Holiday rentals near Wye Landing
We found 360 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:3 Oct - 10 Oct
Image gallery for Secluded Waterfront Property on 3 acres with swimming pool and dock.
1010 out of 10 rating
Exceptional
(47 reviews)
Secluded Waterfront Property on 3 acres with swimming pool and dock.
Bozman, MD
5% off
Price is NZ$9,943
NZ$9,943
NZ$1,420 per night
includes taxes & fees
Image gallery for HGTV quality, private guest suite, country getaway with hot tub & fire pit
1010 out of 10 rating
Exceptional
(5 reviews)
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Centreville, MD
8% off
Price is NZ$3,696
NZ$3,696
NZ$528 per night
includes taxes & fees
Image gallery for St Michaels Retreat, Log Cabin, Family & Pet-Friendly
9.89.8 out of 10 rating
Exceptional
(6 reviews)
St Michaels Retreat, Log Cabin, Family & Pet-Friendly
St. Michaels, MD
16% off
Price is NZ$10,018
NZ$10,018
NZ$1,431 per night
includes taxes & fees
Image gallery for Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
1010 out of 10 rating
Exceptional
(5 reviews)
Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
Chestertown, MD
17% off
Price is NZ$4,856
NZ$4,856
NZ$694 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$11,168
NZ$11,168
NZ$1,595 per night
includes taxes & fees
Image gallery for Studio in Downtown – Walk to Everything!
1010 out of 10 rating
Exceptional
(19 reviews)
Studio in Downtown – Walk to Everything!
St. Michaels, Maryland
12% off
Price is NZ$3,292
NZ$3,292
NZ$470 per night
includes taxes & fees
Image gallery for Waterfront 4 acre home with pool between the towns of St. Michaels & Easton!
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Waterfront 4 acre home with pool between the towns of St. Michaels & Easton!
Easton, MD
8% off
Price is NZ$10,054
NZ$10,054
NZ$1,436 per night
includes taxes & fees
Image gallery for The heart of St Michaels awaits.
1010 out of 10 rating
Exceptional
(39 reviews)
The heart of St Michaels awaits.
St. Michaels, Maryland
7% off
Price is NZ$3,384
NZ$3,384
NZ$483 per night
includes taxes & fees
Image gallery for Chesapeake Bay Waterfront ARTectural Home
1010 out of 10 rating
Exceptional
(28 reviews)
Chesapeake Bay Waterfront ARTectural Home
Stevensville, MD
8% off
Price is NZ$12,570
NZ$12,570
NZ$1,796 per night
includes taxes & fees
Image gallery for Gorgeous Creek Side Ranch-Style Estate With Dock
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Gorgeous Creek Side Ranch-Style Estate With Dock
Queenstown, Maryland
7% off
Price is NZ$7,354
NZ$7,354
NZ$1,051 per night
includes taxes & fees
Image gallery for Waterfront Sunset Bayview: sleeps 6
1010 out of 10 rating
Exceptional
(17 reviews)
Waterfront Sunset Bayview: sleeps 6
Chester, MD
8% off
Price is NZ$5,343
NZ$5,343
NZ$763 per night
includes taxes & fees
Image gallery for Pet-Friendly Cottage – Ideal for Summer Getaways!
1010 out of 10 rating
Exceptional
(6 reviews)
Pet-Friendly Cottage – Ideal for Summer Getaways!
Tilghman, Maryland
11% off
Price is NZ$4,154
NZ$4,154
NZ$593 per night
includes taxes & fees
Image gallery for Eastern Shore Waterside Cottage Near St. Michaels
1010 out of 10 rating
Exceptional
(19 reviews)
Eastern Shore Waterside Cottage Near St. Michaels
Neavitt, MD
12% off
Price is NZ$3,789
NZ$3,789
NZ$541 per night
includes taxes & fees
Image gallery for Circa 1700 Chesapeake Colonial home on the National Register.
9.89.8 out of 10 rating
Exceptional
(53 reviews)
Circa 1700 Chesapeake Colonial home on the National Register.
Stevensville, MD
8% off
Price is NZ$6,468
NZ$6,468
NZ$924 per night
includes taxes & fees
Image gallery for Charming Waterfront Cottage Retreat near St. Michaels
1010 out of 10 rating
Exceptional
(6 reviews)
Charming Waterfront Cottage Retreat near St. Michaels
Bozman, MD
16% off
Price is NZ$4,645
NZ$4,645
NZ$664 per night
includes taxes & fees
Image gallery for Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
1010 out of 10 rating
Exceptional
(45 reviews)
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Rock Hall, MD
12% off
Price is NZ$2,984
NZ$2,984
NZ$426 per night
includes taxes & fees
Image gallery for Peaceful getaway convenient to local amenities including beach, boating & food
9.89.8 out of 10 rating
Exceptional
(113 reviews)
Peaceful getaway convenient to local amenities including beach, boating & food
Rock Hall, MD
8% off
Price is NZ$2,878
NZ$2,878
NZ$411 per night
includes taxes & fees
Image gallery for Dollhouse in Central Historic St Michaels
9.69.6 out of 10 rating
Exceptional
(49 reviews)
Dollhouse in Central Historic St Michaels
St. Michaels, MD
12% off
Price is NZ$3,477
NZ$3,477
NZ$497 per night
includes taxes & fees
Image gallery for Kent Island Luxury Waterfront
1010 out of 10 rating
Exceptional
(6 reviews)
Kent Island Luxury Waterfront
Stevensville, MD
17% off
Price is NZ$8,981
NZ$8,981
NZ$1,283 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$11,168
NZ$11,168
NZ$1,595 per night
includes taxes & fees
Image gallery for Cozy, unique, historic registered cottage on the Corsica River!
1010 out of 10 rating
Exceptional
(5 reviews)
Cozy, unique, historic registered cottage on the Corsica River!
Centreville, MD
8% off
Price is NZ$2,549
NZ$2,549
NZ$364 per night
includes taxes & fees
Image gallery for Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.69.6 out of 10 rating
Exceptional
(119 reviews)
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
St. Michaels, MD
8% off
Price is NZ$4,018
NZ$4,018
NZ$574 per night
includes taxes & fees
Image gallery for Harbor View Suite
1010 out of 10 rating
Exceptional
(24 reviews)
Harbor View Suite
St. Michaels, MD
5% off
Price is NZ$3,485
NZ$3,485
NZ$498 per night
includes taxes & fees
Image gallery for Waterfront Paradise on the Eastern Shore of Chesapeake Bay
1010 out of 10 rating
Exceptional
(64 reviews)
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
Rock Hall, MD
8% off
Price is NZ$11,223
NZ$11,223
NZ$1,603 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Wye Landing
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
122 reviews(122 reviews)
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
99 reviews(99 reviews)
Get Away To The Beautiful Wye River
Sleeps 11 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
44 reviews(44 reviews)
Waterfront! Sunroom, Private Dock, Boat Tie-Up & Near Town
Sleeps 12 · 5 bedrooms · 3 bathrooms
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
23 reviews(23 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