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Compare 332 Vacation Homes in Tilghman with updated reviews, rates, and availability.

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (38)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

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

Walk to Everything House

10.0 out of 10, Exceptional, (76)
"Clean and nice place to stay"
Walk to Everything House

Brand New Spacious Luxury Home

10.0 out of 10, Exceptional, (4)
"Property is great for families!!"
Brand New Spacious Luxury Home

Circa 1700 Chesapeake Colonial home on the National Register.

9.8 out of 10, Exceptional, (50)
"Very cool house with great host. Very spacious. Excellent kitchen and very cozy. It would have been helpful to know about the staircases. We had an 8 month pregnant woman and 2 year old that were not able to come but it would have been an issue as getting to the single bed rooms is challenging."
Circa 1700 Chesapeake Colonial home on the National Register.

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

10.0 out of 10, Exceptional, (21)
"Convenient to restaurants and a warm, comfortable place to gather and relax after a hard, cold waterfowl hunt"
The price is SAR 272
SAR 920 total
includes taxes & fees
9 Feb - 10 Feb
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Waterfront Cheerful 6 BR Home with Private Pier

9.8 out of 10, Exceptional, (30)
"This home accommodated our multigenerational family of 12 perfectly. The well stocked kitchen was spacious and allowed for multiple people to do either meal prep, eat or cook simultaneously. There are plenty of restaurant options nearby too. Annapolis is an easy 30 minutes away. One evening we inexplicably lost water pressure, but John was a text away and he showed up the next morning and took care of it. He was attentive and a pleasure to rent from. Thank you, John, for a fabulous week!"
Waterfront Cheerful 6 BR Home with Private Pier

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2.0 star property
9.6 out of 10, Exceptional, (4)
"Very clean, well stocked with towels, paper products and everything else you need. Lots of space for a large group. I liked the master bedroom on the first floor. Having a second coffee maker upstairs is a nice touch. Walking distance to downtown. "
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

Serene waterfront sunsets in this sprawling historic Annapolis home

9.6 out of 10, Exceptional, (28)
"Gorgeous neighborhood and a very cool house. The view is amazing and the sunsets were incredible. The house could have been cleaner, there were stains on some of the furniture, and the kitchen was a mess -- we had to wash every pot or pan before using it and the cabinets above the stove were grimy. There was only 1 dish towel in the house. Most of the towels and sheets were pretty old and threadbare and needed to be replaced. Overall very good but not 5 star which is what they are striving...
Serene waterfront sunsets in this sprawling historic Annapolis home

Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D

9.8 out of 10, Exceptional, (9)
"This was a perfect home away from home for four adults and two children, ages 5 and 7. The children loved the loft area and named it the "Kids Zone." The pool and the massive amount of toys were a big hit too. Lots of towels, kitchen equipment, beautiful bed linens, outdoor and indoor spaces made this a wonderful vacation home. While the waterfront was beautiful the front porch was our favorite spot in the morning, Just lovely."
Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D

Pet-Friendly Annapolis Home: Walk to Beach!

10.0 out of 10, Exceptional, (6)
"Property is very well maintained and you feel at home. Proximity of the little park is perfect for young kids. Street very quiet. Parking space is great. We had a great family time and we will be back when weather is warmer to enjoy access to the beach."
Pet-Friendly Annapolis Home: Walk to Beach!

Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

10.0 out of 10, Exceptional, (5)
"Nice location. The house had everything we needed for our stay. The host was available by phone for any questions we had. I would stay again the next time I visit North Beach"
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

9.6 out of 10, Exceptional, (20)
"Terrific house, beautiful scenery, property management was very responsive and helpful. Would stay again. Thank you. "
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (33)
"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Waterfront Escape Near Annapolis

10.0 out of 10, Exceptional, (13)
"Good stay. Excellent location and facility es"
Waterfront Escape Near Annapolis

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (49)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

10.0 out of 10, Exceptional, (7)
"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didn’t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. There’s a place to buy fresh crabs, oysters, and shrimp very close by, and the house has everything you need for a crab night. The owner was incredibly responsive and kind."
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Adorable waterside cottage with pool Beach community

9.4 out of 10, Exceptional, (39)
"Neighborhood was cute, perfect spot to relax. Pool was awesome. Kitchen was large and had a great veiw. It was just what we needed to get away."
Adorable waterside cottage with pool Beach community

7 mins away from Downtown Annapolis

9.8 out of 10, Exceptional, (16)
"Loved the house, we were glad to be able to book it on short notice for a large group! Beds were insanely comfortable, and the house had everything we needed. It was clean, comfortable, and a fantastic location. Only downside is that the common areas (living room/kitchen/dining area) are a bit small if you have a larger group (8). Overall a great stay and would stay again!!"
7 mins away from Downtown Annapolis

The Cottage

10.0 out of 10, Exceptional, (2)
"Couldn’t have asked for better- I appreciate the communication and willingness to work with us on a quick turn around trip. Clean. Easy to get to. Accurate description. Quiet neighborhood. 10/10 would stay again. "
The price is SAR 863
SAR 1,599 total
includes taxes & fees
8 Feb - 9 Feb
The Cottage
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

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (38)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (21)
"We really enjoyed our stay. Looking forward to staying again!"
The price is SAR 450
SAR 1,093 total
includes taxes & fees
19 Feb - 20 Feb
Cass-N-Reel Luxury Houseboat

Cozy Cottage with access to and partially obstructed views of the bay.

9.6 out of 10, Exceptional, (17)
"My wife and I stayed two nights to visit family. Cottage was as described, very roomy and comfortable. Great location. Host was very kind. Only dislike was smell from oil heat, I've never had oil heat and not sure if that is normal."
Cozy Cottage with access to and partially obstructed views of the bay.
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.