
House holiday rentals in Tilghman Island
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Top-rated house rentals in Tilghman Island
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Popular amenities for Tilghman Island house rentals
House rentals with a pool

House in Edgewater Maryland
The house was beautiful and clean. The lication was great! Too bad it rain during out stay so we couldn’t enjoy the pool and the backyard. Thank you!

Waterfront Retreat Beach+Pool | Gamerm | Dog+EV OK
What a find! We were attending a wedding on the Potomac and found this gem of a place basically right next door. A perfectly appointed home in a peaceful, tranquil, beautiful setting. Connie was great! Responsive to our need to find the iron, not exactly an emergency, Connie responded immediately with it's location. Loved it!

Bay Breeze Retreat
Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.

The Glebe
A great stay on the river. The kitchen was well equipped and the rest of the house was comfortable. The screened in porch and access to the dock/beach/river was our favorite part. Our dogs were in HEAVEN. The location is rather remote, so recommend bringing any food you'll want as there are no close stores or restaurants.

Gorgeous, waterfront home - Perfect for Families.
Clare and Chris could not be nicer and easier to work with. My family/friends have been getting together since 1994 and have been to many great Airbnb's and VRBO's. My group could not stop telling me how great of a week we had. The primary features that were import to us which the house scored big are as follows: It has a dock (we arrived via boat), The kitchen is big, laid out for many "Cooks", The kitchen was open to the dining room table, The dining room table is open to the sitting areas, The pool was clean and inviting, The fire pit with seasoned firewood was a big hit for our group, All the beds were comfortable, The bedrooms were large and comfortable, The baths were clean, modern & large and The location to "What to do in Cambridge" is only 7-10 miles away. We made prearrangements: Richardson Maritime Museum to have a guided tour with David Williams on Friday and Spocott Windmill with George Radcliff. Both of these tours were fascinating. Our weekend was 5-Stars.

Large Home with Pool & 7 bedrooms; sleeps 21
This home was the perfect place to celebrate my daughter’s graduation! We had family travel in from several states, and everyone felt comfortable and truly enjoyed the spacious layout. It was a bit too chilly to use the pool, but I’m already looking forward to booking this home again. I’ll definitely be a repeat renter!

Beach Please! River cottage w/private beach & dock
My family and I stayed here for a week for our family vacation. We are a group of 8 (6 adults and 2 kids) and there was plenty of room for all of us. We barely left the house because with the beautiful view, dock, beach area, canoe, kayaks, hot tub, game room/ library, corn hole, and fire pit we all had plenty to keep us entertained. Everyone loved Mary & Shelly’s place, and it provided the perfect space for us to enjoy the river and each other’s company!

5 BEDR, Inground Pool+Billiard Table, Close To D.C
Daniel’s Home was beautiful and he made this special event for me and my family able to celebrate my sons 26th Heavenly Birthday a success We were very comfortable and it really felt like home the pool was very clean and the Home was very spacious and squeaky clean I would love to Book Daniel again He was a very nice and friendly Host that responded to any questions we had he made communication easy me and my family really enjoyed our self and yes he’s reasonable and you definitely get what you paid for and more Thank you again Daniel
Weekly house rentals

Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck
Wish we could have stayed longer! We didn’t need to bring anything. All linens, paper products, towels, and kitchenware were provided. Right down to mosquito spray. picnic blankets, and s’mores. Charles was helpful, flexible, kind, and available. He was willing to give my kids and I an up close lesson on beekeeping. He has 5 well maintained hives on his property and was eager for us to come along checking in on them. It was very impressive! The property was beautiful, peaceful, and quiet. There are a few paths to venture out on. One lead to the private beach, another out to a close view of the bay. The deck was the show stopper. The view of the water was amazing. While sitting on the deck, there were hummingbirds, butterflies, and deer passing through. And we could see all of this from the comfort of the hot tub . The game room was a nice bonus. There was something for everyone: darts, poker, drawing, puzzles, movies, board games. I appreciate you sharing your cottage with us!

Mid-Century Modern: Direct Private Beach Access
We returned to this gorgeous home for a second time this summer for a full week’s stay. Not only is the home, landscaping and views beautiful, the house is well equipped with everything we needed for a very comfortable stay, especially the kitchen. We enjoyed finding shark teeth on the private beach, relaxing in the hammock and taking drives into town which is just a short trip away. Nicholas was a super helpful and responsive host. Thank you for your hospitality and sharing your beautiful home! We’ll be back next year!

Bay Breeze - 3BR Waterfront Chester River Retreat
This house was in a beautiful location. Everything was clean and comfortable, thoroughly enjoyed our stay. You cannot beat the views from the main level. Katie was communicative and we were even able to get an early check in!

Ruby Of The Bay
Ruby on the bay lives up to its name. Such beautiful surroundings - loved being on the deck hearing the wind in the pines. I was grateful to unplug! Excellent size for my sister, me and our fur bosses. Could have comfortably fit 2 - 3 more adults. Nikki was instantly responsive & informative. I would love to return.

