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Browse Select Claiborne Cottages

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
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, Commissioning Week
10.0 out of 10, Exceptional, (58)
"This was our sixth stay with Ken and Pat at Firefly Cottage. It is close to our son’s home and works absolutely perfectly for us whenever we’re in town to visit. Pat and Ken are great hosts, and the property has every amenity that we could need and more!"
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, Commissioning Week
Updated North Beach Cottage: Pet Friendly!
9.8 out of 10, Exceptional, (8)
"This location was perfect for our trip for a wedding. Being only a three minute walk from the rehearsal, ceremony, and reception was absolutely perfect. Being close to the deli/market as well came in handy. The house was clean and welcoming. Overall I would absolutely stay here again."
Updated North Beach Cottage: Pet Friendly!
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Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (64)
"Overall great weekend. House was better than described, views were excellent, and location was perfect! Jim was an excellent host and was incredibly helpful with the restaurant suggestions! We will be back!"
Amazing views, short walks to great dining!
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (89)
"Lovely visit. I have a 1 and 3 year old. They loved the water and meeting the llama. The room set up is confusing in the listing. Its 3 bedrooms with 2person beds and a forth bedroom w a 1person bed."
Secluded Waterfront Cottage on 200 acre farm near Queenstown
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (103)
"Really enjoyed the house and it’s location, perfect for a couples weekend!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Waterfront, cozy cottage with private pool on 27 acres of privacy
9.8 out of 10, Exceptional, (85)
"We came for the Ironman 140.6 and we lucked out finding this lovely cottage! It was the perfect location, the property was beautful, and the house was very clean and had everything we needed. Dave and Cindy were so kind and helpful! They welcomed us to the property, gave us restaurant recommendations, let us pick some figs, and were very helpful when I left something behind. We would love to stay again!"
Waterfront, cozy cottage with private pool on 27 acres of privacy
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (125)
"A lovely cottage to stay in. Lots of old world charm and location is unbeatable when want to stay in St. Michaels"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
9.8 out of 10, Exceptional, (17)
"This was the perfect space for our family of five. Check-in was a breeze and Isaac even went as far as to leave the lights on for us knowing we were getting in late. Isaac let us know he was available if we needed anything, but we did not. Despite the rain, we were able to enjoy the hot tub overlooking the creek. The view was stunning! If you are looking for a peaceful stay, this is it!"
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
10.0 out of 10, Exceptional, (20)
"Beautiful house in peaceful West Annapolis, a short distance from the local shops and restaurants and the Naval College. Well equipped, everything you need, a real home from home and a very friendly, helpful and accommodating host. Highly recommended place to stay!"
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Cottage at Goose Neck Point
10.0 out of 10, Exceptional, (20)
"We have been VRBO'ing for quite a few years now and have had lots of positive experiences - but THIS property goes beyond all expectations in ways others can't. I can't think of another property layout that could offer what this one does - soothing water in every direction (where else can you see sunrise AND sunset over water?) and the large screened in porch with a view of the water was so comfortable and relaxing that we had to talk ourselves into leaving to go anywhere! The host could not...
Cottage at Goose Neck Point
North Beach Cottage - Walk to Chesapeake Bay
10.0 out of 10, Exceptional, (19)
"Wonderful house close to the water. Great hosts."
North Beach Cottage - Walk to Chesapeake Bay
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
10.0 out of 10, Exceptional, (48)
"The property was very clean and well decorated. You could tell care and love is placed into the house and landscaping. The backyard and pool area is gorgeous! Despite unlucky/rainy weather and temperatures in the 60s, the pool was heated so warm that we went in everyday with the kids which was so nice. Annapolis is very close by. Plenty of fluffy towels, comfortable beds, nice small touches of welcome goodies and quality soap/shampoo, etc."
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
Cozy, unique, historic registered cottage on the Corsica River!
10.0 out of 10, Exceptional, (4)
"Very nice property. Enjoy the weekend. Would recommend to anyone visiting the Chestertown and Centreville area."
Cozy, unique, historic registered cottage on the Corsica River!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (106)
"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
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (195)
"We enjoyed our stay very much. It was lovely to sit either on the screened in porch or in the living room and look out onto the water. It happened to be chilly & rainy during our stay but with views of the water, we didn’t even mind that."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
10.0 out of 10, Exceptional, (151)
"Quaint yet period correct. Plenty of room with decent kitchen. Especially love location and screaned back porch. Have stayed in house several times and does not disappoint!! Will go again for sure!"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
The Middle Point Cabin in Saint Michaels
9.8 out of 10, Exceptional, (47)
"Looked just like the pictures. Everything was new clean and comfortable. Enclosed patio was a hit with our cat."
The Middle Point Cabin in Saint Michaels
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, (5)
"We loved Waterside Cottage. It was so quite & the crabbing was wonderful which is what we were looking for. Topher was wonderful to work with both before we arrived & on the day of arrival. My husband is already asking if we can book it again next year."
Eastern Shore Waterside Cottage Near St. Michaels
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.

Other property types in Claiborne

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (2)
"My rugby team traveled down for a competition. Erin met us there walked us around the property and gave us great recommendations for food in the area. She was an amazing manager, always answering questions and getting us anything we needed. The property was beautiful and fit our entire team comfortably. The large slace and outdoor activity allowed for a lot of team building and we had a blast llaying pickle ball and basketball with each other. We wish we coukd have spent more time there."
The price is £1,162
per night
13 May - 14 May
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (37)
"This property is in a great location! The house is adorable and the owner was very responsive and accommodating when I needed to add an extra day. I would definitely recommend!"
The Blue Crab Beach House - Free beach passes
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.

Frequently asked questions

How much do holiday cottages in Claiborne cost?
Holiday cottages in Claiborne range between and per night. These properties offer a chance to get in tune with nature — at a price you can afford. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many holiday cottages are there in Claiborne?
Pick from holiday cottages in Claiborne. Whether you’re holidaying with the kids or organising a weekend escape with your besties, Expedia will help you find the right place to get back to nature.
Why book your cottage in Claiborne with Expedia?
We think that a vacay should be stress-free, so if you’re seeking holiday cottages in Claiborne at an affordable rate, Expedia has you covered. Stick to the budget and choose a thrifty option far from the rush of the city, or splurge on an upscale cottage to pamper your favourite people.
How can I find cheap cottages in Claiborne?
Expedia is here to help you easily source cheap cottages in Claiborne. To book your special stay in just a few clicks, try out our convenient filter tool to tailor your search results by budget, star rating and amenities.
What is there to do in Claiborne near my cottage?
After you’ve unpacked and settled in, set out and discover the amazing things Claiborne has to offer. St. Michaels Winery is a great attraction to add to your itinerary.