Tilghman holiday rentals

We found 383 holiday rentals — enter your dates for availability
Discover a selection of 16 homes and other holiday rentals in Tilghman that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for spending time at your holiday home, which might include a fireplace and a washer and dryer. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Tilghman

Showing deals for:25 Dec - 1 Jan

View from Foyer into Great Room
Pool
View from Pier back to house!
screened porch
Exceptional
(145 reviews)

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton

8% off
AU$11,039
for 7 nights, 1 home
AU$1,577 per night
includes taxes & fees
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Pool
The view off of the point, breathtaking.
Interior
Another view from above.
Exceptional
(46 reviews)

Grandview- Main House

Bozman

25% off
AU$6,685
for 7 nights, 1 home
AU$955 per night
includes taxes & fees
Grandview- Main House
Rear Porch for relaxing or for barbecues!
View of Side of Harrison House and St. Michaels Harbor from Locust Street
View of St Michaels Harbor from french doors in Living Room, and from Side Patio
Thomas Harrison House looking from St. Michaels Town Harbor
Exceptional
(145 reviews)

Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!

St. Michaels

8% off
AU$8,620
for 7 nights, 1 home
AU$1,231 per night
includes taxes & fees
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
Dining
Interior
Living area
Exterior
Excellent
(6 reviews)

Spacious waterfront house in charming Royal Oak with WiFi, AC, dock

Royal Oak

9% off
AU$12,459
for 7 nights, 1 cottage
AU$1,780 per night
includes taxes & fees
Spacious waterfront house in charming Royal Oak with WiFi, AC, dock
Living area
Dining
Private kitchen
Private kitchen
Exceptional
(11 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

8% off
AU$5,438
for 7 nights, 1 cottage
AU$777 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Dining
Exterior
Private kitchen
Living area
Exceptional
(25 reviews)

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman

8% off
AU$4,083
for 7 nights, 1 cottage
AU$583 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Property grounds
Outdoor dining
Terrace/patio
Living area
Exceptional
(11 reviews)

Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck

Huntingtown

8% off
AU$5,057
for 7 nights, 1 cottage
AU$722 per night
includes taxes & fees
Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck
Private kitchen
Living area
Dining
Exterior
Exceptional
(51 reviews)

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Stevensville

8% off
AU$9,049
for 7 nights, 1 home
AU$1,293 per night
includes taxes & fees
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Interior
Private kitchen
Dining
Interior
Exceptional
(7 reviews)

Arcadia Shores on the Cove.

Easton

8% off
AU$6,790
for 7 nights, 1 home
AU$970 per night
includes taxes & fees
Arcadia Shores on the Cove.
Sit and stay a while!
View down the lane
Living Room with flat screen TV and sleeper sofa
Dining Room - Seats 6
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
AU$2,818
for 7 nights, 1 cottage
AU$403 per night
includes taxes & fees
Perfect Waterview Cottage - St. Michaels Getaway
Open-concept living area and kitchen
Beautiful North Beach, MD
Directly next door to Sunrise Garden park
Beautiful views from your own private balcony!
Exceptional
(21 reviews)

Unbelievable beach views for 6

North Beach

8% off
AU$3,844
for 7 nights, 1 apartment
AU$549 per night
includes taxes & fees
Unbelievable beach views for 6
Interior
Living area
Exterior
Private kitchen
Exceptional
(7 reviews)

Waterfront- 5-bedroom house with dock in charming North Beach

North Beach

8% off
AU$11,041
for 7 nights, 1 home
AU$1,577 per night
includes taxes & fees
Waterfront- 5-bedroom house with dock in charming North Beach
Living area
Be ready to float! Bring your own inner tubes and tennis shoes!
Living area
Exterior detail
Exceptional
(144 reviews)

Charming cottage along water with private pier, near St. Michaels Winery

Bozman

12% off
AU$2,886
for 7 nights, 1 cottage
AU$412 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Kitchen with peak into living room
Foyer into Living Room
Kitchen/dining
Living Room into Kitchen/Dining
Exceptional
(92 reviews)

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Taylors Island

8% off
AU$6,048
for 7 nights, 1 home
AU$864 per night
includes taxes & fees
Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball
Private kitchen
Living area
Interior
Property grounds
Exceptional
(414 reviews)

Stay in the HEART of Saint Michaels!

St. Michaels

17% off
AU$2,860
for 7 nights, 1 home
AU$409 per night
includes taxes & fees
Stay in the HEART of Saint Michaels!
Property grounds
Foyer
Exterior
Bathroom
Exceptional
(27 reviews)

Guest Quarters at the Inn - 102

North Beach

8% off
AU$2,027
for 7 nights, 1 apartment
AU$290 per night
includes taxes & fees
Guest Quarters at the Inn - 102
Living area
Exterior
Private kitchen
Exterior
Exceptional
(28 reviews)

Spacious waterfront home with amazing views, private pier, fishing and crabbing.

