Photo by Kacy Kish

Tilghman Island holiday homes

We found 175 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Tilghman Island

Showing deals for:18 Dec - 25 Dec

Interior
The view off of the point, breathtaking.
Another view from above.
Interior
Exceptional
(46 reviews)

Grandview- Main House

Bozman

25% off
NZ$8,340
for 7 nights, 1 home
NZ$1,191 per night
includes taxes & fees
Grandview- Main House
Interior
Interior
Exterior
Living area
Excellent
(6 reviews)

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

Royal Oak

8% off
NZ$16,492
for 7 nights, 1 cottage
NZ$2,356 per night
includes taxes & fees
Spacious waterfront house in charming Royal Oak with WiFi, AC, dock
"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental
Shaded view of wrap-around deck; stainless Saber outdoor gas grill
Custom, open-concept home (photo prior to new red-oak hardwood flooring)
Convenient open-concept design:  kitchen, dining and living areas
Exceptional
(163 reviews)

Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

Sherwood

10% off
NZ$4,179
for 7 nights, 1 home
NZ$597 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Private kitchen
Dining
Private kitchen
Interior
Exceptional
(11 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

8% off
NZ$6,119
for 7 nights, 1 cottage
NZ$874 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Dining Room - Seats 6
View down the lane
Custom kitchen
Living Room with flat screen TV and sleeper sofa
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
NZ$3,504
for 7 nights, 1 cottage
NZ$501 per night
includes taxes & fees
Perfect Waterview Cottage - St. Michaels Getaway
two twin beds and play area in loft
Exterior
Outdoor banquet area
view from balcony overlooking playhouse, pergola and Brooks Creek
Exceptional
(276 reviews)

Family and Pet-Friendly, Waterfront with Pier

Cambridge

8% off
NZ$3,920
for 7 nights, 1 cottage
NZ$560 per night
includes taxes & fees
Family and Pet-Friendly, Waterfront with Pier
Dining
Exterior
Living area
Private kitchen
Exceptional
(25 reviews)

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

Tilghman

8% off
NZ$5,117
for 7 nights, 1 cottage
NZ$731 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
New and fully equipped Kitchen
Front of W Melson House
Eating Area adjacent Kitchen
Large Screened Porch with rocking chairs
Exceptional
(208 reviews)

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

St. Michaels

8% off
NZ$5,496
for 7 nights, 1 cottage
NZ$785 per night
includes taxes & fees
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Living area
Be ready to float! Bring your own inner tubes  and tennis shoes!
Exterior detail
Interior
Exceptional
(144 reviews)

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

Bozman

12% off
NZ$3,621
for 7 nights, 1 cottage
NZ$517 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Interior
Living area
Terrace/patio
Living area
Exceptional
(7 reviews)

Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels

St. Michaels

17% off
NZ$4,512
for 7 nights, 1 home
NZ$645 per night
includes taxes & fees
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
Exterior
Living area
Property grounds
Interior
Exceptional
(412 reviews)

Stay in the HEART of Saint Michaels!

St. Michaels

17% off
NZ$3,589
for 7 nights, 1 home
NZ$513 per night
includes taxes & fees
Stay in the HEART of Saint Michaels!
Large screened porch with ceiling fan allows outdoor dining and relaxing.
St. Michaels Harbor from Park down street
Park half block from house
Eating area in panelled Family Room. Eat here, in dining room, or on porch!
Exceptional
(150 reviews)

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St. Michaels

8% off
NZ$5,072
for 7 nights, 1 cottage
NZ$725 per night
includes taxes & fees
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Dining
Exterior
Exterior
Private kitchen
Exceptional
(28 reviews)

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

Cambridge

8% off
NZ$8,230
for 7 nights, 1 home
NZ$1,176 per night
includes taxes & fees
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Tilghman Island getaway

Learn about the unique charm of Tilghman Island with a stay in a holiday home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Tilghman Island

Are you hoping to find things to do while you're in town? Venture out of your holiday home and check out everything that makes Tilghman Island a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • St. Michaels Winery (8.4 mi / 13.6 km)
  • Chesapeake Beach Water Park (10.8 mi / 17.3 km)
  • Phillips Wharf Environmental Center (1.3 mi / 2.2 km)
  • Talbot Massage (15.7 mi / 25.3 km)

Exploring the natural landscape of Tilghman Island

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Tilghman Island is a great place to get out in nature. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Breezy Point Beach (10.9 mi / 17.6 km)
  • Gerry Boyle Park at Great Marsh (15.9 mi / 25.6 km)
  • Long Wharf Park (16.4 mi / 26.4 km)
  • Northern Chesapeake Bay (18.5 mi / 29.8 km)
  • Blackwater National Wildlife Refuge (22.3 mi / 35.9 km)
  • Shadyside Park (14.2 mi / 22.8 km)

More holiday ideas