Photo by Kacy Kish

Tilghman Island holiday rentals

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.
Pool
Exceptional
(46 reviews)

Grandview- Main House

Bozman

25% off
AU$6,737
for 7 nights, 1 home
AU$962 per night
includes taxes & fees
Grandview- Main House
Exterior
Interior
Interior
Living area
Excellent
(6 reviews)

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

Royal Oak

8% off
AU$12,530
for 7 nights, 1 cottage
AU$1,790 per night
includes taxes & fees
Spacious waterfront house in charming Royal Oak with WiFi, AC, dock
Custom, open-concept home (photo prior to new red-oak hardwood flooring)
Shaded view of wrap-around deck; stainless Saber outdoor gas grill
"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental
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
AU$3,375
for 7 nights, 1 home
AU$482 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Interior
Dining
Private kitchen
Living area
Exceptional
(11 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

8% off
AU$4,942
for 7 nights, 1 cottage
AU$706 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Dining Room - Seats 6
View down the lane
Sit and stay a while!
Custom kitchen
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
AU$2,830
for 7 nights, 1 cottage
AU$404 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
AU$3,169
for 7 nights, 1 cottage
AU$453 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
AU$4,135
for 7 nights, 1 cottage
AU$591 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Eating Area adjacent Kitchen
Front of W Melson House
Family Room for reading, playing games, watching television, or just relaxing.
New and fully equipped Kitchen
Exceptional
(208 reviews)

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

St. Michaels

8% off
AU$4,440
for 7 nights, 1 cottage
AU$634 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!
Interior
Living area
Exceptional
(144 reviews)

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

Bozman

12% off
AU$2,925
for 7 nights, 1 cottage
AU$418 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Terrace/patio
Living area
Living area
Interior
Exceptional
(7 reviews)

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

St. Michaels

17% off
AU$3,644
for 7 nights, 1 home
AU$521 per night
includes taxes & fees
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
Interior
Living area
Property grounds
Private kitchen
Exceptional
(412 reviews)

Stay in the HEART of Saint Michaels!

St. Michaels

17% off
AU$2,897
for 7 nights, 1 home
AU$414 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
AU$4,098
for 7 nights, 1 cottage
AU$585 per night
includes taxes & fees
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Private kitchen
Exterior
Living area
Exterior
Exceptional
(28 reviews)

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

Cambridge

8% off
AU$6,611
for 7 nights, 1 home
AU$944 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