Winfield Vacation Rentals

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Vacation Rentals in Winfield

Microwave, stovetop, dishwasher
The blissful house in Howard County with 3 bedrooms 3 bathrooms.

The blissful house in Howard County with 3 bedrooms 3 bathrooms.

Marriottsville
$802 nightly
The price is $850
Dec 7 - Dec 8
Total with taxes and fees
The blissful house in Howard County with 3 bedrooms 3 bathrooms.
Exterior
19th Century Mansion/Farm House

19th Century Mansion/Farm House

Taneytown
10.0 out of 10, Exceptional, (47)
"Great stay again! Mike is a great host and the place works great for a golf weekend with eight buddies!Well equipped place with interesting history."
United States
Adam M.
19th Century Mansion/Farm House
Dining
Charming 7-bedroom house near Reisterstown

Charming 7-bedroom house near Reisterstown

Reisterstown
10.0 out of 10, Exceptional, (1)
"Nice property. Two spacious dining rooms."
United States
michael b.
Charming 7-bedroom house near Reisterstown
Fridge, microwave, oven, stovetop
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>

Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>

Frederick
10.0 out of 10, Exceptional, (79)
"Convenient to downtown Frederick, quiet, enjoyable location."
United States
ELIZABETH L.
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>
Fridge, microwave, oven, stovetop
Gorgeous 1840 Log Cabin- Downtown

Gorgeous 1840 Log Cabin- Downtown

Downtown Frederick
10.0 out of 10, Exceptional, (151)
"Excellent accommodations, quiet, peaceful, and convenient to many walking distance locations. "
United States
Kathleen S.
Gorgeous 1840 Log Cabin- Downtown
TV, fireplace
Spacious Home with Private Pool

Spacious Home with Private Pool

2.0 star property
Reisterstown
Spacious Home with Private Pool
Terrace/patio
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

2.0 star property
Gaithersburg
10.0 out of 10, Exceptional, (1)
"This property is, without question, one of the finest vacation rentals I have ever experienced. I was searching for a family-friendly space suitable for hosting a dinner, and this home exceeded all expectations. The photos do not fully capture its beauty. Ms. Mohammed was an exceptional host—responsive, professional, and clearly dedicated to maintaining a high standard of hospitality.Backyard: The outdoor area is stunning—featuring a firepit, grill, swing set, zipline, and multiple seating areas...
United States
Asher C.
$794 nightly
The price is $897
Dec 5 - Dec 6
Total with taxes and fees
DC Luxury Family Retreat in Forest—Spacious Full of Fun w/ Zipline Waterfall
Dining
Lovely 4-bedroom estate in brilliant Owings Mills 23 miles from John Hopkins

Lovely 4-bedroom estate in brilliant Owings Mills 23 miles from John Hopkins

Owings Mills
4.0 out of 10, (3)
"During our stay there was no clean water because debris was coming through the pipes. The bathroom near the office didn’t work and the pool wasn’t ready and that was one of the reasons why I chose this house. But I do appreciate the communication given to me during our stay"
United States
Paulette T.
Lovely 4-bedroom estate in brilliant Owings Mills 23 miles from John Hopkins
Fridge, microwave, oven, stovetop
Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown

Frederick
10.0 out of 10, Exceptional, (26)
"Super cute and was the PERFECT location! We had a great stay! "
United States
Sarah S.
$186 nightly
The price is $197
Dec 7 - Dec 8
Total with taxes and fees
Cozy, dog-friendly, downtown
Dining
1850 Historic Log Cabin

1850 Historic Log Cabin

Westminster
9.4 out of 10, Exceptional, (42)
"Great property!"
United States
Katie S.
1850 Historic Log Cabin
Interior
Large Open Suite nestled among the Trees

Large Open Suite nestled among the Trees

Marriottsville
10.0 out of 10, Exceptional, (10)
"The best VRBO I have ever stayed in. Host was great, check in was easy. I can't say enough good things about this stay!!"
United States
Paul
Large Open Suite nestled among the Trees
Microwave, stovetop, dishwasher, highchair
A private and peaceful oasis with all amenities in quiet scenic Brookeville

