Villa holiday rentals in Maryland

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Popular amenities for Maryland villa rentals

Private villa rentals

Villa in Germantown
4.83 out of 5 average rating, 18 reviews

Villa du Film -- a luxury 7-beds villa in Potomac

JanelleRating, 5 stars6 months ago
The house is as described full of amenities. I particularly enjoyed the piano and sauna. The host was very responsive and accommodating. Thank you for everything
Guest favourite
Villa in Stevensville
4.86 out of 5 average rating, 44 reviews

Luxurious Waterfront Kent Island Home

MikeRating, 5 stars3 months ago
What a cool spot! I took my family to Annapolis to celebrate my sister’s 60th and we stayed on Kent Island at Nila’s place. The drive here is gorgeous. Thinks scenic with mature trees and headed to the water. The grounds are gorgeous with the golf course meandering throughout. Everyone is friendly driving their golf carts and waving. The house is sick! Think mad men for 2024. Felt like I was staying in an upscale hotel with family, cozy bedrooms upstairs. Plus the second living room. Soooo cool. I did get the projector to work and watched a few dvds with the surround sound. That was pretty cool!! I do Airbnb a lot and I would give this experience a 10/10 on all the things that matter - value, comms, thoughtfulness, cleanliness, location etc. thank you Nila!
Villa in Ocean Pines
4.44 out of 5 average rating, 68 reviews

Luxe Homey Get-Away Beach Cove

GaryRating, 5 stars6 months ago
it was nice to be kind of like in the woods, but only minutes from THE BEACH 🤩⛱️
Superhost
Villa in Clarksburg
4.63 out of 5 average rating, 27 reviews

karma~Entire walkout basement ,4B / 3 rooms,DC sub

RodrigoRating, 5 stars5 months ago
May was very helpful through with all the booking needs.
Guest favourite
Villa in Earleville
5 out of 5 average rating, 27 reviews

Stunning Waterfront Villa w/ indoor saltwater pool

BetsyRating, 5 stars1 month ago
Everything about this house was beautiful. It made us feel like we were in Italy. The only disappointment we had was that the 16 of us could not sit down together for one formal meal, but there was plenty of spaces to sit, plus, we were pleasantly surprised at all the things that were in the house that weren’t mentioned which made our stay that much more enjoyable. It was close to the water. It was close to restaurants and yet it was private in its own little wooded area. We had a great time and would definitely stay again.
Guest favourite
Villa in Annapolis
4.84 out of 5 average rating, 112 reviews

Crow's Nest Cottage: Chesapeake Bay View*HOT TUB*

MarthaRating, 5 stars5 months ago
Our family and friend group of 11 stayed here for three nights. The house was perfect for us and had everything you would possibly need. We loved it so much that we punted some things we were going to do to hang out there. The fire pit on the deck was a fan favorite at night which all of us sat around, talking and laughing. Some people got up early to fish at the pier that we had access to, and my daughter spent time at the beach there. I can't say enough kind words about Paul as a host. He answered all our questions in a timely manner by texting us which not all hosts do. Today, he gave us a later check out time which was helpful in getting so many people up and out! Paul was there when we arrived and was just so gracious. I would highly recommend this place to anyone and would love to come back someday. Thank you so much, Paul!
Guest favourite
Villa in Easton
4.95 out of 5 average rating, 44 reviews

St. Michaels Waterfront-Pool/Kayak/Pier/Firepit

McIntyreRating, 5 stars4 months ago
Absolutely beautiful home. We loved our stay. Mindy was so communicative and helpful. Location is private but also only ~10 minute drive to downtown Easton. We will come back!
Guest favourite
Villa in Neavitt
4.95 out of 5 average rating, 74 reviews

Breathtaking Waterfront Estate

AngieRating, 5 stars4 months ago
Don't think about it for another minute - book this property. You will not be disappointed. While it might not seem possible, the pictures do not do this place justice. Everything was top notch from the accommodations to the decorating detail. The cleanliness was unmatched. We were welcomed with music playing throughout the house, fresh baked cookies and beautiful flowers. What a special way to kick off our 14th semi-annual girls weekend! The sunrises were too spectacular to miss, so that is how we started each day. We also took time to enjoy the sauna, crabs on the pier, a bike ride to watch the sunset across the street, use of both the firepit by the water and the gas powered fire on the porch, and one of us took a dip in the pool! The experience was so wonderful that we are already planning our next trip in the spring and look forward to treating ourselves to a stay at another one of their properties.

