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Compare 344 Vacation Homes in Tilghman with updated reviews, rates, and availability.

Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Grill no longer works
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (87)
"This lovely home sets in a beautful location. The hosts are available and accommodating. They are definitely available if needed. The house itself is very comfy. All amenities you need are there. "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Enjoy the sunset from Long Wharf Marina across the street
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
10.0 out of 10, Exceptional, (5)
"We had a nice stay in a comfortable house!"
The price is SAR 657
SAR 1,473 total
includes taxes & fees
12 Nov - 13 Nov
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Bay views with kayaks, bikes, fire pit, crabbing and more
Living room with tv and gas fireplace
Bay views with kayaks, bikes, fire pit, crabbing and more
9.4 out of 10, Exceptional, (16)
"We had a great stay in this beautiful property. Three good size bedrooms and two nice baths. Well equipped kitchen and nice living area. Large yard for kids or dogs and just relaxing. Convenient to restaurants and markets. Hope to visit again soon."
Bay views with kayaks, bikes, fire pit, crabbing and more
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Exterior
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
2.0 star property
10.0 out of 10, Exceptional, (3)
"The house was very clean and was great for our home base while visiting family in St. Michael’s. The owner was very response and friendly. The house included all basic amenities and then some! The owner really took the time and care preparing this place for guests. Downtown Cambridge is a short drive and a cute little town with shops and restaurants. We didn’t have a ton of time to explore downtown but plan to on our next stay! "
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Your Annapolis Adventure Starts Here!!
Annapolis Adventure Awaits - Book Now For March 2023 Festivities!
Your Annapolis Adventure Starts Here!!
10.0 out of 10, Exceptional, (134)
"Beautifully decorated home in a safe neighborhood. Centrally located to Annapolis for shopping , dining and sight seeing. Loved the cozy seating in living space and the inviting patio. Perfect place for a girl’s get-away. Highly recommend. Five stars all the way. "
Your Annapolis Adventure Starts Here!!
Waterfront Home on the Chesapeake Bay!
Private Pier
Waterfront Home on the Chesapeake Bay!
10.0 out of 10, Exceptional, (23)
"Very nice getaway for a family reunion group of 8 while we visited our son at the USNA. Location is 35 min from US Naval academy; perfect to feel like he's really getting off the Yard. Having such a huge yard really offered lots to do (corn hole, frisbee, etc.). The incredible water views drew us all back home every night, along with the gorgeous sunsets. Had really nice weather so we took advantage of the 3 kayaks and paddled around the marina. Bikes were convenient too, as well as small...
Waterfront Home on the Chesapeake Bay!
Edgewater/Mayo Getaway!
Room
Edgewater/Mayo Getaway!
9.8 out of 10, Exceptional, (8)
"A great property for two families with young kids to stay. Children loved the big backyard and there was plenty of space for everyone to have their own place. We loved Beverly Triton Beach and it was easy to get downtown for the Sailboat Show as well."
The price is SAR 875
SAR 2,196 total
includes taxes & fees
6 Nov - 7 Nov
Edgewater/Mayo Getaway!
Charming Annapolis WaterVIEW Home
3 covered balconies, a ground floor patio, and ceramic and propane grills.
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (48)
"This house was perfect for our group of friends especially with infants. Easy check in, comfortable beds and room for pack and plays. Water view is amazing. Definitely worth the rent and would be interested in coming back!"
Charming Annapolis WaterVIEW Home
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Living Area
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (31)
"Other than arriving with no sheets on beds, no towels, and no basic toiletries or kitchen cleaning set, place is very good. Cleaning service, owner, or property management firm mismanaged the prep for our arrival. Absence of sheets, towels, etc. was rectified in a bit more than 1 hour. Nice place and superb location for seeing the village. Quiet, but right in the middle of all shops, farmers market, restaurants, etc. There was a bit of a pet odor in the 1st floor bedroom. Only other comment is...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Charming Home in Annapolis, MD !
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
9.6 out of 10, Exceptional, (105)
"The only downside and it was miniscule in relation to the overall experience was the amount of debris on the front porch that came from storms blowing off of the trees. Couldn't really be helped and again very minor issue. The rest of the house was fabulous!!"
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Beautiful Waterfront Retreat in Cambridge!
