Wye Mills Holiday Rentals from NZ$478: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Wye Mills has to offer?

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

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In two weeks

In two months

In three months

In four months

Our top choices for Wye Mills holiday rentals

A modern kitchen with dark cabinets, a white countertop, and a large window.

1. Cass-N-Reel Luxury Houseboat

Grasonville

Danny B.

includes taxes & fees

8 Oct - 9 Oct

A lighthouse with a white exterior, a balcony, and a metal roof.

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

Stevensville

Michelle P.

includes taxes & fees

7 Oct - 8 Oct

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

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

Stevensville

Dawn G.

includes taxes & fees

5 Oct - 6 Oct

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

4. First Floor Studio Apartment in Historic Chestertown

Chestertown

"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"

Charr

includes taxes & fees

5 Oct - 6 Oct

A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

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

Rock Hall

lisa p.

includes taxes & fees

13 Oct - 14 Oct

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.

6. Turnbridge Manor

Denton

Glenn S.

includes taxes & fees

6 Oct - 7 Oct

Three birds perched on a wooden structure by the water.

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

Stevensville

barbara s.

includes taxes & fees

5 Oct - 6 Oct

A spacious living area with a dining table, sofa, and a kitchen in the background.

8. Newly restored apartment in the heart of Chestertown

Chestertown

Anonymous traveller

includes taxes & fees

7 Oct - 8 Oct

A building with a gabled roof and a circular vent on the roof.

9. BAYSIDE BUNGALOW

Rock Hall

Diane V.

includes taxes & fees

5 Oct - 6 Oct

A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

10. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

includes taxes & fees

8 Oct - 9 Oct

A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

11. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stevensville

David R.

includes taxes & fees

5 Oct - 6 Oct

A deck with outdoor furniture, a potted plant, and a house in the background.

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

Chestertown

"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...

Miriam G.

includes taxes & fees

12 Oct - 13 Oct

A two-story house with a red roof, a brick chimney, and a small porch.

13. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

"We arrived and the air conditioning was broken.The owner did not inform us but installed portable AC’s running vents out of doors that would not close or lock. The old AC unit was installed incorrectly &BR below flooded by 12 am. contacted owner and then was told not to run AC & we would be refunded. Covered mattresses that were being soaked, cleaned up flood, washed all bedding. Owner said trying to find us another rental but there were none & I had service dog. If we moved we would miss...

Suzanne R.

includes taxes & fees

6 Oct - 7 Oct

A hallway with wooden flooring, a door on the right, and a window at the end.

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

Chestertown

Mandy D.

includes taxes & fees

7 Oct - 8 Oct

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Top Wye Mills Hotel Reviews

Best Western Plus Easton Inn & Suites

10/10 Excellent

"I believe the gentleman at the front desk was named Ron? He was great. Took care of my reservation right away even though I was early."

Inn at Perry Cabin

10/10 Excellent

"Outstanding experience in every way. Staff was superior — everyone greeted us by name and was eager to ensure we had everything we needed. Meals at Stars were excellent — and the gorgeous views of the water and property enhanced the dining experience. The lit firepits and comfy seating outside were a welcome retreat in the early evening so we could sit and take in the views. We strolled the grounds via the walking paths and enjoyed the lush gardens and plantings. All in all, an amazing getaway."

Find out more about Wye Mills

Everything you need to know about Wye Mills holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wye Mills holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wye Mills holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wye Mills holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wye Mills. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wye Mills holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wye Mills holiday rentals we have selected for you start as low as NZ$478 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wye Mills rentals

At Expedia, we put the best Wye Mills holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Wye Mills rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wye Mills holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wye Mills. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a holiday rental in Wye Mills?

Yes, there are holiday rentals close to the most popular sights in Wye Mills, or you can select a more secluded option if you're looking for a relaxing stay. Wye Mills is known for its waterfront.

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

Dollhouse in Central Historic St Michaels: This holiday home rental outside of Wye Mills offers a garden, a BBQ 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 holiday rentals like in Wye Mills?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Wye Mills. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.

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Check prices for these dates

Our top choices for Wye Mills holiday rentals

1. Cass-N-Reel Luxury Houseboat

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

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

4. First Floor Studio Apartment in Historic Chestertown

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

6. Turnbridge Manor

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

8. Newly restored apartment in the heart of Chestertown

9. BAYSIDE BUNGALOW

10. Secluded Cottage in Middle of Chestertown

11. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

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

13. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

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

Find holiday rentals that suit your style

Top Wye Mills Hotel Reviews

Best Western Plus Easton Inn & Suites

St Michaels Inn

Baymont by Wyndham Easton

The Tilghman Island Inn

Hilton Garden Inn Kent Island Marina

Inn at Perry Cabin

Holiday Inn Express Easton by IHG

Sandaway Suites & Beach

Holiday Inn Express Annapolis East-Kent Island by IHG

Find out more about Wye Mills

Frequently asked questions

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