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:8 Jan - 15 Jan

two twin beds and play area in loft
Exterior
dining room
view from balcony overlooking playhouse, pergola and Brooks Creek
Exceptional
(277 reviews)

Family and Pet-Friendly, Waterfront with Pier

Cambridge

8% off
S$3,011
for 7 nights, 1 cottage
S$430 per night
includes taxes & fees
Family and Pet-Friendly, Waterfront with Pier
Dining
Interior
Living area
Interior
Wonderful
(7 reviews)

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

Royal Oak

8% off
S$11,486
for 7 nights, 1 cottage
S$1,641 per night
includes taxes & fees
Spacious waterfront house in charming Royal Oak with WiFi, AC, dock
Exterior
Aerial view
Aerial view
Exterior
Exceptional
(70 reviews)

Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay

Cambridge

8% off
S$9,644
for 7 nights, 1 home
S$1,378 per night
includes taxes & fees
Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay
Another view from above.
The view off of the point, breathtaking.
Interior
Interior
Exceptional
(46 reviews)

Grandview- Main House

Bozman

25% off
S$6,370
for 7 nights, 1 home
S$910 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
View of St. Michaels Harbor from Town Park in front of Thomas Harrison House
Exceptional
(147 reviews)

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

St. Michaels

8% off
S$7,754
for 7 nights, 1 home
S$1,108 per night
includes taxes & fees
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
Delightful front garden welcomes you when approaching house from driveway
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
(165 reviews)

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

Sherwood

10% off
S$2,782
for 7 nights, 1 home
S$397 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Eating Area adjacent Kitchen
Front of W Melson House
Large Screened Porch with rocking chairs
Family Room for reading, playing games, watching television, or just relaxing.
Exceptional
(211 reviews)

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

St. Michaels

8% off
S$4,131
for 7 nights, 1 cottage
S$590 per night
includes taxes & fees
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Private kitchen
Dining
Living area
Interior
Exceptional
(11 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

8% off
S$3,234
for 7 nights, 1 cottage
S$462 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Room
Living area
Living area
Interior
Exceptional
(7 reviews)

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

St. Michaels

16% off
S$2,814
for 7 nights, 1 home
S$402 per night
includes taxes & fees
Private+Cozy-3br+2ba-1mile to Historic Downtown 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
(151 reviews)

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

St. Michaels

8% off
S$3,820
for 7 nights, 1 cottage
S$546 per night
includes taxes & fees
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Exterior detail
Be ready to float! Bring your own inner tubes  and tennis shoes!
Living area
Interior
Exceptional
(145 reviews)

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

Bozman

12% off
S$2,746
for 7 nights, 1 cottage
S$392 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Exterior
Exterior
Living area
Dining
Exceptional
(28 reviews)

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

Cambridge

8% off
S$6,659
for 7 nights, 1 home
S$951 per night
includes taxes & fees
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
Private kitchen
Living area
Exterior
Interior
Exceptional
(418 reviews)

Stay in the HEART of Saint Michaels!

St. Michaels

16% off
S$2,733
for 7 nights, 1 home
S$390 per night
includes taxes & fees
Stay in the HEART of Saint Michaels!
  • 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)
  • Romancoke Wharf County Park (12.7 mi / 20.4 km)

More holiday ideas