Exterior
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (31)
"This house exceeded our expectations in every way. The kitchen is large and well-appointed, the beds are comfortable, and the peace and quiet is priceless. We enjoyed morning coffee in the sunroom, table tennis in the crab house, sunsets from the dock, and stargazing at the firepit. If you desire peace and quiet this house is a perfect choice!"
The price is SAR 1,033
SAR 1,927 total
includes taxes & fees
12 Nov - 13 Nov
Beautiful Waterfront Retreat in Cambridge!
Charming Cottage with Hot Tub 1 Block from the Bay
Marina
Charming Cottage with Hot Tub 1 Block from the Bay
10.0 out of 10, Exceptional, (8)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is SAR 1,014
SAR 2,180 total
includes taxes & fees
3 Dec - 4 Dec
Charming Cottage with Hot Tub 1 Block from the Bay
Walk to Everything House
Front of House
Walk to Everything House
10.0 out of 10, Exceptional, (72)
"We thoroughly enjoyed the convenience of walking to shops, restaurants, and waterfront! Residence was charming and clean! Only minor issue was we couldn’t locate the iron- just the ironing board! We still had fun but we’re just a bit wrinkled!😁"
Walk to Everything House
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Exterior
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
10.0 out of 10, Exceptional, (31)
"House was spacious, clean, and exactly as described in the listings. We had a great time!"
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Coastal Edgewater Home w/ Private Hot Tub!
Edgewater Vacation Rental | 5BR | 2BA | Access Only By Stairs | 2,350 Sq Ft
Coastal Edgewater Home w/ Private Hot Tub!
9.0 out of 10, Wonderful, (11)
"It was just my husband and me. We were visiting family, and this house was a very convenient 3-minutes from their house. Quiet location; nice water view. House was very clean and comfortable."
Coastal Edgewater Home w/ Private Hot Tub!
Grasonville Home w/ Private Pool on the Water
Grasonville Vacation Rental | 3BR | 2BA | Stairs Required for Access
Grasonville Home w/ Private Pool on the Water
9.8 out of 10, Exceptional, (19)
"Location was great for our stay"
Grasonville Home w/ Private Pool on the Water
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.8 out of 10, Exceptional, (8)
"Stayed here for a wedding was perfect for the group of 4 of us. Living room is bigger than it looks in the photos and the house was well kept/ clean. Host was great and responsive as well!"
The price is SAR 751
SAR 1,362 total
includes taxes & fees
6 Nov - 7 Nov
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Exterior
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
9.6 out of 10, Exceptional, (19)
"The house was just as it was listed!! Our annual family vacation was so much fun here! Plenty of room, very clean, and fully stocked! Peddle boats, kayaks, and pool used daily!! Fire every night!!! Thank you for the wonderful hospitality!!!"
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!
Front of home with view of path to pier and dock
Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!
9.8 out of 10, Exceptional, (21)
"We went to this wonderful home for our 32nd wedding anniversary and it was so lovely. The home was so comfy and well stocked, the beds were very comfortable and the sunsets were spectacular. We enjoyed every minute! Barbara was just so delightful and helpful. She made everything perfect! Would love to stay again some time."
Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!
Beautiful Peaceful Home
Living area
Beautiful Peaceful Home
7.4 out of 10, Good, (3)
"Owner canceled the day before with no notice"
Beautiful Peaceful Home
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 Tilghman

Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
View
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
9.4 out of 10, Exceptional, (6)
"The home was beautiful, the indoor pool was great Everything about the home was perfect for our family vacation (4generations). The only thing that was not enjoyable was the flooding caused by hurricane Debby but it did leave us with memories. . Eastern Shores is a great host and kept us informed "
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
Charming Annapolis WaterVIEW Home
3 covered balconies, a ground floor patio, and ceramic and propane grills.
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (48)
"This house was perfect for our group of friends especially with infants. Easy check in, comfortable beds and room for pack and plays. Water view is amazing. Definitely worth the rent and would be interested in coming back!"
Charming Annapolis WaterVIEW Home
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (202)
"This was a lovely home. I especially appreciated how clean and well-stocked it was. Liz and Tom were very responsive and accommodating! This truly added to a wonderful reunion weekend with friends and family. Thank you!"
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
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.