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Tilghman Vacation Rentals

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Vacation Rentals in Tilghman

Fridge, microwave, oven, stovetop
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
9.0 out of 10, Wonderful, (2)
"We enjoyed a long weekend at this property. The location being right on the water made the views incredible. We unfortunately were there during a rainy weekend, but the indoor pool saved us for sure. The main living areas of this property are gorgeous (kitchen, multiple living rooms). The furniture in the living rooms though are low to the ground, which was a challenge for the age 65+ individuals in our group. The bedrooms were nice and beds were super comfortable. Three of the five showers were...
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (25)
"My family and I enjoyed our stay at the Carpenter Alley Cottage in Saint Michaels! The location was perfect -- walking distance from everything! Appreciated that there was a ground floor bedroom for my parents so they didn't have to climb the stairs and my daughter loved having her own bunk bed room! I did have a few questions about the cottage and the check-in process and my inquiries were all met with a prompt response. Would love to stay here again! (One note though is that it is a smaller,...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Exterior
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
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Exterior
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (19)
"We have nothing but great things to say about Adam and his beautiful home! He was so accommodating and the home was comfortable and spacious for our family of 5! Couldn’t have had a better experience :)"
The price is CA $137
CA $390 total
includes taxes & fees
May 27 - May 28
Relax on Kent Island in 3 Bedroom Home w/Waterview
Outdoor spa tub
Bay View Studio Apartment
10.0 out of 10, Exceptional, (25)
"If you are looking for a very spacious well-appointed one bedroom apt. style accommodation in a residential setting with lovely waterfront bay views, I highly recommend this place!"
Bay View Studio Apartment
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (107)
"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
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
10.0 out of 10, Exceptional, (73)
"The cottage provides a wonderful way to experience Deale and the surrounding area. Well equipped and clean, I had everything I needed and didn't want to leave,"
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Beach nearby, sun loungers, beach umbrellas, beach towels
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (39)
"It was clean and had everything we needed. We had a very comfortable stay. There are one or two steps between many of the rooms so keep that in mind."
The Blue Crab Beach House - Free beach passes
Property grounds
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
Property grounds
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, (24)
"This house and property is GORGEOUS. Well maintained, beautiful setting. Amazing amenities (pool, hot tub) which enhanced our stay. We had no problem finding multiple places to all hang out and chat- the living room with plenty of seating, the dining room table with seating for at least 14, and outside in the hot tub. It was a perfect setting for valuable time away with friends! Additionally, the owner was STELLAR in communication. I very much appreciated his quick and attentive responses...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Property grounds
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, (4)
"Had a great time fishing from the dock while we got out of the city for a weekend."
Maryland Vacation Rental w/ Private Pool & Dock
Fridge, microwave, stovetop, dishwasher
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (4)
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (104)
"Loved this historic house! Perfect location, peaceful neighborhood and walking distance to entire town."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
3 bedrooms, desk, iron/ironing board, free WiFi
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
10.0 out of 10, Exceptional, (101)
"The house was very well maintained, beach access and views were wonderful. This location was very quiet, and if you are a nature lover this location is perfect. Many miles to walk and explore, lots of birds to watch. Very enjoyable weekend. Hope to return."
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
Property grounds
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (43)
"Beautiful house and views. Amenities and grounds were great. Loved the playground and beach. Peace and quiet at its finest in nature."
The price is CA $452
CA $925 total
includes taxes & fees
May 28 - May 29
Charming Annapolis WaterVIEW Home
Outdoor pool
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (21)
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Property grounds
Quaint cottage with serene water view!
10.0 out of 10, Exceptional, (24)
"Studio with plenty of space for one. Nicely decorated, ample supplies. Petite front porch to watch the river from. Pam was friendly and welcoming, and I will certainly happily stay here again!"
Quaint cottage with serene water view!
Property grounds
Charming Cottage with Hot Tub 1 Block from the Bay
10.0 out of 10, Exceptional, (6)
"Was a super comfortable spot my 5 friends and I. Super comfy couches and beds, nice TV, well appointed kitchen. Took a nice walk down to the water in the am. Would stay again!"
The price is CA $418
CA $852 total
includes taxes & fees
May 27 - May 28
Charming Cottage with Hot Tub 1 Block from the Bay
Fridge, microwave, oven, stovetop
Waterfront Cottage on the Eastern Shore
The price is CA $820
CA $1,552 total
includes taxes & fees
Jun 17 - Jun 18
Waterfront Cottage on the Eastern Shore
Fridge, microwave, oven, stovetop
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
9.6 out of 10, Exceptional, (99)
"Our daughter was married at the Annapolis Maritime Museum and the property is literally right around the corner. The house is spacious and included everything we needed for a wonderful weekend. Would highly recommend staying at this property to anyone looking to visit Annapolis/Eastport!!!"
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Don't see what you're looking for?
See all available properties in Tilghman
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 types of properties in Tilghman you may be interested in

