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Wye Mills Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Wye Mills vacation rentals

A deck with a view of a marina, including boats and docks.

1. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
The price is ￥14,180
￥40,441 total
includes taxes & fees
Nov 12 - Nov 13
Cass-N-Reel Luxury Houseboat
A kitchen with wooden cabinets, a dining table, and a refrigerator.

2. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (13 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
Family Retreat at Lansdowne Manor
Living area

3. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
Easton
10.0 out of 10, Exceptional, (1 review)
"Fabulous location in town location! It was much larger than we expected - 2 levels. Nice open layout on the main level with 2 BR/BA and a 3rd BR/BA on 2nd floor. Owners are very responsive before and during the trip. We could not connect to the TV, but owner quickly offered assistance. Bathrooms can use some towel racks and shelves. Beds/pillows were comfy! We were very happy with our stay."
United States
Lynn G.
The price is ￥35,451
￥63,131 total
includes taxes & fees
Nov 10 - Nov 11
EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

4. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is ￥11,912
￥42,951 total
includes taxes & fees
Nov 2 - Nov 3
Charming Coastal/Country Home w/3 Acres & Sauna!
A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

5. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (56 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is ￥23,634
￥57,465 total
includes taxes & fees
Nov 23 - Nov 24
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

6. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (132 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is ￥15,598
￥23,690 total
includes taxes & fees
Nov 3 - Nov 4
First Floor Studio Apartment in Historic Chestertown
A house with a blue front door, two windows, and a small porch.

7. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (32 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is ￥19,405
￥44,118 total
includes taxes & fees
Nov 2 - Nov 3
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A garden path leading to a wooden building with a rustic appearance.

8. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is ￥28,928
￥43,335 total
includes taxes & fees
Nov 3 - Nov 4
Secluded Cottage in Middle of Chestertown
A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

9. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful home. Plenty of space inside with great outdoor spaces. Very clean and easy to contact host. Family friendly-would highly recommend!"
United States
Jessica H.
The price is ￥56,722
￥91,691 total
includes taxes & fees
Nov 2 - Nov 3
Turnbridge Manor
A spacious living area with a dining table, sofa, and a kitchen in the background.

10. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is ￥35,451
￥52,978 total
includes taxes & fees
Nov 2 - Nov 3
Newly restored apartment in the heart of Chestertown
A building with a gabled roof and a circular vent on the roof.

11. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is ￥31,512
￥47,397 total
includes taxes & fees
Nov 2 - Nov 3
BAYSIDE BUNGALOW
Three birds perched on a wooden structure by the water.

12. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is ￥110,134
￥195,760 total
includes taxes & fees
Dec 1 - Dec 2
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

13. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (44 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is ￥110,134
￥195,760 total
includes taxes & fees
Dec 1 - Dec 2
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

14. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is ￥31,197
￥43,591 total
includes taxes & fees
Nov 7 - Nov 8
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A covered porch with a wooden bench, potted plants, and a decorative railing.

15. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is ￥47,986
￥71,987 total
includes taxes & fees
Nov 2 - Nov 3
Wren Retweet- Country Estate in Center of C’Town
A two-story house with a red roof, a brick chimney, and a small porch.

16. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
8.4 out of 10, Very good, (6 reviews)
"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."
United States
Anonymous traveler
The price is ￥113,443
￥157,828 total
includes taxes & fees
Nov 3 - Nov 4
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
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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Top Wye Mills Hotel Reviews

St Michaels Inn

St Michaels Inn

10/10 Excellent
"We enjoyed our stay. It was close to our event and our room was quite comfortable. The staff was very helpful to us and accommodating."
Phyllis 1-night trip
Posted 14 hours ago
St Michaels Inn

Find out more about Wye Mills

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Frequently asked questions

Can I find a vacation rental in Wye Mills?

Yes, we have vacation rentals near the most popular attractions in Wye Mills, or you can go with a secluded option if you want a relaxing place to stay. Wye Mills is known for its waterfront.

What are some of the best vacation home rentals that Wye Mills has to offer?

Dollhouse in Central Historic St Michaels: This vacation home rental outside of Wye Mills offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Wye Mills?

While exploring the area, visit family-friendly sights like Chesapeake Bay Maritime Museum, or get outside and enjoy nature at Chesapeake Bay Environmental Center. Wye Landing and Wye Oak State Park are other places to visit while you're in town.

What are vacation rentals like in Wye Mills?

Vacation rentals are private properties you can reserve for several days or more in Wye Mills. Vacation rentals feature amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a small group gathering.