Cambridge

8% off
AU$6,670
for 7 nights, 1 home
AU$953 per night
includes taxes & fees
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
Exterior
Foyer
Living area
Living area
Exceptional
(21 reviews)

Guest quarters at the inn - 205

North Beach

8% off
AU$2,489
for 7 nights, 1 apartment
AU$356 per night
includes taxes & fees
Guest quarters at the inn - 205
Property grounds
Foyer
Bathroom
Room
Exceptional
(18 reviews)

Guest Quarters at the Inn - 101

North Beach

8% off
AU$2,027
for 7 nights, 1 apartment
AU$290 per night
includes taxes & fees
Guest Quarters at the Inn - 101
Exterior
Foyer
Property grounds
Room
Exceptional
(20 reviews)

Guest quarters at the inn - 204

North Beach

8% off
AU$2,489
for 7 nights, 1 apartment
AU$356 per night
includes taxes & fees
Guest quarters at the inn - 204
Exterior
Foyer
Room
Property grounds
Exceptional
(32 reviews)

Guest Quarters at the Inn - 103

North Beach

8% off
AU$2,027
for 7 nights, 1 apartment
AU$290 per night
includes taxes & fees
Guest Quarters at the Inn - 103

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The waterfront setting of Tilghman is ready to explore

The island views and wildlife provide a pleasant backdrop to your holiday home in Tilghman. This city's fishing, bird watching and boating draw many visitors. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Tilghman

Are you hoping to find top things to see and do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Tilghman a one-of-a-kind holiday spot. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • St. Michaels Winery (8.2 mi / 13.3 km)
  • Chesapeake Beach Water Park (10.7 mi / 17.2 km)
  • Phillips Wharf Environmental Center (1 mi / 1.6 km)
  • Talbot Massage (15.7 mi / 25.2 km)

Exploring the natural landscape of Tilghman

Travellers enjoy Tilghman for its island views and sunsets. Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Tilghman is a great place to get outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Breezy Point Beach (11.1 mi / 17.8 km)
  • Gerry Boyle Park at Great Marsh (16.2 mi / 26.1 km)
  • Long Wharf Park (16.8 mi / 27 km)
  • Northern Chesapeake Bay (18.1 mi / 29.1 km)
  • Blackwater National Wildlife Refuge (22.8 mi / 36.6 km)
  • Brownies Beach (10.6 mi / 17.1 km)

Transport to and around Tilghman

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 16.5 mi (26.6 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Baltimore Washington International Airport (BWI), which is 37.4 mi (60.1 km) away.

