to see an invoice from Expedia that included taxes yet also be charged taxes upon checkout of the motel. I did not appreciate that surprise."
Katharine 2-night trip
Posted 12 hours ago
St Michaels Inn

Find out more about Chesapeake Beach

Chesapeake Beach Condo Rentals information

Number of reviews
8,338
Accommodation
3 Condo Rentals
Lowest Price
$86
Highest Price
$493

Frequently asked questions

Why book your condo in Chesapeake Beach with Expedia?
Booking a condo in Chesapeake Beach is as simple as working out your travel dates and selecting a place that meets your needs. Chasing something low cost or luxurious, or a stay that also offers a pool and free WiFi? Use Expedia's search filters to narrow your results even further and find your ideal pad.
How can I find cheap condos in Chesapeake Beach?
With Expedia's handy filter tool, getting your hands on cheap condos in Chesapeake Beach is a piece of cake. To discover stays that'll make your wallet happy, fine-tune your search results by budget, amenities and star rating.
What is there to do in Chesapeake Beach near my condo?
Once you've unpacked and settled in, venture out and explore the awesome things Chesapeake Beach has on offer. Breezy Point Beach is a top attraction to add to your must-see list.

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