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Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

Compare 410 Vacation Homes in Chesapeake Beach with updated reviews, rates, and availability.

The Blue Crab Beach House - Free beach passes
Fridge, microwave, oven, stovetop

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (52)
"The Blue Crab Beach House was perfect for my wife and I and our dog. Very comfortable with a great backyard space for our dog. We loved the location - it’s just a short walk to restaurants and the bay. Very enjoyable stay and we hope to return."
The Blue Crab Beach House - Free beach passes
Modern Waterfront House with amazing views of the ChesapeakeBay!
Fridge, microwave, oven, stovetop

Modern Waterfront House with amazing views of the ChesapeakeBay!

Modern Waterfront House with amazing views of the ChesapeakeBay!
Sweet Bamboo Beach Cottage
Property grounds

Sweet Bamboo Beach Cottage

10.0 out of 10, Exceptional, (73)
"Needed a little quiet time, and the fresh air. Had a nice time. The house is clean,stocked with basic essentials. The beds are comfortable, that is super important to me, I also enjoyed the color choices and decorations. Tracy was prompt and thorough. I’d stay again . "
Sweet Bamboo Beach Cottage
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Property grounds

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (88)
"Ritchie, our host was extremely accommodating. Home looked exactly like the pictures. Very clean and comfortable. Water front! Many good restaurants within walking distance."
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
3 bedrooms, free WiFi, bed sheets

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (34)
"Great location with two parking spots and a small yard. Great for family vacation. "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Interior

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (113)
"This place was a wonderful spot for our family to have a long weekend getaway. It's on a bluff right next to the ocean with a glorious view and a stairway access to the beach. The beds are comfortable, the house has lots of great spaces to relax or play games, and the beach is a wonderful space to explore, find seashells and possibly a fossil sharks tooth (we had no luck there, but we did find a whale vertebrae, so that's something!). But in any event, we highly recommend! "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Interior

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

2.0 star property
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
The Lazy Crab Beach House - Free beach passes
Exterior

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (46)
"Exactly as described. Appreciated coffee & cream upon arrival too."
The Lazy Crab Beach House - Free beach passes
Relax on Kent Island in 3 Bedroom Home w/Waterview
Smart TV

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (34)
"Clean, Spacious, and exactly as advertised! "
The price is SAR 361
SAR 1,039 total
includes taxes & fees
20 Apr - 21 Apr
Relax on Kent Island in 3 Bedroom Home w/Waterview
The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (4)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is SAR 732
SAR 1,407 total
includes taxes & fees
8 May - 9 May
The Cottage
7 mins away from Downtown Annapolis
Fridge, microwave, oven, coffee/tea maker

7 mins away from Downtown Annapolis

9.8 out of 10, Exceptional, (16)
"Loved the house, we were glad to be able to book it on short notice for a large group! Beds were insanely comfortable, and the house had everything we needed. It was clean, comfortable, and a fantastic location. Only downside is that the common areas (living room/kitchen/dining area) are a bit small if you have a larger group (8). Overall a great stay and would stay again!!"
7 mins away from Downtown Annapolis
Walk to Everything House
Smart TV

Walk to Everything House

10.0 out of 10, Exceptional, (78)
"Great location. Loved being near town and the Blue Crab. "
Walk to Everything House
Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub
Fridge, microwave, oven, stovetop

Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub

9.6 out of 10, Exceptional, (24)
"The property is beautiful. The house is spacious and has comfortable beds and excellent bathrooms. There were some things that could make a stay so much better. The bedrooms need at least one chair. Although there were books in a drawer with directions for the high end appliances, each one should have a quick explanation on usage next to it. The information said the table seated 8 and yet there were only six chairs! A putting green was described and even showed a picture of one in the original...
Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub
25-50% Off~Private Beach~Hot Tub~Fire Table~
Terrace/patio

