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Compare 538 Vacation Homes in Claiborne with updated reviews, rates, and availability.

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
10.0 out of 10, Exceptional, (5)
"This property is a gem! Close to everything but without too much hustle or bustle! Great amenities. Kimberley is very easy to work with and graciously accommodated my need for late check out. Parking is private and off street!"
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (26)
"Great house and location. Very family friendly! "
The price is AED 1,010
AED 1,892 total
includes taxes & fees
25 Sep - 26 Sep
Beautiful Waterfront Retreat in Cambridge!
Walk to Everything House
10.0 out of 10, Exceptional, (69)
"We enjoyed this lovely historic home that is a short walk to attractions in St Michaels. It has a nice patio out back and is very close to a coffee shop."
Walk to Everything House
Blocks to the Boardwalk!
9.8 out of 10, Exceptional, (31)
"We had fun"
Blocks to the Boardwalk!
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
10.0 out of 10, Exceptional, (5)
"Our stay here with Brenda was amazing! She was very pleasant and professional! She even suggested a few things for us to do in the area. The home had everything we could have needed and wanted. The place looks even better in person than the pictures! We can’t wait to book again!"
The price is AED 643
AED 1,219 total
includes taxes & fees
24 Sep - 25 Sep
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
River Front, Private Single Family Home
10.0 out of 10, Exceptional, (4)
"We loved the house with all the amenities and especially the expansive yard, bay view, hot tub and fire ring. "
River Front, Private Single Family Home
Waterfront Cottage on the Eastern Shore
9.6 out of 10, Exceptional, (7)
"We rented the house for the weekend and to host a surprise birthday party. We had the party right at the beach and the host/concierge were able to help us with everything we needed. They really went out of their way for us, and it made a huge difference in the party’s success! Plus, you can’t beat the view and the Chesapeake Bay sunsets !!"
The price is AED 1,282
AED 3,008 total
includes taxes & fees
1 Oct - 2 Oct
Waterfront Cottage on the Eastern Shore
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (96)
"We took a quick weekend getaway to Annapolis. It was our first time there and we loved it. The location of the house is perfect. We were so close to the bay with tons of restaurants nearby. It was a quiet neighborhood though so we didn’t feel like we were in a party scene. The house was so clean. The pool was huge (bigger than expected), and the host went above and beyond. Liz was an excellent communicator. She had more than enough essentials at the house that made our stay so relaxing. I felt...
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (29)
"Perfect for a 3 day visit! "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Dollhouse in Central Historic St Michaels
9.6 out of 10, Exceptional, (44)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
9.6 out of 10, Exceptional, (39)
"I was very impressed with this property. It's a cute little house that was comfortable for our group of 6. It was at a great location, too. The owner was quick to respond to my questions. If we visit North Beach again, I will definitely book here again."
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
10.0 out of 10, Exceptional, (89)
"It was nice to get outside DTA and see another part of Annapolis. 15 minutes from DTA it was quiet and beautiful small cottage perfect for our family. The home was clean and designed well. We would stay again. Thank you!!!"
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Nautical charmer near the City Dock with open layout, W/D, & AC
10.0 out of 10, Exceptional, (5)
Nautical charmer near the City Dock with open layout, W/D, & AC
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
2.5 star property
10.0 out of 10, Exceptional, (4)
"Cannot recommend enough! Lauren was so sweet and accommodating. The home is gorgeous and filled with so much charm. Perfect location. An absolute 10/10! "
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Charming 3-bedroom house in Annapolis ⚓️🛥️⛵️ on the Chesapeake Bay
8.0 out of 10, Very Good, (1)
"The house was quiet, cozy and fit our needs perfectly. The location was convenient for our trips to and from DTA. Our host, Abber was available for any questions we had and made our stay enjoyable. "
Charming 3-bedroom house in Annapolis ⚓️🛥️⛵️ on the Chesapeake Bay
Pet-Friendly Annapolis Home: Walk to Beach!
Pet-Friendly Annapolis Home: Walk to Beach!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (15)
"We stayed at this beautiful property for my 50th birthday Girls trip. We were 15 of us. The house is very spacious, attractive pool and water facing sun room. Some of the rooms have gorgeous views of the water. They have a pickleball court, large family room where we could all hang out together"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (198)
"While the cottage may have some of the historic/ older quirks, it is a wonderful (and beautiful ) property that we would highly recommend! We loved the walk-ability to downtown Annapolis and the Naval Academy. Despite its close location, it’s quiet at night lending to a good nights sleep 😊. The owner provided us some great insight on the location as well. "
Directly Across from Gate One & Steps from the Waterfront
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (47)
"Great house qoth ocean view"
Charming Annapolis WaterVIEW Home
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (14)
"Amazing time with friends and family at this property. I just need to remember to buy more bug spray haha. Regardless though- it was worth it"
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
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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 Claiborne

Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (83)
"The house was clean and comfortable. Walking distance to a local restaurant. Screened porch was great for watching the sunrise in the morning and the boats coming in and out of harbor "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
10.0 out of 10, Exceptional, (75)
"Lovely house and location! Pat and Ken were rapid and personable with every interaction."
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (15)
"We stayed at this beautiful property for my 50th birthday Girls trip. We were 15 of us. The house is very spacious, attractive pool and water facing sun room. Some of the rooms have gorgeous views of the water. They have a pickleball court, large family room where we could all hang out together"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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.