Holiday rentals near Wye Landing
We found 353 holiday rentals — enter your dates for availability
If you'd like to stay close to Wye Landing, scroll through and discover holiday rentals to find the perfect one for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include a pool and a washer and dryer. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Wye Landing
Showing deals for:1 Aug - 8 Aug
Image gallery for Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
1010 out of 10 rating
Exceptional
(8 reviews)
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Rock Hall, MD
8% off
Price is NZ$3,366
NZ$3,366
NZ$481 per night
includes taxes & fees
Image gallery for Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
1010 out of 10 rating
Exceptional
(13 reviews)
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
Rock Hall, MD
16% off
Price is NZ$3,063
NZ$3,063
NZ$438 per night
includes taxes & fees
Image gallery for 4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues
1010 out of 10 rating
Exceptional
(33 reviews)
4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues
Stevensville, MD
8% off
Price is NZ$11,684
NZ$11,684
NZ$1,669 per night
includes taxes & fees
Image gallery for Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
1010 out of 10 rating
Exceptional
(118 reviews)
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester, MD
8% off
Price is NZ$5,359
NZ$5,359
NZ$766 per night
includes taxes & fees
Image gallery for Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.
1010 out of 10 rating
Exceptional
(7 reviews)
Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.
Rock Hall, MD
8% off
Price is NZ$3,898
NZ$3,898
NZ$557 per night
includes taxes & fees
Image gallery for Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
1010 out of 10 rating
Exceptional
(75 reviews)
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
Stevensville, MD
8% off
Price is NZ$11,684
NZ$11,684
NZ$1,669 per night
includes taxes & fees
Image gallery for Annapolis Charm - Waterfront Private Fishing Dock Pier Near Beach - Navy Academy
9.89.8 out of 10 rating
Exceptional
(21 reviews)
Annapolis Charm - Waterfront Private Fishing Dock Pier Near Beach - Navy Academy
Annapolis, MD
8% off
Price is NZ$6,324
NZ$6,324
NZ$903 per night
includes taxes & fees
Image gallery for St Michaels Retreat, Log Cabin, Family & Pet-Friendly
9.69.6 out of 10 rating
Exceptional
(5 reviews)
St Michaels Retreat, Log Cabin, Family & Pet-Friendly
St. Michaels, MD
16% off
Price is NZ$10,248
NZ$10,248
NZ$1,464 per night
includes taxes & fees
Image gallery for Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
1010 out of 10 rating
Exceptional
(40 reviews)
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
Stevensville, MD
8% off
Price is NZ$9,007
NZ$9,007
NZ$1,287 per night
includes taxes & fees
Image gallery for Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
1010 out of 10 rating
Exceptional
(6 reviews)
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
St. Michaels, MD
17% off
Price is NZ$5,284
NZ$5,284
NZ$755 per night
includes taxes & fees
Image gallery for In Town, Rock Hall, Fenced-In Yard, 1 Block to Bay!!
9.89.8 out of 10 rating
Exceptional
(9 reviews)
In Town, Rock Hall, Fenced-In Yard, 1 Block to Bay!!
Rock Hall, MD
8% off
Price is NZ$2,957
NZ$2,957
NZ$422 per night
includes taxes & fees
Image gallery for Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
1010 out of 10 rating
Exceptional
(38 reviews)
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Stevensville, MD
8% off
Price is NZ$11,684
NZ$11,684
NZ$1,669 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 rating
Exceptional
(132 reviews)
Charming cottage along water with private pier, near St. Michaels Winery
Bozman, MD
12% off
Price is NZ$3,485
NZ$3,485
NZ$498 per night
includes taxes & fees
Image gallery for Kent Island Waterfront Cottage
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Kent Island Waterfront Cottage
Stevensville, MD
16% off
Price is NZ$4,179
NZ$4,179
NZ$597 per night
includes taxes & fees
Image gallery for A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels
1010 out of 10 rating
Exceptional
(18 reviews)
A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels
Easton, MD
8% off
Price is NZ$5,509
NZ$5,509
NZ$787 per night
includes taxes & fees
Image gallery for Perfect Waterview Cottage - St. Michaels Getaway
9.89.8 out of 10 rating
Exceptional
(110 reviews)
Perfect Waterview Cottage - St. Michaels Getaway
Wittman, MD
8% off
Price is NZ$3,177
NZ$3,177
NZ$454 per night
includes taxes & fees
Image gallery for Jellyfish Cottage - Waterfront. Spectacular Sunsets over Chesapeake Bay
9.69.6 out of 10 rating
Exceptional
(23 reviews)
Jellyfish Cottage - Waterfront. Spectacular Sunsets over Chesapeake Bay
Tilghman, MD
12% off
Price is NZ$5,438
NZ$5,438
NZ$777 per night
includes taxes & fees
Image gallery for Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
9.89.8 out of 10 rating
Exceptional
(60 reviews)
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
Rock Hall, MD
8% off
Price is NZ$3,839
NZ$3,839
NZ$548 per night
includes taxes & fees
Image gallery for The heart of St Michaels awaits.
1010 out of 10 rating
Exceptional
(34 reviews)
The heart of St Michaels awaits.
St. Michaels, Maryland
7% off
Price is NZ$4,283
NZ$4,283
NZ$612 per night
includes taxes & fees
Image gallery for Charming Waterfront Cottage Outside St. Michaels Close to the Oaks
1010 out of 10 rating
Exceptional
(93 reviews)
Charming Waterfront Cottage Outside St. Michaels Close to the Oaks
Royal Oak, MD
8% off
Price is NZ$6,119
NZ$6,119
NZ$874 per night
includes taxes & fees
Image gallery for Easter Weekend open WATERFRONT St Michaels area historic home, dog friendly
1010 out of 10 rating
Exceptional
(51 reviews)
Easter Weekend open WATERFRONT St Michaels area historic home, dog friendly
Neavitt, MD
8% off
Price is NZ$5,260
NZ$5,260
NZ$751 per night
includes taxes & fees
Image gallery for Waterfront 4 BR home with private pier and boat dock
1010 out of 10 rating
Exceptional
(8 reviews)
Waterfront 4 BR home with private pier and boat dock
Grasonville, MD
12% off
Price is NZ$8,298
NZ$8,298
NZ$1,185 per night
includes taxes & fees
Image gallery for Grace Cottage, Saint Michaels Walk to everything!
1010 out of 10 rating
Exceptional
(7 reviews)
Grace Cottage, Saint Michaels Walk to everything!
St. Michaels, MD
8% off
Price is NZ$7,383
NZ$7,383
NZ$1,055 per night
includes taxes & fees
Image gallery for Brand New Cottage Steps from the Beach!
1010 out of 10 rating
Exceptional
(58 reviews)
Brand New Cottage Steps from the Beach!
Rock Hall, MD
8% off
Price is NZ$3,204
NZ$3,204
NZ$458 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Wye Landing
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
Eastern Shore Waterside Cottage Near St. Michaels
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
19 reviews(19 reviews)
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Sleeps 6 · 3 bedrooms · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
34 reviews(34 reviews)
Tilghman | Pool | Private Dock | Pet Friendly
Sleeps 6 · 3 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres
Sleeps 8 · 4 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
59 reviews(59 reviews)
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
118 reviews(118 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