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Search Vacation Homes in Chesapeake Beach

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Compare 320 Vacation Homes in Chesapeake Beach with updated reviews, rates, and availability.

Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (87)
"This lovely home sets in a beautful location. The hosts are available and accommodating. They are definitely available if needed. The house itself is very comfy. All amenities you need are there. "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
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
Your Annapolis Adventure Starts Here!!
10.0 out of 10, Exceptional, (136)
"My family and I love staying here! It's clean, beautiful, spacious, and comfortable. It's home away from home. I love all the special touches--lots of cozy blankets, the beautiful decor, the comfortable beds. And, of course, it's close to anything you want to do in Annapolis or the surrounding areas. During this stay, we were able to enjoy the patio, which was especially wonderful to be able to do in November. My favorite spot is the sitting area next to the kitchen; it's a perfect place to...
Your Annapolis Adventure Starts Here!!
Waterfront Home on the Chesapeake Bay!
10.0 out of 10, Exceptional, (23)
"Very nice getaway for a family reunion group of 8 while we visited our son at the USNA. Location is 35 min from US Naval academy; perfect to feel like he's really getting off the Yard. Having such a huge yard really offered lots to do (corn hole, frisbee, etc.). The incredible water views drew us all back home every night, along with the gorgeous sunsets. Had really nice weather so we took advantage of the 3 kayaks and paddled around the marina. Bikes were convenient too, as well as small...
Waterfront Home on the Chesapeake Bay!
Edgewater/Mayo Getaway!
9.8 out of 10, Exceptional, (10)
"We only stayed one night but the house was perfect for our needs. The main family room/kitchen area was perfect for all of us to comfortably sit together, and the bedroom layout was great for two families (two “wings”). The hosts were super responsive and accommodating. Would just suggest two hairdryers (one in each bathroom - if there was a second, we did not see it) and shower soap. The bed in the primary bedroom was very comfortable and everything went smoothly. "
The price is AED 735
AED 1,991 total
includes taxes & fees
3 Dec - 4 Dec
Edgewater/Mayo Getaway!
La Maison - Stunning waterfront views with pool
10.0 out of 10, Exceptional, (90)
"Gorgeous, serene and well-appointed property! It was very comfortable for our group of four women. Highly recommend for a family or friends."
La Maison - Stunning waterfront views with pool
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (49)
"Wonderful location to downtown Annapolis! Beautiful home, well maintained and plenty of room. The porch overlooking the bay has a table for 10 which provided a wonderful setting for our family. This is our second stay and we’ll absolutely stay again "
Charming Annapolis WaterVIEW Home
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
9.6 out of 10, Exceptional, (12)
"We appreciate the hospitality and responsiveness of our gracious host. We would stay again and look forward to our next visit. Recommend staying to all looking for a tranquil getaway in the Annapolis area."
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (32)
"We were able to walk to most places we wanted to go in town. The house was a little small but everything we needed was there and the property managers were easy to reach. We had a great time!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (31)
"This house exceeded our expectations in every way. The kitchen is large and well-appointed, the beds are comfortable, and the peace and quiet is priceless. We enjoyed morning coffee in the sunroom, table tennis in the crab house, sunsets from the dock, and stargazing at the firepit. If you desire peace and quiet this house is a perfect choice!"
The price is AED 1,010
AED 1,884 total
includes taxes & fees
3 Dec - 4 Dec
Beautiful Waterfront Retreat in Cambridge!
Charming Cottage with Hot Tub 1 Block from the Bay
10.0 out of 10, Exceptional, (8)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is AED 992
AED 2,131 total
includes taxes & fees
3 Dec - 4 Dec
Charming Cottage with Hot Tub 1 Block from the Bay
Walk to Everything House
10.0 out of 10, Exceptional, (72)
"We thoroughly enjoyed the convenience of walking to shops, restaurants, and waterfront! Residence was charming and clean! Only minor issue was we couldn’t locate the iron- just the ironing board! We still had fun but we’re just a bit wrinkled!😁"
Walk to Everything House
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
10.0 out of 10, Exceptional, (32)
"Perfect large space on a quiet and pretty area. Really great space. "
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Coastal Edgewater Home w/ Private Hot Tub!
9.0 out of 10, Wonderful, (11)
"It was just my husband and me. We were visiting family, and this house was a very convenient 3-minutes from their house. Quiet location; nice water view. House was very clean and comfortable."
Coastal Edgewater Home w/ Private Hot Tub!
WATERFRONT!!! The River's Roost on The Patuxent River
10.0 out of 10, Exceptional, (18)
"This house is absolutely fabulous! Very spacious, stocked with necessary supplies and many amenities. Beautiful property and views of the water, sunrises and sunsets. We especially liked all the wonderful decks, kitchen on the bottom level, many bathrooms, and comfortable furnishings. John and Christina were excellent host. They responded immediately to any concerns or questions. They were easy to communicate with during the check-in and check-out process. I would definitely love to...
WATERFRONT!!! The River's Roost on The Patuxent River
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
9.6 out of 10, Exceptional, (19)
"The house was just as it was listed!! Our annual family vacation was so much fun here! Plenty of room, very clean, and fully stocked! Peddle boats, kayaks, and pool used daily!! Fire every night!!! Thank you for the wonderful hospitality!!!"
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!
9.8 out of 10, Exceptional, (21)
"We went to this wonderful home for our 32nd wedding anniversary and it was so lovely. The home was so comfy and well stocked, the beds were very comfortable and the sunsets were spectacular. We enjoyed every minute! Barbara was just so delightful and helpful. She made everything perfect! Would love to stay again some time."
Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!
Blue Heron Retreat on the Water
10.0 out of 10, Exceptional, (10)
"The place was as described. Great communication and check in. All professional."
Blue Heron Retreat on the Water
One-level waterfront home with beach and views all the way to the Bay Bridge
2.0 star property
9.6 out of 10, Exceptional, (5)
"We enjoyed our time here. The location is perfect, right on the water with beautiful sunset views. I thought the home could have some more seating space in the main living room area, but it worked well for our family of 5 (4 adults, 1 child). There was a bit of a musty smell throughout the duration of the stay, but it didn't hinder our enjoyment of the property. We'd definitely stay there again."
One-level waterfront home with beach and views all the way to the Bay Bridge
Spacious 5-bedroom house with Pier, AC and WiFi in delightful Edgewater
2.0 out of 10, (1)
"The property should not be rented. The house structurally is not safe, there are many safety hazards. There is no front door. A storm door is not a door. We felt unsafe at night. The stove was not useable. There is no range to it. You cannot use it without a range above it. There were several outlets without outlet covers and were pulled out, the fridge does not work - it does not get cold enough, the freezer was full of someone else’s food. bugs, mice, everywhere in the basement and upstairs....
Spacious 5-bedroom house with Pier, AC and WiFi in delightful Edgewater
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

Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (70)
"The house was amazing! From the moment the front door opened it was a visual feast. The views are incredible, it's quiet, private and very relaxing. There were personal elements reflecting the current and original owners which we found very interesting and the attention to detail throughout was superb! Everything was incredibly well stocked with a multitude of extras. "
Mid-Century Modern and Marvelous on the Bay
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 AED 624
AED 1,766 total
includes taxes & fees
23 Nov - 24 Nov
Family Beach House: Spacious Deck, Grill & Views
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (217)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, 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.