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Winfield Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Winfield vacation rentals

A ping pong table in a room with a television, a plant, and a sofa.

1. Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV

Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
Woodbine
8.0 out of 10, Very Good, (2 reviews)
"The stay was at a beautiful new home. Great host. Location close to Interstate 70. I had everything I needed. Took in the sights in DC via the Greenline Metro. I would definitely stay here again."
United States
Scott C.
$140 nightly
The price is $148
Aug 29 - Aug 30
Total with taxes and fees
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
A modern hotel room with a large bed, two bedside tables, a flat-screen TV, a seating area with a chair and a small table, and a decorative plant.

2. Newly Renovated Cozy Basement w/Private Entrance

Newly Renovated Cozy Basement w/Private Entrance
Reisterstown
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and quiet studio. I would highly recommend."
United States
Jim S.
$145 nightly
The price is $167
Aug 30 - Aug 31
Total with taxes and fees
Newly Renovated Cozy Basement w/Private Entrance
A bedroom with a bed, a bedside table with a lamp, a window with a view, and a decorative wall piece.

3. Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (36 reviews)
"Great location, clean place. "
United States
Warren B.
$199 nightly
The price is $211
Aug 31 - Sep 1
Total with taxes and fees
Cozy, dog-friendly, downtown
A storefront with a large glass window, a wooden door, and a brick sidewalk.

4. Huge 1br apt, baby-friendly, dogs, walkable downtown

Huge 1br apt, baby-friendly, dogs, walkable downtown
Downtown Frederick
10.0 out of 10, Exceptional, (11 reviews)
"Great location for a peaceful solo night away -- thanks!"
United States
Kristina S.
Huge 1br apt, baby-friendly, dogs, walkable downtown
A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

5. Rural & Historic Detour Escape w/ Horses On-site!

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
$408 nightly
The price is $432
Aug 30 - Aug 31
Total with taxes and fees
Rural & Historic Detour Escape w/ Horses On-site!
A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

6. Rural & Historic Detour Escape w/ Horses On-Site!

Rural & Historic Detour Escape w/ Horses On-Site!
Detour
9.0 out of 10, Wonderful, (6 reviews)
"We had a great time. It is an older house but wonderful. It is in the country with lots of green fields surrounding it. The porch with the rockers was my favorite place to be when we weren’t site seeing, It was so peaceful. I would definitely stay here again."
United States
Charla H.
$415 nightly
The price is $440
Aug 30 - Aug 31
Total with taxes and fees
Rural & Historic Detour Escape w/ Horses On-Site!
A living room with a large mirror, a sofa with cushions, a television, and decorative items on a wooden console.

7. Downtown Frederick retreat with parking. Dog- and baby-friendly!

Downtown Frederick retreat with parking. Dog- and baby-friendly!
Frederick
9.8 out of 10, Exceptional, (7 reviews)
"This place looked exactly like the photos, very clean, super organized, and well designed. We were very comfortable during our stay and would stay here again."
United States
Dvorak A.
$270 nightly
The price is $286
Aug 30 - Aug 31
Total with taxes and fees
Downtown Frederick retreat with parking. Dog- and baby-friendly!
A corner room with a sliding glass door closet, a wooden cabinet with glass doors, and a small rug on the floor.

8. Private Sauna, Fireplace and Country Views

Private Sauna, Fireplace and Country Views
Mount Airy
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful location with a beautiful field where wild animals visited. Hosts really took care of the amenities (great coffee bar). Close to Mt Airy and vineyards."
United States
Richard B.
$381 nightly
The price is $404
Sep 1 - Sep 2
Total with taxes and fees
Private Sauna, Fireplace and Country Views
A small building labeled "The Snowball Stand" with a sign above the entrance.

9. Cozy Guesthouse in Woodstock, MD

Cozy Guesthouse in Woodstock, MD
Woodstock
2.0 out of 10, (1 review)
"We didn’t stay. We when arrived, instead of a room in the guest house, we were expected to stay in a tentlike structure. In addition, the bathroom facilities were outdoor showers and commodes that required a climb up a set of stairs. Luckily we were able to secure a room at another facility. The owner supposedly requested a refund for me but I haven’t heard whether this has been approved."
United States
Marie E M.
$204 nightly
The price is $236
Aug 29 - Aug 30
Total with taxes and fees
Cozy Guesthouse in Woodstock, MD
A modern apartment with a living room, kitchen, and dining area.

10. Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (9 reviews)
"Great location. We did not bring a pet but they thoughtfully provided a dog bed for those who do, which was very cute. It was great that they provide dishes for use on property and the kitchen cabinets were well labelled. There is a good ice cream place a block away and it was quick and easy to walk to the major downtown areas. We would stay here again in the future"
United States
Erica B.
$221 nightly
The price is $234
Sep 3 - Sep 4
Total with taxes and fees
Pet-friendly, heart of downtown
A modern kitchen with stainless steel appliances, dark cabinetry, and pendant lighting.

11. Cozy & inviting 2BD 2BTH Apt Home

Cozy & inviting 2BD 2BTH Apt Home
Owings Mills
$226 nightly
The price is $261
Sep 27 - Sep 28
Total with taxes and fees
Cozy & inviting 2BD 2BTH Apt Home
A modern kitchen with dark cabinets, a large island with stools, a stainless steel refrigerator, and a built-in oven.

12. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (20 reviews)
"It was a great place to relax, sleep and come home to after busy days in Frederick area. We would definitely stay here again!"
United States
Janice M.
$472 nightly
The price is $500
Aug 30 - Aug 31
Total with taxes and fees
Newly constructed 6 bedroom home
A room with a blue wall, a wooden dining table, a blue sofa, a white fireplace, and a window with white curtains.

13. Huge, Downtown, Walkable, Coffee, Breweries, Dogs

Huge, Downtown, Walkable, Coffee, Breweries, Dogs
Downtown Frederick
$220 nightly
The price is $233
Sep 22 - Sep 23
Total with taxes and fees
Huge, Downtown, Walkable, Coffee, Breweries, Dogs
A wooden deck with a fire pit, outdoor furniture, and string lights.

14. Backyard Oasis | Swim Spa, Fire Pit & Relaxing Outdoor Retreat

Backyard Oasis | Swim Spa, Fire Pit & Relaxing Outdoor Retreat
Westminster
8.0 out of 10, Very Good, (7 reviews)
"The stay was nice and as advertised. It was a little noisy at night with the split house and close neighbors, but it was a nice place. "
United States
Payson D.
$477 nightly
The price is $506
Aug 30 - Aug 31
Total with taxes and fees
Backyard Oasis | Swim Spa, Fire Pit & Relaxing Outdoor Retreat
A brick building with a waterfall feature in front.

15. New townhouse

New townhouse
Frederick
9.6 out of 10, Exceptional, (11 reviews)
"We had a great time. It was perfect for us. I would highly recommend it to others and would not hesitate to return there when back in the area. "
United States
Tereasa G.
$476 nightly
The price is $505
Sep 2 - Sep 3
Total with taxes and fees
New townhouse

16. Downtown Loft on Market Street-Great Location

Downtown Loft on Market Street-Great Location
Downtown Frederick
$114 nightly
The price is $121
Sep 28 - Sep 29
Total with taxes and fees
Downtown Loft on Market Street-Great Location

17. DC Luxury Family Retreat in Forest—Spacious Full of Fun w/ Zipline Waterfall

DC Luxury Family Retreat in Forest—Spacious Full of Fun w/ Zipline Waterfall
Gaithersburg
10.0 out of 10, Exceptional, (3 reviews)
"Had a great stay home was amazing "
United States
Darinda h.
$795 nightly
The price is $898
Sep 8 - Sep 9
Total with taxes and fees
DC Luxury Family Retreat in Forest—Spacious Full of Fun w/ Zipline Waterfall
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 Winfield Hotel Reviews

Hampton Inn Baltimore/Owings Mills

Hampton Inn Baltimore/Owings Mills

10/10 Excellent
"Room was very clean. Over all property was clean. Microwave, refrigerator, shower etc was functioning properly. Staff was very friendly, specially Ms Angel and the staff who takes care of Breakfast. My family loved it."
Mahmood 2-night trip
Posted 7 hours ago
Hampton Inn Baltimore/Owings Mills

Find out more about Winfield

Everything you need to know about Winfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Winfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winfield vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $211 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winfield rentals

At Expedia, we put the best Winfield vacation 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 Winfield 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 Winfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winfield. 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 vacation rental in Winfield?

Yes, you can find vacation rentals near top sights in Winfield, or you can go with a more remote option if you want a relaxing place to stay.

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

19th Century Mansion/Farm House: Visitors like this Winfield vacation home rental. It offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Winfield?

Explore the area and family-friendly sights such as Adventure Park USA, or get out into nature at a spot like Union Mills Homestead Park. Elk Run Vineyards and Old Westminster Winery are a couple of places you'll find in the larger area.

What’s a vacation rental in Winfield like?

Vacation rentals are privately owned properties you can book for several days or longer in Winfield. Vacation rentals provide amenities like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a family getaway.