Holiday rentals in Cambridge

4.98 out of 5 average rating, 128 reviews

Home in Church Creek

Church Creek Charm (close to Blackwater Refuge)

Charming Eastern Shore home built in 1900, located in CHURCH CREEK, MD, less than 10-15 mins from Cambridge, Blackwater National Wildlife Refuge & the Harriet Tubman Underground Railroad museum. Ideal spot for cycling, birding, fishing, canoeing, relaxing, or exploring the many cute towns of Maryland's Eastern Shore. Just over an hour from Ocean City & Assateague Nat'l Seashore. Pet-friendly with a fenced backyard. The Eastern Shore is famous for its seafood, history, nature & fresh produce!

4.98 out of 5 average rating, 198 reviews

Farm stay in Madison

Madison Nature Getaway

We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.

Superhost

Flat in Cambridge

4.9 out of 5 average rating, 130 reviews

Little Slice of Cambridge. 2 bedroom, pet friendly

You’ll be staying right in the center of the Historic district, close enough to walk to town and enjoy shopping or some of the great restaurants. Just two blocks from the water, a short stroll to the lighthouse or down to the water front and enjoy the park. This newly listed 2 bedroom , pet- friendly apartment has everything you will need to explore the history, food and waterfowl found in this area. Park your boat here. We can’t wait for you to experience Cambridge and relax in the “West End”.

4.98 out of 5 average rating, 201 reviews

Tiny home in Cambridge

The Little House on the Farm, Water Access

Peaceful, Quaint & located on the Little Blackwater River, & 1.5 miles from the Blackwater National Wildlife Refuge & The Harriet Tubman Underground Railroad State Park & Museum. A bird watching, kayaking, and bicycling paradise awaits. Perfect for a couples retreat, girls getaway or a solo vacation to relax & unwind. Hunters and Fishermen are welcome also! Route 50 & downtown Cambridge are 10 mins away for local eateries and shopping! This is the perfect location to explore the Eastern Shore!

4.99 out of 5 average rating, 172 reviews

Sunset Breezes - quiet waterfront retreat

Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. Gather with family and friends around the fire pit. Take in the beautiful water sights while paddling in a kayak, canoe, or paddleboard. Laugh with family and friends while playing corn hole, croquet, or bocce ball waterside. Photograph abundant wildlife - bald eagles, blue herons, osprey, deer, turkey and numerous waterfowl. Dine on the deck while enjoying beautiful sunsets.

4.94 out of 5 average rating, 141 reviews

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

4.99 out of 5 average rating, 122 reviews

Guest house in Cambridge

Rosses Chance Guest House

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

4.99 out of 5 average rating, 606 reviews

Guest house in Easton

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

4.89 out of 5 average rating, 603 reviews

Tiny home in Cambridge

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette, making your visit even more memorable! Just a 5 min drive from Blackwater Refuge! It's an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! The Tiny Cabin is located 50 steps away from Pitcher Dam Creek which leads to the Little Blackwater! Kayaks on site! Bring your fishing rod to catch popular Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining!

4.97 out of 5 average rating, 417 reviews

Flat in Church Creek

Church Creek Natures' Rest

Nature's Rest is ideally located, just minutes to Blackwater Wildlife Refuge The Harriet Tubman Museum, as well as boat ramps for easy access to the Chesapeake Bay and it's tributaries for enjoying Maryland's Eastern Shore. We have plenty of parking, so bring your boat, bikes, and binoculars. Just mins from downtown Cambridge for dining & shopping. Discover the many quaint towns the area has to offer, come for a night, or stay as long as you'd like, look forward to meeting you.

4.96 out of 5 average rating, 148 reviews

Cottage in Cambridge

Church Creek - waterfront cottage & pool - private

Close to Blackwater NWR and the Harriet Tubman Center, enjoy peaceful days at our secluded waterfront cottage on Church Creek. Our closest neighbor is across a cove. Our estate offers 50 acres of privacy and one of the best waterfront views on the Chesapeake. Enjoy a view from every window and nature all around you. Excellent walking, swimming (in-ground pool-May 3-Oct 1), great birding and bicycling. Launch your kayak from the backyard. Perfect private getaway!

