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Dickerson vacation rentals

We found 101 vacation rentals — enter your dates for availability

Discover a selection of 101 vacation rentals in Dickerson, MD that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $124 per night, and houses and condos are popular options for a stay in Dickerson. Either way, you'll find a rental for everyone's needs.
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Find spaces that suit your style

Houses

View 68 Houses

Condos/Apartments

View 18 Condos/Apartments

Studios

View 18 Studios

Find the best place to stay — Dickerson

Log House at Sugarloaf Mountain MD

Sleeps 15 · 5 Bedrooms · 5 Bathrooms
$971 avg/night
(2)

Studio apartment at Sugarloaf Log House

Sleeps 2 · 1 Bedroom · 1 Bathroom
$124 avg/night

Tall Oaks Cabin, Walk to Wineries and Breweries!

Sleeps 12 · 4 Bedrooms · 3 Bathrooms
$200 avg/night
(15)

Villa with Majestic Views of Monocacy River. Sleeps 5, 2 Bath, Full Kitchen

Sleeps 5 · 2 Bedrooms · 2 Bathrooms
$155 avg/night
(18)

Gorgeous 1840 Log Cabin- Downtown

Sleeps 7 · 3 Bedrooms · 2 Bathrooms
$163 avg/night
(38)

The Cottage at Twin Notch Farm

Sleeps 6 · 2 Bedrooms
$162 avg/night
(65)

Search 101 vacation rentals

Top rated rentals — Dickerson
Stayed Feb 2021

Weekend getaway

We needed a weekend getaway from all the craziness. We loved the pictures and description on VRBO and the actual house did not disappoint. Very uniquely renovated cabin with modern amenities. Refreshing short walk to dining and sight seeing just a fe...

Justin S.
Justin S.
Stayed Feb 2021

The property is beautiful.

Sugarloaf is a beautiful home, with a lovely landscape and mountain scenery to match. Our overall experience for our annual couple’s retreat this Valentine’s weekend was satisfactory. We adhered to our lease agreement and any issues or concerns we ...

Tamara W.
Tamara W.
Stayed Feb 2021

Pandemic getaway

Exactly as advertised. Older home steps away from town. That comes with a few drafty windows but the hosts provided lovely space heaters and warm blankets to watch TV under. Some local town noise was taken care of by the little sound machine provided...

Michele T.
Michele T.

Middletown, DE

Stayed Feb 2021

Cozy Winter Getaway

After our first trip in October 2020, we could not wait to come back! While we enjoyed beautiful fall foliage in October, this time we were treated to lovely snow covered trees and crisp air. With the colder temperatures, we utilized the pellet stove...

Alexis H.
Alexis H.
Stayed Feb 2021

Exactly What We Were Looking For

This is a terrific property if you want to feel like you are really getting away from it all. The cabin feels remote - surrounded by trees and off the beaten track. That said, you are minutes away from downtown Leesburg. There are wineries and brewer...

Rachel K.
Rachel K.
Stayed Feb 2021

Wonderful time at the farm. Enjoyed the lovely cottage -- everything we needed!

The farm is beautiful! Very easily accessible to Harper's Ferry and surrounding area. The cottage was very well equipped with everything we needed. Walks around the property, meeting the horses, dogs, cats, chickens, roosters, sheep and llamas was ju...

Diane (Shelley) C.
Diane (Shelley) C.

Elkton, MD USA

Stayed Dec 2020

Great!!

Fantastic property and property owners! Ali was very communicative and extremely amendable to our needs (which included letting us use the pack and play and high chair for our 1 year old son). The property is very nice with homey touches. I wish we c...

Kristen D.
Kristen D.
Stayed Dec 2020

Wonderful farm retreat

We had a fantastic time at this rental property. The farmhouse was large, yet cozy with a modernized kitchen. We used the indoor fireplace every evening. Lots of games and toys for the kids. The outdoor space is amazing. The children enjoyed feeding ...

Kimberly H.
Kimberly H.
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How many vacation rentals are available around Dickerson, MD?

Our 2021 property listings offer a large selection of 101 vacation rentals around Dickerson. From 68 house rentals to 18 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Dickerson?

Yes, of course. Vrbo has 68 Houses in Dickerson. Our other popular types of vacation rentals in Dickerson include:

  • Condos/Apartments: 18 rentals available
  • Cabins: 5 rentals available
  • Cottages: 5 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Studios and more.

Can I find a vacation rental with pool in Dickerson?

Yes, you can select your preferred vacation rental with pool among our 16 vacation rentals with pool available in Dickerson. Please use our search bar to access the selection of vacation rentals available.