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Top Holiday Rentals in Claiborne

Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (3)
"Wonderful place to stay and Erin was great. Asked about a Grill on the property and the next day we had a grill. The young adults loved the pool and water activities while the older adults enjoyed sitting on the docks watching the sunrise with a cuppa coffee. Would highly recommend this property."
The price is £1,136
per night
4 Jun - 5 Jun
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (180)
"Charming spot in the heart of Annapolis, just a few moments walk from anything you might need."
Directly Across from Gate One & Steps from the Waterfront
Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (186)
"The cottage is fully stocked, clean, and cozy. We thoroughly enjoyed sitting on the deck and watching all the wildlife."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
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Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (25)
"My family and I enjoyed our stay at the Carpenter Alley Cottage in Saint Michaels! The location was perfect -- walking distance from everything! Appreciated that there was a ground floor bedroom for my parents so they didn't have to climb the stairs and my daughter loved having her own bunk bed room! I did have a few questions about the cottage and the check-in process and my inquiries were all met with a prompt response. Would love to stay here again! (One note though is that it is a smaller,...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Exterior
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (19)
"We have nothing but great things to say about Adam and his beautiful home! He was so accommodating and the home was comfortable and spacious for our family of 5! Couldn’t have had a better experience :)"
The price is £228
per night
27 May - 28 May
Relax on Kent Island in 3 Bedroom Home w/Waterview
Beach nearby, sun-loungers, beach umbrellas, beach towels
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (39)
"It was clean and had everything we needed. We had a very comfortable stay. There are one or two steps between many of the rooms so keep that in mind."
The Blue Crab Beach House - Free beach passes
Property grounds
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, (14)
"We really enjoyed our (much too short) stay at this waterfront gem!! The property was very clean, had all the amenities that we needed for our time away.... the only complaint is that we didn't have enough time to enjoy it all!! : ) thank you so much, we will be back!"
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
10.0 out of 10, Exceptional, (60)
"We had a great stay here for my husband’s birthday. Pat and Ken were fantastic hosts and even decorated for this birthday. They provided everything we would need for our toddler and if the weather had cooperated we’d have spent hours and hours in the backyard. Really appreciative of all the attention to detail and would highly recommend this listing if you’re looking for a low-key, relaxing stay where you don’t need to worry about the details."
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (107)
"Wonderful return visit to St Michaels. This time at a fantastic historical home in perfect location. Home was everything you could ask for and more. Park your car and walk anywhere, within a very quiet neighborhood, yet minutes from all St Michaels offers. Highly recommend this Property and host."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
10.0 out of 10, Exceptional, (73)
"The cottage provides a wonderful way to experience Deale and the surrounding area. Well equipped and clean, I had everything I needed and didn't want to leave,"
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Property grounds
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (43)
"Beautiful house and views. Amenities and grounds were great. Loved the playground and beach. Peace and quiet at its finest in nature."
The price is £543
per night
27 May - 28 May
Charming Annapolis WaterVIEW Home
Outdoor pool
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (21)
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Exterior
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, (24)
"This house and property is GORGEOUS. Well maintained, beautiful setting. Amazing amenities (pool, hot tub) which enhanced our stay. We had no problem finding multiple places to all hang out and chat- the living room with plenty of seating, the dining room table with seating for at least 14, and outside in the hot tub. It was a perfect setting for valuable time away with friends! Additionally, the owner was STELLAR in communication. I very much appreciated his quick and attentive responses...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Fridge, microwave, oven, stovetop
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (80)
"This is an absolutely fantastic place to stay!! The host Liz was so easy to work with and quick to respond to any inquiries we had. We booked for the Herndon climb (#plebenomore) and cannot say enough about how perfect this house was for us. It was an easy walk to DTA and gate #1. The kitchen was well stocked and had everything needed to make several home cooked meals for our son and his friends. The sun room is beautiful and the perfect spot to enjoy a cup of coffee or breakfast! The pool was...
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Fridge, microwave, oven, stovetop
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (44)
"This house was perfect for a group of friends celebrating a 50th birthday! The house was so clean and well cared for! The front porch and outdoor backyard space provided even more room for us to gather together. We will be back!"
Recently Renovated Annapolis Home - Conveniently Located
Property grounds
Bay View Studio Apartment
10.0 out of 10, Exceptional, (25)
"If you are looking for a very spacious well-appointed one bedroom apt. style accommodation in a residential setting with lovely waterfront bay views, I highly recommend this place!"
Bay View Studio Apartment
Fridge, microwave, oven, stovetop
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
9.4 out of 10, Exceptional, (8)
"The home was lovely. We very much enjoyed our stay. The one thing that I would recommend is direction on the heat and air. We were unable to figure out what to do The downstairs was cold and when we tried to raise the temp the upstairs was unbearably hot. I also wanted to let you know there was a leak from the ceiling in the master bedroom. Lastly, My daughter lost a small hoop earring. If you find it could you please contact me to have it returned. Thank you,"
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Fridge, microwave, oven, stovetop
Waterfront Cottage on the Eastern Shore
8.0 out of 10, Very good, (1)
The price is £911
per night
17 Jun - 18 Jun
Waterfront Cottage on the Eastern Shore
Smart TV, Netflix, DVD player, streaming services
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (65)
"Extremely responsive host and beautiful cottage. Incredible location with tranquil views of the water. 5 minute walk to ice cream and nice restaurants. Easy walk (20-25 mins) otherwise into more bustling downtown Annapolis."
Amazing views, short walks to great dining!
Fridge, microwave, stovetop, dishwasher
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (4)
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Don't see what you're looking for?
See all available properties in Claiborne
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.