Luxury villa rentals

Villa in Germantown
4.83 out of 5 average rating, 18 reviews

Villa du Film -- a luxury 7-beds villa in Potomac

JanelleRating, 5 stars6 months ago
The house is as described full of amenities. I particularly enjoyed the piano and sauna. The host was very responsive and accommodating. Thank you for everything
Guest favourite
Villa in Bel Alton
5 out of 5 average rating, 8 reviews

Leo Farm Villa - Beautiful Country Retreat

TaneishaRating, 5 stars5 months ago
This was an amazing place to stay!
Guest favourite
Villa in Earleville
5 out of 5 average rating, 27 reviews

Stunning Waterfront Villa w/ indoor saltwater pool

BetsyRating, 5 stars1 month ago
Everything about this house was beautiful. It made us feel like we were in Italy. The only disappointment we had was that the 16 of us could not sit down together for one formal meal, but there was plenty of spaces to sit, plus, we were pleasantly surprised at all the things that were in the house that weren’t mentioned which made our stay that much more enjoyable. It was close to the water. It was close to restaurants and yet it was private in its own little wooded area. We had a great time and would definitely stay again.
Guest favourite
Villa in Annapolis
4.84 out of 5 average rating, 112 reviews

Crow's Nest Cottage: Chesapeake Bay View*HOT TUB*

MarthaRating, 5 stars5 months ago
Our family and friend group of 11 stayed here for three nights. The house was perfect for us and had everything you would possibly need. We loved it so much that we punted some things we were going to do to hang out there. The fire pit on the deck was a fan favorite at night which all of us sat around, talking and laughing. Some people got up early to fish at the pier that we had access to, and my daughter spent time at the beach there. I can't say enough kind words about Paul as a host. He answered all our questions in a timely manner by texting us which not all hosts do. Today, he gave us a later check out time which was helpful in getting so many people up and out! Paul was there when we arrived and was just so gracious. I would highly recommend this place to anyone and would love to come back someday. Thank you so much, Paul!
Guest favourite
Villa in Easton
4.95 out of 5 average rating, 44 reviews

St. Michaels Waterfront-Pool/Kayak/Pier/Firepit

McIntyreRating, 5 stars4 months ago
Absolutely beautiful home. We loved our stay. Mindy was so communicative and helpful. Location is private but also only ~10 minute drive to downtown Easton. We will come back!
Villa in Bethesda
4.78 out of 5 average rating, 105 reviews

Italy meets Moroccan oasis with huge pool for 10

DavidRating, 5 stars1 month ago
My partner, two dogs and I had a wonderful stay here. First and foremost, the home was on a quiet, beautiful street, and the home itself was lovely and as described. Plenty of nooks and crannies to curl up with a book, do some work, or just ponder. It is a easily drivable to the metro and to plenty of things in and around Bethesda to do. Second, Kate was a great host. Very accommodating, incredibly nice, and always responsive. Two key points for travelers: 1. We are dog owners and travel frequently with our dogs. If you are too, we particularly recommend Kate as she was accommodating of our dogs (even let us know of the treat stash), which is very important. 2. Relatedly, if you are not a dog person, you should still stay here because there was absolutely no evidence that any dog had ever stayed there (not that we would mind, but we understand others may). No dog fur, not dog stains, no dog smell. The place was pristine. So don't let the positive review dogs, concern you. A+++
Guest favourite
Villa in Neavitt
4.95 out of 5 average rating, 74 reviews

Breathtaking Waterfront Estate

AngieRating, 5 stars4 months ago
Don't think about it for another minute - book this property. You will not be disappointed. While it might not seem possible, the pictures do not do this place justice. Everything was top notch from the accommodations to the decorating detail. The cleanliness was unmatched. We were welcomed with music playing throughout the house, fresh baked cookies and beautiful flowers. What a special way to kick off our 14th semi-annual girls weekend! The sunrises were too spectacular to miss, so that is how we started each day. We also took time to enjoy the sauna, crabs on the pier, a bike ride to watch the sunset across the street, use of both the firepit by the water and the gas powered fire on the porch, and one of us took a dip in the pool! The experience was so wonderful that we are already planning our next trip in the spring and look forward to treating ourselves to a stay at another one of their properties.
Villa in Princess Anne
4.82 out of 5 average rating, 138 reviews

Waterfront Retreat & Guest House

LaurenRating, 5 stars1 month ago
Beautiful big house with unique charm, in a beautiful area with the Chesapeake as the back drop. Great location for family to meet mid point from NJ, PA, and Virginia. The huge family table in the breezeway was a great place to gather for meals and games. The house worked for one of our family members with mobility issues with full bathrooms, and bedrooms on the 1st floor and no stairs to get in the back door. Went for over a 4 mile walk around the town one morning, beautiful landscapes, birds, boat docks, and a park. We enjoyed the fire pit, grilling food in winter, the dock on the property, hearing the church bells from a distance. Kyle is a great host! Would definitely return.

