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Compare 321 Vacation Homes in Chesapeake Beach with updated reviews, rates, and availability.

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

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

9.6 out of 10, Exceptional, (19)
"We visited with our family with ages ranging from 5-66. Everyone enjoyed their stay. There were plenty of things to do on the water (kayak, SUP, fish, etc). The pool was a great place to cool off. The house was secluded but close enough to town to pop in for dinner, supplies, etc. We had a blast!"
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Walk to Everything House

10.0 out of 10, Exceptional, (76)
"Clean and nice place to stay"
Walk to Everything House

Brand New Spacious Luxury Home

10.0 out of 10, Exceptional, (5)
"This home was exactly as described. Very clean, comfortable and well equipped. This home was beautifully designed, well furnished and had everything we need to enjoy a short friends getaway. Thank you for a wonderful stay. "
Brand New Spacious Luxury Home

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

9.4 out of 10, Exceptional, (30)
"This was our third year celebrating our family Thanksgiving in this home. Three generations coming from three different states. Location offers an easy drive for everyone, and the home is large enough for us spread out yet gather for meals. The host listened to our comments from previous years and addressed all of our concerns. Will be returning again."
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

Waterfront Cheerful 6 BR Home with Private Pier

9.8 out of 10, Exceptional, (31)
"The property was clean and comfy. Our group of 11 were very comfortable in this beautiful house "
Waterfront Cheerful 6 BR Home with Private Pier

Serene waterfront sunsets in this sprawling historic Annapolis home

9.6 out of 10, Exceptional, (28)
"Gorgeous neighborhood and a very cool house. The view is amazing and the sunsets were incredible. The house could have been cleaner, there were stains on some of the furniture, and the kitchen was a mess -- we had to wash every pot or pan before using it and the cabinets above the stove were grimy. There was only 1 dish towel in the house. Most of the towels and sheets were pretty old and threadbare and needed to be replaced. Overall very good but not 5 star which is what they are striving...
Serene waterfront sunsets in this sprawling historic Annapolis home

Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D

9.8 out of 10, Exceptional, (9)
"This was a perfect home away from home for four adults and two children, ages 5 and 7. The children loved the loft area and named it the "Kids Zone." The pool and the massive amount of toys were a big hit too. Lots of towels, kitchen equipment, beautiful bed linens, outdoor and indoor spaces made this a wonderful vacation home. While the waterfront was beautiful the front porch was our favorite spot in the morning, Just lovely."
Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D

Pet-Friendly Annapolis Home: Walk to Beach!

10.0 out of 10, Exceptional, (6)
"Property is very well maintained and you feel at home. Proximity of the little park is perfect for young kids. Street very quiet. Parking space is great. We had a great family time and we will be back when weather is warmer to enjoy access to the beach."
Pet-Friendly Annapolis Home: Walk to Beach!

Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

10.0 out of 10, Exceptional, (5)
"Nice location. The house had everything we needed for our stay. The host was available by phone for any questions we had. I would stay again the next time I visit North Beach"
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

9.6 out of 10, Exceptional, (20)
"Terrific house, beautiful scenery, property management was very responsive and helpful. Would stay again. Thank you. "
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

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

9.8 out of 10, Exceptional, (33)
"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Waterfront Escape Near Annapolis

10.0 out of 10, Exceptional, (13)
"Good stay. Excellent location and facility es"
Waterfront Escape Near Annapolis

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (49)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes

Adorable waterside cottage with pool Beach community

9.4 out of 10, Exceptional, (39)
"Neighborhood was cute, perfect spot to relax. Pool was awesome. Kitchen was large and had a great veiw. It was just what we needed to get away."
Adorable waterside cottage with pool Beach community

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

The Cottage

10.0 out of 10, Exceptional, (2)
"Couldn’t have asked for better- I appreciate the communication and willingness to work with us on a quick turn around trip. Clean. Easy to get to. Accurate description. Quiet neighborhood. 10/10 would stay again. "
The price is SAR 863
SAR 1,603 total
includes taxes & fees
24 Feb - 25 Feb
The Cottage

Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

10.0 out of 10, Exceptional, (1)
"This property is a phenomenal place to spend time with family and enjoy beautiful St. Michael’s. The house is well stocked and convenient to town. We’d love to come back. "
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

Jackson's Bunker in Eastport with fenced-in backyard

9.8 out of 10, Exceptional, (9)
"We were just minutes away from all the good restaurants, shops, sights, and harbor. Safe area. Place as described, but no nightstands by any of the beds. One room had a closet and no drawers, the other drawers and no closets. Manager responded immediately to any questions. Great customer service. We would stay there again."
Jackson's Bunker in Eastport with fenced-in backyard

6 Mi to Dtwn: Family-Friendly Home in Annapolis!

9.4 out of 10, Exceptional, (3)
"We were in Annapolis for our Midshipman’s birthday. There was plenty of room to have friends over for dinner. The house was clean , kitchen well stocked, and our college kids had fun playing the games provided. The proximity to The Yard was very nice. We all enjoyed our stay. "
6 Mi to Dtwn: Family-Friendly Home in Annapolis!
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 on Private Beach, Designed by Award Winning Architect!

10.0 out of 10, Exceptional, (75)
"Panoramic views of the water and sunsets. Loved the elevation of the property and the gorgeous trees that framed but did not obstruct the view. The layout was great and attention to detail throughout the home impressive."
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

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 1,641 total
includes taxes & fees
3 Mar - 4 Mar
Family Beach House: Spacious Deck, Grill & Views

Cozy Cottage with access to and partially obstructed views of the bay.

9.4 out of 10, Exceptional, (18)
"This home was lovely and superrrr amazing! Property was clean in a beautiful spot with great scenery and not to mention the loads of snacks for us. Thank you Lisa for also being so communicative with us, our trip absolutely rocked because of your lovely home."
Cozy Cottage with access to and partially obstructed views of the bay.
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.