A private and peaceful oasis with all amenities in quiet scenic Brookeville

2.0 star property
Brookeville
9.2 out of 10, Wonderful, (5)
"The property was located in a beautiful spacious neighborhood and was very peaceful and relaxing! Very clean and spacious. Janice was very nice and easy going. Highly recommend! "
United States
Adam H.
A private and peaceful oasis with all amenities in quiet scenic Brookeville
Property grounds
Charming 1 Bedroom Apt- Best Location Near Downtown Frederick & DC

Charming 1 Bedroom Apt- Best Location Near Downtown Frederick & DC

Frederick
10.0 out of 10, Exceptional, (37)
"Owner was always available and helpful."
United States
Donald G.
Charming 1 Bedroom Apt- Best Location Near Downtown Frederick & DC
Fridge, microwave, oven, stovetop
Newly constructed 6 bedroom home

Newly constructed 6 bedroom home

Frederick
10.0 out of 10, Exceptional, (14)
"This is our second time staying here and we really love how easily we all fit in. It's clean, family friendly, and have lots of space."
United States
Bonnie S.
$441 nightly
The price is $467
Dec 7 - Dec 8
Total with taxes and fees
Newly constructed 6 bedroom home
Interior
Cozy Peaceful Basement Cabin Vibes

Cozy Peaceful Basement Cabin Vibes

Ijamsville
10.0 out of 10, Exceptional, (5)
"Good trip."
United States
Jewell F.
$341 nightly
The price is $361
Jan 3 - Jan 4, 2026
Total with taxes and fees
Cozy Peaceful Basement Cabin Vibes
Exterior detail
NEW! Cozy Pikesville Penthouse with Basketball Arcade

NEW! Cozy Pikesville Penthouse with Basketball Arcade

Pikesville
NEW! Cozy Pikesville Penthouse with Basketball Arcade
Exterior
“The Train Depot” 2nd oldest in the US

“The Train Depot” 2nd oldest in the US

Downtown Frederick
10.0 out of 10, Exceptional, (91)
"Beautiful property within walking distance of downtown "
United States
Adriaan B.
“The Train Depot” 2nd oldest in the US
Paper towels
Cozy Studio with Private Entrance.

Cozy Studio with Private Entrance.

Lochearn
$150 nightly
The price is $173
Dec 5 - Dec 6
Total with taxes and fees
Cozy Studio with Private Entrance.
Private kitchen
Spacious Downtown Frederick, 3 BR, Full Kitchen Off Street Parking

Spacious Downtown Frederick, 3 BR, Full Kitchen Off Street Parking

2.0 star property
Downtown Frederick
10.0 out of 10, Exceptional, (1)
"Great location "
United States
Edith J.
Spacious Downtown Frederick, 3 BR, Full Kitchen Off Street Parking
Fridge, microwave, oven, stovetop
Experience Elevated Comfort: Luxe Breeze Townhouse.

Experience Elevated Comfort: Luxe Breeze Townhouse.

Owings Mills
9.6 out of 10, Exceptional, (4)
"Awesome stay and great location. Very quiet neighborhood, made the stay comfortable and relaxing. Very spacious and modern. "
United States
Jesse H.
$497 nightly
The price is $574
Jan 1 - Jan 2, 2026
Total with taxes and fees
Experience Elevated Comfort: Luxe Breeze Townhouse.
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

Hyatt Place Baltimore/Owings Mills

Hyatt Place Baltimore/Owings Mills

10/10 Excellent
"Staff very courteous "
barbara 2-night trip
Posted 3 days ago
Hyatt Place 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 $173 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.

Explore a world of travel with Expedia

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?

DC Luxury Family Retreat in Forest—Spacious Full of Fun w/ Zipline Waterfall: Visitors like this Winfield vacation home rental. It offers a fireplace, a selection of games, 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 stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a hot tub.

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 Bear Branch Nature Center. Serpent Ridge Vineyard and Elk Run Vineyards 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.