Frequently asked questions

What is the best area to stay in Tilghman when booking a holiday rental?
When considering a holiday rental in Tilghman, Maryland, the best area to stay is near the waterfront. This picturesque neighbourhood offers a charming atmosphere with stunning views of the Chesapeake Bay. There are a variety of properties available, ranging from cosy cottages to larger family homes, allowing for a delightful stay.One of the top attractions in this area is the Tilghman Island Maritime Museum, which provides fascinating insights into the local history and maritime culture. Additionally, visitors can enjoy the serene beauty of the nearby Black Walnut Point Inn, where you can indulge in scenic walks or simply relax while taking in the breathtaking sunsets over the water.Staying near the waterfront not only immerses you in the natural beauty of Tilghman but also places you within easy reach of local dining options, where you can savour fresh seafood and regional delicacies.
Where are the best areas for renting a beach house in Tilghman?
For renting a beach house in Tilghman, Maryland, the area along the Chesapeake Bay is particularly appealing. The waterfront properties near Tilghman Island's historic district offer easy access to sandy beaches and picturesque views of the bay. Many of these homes come with desirable amenities such as private docks, outdoor terraces, and spacious living areas, making them great for families or groups seeking a relaxing getaway.The nearby Black Walnut Point is also a great location, where you'll find charming cottages that often feature modern kitchens, comfortable seating areas, and sometimes even access to kayaks or bicycles for exploring the scenic surroundings. This area is known for its tranquil atmosphere, ideal for those looking to unwind while enjoying water-based activities.Additionally, Tilghman Island is close to local attractions like the Chesapeake Bay Maritime Museum in nearby St. Michaels, which provides cultural insights into the region's maritime history. Rentals in this area often have access to local restaurants serving fresh seafood, adding to the overall experience.
What is the most popular type of holiday rental accomodation in Tilghman?
In Tilghman, holiday houses are the predominant type of holiday rental, with around 68 available throughout the charming waterfront community. These properties typically feature spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking a comfortable home away from home. Many holiday houses also offer outdoor spaces, such as decks or patios, where guests can enjoy views of the bay and relax after a day of exploring the local attractions. Additionally, there are about 16 cottages available, which provide a cozier option for couples or smaller groups. These cottages often come with rustic charm and amenities like kitchens and sitting areas, great for a peaceful retreat.
Are there any family house rentals in Tilghman?
In Tilghman, Maryland, there are some family-friendly house rentals available, with around 14 options to choose from. This charming locale offers a delightful mix of waterfront views and serene countryside. Families can find spacious homes featuring amenities such as fully equipped kitchens for preparing family meals, comfortable living areas for relaxation, and outdoor spaces great for children to play or for gatherings.Nearby, visitors can explore the picturesque Tilghman Island, known for its beautiful landscapes and rich maritime history. Activities like kayaking, fishing, and cycling along scenic routes provide great opportunities for family bonding. The area is also close to local eateries serving fresh seafood, ensuring that guests can enjoy the culinary delights of the Chesapeake Bay.
Can I rent a holiday home with a pool or hot tub in Tilghman?
In Tilghman, Maryland, there are several holiday homes available for rent that feature pools and hot tubs, making it a delightful choice for travellers seeking relaxation. This charming waterfront community offers a serene atmosphere, ideal for unwinding. Many properties boast amenities such as private swimming pools, hot tubs, spacious outdoor decks, and fully equipped kitchens, superb for enjoying meals with family and friends after a day of exploring the beautiful surroundings.The area is known for its stunning views of the Chesapeake Bay, and some rentals may even offer direct waterfront access, enhancing the overall holiday experience.
Are there pet-friendly house rentals in Tilghman?
In Tilghman, there are several pet-friendly house rentals available, making it an excellent destination for those travelling with their furry companions. The area is known for its charming waterfront properties, many of which offer amenities such as private docks, outdoor spaces, and fully equipped kitchens, superb for families or groups seeking a relaxing getaway.The picturesque setting of Tilghman provides easy access to the Chesapeake Bay, where you can enjoy activities like kayaking and fishing. Additionally, nearby parks and nature reserves offer lovely walking trails and scenic views, making it ideal for pet owners looking to explore the outdoors with their pets.
Are there any remote work holiday rentals in Tilghman?
In Tilghman, Maryland, there are approximately 80 remote work-friendly holiday rentals available, making it an excellent choice for those looking to combine work and leisure. The area offers a picturesque setting, with properties often featuring essential amenities for remote work, such as reliable Wi-Fi, dedicated office spaces, and comfortable desks in the accommodations.Many of these rentals are situated near the waterfront, providing serene views and a tranquil atmosphere that can help enhance productivity. Additionally, guests can expect to find well-equipped kitchens, spacious living areas, and outdoor spaces superb for relaxation after a day of work.Exploring the local charm of Tilghman is also easy, with nearby attractions like beautiful coastal landscapes and quaint shops, ensuring that when the workday is done, there's plenty to see and do. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Tilghman?
In Tilghman, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature coffee and tea makers, making it easy to enjoy a warm beverage at any time. Onsite parking is typically available, providing convenience for those travelling by car. Additionally, several rentals offer decks or patios, where visitors can relax and take in the serene surroundings. Gardens are also a common feature, providing a lovely outdoor space for leisure and enjoyment.
When is the best time to visit Tilghman for a holiday rental?
The best time to visit Tilghman for a holiday rental is during the summer months, particularly in July, when the area is bustling with activity and charm. This peak season, spanning from June to August, attracts visitors seeking warmth and outdoor adventures, making it a vibrant time to explore this picturesque coastal destination.In July, you can expect delightful temperatures, typically ranging from 20 to 30 degrees Celsius, superb for enjoying the beautiful waterfront and indulging in activities like kayaking, sailing, or simply relaxing on the beach. The community comes alive with local events and festivals, allowing you to immerse yourself in the laid-back culture of Tilghman.For those looking for a more tranquil experience, consider visiting in November, when the crowds have thinned out. This quieter month offers a unique opportunity to enjoy the stunning autumn views and the peacefulness of the area without the hustle and bustle of peak tourist season.Whether you prefer the lively summer atmosphere or the serene charm of the off-peak months, Tilghman has something to offer every type of traveller.
What are the top attractions in Tilghman?
In Tilghman, Maryland, visitors can enjoy a serene escape with a range of attractions that highlight the area's natural beauty and maritime culture. The Tilghman Island Museum offers insight into the local history and heritage, showcasing the region's fishing industry and boat-building traditions. For those interested in outdoor activities, the nearby Chesapeake Bay provides ample opportunities for boating, fishing, and kayaking, with stunning views of the water and surrounding landscapes.The charming waterfront area is great for leisurely strolls, and the local seafood restaurants serve fresh catches, allowing guests to indulge in the region's culinary delights. Additionally, the nearby Blackwater National Wildlife Refuge offers opportunities for birdwatching and hiking, attracting nature enthusiasts looking to explore the diverse ecosystems of the Eastern Shore.
Are all fees included in the Tilghman holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Tilghman holiday homes with parking?
Stayz offers a wide selection of holiday homes in Tilghman with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Tilghman holiday homes?
You can find great discounts on holiday homes in Tilghman on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Tilghman holiday home booking on Stayz?
To find Tilghman holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Tilghman?
A long-stay holiday home in Tilghman is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Tilghman holiday home?
Book your Tilghman holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Tilghman?
Prices for holiday homes in Tilghman vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Tilghman to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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