Holiday rentals with weekly discounts – Tilghman Island
Showing deals for:5 Feb - 12 Feb
Image gallery for Family and Pet-Friendly, Waterfront with Pier
1010 out of 10, Exceptional, (279 reviews)
Exceptional
(279 reviews)
Family and Pet-Friendly, Waterfront with Pier
Cambridge
8% off
Price is NZ$4,127
NZ$4,127
for 7 nights, 1 cottage
NZ$590 per night
includes taxes & fees
Image gallery for Grandview- Main House
9.89.8 out of 10, Exceptional, (46 reviews)
Exceptional
(46 reviews)
Grandview- Main House
Bozman
26% off
Price is NZ$8,191
NZ$8,191
for 7 nights, 1 home
NZ$1,170 per night
includes taxes & fees
Image gallery for Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay
1010 out of 10, Exceptional, (70 reviews)
Exceptional
(70 reviews)
Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay
Cambridge
8% off
Price is NZ$12,411
NZ$12,411
for 7 nights, 1 home
NZ$1,773 per night
includes taxes & fees
Image gallery for Spacious waterfront house in charming Royal Oak with WiFi, AC, dock
9.09.0 out of 10, Wonderful, (8 reviews)
Wonderful
(8 reviews)
Spacious waterfront house in charming Royal Oak with WiFi, AC, dock
Royal Oak
9% off
Price is NZ$11,767
NZ$11,767
for 7 nights, 1 cottage
NZ$1,681 per night
includes taxes & fees
Image gallery for Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
9.49.4 out of 10, Exceptional, (148 reviews)
Exceptional
(148 reviews)
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
St. Michaels
8% off
Price is NZ$10,526
NZ$10,526
for 7 nights, 1 home
NZ$1,504 per night
includes taxes & fees
Image gallery for Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.89.8 out of 10, Exceptional, (213 reviews)
Exceptional
(213 reviews)
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
St. Michaels
8% off
Price is NZ$5,647
NZ$5,647
for 7 nights, 1 cottage
NZ$807 per night
includes taxes & fees
Image gallery for Charming Waterfront Cottage Retreat near St. Michaels
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Charming Waterfront Cottage Retreat near St. Michaels
Bozman
8% off
Price is NZ$5,908
NZ$5,908
for 7 nights, 1 cottage
NZ$844 per night
includes taxes & fees
Image gallery for Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
1010 out of 10, Exceptional, (167 reviews)
Exceptional
(167 reviews)
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Sherwood
11% off
Price is NZ$3,598
NZ$3,598
for 7 nights, 1 home
NZ$514 per night
includes taxes & fees
Image gallery for Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
1010 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
St. Michaels
17% off
Price is NZ$3,657
NZ$3,657
for 7 nights, 1 home
NZ$522 per night
includes taxes & fees
Image gallery for Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.69.6 out of 10, Exceptional, (153 reviews)
Exceptional
(153 reviews)
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
St. Michaels
8% off
Price is NZ$5,211
NZ$5,211
for 7 nights, 1 cottage
NZ$744 per night
includes taxes & fees
Image gallery for Charming cottage along water with private pier, near St. Michaels Winery
9.69.6 out of 10, Exceptional, (145 reviews)
Exceptional
(145 reviews)
Charming cottage along water with private pier, near St. Michaels Winery
Bozman
12% off
Price is NZ$3,666
NZ$3,666
for 7 nights, 1 cottage
NZ$524 per night
includes taxes & fees
Image gallery for Spacious waterfront home with amazing views, private pier, fishing and crabbing.
9.69.6 out of 10, Exceptional, (28 reviews)
Exceptional
(28 reviews)
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
Cambridge
9% off
Price is NZ$8,409
NZ$8,409
for 7 nights, 1 home
NZ$1,201 per night
includes taxes & fees
Image gallery for Stay in the HEART of Saint Michaels!
1010 out of 10, Exceptional, (423 reviews)
Exceptional
(423 reviews)
Stay in the HEART of Saint Michaels!
St. Michaels
17% off
Price is NZ$3,609
NZ$3,609
for 7 nights, 1 home
NZ$516 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Tilghman Island
1. Peaceful Tilghman Island Cottage – Pet Friendly Chesapeake Bay Escape
Sleeps 6 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
52 reviews(52 reviews)
2. Pet-Friendly Cottage on Tilghman Island | Minutes to St. Michaels
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
3. Vintage Pet-Friendly Cottage | Tilghman Island
Sleeps 4 · 2 bedrooms · 1+ bathroom
4. Family Friendly Cottage - Waterfront. Spectacular Sunsets over Chesapeake Bay
Sleeps 5 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
5. Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026!
Sleeps 8 · 4 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
31 reviews(31 reviews)
6. Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Sleeps 4 · 2 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value