Search Vacation Homes in Wye Mills

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Wye Mills

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (38)
"We had a wonderful weekend at Bayside Bungalow. Chris and Paul have really set up a great spot to enjoy some peace and quiet on the Chesapeake Bay. Thank you for your hospitality and attention to detail!Sincerely,J, J and L"
The price is SAR 750
SAR 1,129 total
includes taxes & fees
6 Jun - 7 Jun
BAYSIDE BUNGALOW

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (49)
"Nice place "
Dollhouse in Central Historic St Michaels

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (35)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is SAR 469
SAR 1,228 total
includes taxes & fees
11 Jun - 12 Jun
Relax on Kent Island in 3 Bedroom Home w/Waterview

Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD

10.0 out of 10, Exceptional, (5)
Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD

25-50% Off~Private Beach~Hot Tub~Fire Table~

10.0 out of 10, Exceptional, (25)
"It was the perfect romantic getaway! "
25-50% Off~Private Beach~Hot Tub~Fire Table~

Minutes from Downtown Easton and St. Michaels | Charming | 4000 ft of Shoreline

10.0 out of 10, Exceptional, (5)
"All day views. Sunrises and sunsets. Quiet and easy to get to. Beautiful property and the house is perfect for a small group. Dock is great for crabbing and fishing. Will be back for sure!"
Minutes from Downtown Easton and St. Michaels | Charming | 4000 ft of Shoreline

A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels

10.0 out of 10, Exceptional, (19)
"This was a good house for a family get together with other people staying in the area. The house was clean and well stocked. Lovely setting on the water. "
A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (186)
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (38)
"Very clean, great location"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

10.0 out of 10, Exceptional, (37)
"Loved the location and the pristine condition of the house. "
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Circa 1700 Chesapeake Colonial home on the National Register.

9.8 out of 10, Exceptional, (52)
"Great and comfortable stay! Beautiful historic house and property Owners were so friendly and helpful"
Circa 1700 Chesapeake Colonial home on the National Register.

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (15)
"Perfect for a family wedding weekend"
River Front, Private Single Family Home

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

10.0 out of 10, Exceptional, (33)
"Perfect large space on a quiet and pretty area. Really great space. "
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Waterfront Annapolis Home: Fire Pit & Fishing Pier

9.2 out of 10, Wonderful, (36)
"We immensely enjoyed our stay! The home is a peaceful retreat yet close enough to Annapolis and DC to visit! It was super clean! It was a joy to sit outside and watch the wildlife on the water during the day! Will definitely come back!"
Waterfront Annapolis Home: Fire Pit & Fishing Pier

Tilghman | Pool | Private Dock | Pet Friendly

9.6 out of 10, Exceptional, (14)
"We really enjoyed this house! It was super clean and spacious. The pool was great and you can’t beat the water view. I would 100% stay here again!"
Tilghman | Pool | Private Dock | Pet Friendly

Thorneton Point Estate

9.8 out of 10, Exceptional, (16)
"Beautiful, well-maintained property in a gorgeous waterside setting. "
Thorneton Point Estate

Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

10.0 out of 10, Exceptional, (15)
"Extremely clean, comfortable, and cozy place to stay for a weekend trip. The host was great to work with. We would definitely stay again."
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

Tilghman Island Retreat By Knapps Narrows!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great little cottage for small family in quiet, low key area. "
Tilghman Island Retreat By Knapps Narrows!

Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien

10.0 out of 10, Exceptional, (2)
"I was all about having a killer water view, and this certainly has that. Entire house was beautiful, and very tastefully decorated. Would strongly recommend to any family. "
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien

New! Stylish downtown home w/awesome outdoor area!

9.8 out of 10, Exceptional, (23)
"Place was clean and well furnished. Very comfortable and close to the venue where we attended an event. Meg (host) was very responsive and helpful."
New! Stylish downtown home w/awesome outdoor area!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in