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Compare 194 Vacation Homes in Wye Mills with updated reviews, rates, and availability.

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (31)
"Other than arriving with no sheets on beds, no towels, and no basic toiletries or kitchen cleaning set, place is very good. Cleaning service, owner, or property management firm mismanaged the prep for our arrival. Absence of sheets, towels, etc. was rectified in a bit more than 1 hour. Nice place and superb location for seeing the village. Quiet, but right in the middle of all shops, farmers market, restaurants, etc. There was a bit of a pet odor in the 1st floor bedroom. Only other comment is...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
10.0 out of 10, Exceptional, (47)
"Beautiful views and spacious comfortable living space. Well supplied kitchen. "
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
Walk to Everything House
10.0 out of 10, Exceptional, (72)
"We thoroughly enjoyed the convenience of walking to shops, restaurants, and waterfront! Residence was charming and clean! Only minor issue was we couldn’t locate the iron- just the ironing board! We still had fun but we’re just a bit wrinkled!😁"
Walk to Everything House
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
10.0 out of 10, Exceptional, (31)
"House was spacious, clean, and exactly as described in the listings. We had a great time!"
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Grasonville Home w/ Private Pool on the Water
9.8 out of 10, Exceptional, (19)
"We stayed at this place for a family wedding at the nearby beach club. In addition to be a convenient location, the views from the house and property were stunning. The style inside the house was quite eclectic which gave it wonderful charm. Coming back at night gave us fits trying to find the driveway but that was a small price to pay for such a great house. "
Grasonville Home w/ Private Pool on the Water
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.8 out of 10, Exceptional, (8)
"Stayed here for a wedding was perfect for the group of 4 of us. Living room is bigger than it looks in the photos and the house was well kept/ clean. Host was great and responsive as well!"
The price is AED 735
AED 1,332 total
includes taxes & fees
11 Nov - 12 Nov
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!
9.8 out of 10, Exceptional, (21)
"We went to this wonderful home for our 32nd wedding anniversary and it was so lovely. The home was so comfy and well stocked, the beds were very comfortable and the sunsets were spectacular. We enjoyed every minute! Barbara was just so delightful and helpful. She made everything perfect! Would love to stay again some time."
Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
7.4 out of 10, Good, (3)
"About a 10 minute walk to main street, 15-20 to the Marinas. The house is cute, has a nice common room, and the bed was comfy."
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
Kent Island Luxury Waterfront
10.0 out of 10, Exceptional, (5)
"Such a beautiful property. . Wonderful experience. Love to come back again. House is way better than we expected. Gorgeous views and had an amazing experience of moonrise abd sunrise"
Kent Island Luxury Waterfront
One-level waterfront home with beach and views all the way to the Bay Bridge
2.0 star property
10.0 out of 10, Exceptional, (4)
"It’s a great property to rent. The location and views are unbelievable. They do not some towel hooks in each bathroom but no other issues with this place at all."
One-level waterfront home with beach and views all the way to the Bay Bridge
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
10.0 out of 10, Exceptional, (1)
"This was the most peaceful and perfect property. I felt like I was on vacation and able to relax! We would definitely return if we are in the area again."
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (33)
"The bay cottage's porch was a perfect spot to enjoy a bottle of wine and snacks provided by the thoughtful hosts. Clever decor , furnishings, and sauna made our stay special and warm. Had crab dinner viewing sunset over the bay at dockside suggested by hosts. we hope to return. "
The price is AED 643
AED 989 total
includes taxes & fees
9 Nov - 10 Nov
BAYSIDE BUNGALOW
St. Michaels Waterfront Home
9.6 out of 10, Exceptional, (25)
"Excellent property ! Had everything we needed and wanted and more. Waterfront views and shorebirds beautiful ! We hope to revisit !!! "
St. Michaels Waterfront Home
New! Stylish downtown home w/awesome outdoor area!
10.0 out of 10, Exceptional, (21)
"Great stay, clean and spacious. Lovely outdoor seating area. Convenient to the town of Stevensville, shopping and dining options, coffee house and great location for Kent Island and Annapolis. Loved the home and would definitely stay again! "
New! Stylish downtown home w/awesome outdoor area!
Waterfront Annapolis Home: Fire Pit & Fishing Pier
9.2 out of 10, Wonderful, (31)
"We loved our stay. The house is well furnished and has a delightful outdoor setting. It was hard to leave the house to go see Annapolis because it was so peaceful and relaxing just to stay there. Everything was easily accessible - tour of the Naval Academy and Annapolis, Quiet Waters Dog Beach, shopping and delicious restaurants. However the best was sitting outside by the water, enjoying the air and the wildlife. "
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
9.8 out of 10, Exceptional, (9)
"Our stay was amazing. The house is beautiful. The views and peaceful location were completely used. We had many fun game nights and dinners around the table, the kitchen easily provided many happy meals. The gas grill, the fire pit were easy to use. The kayaks were a lot of fun. Sitting on the dock enjoying the peaceful quiet mornings was rejuvenating. The pool chairs and umbrellas were really nice. A ping pong table in the garage was a ton of fun too. The extra fridge/freezer was handy and the...
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
Autumn Charm Beautiful Waterfront Retreat Near Historic St. Michaels & Royal Oak
9.8 out of 10, Exceptional, (37)
"Great rental experience. Barb was fantastic at communicating. The house was perfect for our group, including some adults and some young children. Yard and dock were a blast for playing and fishing. "
Autumn Charm Beautiful Waterfront Retreat Near Historic St. Michaels & Royal Oak
Waterfront family resort Lodge with private pier, game room and bar
9.8 out of 10, Exceptional, (22)
"The property was excellent for a large group. We was there for a Sailing Regatta on the lake in front of the house. The perfect house for groups."
Waterfront family resort Lodge with private pier, game room and bar
Downtown Oxford | Charming | Pet Friendly | Bikes
9.2 out of 10, Wonderful, (25)
"The property was just as we remembered it. This is our second stay at this location so no surprises. The driveway is a little tight with the new fence but not an issue, so why mention it you say? As we get older the stairs are very tight and would become an issue. I sent a note to ES people about the plumbing upstairs but an easy fix. All good maybe see you next time."
Downtown Oxford | Charming | Pet Friendly | Bikes
Thorneton Point Estate
9.8 out of 10, Exceptional, (12)
"I have to say that this was one of the best trips I’ve ever taken. I Travel a lot And make sure to have a family vacation every summer and the summer we wanted to stay within driving distance. Thorton estate was a grand slam homer And far exceeded expectations. We literally did not leave the property for the entire time that we were there. Each day we swam in the pool, went paddle boarding/kayaking, sat around in the house, used the game room, played with the pool table, and made a fire pit at...
Thorneton Point Estate
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.
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Other property types in Wye Mills

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (112)
"Our stay in St Michael's was wonderful. The location of this property could not be better. Close to marina, parks, restaurants, historic downtown and the maritime museum. We never needed to use our car! Tom is an excellent host. "
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (216)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (132)
"Fine stay pretty quiet off season"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
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.