Villa rentals with a pool

Guest favourite
Villa in Easton
4.95 out of 5 average rating, 44 reviews

St. Michaels Waterfront-Pool/Kayak/Pier/Firepit

McIntyreRating, 5 stars4 months ago
Absolutely beautiful home. We loved our stay. Mindy was so communicative and helpful. Location is private but also only ~10 minute drive to downtown Easton. We will come back!
Villa in Ocean Pines
5 out of 5 average rating, 3 reviews

Lakeview/Golf course front home - 4 Bed/3 baths

JohnRating, 5 stars31 months ago
My family and I found this rental unit to be very clean and well kept. Rich was very responsive with the few questions that I had for him. I would recommend this rental to others!
Villa in Bethesda
4.78 out of 5 average rating, 105 reviews

Italy meets Moroccan oasis with huge pool for 10

DavidRating, 5 stars1 month ago
My partner, two dogs and I had a wonderful stay here. First and foremost, the home was on a quiet, beautiful street, and the home itself was lovely and as described. Plenty of nooks and crannies to curl up with a book, do some work, or just ponder. It is a easily drivable to the metro and to plenty of things in and around Bethesda to do. Second, Kate was a great host. Very accommodating, incredibly nice, and always responsive. Two key points for travelers: 1. We are dog owners and travel frequently with our dogs. If you are too, we particularly recommend Kate as she was accommodating of our dogs (even let us know of the treat stash), which is very important. 2. Relatedly, if you are not a dog person, you should still stay here because there was absolutely no evidence that any dog had ever stayed there (not that we would mind, but we understand others may). No dog fur, not dog stains, no dog smell. The place was pristine. So don't let the positive review dogs, concern you. A+++
Guest favourite
Villa in Neavitt
4.95 out of 5 average rating, 74 reviews

Breathtaking Waterfront Estate

AngieRating, 5 stars4 months ago
Don't think about it for another minute - book this property. You will not be disappointed. While it might not seem possible, the pictures do not do this place justice. Everything was top notch from the accommodations to the decorating detail. The cleanliness was unmatched. We were welcomed with music playing throughout the house, fresh baked cookies and beautiful flowers. What a special way to kick off our 14th semi-annual girls weekend! The sunrises were too spectacular to miss, so that is how we started each day. We also took time to enjoy the sauna, crabs on the pier, a bike ride to watch the sunset across the street, use of both the firepit by the water and the gas powered fire on the porch, and one of us took a dip in the pool! The experience was so wonderful that we are already planning our next trip in the spring and look forward to treating ourselves to a stay at another one of their properties.
Guest favourite
Villa in Earleville
5 out of 5 average rating, 27 reviews

Stunning Waterfront Villa w/ indoor saltwater pool

BetsyRating, 5 stars1 month ago
Everything about this house was beautiful. It made us feel like we were in Italy. The only disappointment we had was that the 16 of us could not sit down together for one formal meal, but there was plenty of spaces to sit, plus, we were pleasantly surprised at all the things that were in the house that weren’t mentioned which made our stay that much more enjoyable. It was close to the water. It was close to restaurants and yet it was private in its own little wooded area. We had a great time and would definitely stay again.
Superhost
Private room in Cockeysville
4.79 out of 5 average rating, 28 reviews

Westmore Estate II Contemporary Cave Gorgeous B&B

KristinaRating, 5 stars9 months ago
Drs. Ken & Sam were some of the best hosts I’ve had! They were extremely friendly, flexible, and provided very thorough instructions. They offered great amenities and provided a continental breakfast as well! They strived to go above and beyond to accommodate us and even joined us for conversation at breakfast. The estate is to die for and we would be more than happy to book with them again!
Guest favourite
Villa in Annapolis
4.84 out of 5 average rating, 112 reviews

Crow's Nest Cottage: Chesapeake Bay View*HOT TUB*

MarthaRating, 5 stars5 months ago
Our family and friend group of 11 stayed here for three nights. The house was perfect for us and had everything you would possibly need. We loved it so much that we punted some things we were going to do to hang out there. The fire pit on the deck was a fan favorite at night which all of us sat around, talking and laughing. Some people got up early to fish at the pier that we had access to, and my daughter spent time at the beach there. I can't say enough kind words about Paul as a host. He answered all our questions in a timely manner by texting us which not all hosts do. Today, he gave us a later check out time which was helpful in getting so many people up and out! Paul was there when we arrived and was just so gracious. I would highly recommend this place to anyone and would love to come back someday. Thank you so much, Paul!

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