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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
9.4 out of 10, Exceptional, (16)
"We had a great stay in this beautiful property. Three good size bedrooms and two nice baths. Well equipped kitchen and nice living area. Large yard for kids or dogs and just relaxing. Convenient to restaurants and markets. Hope to visit again soon."
Bay views with kayaks, bikes, fire pit, crabbing and more
Your Annapolis Adventure Starts Here!!
10.0 out of 10, Exceptional, (134)
"Beautifully decorated home in a safe neighborhood. Centrally located to Annapolis for shopping , dining and sight seeing. Loved the cozy seating in living space and the inviting patio. Perfect place for a girl’s get-away. Highly recommend. Five stars all the way. "
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, (8)
"A great property for two families with young kids to stay. Children loved the big backyard and there was plenty of space for everyone to have their own place. We loved Beverly Triton Beach and it was easy to get downtown for the Sailboat Show as well."
The price is SAR 909
SAR 2,238 total
includes taxes & fees
4 Nov 2024 - 5 Nov 2024
Edgewater/Mayo Getaway!
La Maison - Stunning waterfront views with pool
10.0 out of 10, Exceptional, (89)
"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, (48)
"This house was perfect for our group of friends especially with infants. Easy check in, comfortable beds and room for pack and plays. Water view is amazing. Definitely worth the rent and would be interested in coming back!"
Charming Annapolis WaterVIEW Home
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
9.6 out of 10, Exceptional, (11)
"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, (31)
"Other than arriving with no sheets on beds, no towels, and no basic toiletries or kitchen cleaning set, place is very good. Cleaning service, owner, or property management firm mismanaged the prep for our arrival. Absence of sheets, towels, etc. was rectified in a bit more than 1 hour. Nice place and superb location for seeing the village. Quiet, but right in the middle of all shops, farmers market, restaurants, etc. There was a bit of a pet odor in the 1st floor bedroom. Only other comment is...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (31)
"Great property!"
The price is SAR 1,033
SAR 1,915 total
includes taxes & fees
3 Nov 2024 - 4 Nov 2024
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 SAR 1,052
SAR 2,226 total
includes taxes & fees
2 Dec 2024 - 3 Dec 2024
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, (31)
"House was spacious, clean, and exactly as described in the listings. We had a great time!"
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, (9)
"We had a relaxing stay at the Blue Heron Retreat. The house is as described. The beds were very comfortable and it was nice sitting out on the decks having our morning coffee and listening to the birds. We used the hot tub every day since it’s shaded by trees so even though we had hot weather, we were still able to use it during the day. "
Blue Heron Retreat on the Water
Waterfront home with beach and views all the way to the Bay Bridge all on one level
2.0 star property
10.0 out of 10, Exceptional, (4)
"It’s a great property to rent. The location and views are unbelievable. They do not some towel hooks in each bathroom but no other issues with this place at all."
Waterfront home with beach and views all the way to the Bay Bridge all on one level
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, (68)
"The ratings were Exceptional, so I was skeptical. However, it was beyond exceptional. The most well equipped rental we have seen. Great location. Well stocked. Excellent communication with the host. Couldn’t have asked for anything more. Definitely recommend, and will stay here again when in the area. We had a great time."
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 SAR 638
SAR 1,824 total
includes taxes & fees
6 Nov 2024 - 7 Nov 2024
Family Beach House: Spacious Deck, Grill & Views
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (48)
"This house was perfect for our group of friends especially with infants. Easy check in, comfortable beds and room for pack and plays. Water view is amazing. Definitely worth the rent and would be interested in coming back!"
Charming Annapolis WaterVIEW Home
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.