4.98 out of 5 average rating, 203 reviews

Flat in Cambridge

Private apt above garage w/ pier and water access

New 2 Bedroom apartment along the picturesque Choptank River. This quiet and spacious 2nd floor Private garage apartment features an open concept with 2 bedrooms, a full kitchen, living room, washer & dryer with optional garage area to store bikes or beach gear. Bike, walk or drive to local restaurants, parks and downtown attractions. Private beach and pier access!!! Close to all of the Ironman festivities and conveniently located to Rt 50. Kayaks on site.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Cambridge holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Cambridge

5 out of 5 average rating, 15 reviews

Guest house in Cambridge

The Place in Cambridge-Summer is in the Air!

PhilRating, 5 stars2 weeks ago

Catherine’s place was perfect location for Ironman eagleman. We were able to walk everywhere we needed to go. The place was clean, quiet, and comfortable. Being able to cool off in the pool was great. They were very friendly and I would stay again.

Loft in Cambridge

4.82 out of 5 average rating, 28 reviews

Modern Cambridge Cottage: Walk to Town, Waterfront

KarenRating, 5 stars1 month ago

This little place was perfect for what we needed. The bed is super comfortable and the space has everything you need. The owner was friendly and very helpful. We enjoyed our stay and would love to come back. There are several cameras around the property that record sound and video. It’s stated in the description. I know it’s for safety reasons and none of them are facing windows, just the yard. It might not be a big deal to others; it just made me feel a little weird. We enjoy sitting outside and knowing that I was on video felt strange. But we still loved the place and would definitely come back

4.87 out of 5 average rating, 157 reviews

Cozy Choptank Oasis home

MiloRating, 5 stars3 weeks ago

Nellie was easy to contact to if we had any issues. The house was very comfortable and had everything we would need for our stay. Close to everything we needed to see or do. Nellie visited us the first day to see if we needed anything and informed us of places to fish or crab. I would be willing to stay there again on another fishing trip. Recommend anyone to stay at this place.

5 out of 5 average rating, 13 reviews

Apartment in Cambridge

The Drinking Gourd: Stunning Cambridge Penthouse

MelanieRating, 5 stars1 month ago

We had a great stay at Jen's place! It was very spacious and comfortable, and walkable to downtown Cambridge which had plenty of restaurants and bars to explore. The beds were comfortable and the amenities were as described. Jen was a very responsive host and helped out with all our questions. She also offered lots of local recommendations in Cambridge and the surrounding area. I'd definitely recommend Jen's place if you find yourself in Cambridge, MD :)

4.96 out of 5 average rating, 47 reviews

Historic 1740 Home Near Waterfront

MelanieRating, 5 stars1 day ago

I knew our stay here would be a wonderful experience even before our arrival based on Annie's detailed responses to my questions and genuine support of our group's needs to include our 2 dogs. The house is as pictured...warm, inviting and comfortable with all the modern amenities not always found in historic properties...full channel streaming and fast wifi. The beds are extremely comfortable with high quality linens and the showers have great water pressure. The temperature was in the high 90's for 3 days straight during our stay and the house stayed cool and comfortable. The garden is beautiful...Our dogs loved the space and the adjoining path. The neighborhood is quiet which allowed for some very enjoyable cocktail hours on the veranda in the evenings. There are several upscale eateries within walking distance. Ava's pizza and wine bar was a favorite in our group (Thin crust mushroom tart...yum). I highly recommend this property. Kudos to Annie for being an impeccable host.

4.88 out of 5 average rating, 130 reviews

Dorothy's Chesapeake Delight

AnitaRating, 5 stars1 week ago

What a great place to stay and relax. Sitting with your feet in the sand , kayaking , crabbing and fishing . We will definitely boom again .

4.98 out of 5 average rating, 53 reviews

You'll enjoy the The Great Escape in Cambridge!

IngridRating, 5 stars3 weeks ago

Clare was super responsive, and got right back to me with recommendations for restaurants and answering any questions. The home was great for our party and we were able to walk downtown to restaurants and shops. Beds and pillows were very comfortable. Overall a great stay!