Garden View Double Queen First Level - Not Dog Friendly | View from room
The Tilghman Island Inn
3.5 star property
9.8 out of 10, Exceptional, (51)
"Lovely place! "
The price is CA $404
CA $444 total
includes taxes & fees
Jun 9 - Jun 10
The Tilghman Island Inn
Exterior
Knapps Narrows Marina & Inn
3.0 star property
9.4 out of 10, Exceptional, (307)
"Excellent Inn and Marina. Perfect for boaters and people fishing the area. It’s also a nice place outside of St Michaels. The two main restaurants in the area need attention. The breakfast restaurant on the island “Two if by Sea” is excellent!"
The price is CA $233
CA $257 total
includes taxes & fees
May 31 - Jun 1
Knapps Narrows Marina & Inn
Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers
Hyatt Regency Chesapeake Bay
4.0 star property
8.8 out of 10, Excellent, (1000)
"Gorgeous property. Beautiful views. Well maintained and kept clean. The bed was the best lullaby ever. I slept ever so soundly. Breakfast was bountiful and delicious. The young lady that checked us in was on the surly side and could use some professional development on friendliness and hospitality for people of all cultures. But, the gentleman from Ghana that check me out made up for what she lacked and redeemed my experience. I would definitely stay again. "
The price is CA $246
CA $337 total
includes taxes & fees
May 27 - May 28
Hyatt Regency Chesapeake 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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Tilghman. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Tilghman?

Yes, you can find vacation rentals in Tilghman near Phillips Wharf Environmental Center, or you can go with a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Tilghman has to offer?

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife: You might want to consider this vacation rental near Tilghman, which offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Tilghman?

Expedia has 16 vacation rentals for your stay in Tilghman.

What’s there to see and do in Tilghman?

Cultural attractions include Tilghman Watermen’s Museum, whereas Phillips Wharf Environmental Center is just one of the family-friendly sights. St. Michaels Winery and Chesapeake Bay Maritime Museum are a couple of places you'll find in the larger area.

What’s a vacation rental in Tilghman like?

Vacation rentals are private properties you can book for a long or short time in Tilghman. Vacation rentals offer amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.

Recent reviews of Tilghman properties
Expedia verified reviews

The Wildset

The Wildset

5/5 Excellent
Wonderful Stay
"We stayed one night for the St. Michaels Running Festival. The entire staff was friendly and accommodating, very easygoing and helpful. The location is great, and the rooms were clean, well designed, and spacious. As someone with Celiac, they even have gluten-free breakfast options for guests. The beds were comfy; the shower was nice. One thing I'd love to see is a small lamp for the rooms, because the lighting was too strong at night and in morning when waking early for the race. Yet, there was nothing from wanting us to return to this place the next time we do the running festival (we live in Annapolis, but I'd recommend to those coming in for longer stays)."
A verified traveller stayed at The Wildset
Posted 3 days ago
The Wildset