Wye Island holiday rentals

We found 148 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Wye Island

Showing deals for:1 Jan - 8 Jan

screened porch
Pool
View from Pier back to house!
View from Foyer into Great Room
Exceptional
(147 reviews)

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

Easton

8% off
AU$11,457
for 7 nights, 1 home
AU$1,637 per night
includes taxes & fees
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Kitchen
Kitchen
Exterior
Kitchen
Exceptional
(32 reviews)

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Stevensville

12% off
AU$3,138
for 7 nights, 1 room
AU$448 per night
includes taxes & fees
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
View of St Michaels Harbor from french doors in Living Room, and from Side Patio
View of Side of Harrison House and St. Michaels Harbor from Locust Street
Thomas Harrison House looking from St. Michaels Town Harbor
View of St. Michaels Harbor from Town Park in front of Thomas Harrison House
Exceptional
(146 reviews)

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

St. Michaels

8% off
AU$8,931
for 7 nights, 1 home
AU$1,276 per night
includes taxes & fees
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
Interior
Private kitchen
Interior
Property grounds
Exceptional
(7 reviews)

Arcadia Shores on the Cove.

Easton

8% off
AU$6,897
for 7 nights, 1 home
AU$985 per night
includes taxes & fees
Arcadia Shores on the Cove.
Private kitchen
Dining
Living area
Private kitchen
Exceptional
(11 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

8% off
AU$4,160
for 7 nights, 1 cottage
AU$594 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Property grounds
Pool
Outdoor dining
Interior
Exceptional
(218 reviews)

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

Stevensville

12% off
AU$4,701
for 7 nights, 1 room
AU$672 per night
includes taxes & fees
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Living area
Be ready to float! Bring your own inner tubes  and tennis shoes!
Interior
Exterior detail
Exceptional
(145 reviews)

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

Bozman

12% off
AU$2,996
for 7 nights, 1 cottage
AU$428 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Interior
Living area
Exterior
Property grounds
Exceptional
(417 reviews)

Stay in the HEART of Saint Michaels!

St. Michaels

17% off
AU$2,982
for 7 nights, 1 home
AU$426 per night
includes taxes & fees
Stay in the HEART of Saint Michaels!
Interior
Dining
Room
Exterior
Exceptional
(16 reviews)

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville

8% off
AU$3,279
for 7 nights, 1 home
AU$468 per night
includes taxes & fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
  • 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)
  • Paul Reed Smith Guitars (11.2 mi / 18.1 km)
  • Triple Creek Winery (7.5 mi / 12.1 km)
  • Talbot Massage (8.8 mi / 14.2 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:

  • Eastern Neck National Wildlife Refuge (10.6 mi / 17 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)
  • Chesapeake Bay Environmental Center (5.9 mi / 9.5 km)
  • Romancoke Wharf County Park (9.9 mi / 16 km)

More holiday ideas