*Waterfront Sunset Bayview* sleeps 6
The perfect mom and teen boy getaway! The house is on the water with gorgeous sunsets and super clean! My boys attempted fishing daily even without any luck. Altho we didn't kayak because of the choppy water, its great location (there's a ladder at the private pier or a public launch a few yards away) We cooked and ate in a few nights and also enjoyed a local spot on the water (The Narrows). The neighborhood was quiet, relaxing and peaceful. We enjoyed a visit to the Chesapeake Environmental center (abt a 12 min drive) which was a hidden treasure. The Chesapeake Outdoors (recommended by our host Jeremiah) was a great find for bait and info from the locals. Morning coffee on the patio and evening sunsets on the pier were some of my favorites, along with the spacious open floor plan (yet privacy with bedrooms). Jeremiah was super responsive and kind! We'll be back to kayak, fish more, enjoy the hot tub coming soon, the serenity and gorgeous sunsets! (maybe we'll even bring dad -LOL)

• Peaceful Point • A relaxing waterfront retreat
Peaceful Point was incredible and should be the standard that all other rentals follow. The home was well-stocked, organized and cozy, and I was blown away by the thought that went into preparations for guests. The furniture is well maintained and comfortable, the linens soft and clean, and the kitchen was filled with a variety of helpful items unlike the typical haphazard collection of damaged pots, pans and dishes--at Peaceful Point everything was of good quality and seemed to be purchased specifically for that home. The surrounding property was the epitome of peace and quiet, though activities like kayaking and paddleboarding kept everyone entertained. The local wildlife was plentiful and had us endlessly fascinated. Last but not least, our host Joanna was so helpful and proactive in her communications. She should teach a class on hospitality as she's clearly an expert! Thank you for such a wonderful stay, our family will cherish these memories always--hope to visit again soon!

Kent Island Escape
The place was wonderful. The house was clean. The beds were comfortable. The kitchen was more than well equipped. The setting was beautiful. The outdoors was perfect. Great outdoor furniture. The Bayview was unbelievable. The house in relationship to recreation is spot on. I can’t say enough great things about the place. I will definitely be booking again and again.

Downs By The River
We had a very enjoyable stay at this perfect River House. The place was warm and comforting, with some of the most amazing views you can find. We arrived shortly after check in time, and easily let ourselves in with the lock box code & key. Everything inside looked just like the pictures, and we weren't disappointed! If you're looking for some beautiful river views, right on the water, with your own private water access and dock, this is the place for you. We were in town for a wedding a few houses down, and this place couldn't have been any better for us. We were able to walk to & from, which was a huge bonus for after the reception...Cheers :) We enjoyed eating out a couple times in town, and really liked Brick Wood Fired Bistro & Traders Seafood Steak & Ale. We would highly recommend this property for anyone looking for a peaceful river stay, and will surely return someday in the future! Thanks for your hospitality!
Private house rentals

The Wise Quack 2 - A Taste of the Chesapeake Bay!
The Wise Quack 2 is a cozy, clean Airbnb steps from the Chesapeake Bay, perfect for a relaxing getaway. Sidco’s warm hospitality, comfy beds, and thoughtful touches like the deep tub and hammock make it a gem. The quiet Shady Side location and quick host responses ensure a delightful stay.

Madison Bay Club House
This place is amazing. We loved it and will be coming back soon. Jo was amazing and very responsive. Jo answered all text with questions we had and made our trip amazing. I recommend anyone looking for a peaceful water front getaway choose this house you won’t regret it. Very amazing place and host.

Waterfront Farmhouse Meets Modern Luxury
The house is beautiful and worked well for our family. The host was very helpful and responded quickly to any questions we had. The grounds are lovely and very peaceful. Pictures don’t do this property justice.

WaterfrontHotTubPvtPierFirePitKayakGrillQuietHouse
One of the best places we have stayed! Nice and peaceful! We had the best time at Maria’s place.

Waterfront Home, Spectacular View & Private Beach!
We had a great stay here. Beautiful views of the water. Hosts were quick to respond. Good WiFi. Large deck with teak table and weber grill. Easy walk to water access. The waterfront is the best I’ve seen on the Bay. Sandy with shady and sunny spots against the cliffs. From the water access, you can walk in one direction to the limestone cliffs for shark tooth hunting. The other direction goes all the way to the marina. We hope to stay here again.

Waterfront Chesapeake mansion - Panoramic Bay view
We stayed in this house for our son's Naval Academy graduation/commissioning. It was absolutely perfect for our group. The drive across the bay bridge took anywhere from 35-45 minutes depending on the traffic. At no time was the traffic as bad as we've experienced it on the DC side of Annapolis. We crossed the bridge 1-2 times a day during our 7 day stay. As soon as you get to the island and head south there is no traffic and it's a beautiful, peaceful drive. The house is perfect for entertaining with two large rooms inside on the main floor. There is a large island in the kitchen room which makes for a great serving area. It rained during about half of our visit so we made good use of the space indoors. Our children used the fishing poles, kayak, soccer nets, ping pong and fooseball table. Negin was very responsive in answering our questions and even worked it out so we could check in early. We would definitely stay there again if we had the chance.

Bay Home in Annapolis with Private Dock
Beautiful place, beautiful location. Joel thought of anything you could want.

Beachside Dream
BK was an absolute perfect host. His home is spectacular. Such a special bat visit.
Quick stats about house rentals in Tilghman Island
Total rentals
20 properties
Nightly prices starting at
$266 NZD before taxes and fees
Total number of reviews
270 reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 properties include access to Wi-Fi
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- Nationals Park
- The White House
- Betterton Beach
- National Mall
- Georgetown University
- Hampden
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- Smithsonian National Museum of Natural History
- District Wharf
- M&T Bank Stadium
- Sandy Point State Park
- Arlington National Cemetery
- Washington Monument
- Georgetown Waterfront Park
- Patterson Park
- National Air and Space Museum
- National Harbor
- Smithsonian American Art Museum
- Meridian Hill Park
- Lincoln Park
- Congressional Country Club
- Maryland Renaissance Festival
- Killens Pond State Park