Wye Island holiday homes

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

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

Easton

8% off
NZ$14,749
for 7 nights, 1 home
NZ$2,107 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
NZ$3,895
for 7 nights, 1 room
NZ$556 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
Rear Porch for relaxing or for barbecues!
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
NZ$11,222
for 7 nights, 1 home
NZ$1,603 per night
includes taxes & fees
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
Interior
Private kitchen
Dining
Interior
Exceptional
(7 reviews)

Arcadia Shores on the Cove.

Easton

8% off
NZ$8,614
for 7 nights, 1 home
NZ$1,231 per night
includes taxes & fees
Arcadia Shores on the Cove.
Living area
Dining
Interior
Private kitchen
Exceptional
(11 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

8% off
NZ$5,262
for 7 nights, 1 cottage
NZ$752 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
NZ$5,944
for 7 nights, 1 room
NZ$849 per night
includes taxes & fees
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Exterior detail
Be ready to float! Bring your own inner tubes  and tennis shoes!
Living area
Interior
Exceptional
(145 reviews)

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

Bozman

12% off
NZ$3,721
for 7 nights, 1 cottage
NZ$532 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Property grounds
Living area
Private kitchen
Exterior
Exceptional
(417 reviews)

Stay in the HEART of Saint Michaels!

St. Michaels

17% off
NZ$3,703
for 7 nights, 1 home
NZ$529 per night
includes taxes & fees
Stay in the HEART of Saint Michaels!
Interior
Dining
Room
Living area
Exceptional
(16 reviews)

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

Grasonville

8% off
NZ$4,068
for 7 nights, 1 home
NZ$581 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