Wye Island holiday homes

We found 151 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Wye Island

Showing deals for:20 Nov - 27 Nov

Dining table- seats 10!
Pool
View from Foyer into Great Room
screened porch
Exceptional
(145 reviews)

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton

8% off
NZ$13,818
for 7 nights, 1 home
NZ$1,974 per night
includes taxes & fees
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Interior
Living area
Interior
Room
Exceptional
(15 reviews)

Waterfront 4 BR home with private pier and boat dock

Grasonville

8% off
NZ$9,347
for 7 nights, 1 home
NZ$1,335 per night
includes taxes & fees
Waterfront 4 BR home with private pier and boat dock
Custom kitchen
View down the lane
Sit and stay a while!
Dining Room - Seats 6
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
NZ$3,384
for 7 nights, 1 cottage
NZ$483 per night
includes taxes & fees
Perfect Waterview Cottage - St. Michaels Getaway
Private kitchen
Dining
Interior
Private kitchen
Exceptional
(10 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

8% off
NZ$6,324
for 7 nights, 1 cottage
NZ$903 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Interior
Be ready to float! Bring your own inner tubes  and tennis shoes!
Exterior detail
Living area
Exceptional
(143 reviews)

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

Bozman

12% off
NZ$3,496
for 7 nights, 1 cottage
NZ$499 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Outdoor dining
Pool
Private kitchen
Interior
Exceptional
(216 reviews)

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville

12% off
NZ$5,643
for 7 nights, 1 room
NZ$806 per night
includes taxes & fees
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Eating area in panelled Family Room. Eat here, in dining room, or on porch!
St. Michaels Harbor from Park down street
Front and side view of Blades House from Locust St.
Large screened porch with ceiling fan allows outdoor dining and relaxing.
Exceptional
(150 reviews)

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

St. Michaels

8% off
NZ$4,992
for 7 nights, 1 cottage
NZ$713 per night
includes taxes & fees
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
  • 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

Book a holiday rental for your Wye Island getaway

Learn about the unique charm of Wye Island with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Wye Island

Are you searching for attractions to see in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Wye Island a one-of-a-kind holiday spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Queenstown Harbor Golf (7 mi / 11.3 km)
  • St. Michaels Winery (8.4 mi / 13.5 km)
  • Hog Neck Golf Course (6.6 mi / 10.7 km)
  • Easton Cycle and Sport (9 mi / 14.5 km)
  • Paul Reed Smith Guitars (11.2 mi / 18.1 km)
  • Triple Creek Winery (7.5 mi / 12.1 km)

Exploring the natural landscape of Wye Island

Whether you're an active traveller or just want to take in the scenery, Wye Island is a great place to get outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Chesapeake Bay Environmental Center (5.9 mi / 9.5 km)
  • Northern Chesapeake Bay (11.8 mi / 18.9 km)
  • Sandy Point Beach (15.7 mi / 25.2 km)
  • Bay Ridge Beach (17 mi / 27.3 km)
  • Romancoke Wharf County Park (9.9 mi / 16 km)
  • Eastern Neck National Wildlife Refuge (10.6 mi / 17 km)

More holiday ideas