Claiborne Holiday Rentals

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Our top choices for Claiborne holiday rentals

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (34 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is AU$385
includes taxes & fees
23 Mar - 24 Mar
Charming Coastal/Country Home w/3 Acres & Sauna!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (43 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is AU$403
includes taxes & fees
19 Mar - 20 Mar
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is AU$584
includes taxes & fees
18 Mar - 19 Mar
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (36 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is AU$468
includes taxes & fees
18 Mar - 19 Mar
Large 2 bedroom house with private parking in a nice neighborhood

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is AU$751
includes taxes & fees
19 Mar - 20 Mar
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (19 reviews)
"Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed"
United States
Elaine D.
The price is AU$459
includes taxes & fees
18 Mar - 19 Mar
Walk to Beach! King Bed & Free Beach Passes

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is AU$667
includes taxes & fees
18 Mar - 19 Mar
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is AU$633
includes taxes & fees
23 Mar - 24 Mar
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AU$568
includes taxes & fees
18 Mar - 19 Mar
Waterfront Oasis of Annapolis Star

Waterfront Getaway, Dock Your Boat & Play!

Waterfront Getaway, Dock Your Boat & Play!
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
The price is AU$461
includes taxes & fees
18 Mar - 19 Mar
Waterfront Getaway, Dock Your Boat & Play!

Luxury Pool Loft sleeps 4

Luxury Pool Loft sleeps 4
Cape Saint Claire
10.0 out of 10, Exceptional, (4 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is AU$538
includes taxes & fees
18 Mar - 19 Mar
Luxury Pool Loft sleeps 4

40' Bristol sailboat with spectacular views

40' Bristol sailboat with spectacular views
Stevensville
The price is AU$599
includes taxes & fees
18 Mar - 19 Mar
40' Bristol sailboat with spectacular views

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is AU$731
includes taxes & fees
18 Mar - 19 Mar
Cute bungalow blocks to Stadium

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is AU$760
includes taxes & fees
24 Mar - 25 Mar
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Shady Side
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
The price is AU$615
includes taxes & fees
18 Mar - 19 Mar
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

London Towne Bungalow w/Loft - Walk to the Beach!

London Towne Bungalow w/Loft - Walk to the Beach!
Edgewater
9.0 out of 10, Wonderful, (4 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is AU$641
includes taxes & fees
18 Mar - 19 Mar
London Towne Bungalow w/Loft - Walk to the Beach!

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
The price is AU$464
includes taxes & fees
30 Mar - 31 Mar
Cozy 2br home w/ parking in downtown Annapolis

Annapolis Garden Suite

Annapolis Garden Suite
Epping Forest
10.0 out of 10, Exceptional, (14 reviews)
"We had a quick overnight stay to attend an event at the Naval Academy! This was the perfect spot!! The accommodations were exactly what we needed!! Thanks for a great stay!!! "
United States
Mary S.
The price is AU$566
includes taxes & fees
19 Mar - 20 Mar
Annapolis Garden Suite

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is AU$1,006
includes taxes & fees
18 Mar - 19 Mar
Historic Row Home | Hot Tub - 1 Block from Gate 1!

Wright's Cottage- Pet's Welcome & EV Charging

Wright's Cottage- Pet's Welcome & EV Charging
Annapolis
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
The price is AU$524
includes taxes & fees
23 Mar - 24 Mar
Wright's Cottage- Pet's Welcome & EV Charging
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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Top Claiborne Hotel Reviews

Find out more about Claiborne

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, 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 favourite 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 depend 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 AU$385 per night. Entering your travel dates in the search wizard might find you 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?

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac: This holiday home rental outside of Claiborne is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ to put you at ease 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. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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 CL Open Field. In the wider area, you’ll find St. Michaels Marina and St. Michaels Winery.

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.