25-50% Off~Private Beach~Hot Tub~Fire Table~

10.0 out of 10, Exceptional, (22)
"Our girls' weekend at this VRBO was absolutely perfect! From the moment we walked in, we were blown away by the gorgeous interior and stunning views. The house was fully equipped with everything we needed, making our stay incredibly comfortable and convenient. The hot tub was a huge hit and added an extra touch of luxury to our getaway.The beds were incredibly comfortable, and the entire house was spotlessly clean upon our arrival. We truly appreciated the attention to detail.The host was...
25-50% Off~Private Beach~Hot Tub~Fire Table~
Wright's Cottage- Pet's Welcome & EV Charging
1 bedroom, iron/ironing board, WiFi, bed sheets

Wright's Cottage- Pet's Welcome & EV Charging

9.8 out of 10, Exceptional, (6)
"Great location, cozy cottage, good for dogs, lots to do in and around Annapolis. "
The price is SAR 375
SAR 1,318 total
includes taxes & fees
21 Apr - 22 Apr
Wright's Cottage- Pet's Welcome & EV Charging
Cozy Cottage 3 beds 2 baths
Fridge, microwave, oven, stovetop

Cozy Cottage 3 beds 2 baths

9.8 out of 10, Exceptional, (78)
"Absolutely perfect, will stay here again and again when visting family in Maryland. "
Cozy Cottage 3 beds 2 baths
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Outdoor pool, a heated pool

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (38)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
5 bedroom, 8 bed, 3 story house a block from beach
Fridge, microwave, oven, stovetop

5 bedroom, 8 bed, 3 story house a block from beach

9.6 out of 10, Exceptional, (13)
"Everything went extremely smooth. Check in was easy. House was nice and clean. Had a lot of fun with the gaming stuff they had set up! The house had everything you could imagine and more! Owners were extremely nice and informative. Recommended good places to go and eat. Overall great experience and would definitely go again."
5 bedroom, 8 bed, 3 story house a block from beach
Beautiful Waterfront Retreat in Cambridge!
Fridge, microwave, oven, stovetop

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (33)
"The perfect Thanksgiving. House was just right for family of three although more people would have been fine too. Lived the crab shack and played lots of pool and ping pong. Kitchen well stocked. Owners were prompt in responding to any questions. We would come back in a heartbeat."
The price is SAR 1,032
SAR 1,909 total
includes taxes & fees
12 May - 13 May
Beautiful Waterfront Retreat in Cambridge!
Bay views with kayaks, bikes, fire pit, crabbing and more
Fridge, microwave, oven, stovetop

Bay views with kayaks, bikes, fire pit, crabbing and more

9.6 out of 10, Exceptional, (17)
"Very clean, everything as described. Awesome host, communication an A+. Would definitely stay again, if we are in the area."
Bay views with kayaks, bikes, fire pit, crabbing and more
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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Other property types in Chesapeake Beach

Family Beach House: Spacious Deck, Grill & Views
Pool

Family Beach House: Spacious Deck, Grill & Views

9.6 out of 10, Exceptional, (4)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is SAR 1,032
SAR 2,099 total
includes taxes & fees
14 May - 15 May
Family Beach House: Spacious Deck, Grill & Views
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
Exterior

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

10.0 out of 10, Exceptional, (77)
"An absolutely beautiful, architecturally fascinating, spotlessly clean, well stocked home with views that go on for literally miles. We spent a late winter weekend there with a fire roaring in the fireplace and mussels on the stove. Hosts were exceptionally responsive and very attentive. Highly recommended. One of the best experiences we've ever had in home rentals! "
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
Chesapeake Houseboat Getaway on Kent Island, Maryland
Smart TV, fireplace

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (24)
"Our weekend stay at Julia’s Arc was truly the perfect weekend!!! The location is perfect and the boat is so clean, cozy, beautifully decorated, and generously stocked. We felt so calm and happy during our whole stay. The top deck is a perfect spot to have a cup of coffee or watch the sunset. Plus, the host, Julia was so accommodating and sweet. We really hope to go back soon! "
Chesapeake Houseboat Getaway on Kent Island, Maryland
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.