Claiborne Holiday Rental Travel Info

Number of holiday rentals
15
Popular accommodation
Claiborne private holiday homes
Known landmarks
St. Michaels Winery, St. Michaels Museum and Chesapeake Bay Maritime Museum
International airport
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)

Other types of properties in Claiborne you may be interested in

Exterior
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1614)
"overall the room was very clean, very spacious and service with housekeeping was fabulous. The only complain we had was we kept hearing this noise coming from the wall like if there was some kind of machine that kept going off and on, humming sound"
The price is £158
per night
9 Jun - 10 Jun
Historic Inns of Annapolis
View from property
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1045)
"Unique property, close to everything. Costly, but every hotel in the area is. "
The price is £190
per night
9 Jun - 10 Jun
Graduate Annapolis
Lobby
DoubleTree by Hilton Hotel Annapolis
4.0 star property
8.6 out of 10, Excellent, (1001)
"I was sadly visiting for a funeral and was there for a 4 nite stay. The staff was so kind and very helpful. The room was clean and comfortable. Perfect location to everything I needed. I will 100% stay at this double tree when I come back into town. "
The price is £114
per night
4 Jun - 5 Jun
DoubleTree by Hilton Hotel 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.

Everything you need to know about Claiborne holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Claiborne holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Claiborne holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Claiborne holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Claiborne. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Claiborne holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Claiborne holiday rentals we have selected for you start as low as £228 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Claiborne rentals

At Expedia, we put the best Claiborne holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Claiborne rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Claiborne holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Claiborne. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Claiborne?

Yes, there are holiday rentals close to the most popular sights in Claiborne, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Claiborne has to offer?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Claiborne offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

What’s there to see and do in Claiborne?

Explore the area and family-friendly sights such as Chesapeake Bay Maritime Museum, or get out into nature at a spot like Chesapeake Bay Environmental Center. In the wider area, you’ll find St. Michaels Winery and Matapeake State Park.

What’s a holiday rental in Claiborne like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Claiborne. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips.

Recent reviews of Claiborne properties
Expedia verified reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

5/5 Excellent
EXCELLENT LOCATION.
"Outstanding hotel in downtown Annapolis within walking distance to EVERYTHING. Parking can be a challenge but we were able to find inexpensive parking at the Whitmore Garage. A bit of a hike; however, the total bill for 2 days of parking was $10."
A verified traveller stayed at Historic Inns of Annapolis
Posted 2 days ago
Historic Inns of Annapolis