Villa vacation rentals in Eastern Shore of Virginia

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Popular amenities for Eastern Shore of Virginia villa rentals

Private villa rentals

The exterior of a spacious home is surrounded by greenery, featuring large windows that invite natural light. A gravel driveway leads to the entrance, which is accented with steps and a circular front window.
Villa in Ocean Pines
4.44 out of 5 average rating, 68 reviews

Luxe Homey Get-Away Beach Cove

GaryRating, 5 stars8 months ago
it was nice to be kind of like in the woods, but only minutes from THE BEACH 🤩⛱️
Guest favorite
A spacious entryway is highlighted by a decorative chandelier above a patterned area rug. Dark wooden doors and large windows frame the entrance, offering natural light. Slate and hardwood flooring create a blend of textures, while wooden chairs are positioned against the wall.
Villa in Claremont
4.92 out of 5 average rating, 50 reviews

River Retreat with Eagle's Eye View

LoriRating, 5 stars4 months ago
We had a wonderful stay celebrating family birthdays! The house was spacious and had plenty of bathrooms. It was decorated beautifully for the holidays. We especially enjoyed the porches overlooking the spectacular views!
Superhost
A compact bathroom is presented with neutral-colored walls and a tiled floor. A round mirror is mounted above a small pedestal sink, and a toilet is positioned against the wall. A shelf is located above the sink, providing additional storage.
Villa in Chincoteague
4.62 out of 5 average rating, 13 reviews

Surfers Villa

Maurice DejongRating, 5 stars4 months ago
Hands down one of my best stays to date. I travel 300+ days out of the year for work and to have a place that feels like home to myself and my employees is important. The reef went above and beyond that expectation.
Guest favorite
The image captures a waterfront view of the condo complex, showcasing a series of boats docked at wooden piers. Calm water reflects the blue sky, while landscaped areas with low-growing plants line the docks. The colorful buildings of the complex are visible in the background.
Villa in Chincoteague
4.94 out of 5 average rating, 17 reviews

Sunset Bay 105-Waterfront POOL & BOAT SlIP

RobinRating, 5 stars10 months ago
We loved staying in this first floor condo with a view of the bay. One morning while sitting on the deck, dolphins swam by, it was a very beautiful view of the sunset each evening, and I enjoyed watching all of the birds around the docks. We had an issue with the lock, and our host quickly had it resolved and was very polite.
Superhost
An open living area features a comfortable brown sofa and a woven armchair positioned beside a rectangular coffee table. A staircase leads to the upper level, while a dining area with a wooden table and chairs is visible beyond. Large windows allow natural light to fill the space.
Villa in Chincoteague
4.14 out of 5 average rating, 7 reviews

Shallow Waters Villa

LeslieRating, 5 stars20 months ago
The REEF accommodations we had were great. Super great location right before the entry to the national refuge (beach and park) and all the great shops and water park in the other direction. The pool was heated and had toys for the kids. There’s 2 water park passes to use as well! There’s plenty of bikes to grab and go around the island for the whole family! Ed was super responsive and helpful all of the time! Couldn’t ask for a better host.
Superhost
An entranceway features a sliding glass door leading to a small balcony with a white chair. Natural light illuminates the space, highlighting the pale green tile flooring. A staircase with blue railings ascends to the upper level, while a decorative wreath adorns the wall.
Villa in Chincoteague
4.44 out of 5 average rating, 9 reviews

Shipwreck Villa

SaudiaRating, 5 stars26 months ago
It was very fun I had a great time the host had great communication and the place was very clean thank you
Guest favorite
The living area features a brown sofa with light cushions, a dark coffee table, and a textured rug. A sliding glass door leads to an outdoor space, while a staircase ascends in the background. An air conditioning unit and a small dining table are also visible.
Villa in Chincoteague
4.76 out of 5 average rating, 17 reviews

Palm Villa

KatieRating, 5 stars9 months ago
right in the middle of local shops, water park, and beach! this place was very clean and host was responsive and accommodating. can't beat the free water park tickets for the entire duration of our stay. water park was perfect for people with children 🙂
Superhost
A functional kitchen is displayed, featuring a white refrigerator, microwave, and coffee maker. Dark wood cabinetry lines the walls, complemented by a light-colored countertop. A door leads outside, allowing natural light to illuminate the space, while a window invites fresh air.
Villa in Chincoteague
4.5 out of 5 average rating, 8 reviews

Coral Villa

ArthurRating, 5 stars7 months ago
We had a great time ! The location was excellent, however a bathroom door needs fixing, but we got a good price for location!!! Thanks

Luxury villa rentals

Guest favorite
A spacious outdoor deck is furnished with a dining table and several chairs, offering ample seating. A large umbrella provides shade, while lounge chairs invite relaxation. The surrounding greenery adds a serene backdrop, enhancing the inviting atmosphere for outdoor gatherings.
Villa in Bel Alton
5 out of 5 average rating, 8 reviews

Leo Farm Villa - Beautiful Country Retreat

TaneishaRating, 5 stars8 months ago
This was an amazing place to stay!
Top guest favorite
A cheerful living space features light blue walls and a starfish-patterned rug. A navy blue couch is complemented by patterned curtains and decorative poufs. Two windows provide natural light, and a lamp stands on a side table. A wall sign conveys a family-oriented theme.
Villa in Millville
5 out of 5 average rating, 10 reviews

Firepit/Beach Shuttle/Pools/Office/Smart TVs

JhoannaRating, 5 stars9 months ago
Our family enjoyed our vacation and stay in Judie’s home. She was a very responsive host throughout our stay. The home had everything we needed and more- which made things very convenient for us. The kitchen was well equipped, the rooms were all comfy and cozy and very clean. Bathrooms had all toiletries including makeup remover! We literally did not need to pack any towels from home because Judie had everything! We traveled with two kids ages 3 and 4 so the fact that she had beach toys and chairs for them and a wagon in the garage for us to use was very convenient. It was overall less things I had to worry about packing. We love the Bishop’s Landing community pools; the one pool is within a short walking distance from Judie’s home. The location to stores and restaurants are easy and quick as well. This is our second year staying in Bishop’s Landing and we hope to be back again. Judie’s home would be at the top of our list.
A large, inviting pool area features clear blue water, surrounded by lounge chairs and umbrellas for shade. The clubhouse, with expansive glass windows, provides a comfortable area for relaxation, overlooking the pool and the nearby landscape.
Villa in Selbyville
5 out of 5 average rating, 4 reviews

Fenwick Island-GOLF CART-Bayfront pool and beach!

VeronicaRating, 5 stars10 months ago
This is our second time staying here and we loved everything about it! It’s so peaceful sitting out back on the porch overlooking the pond and it’s also wonderful sitting out by the pool that overlooks the bay. The small beach by the pool is the perfect place for families with little ones who don’t want to haul a bunch of stuff to the real beach. My 6 yr old daughter absolutely loves coming here and has already asked to come back this summer for a third trip. The house is beautifully decorated and has plenty of space for two families. It’s close to some great restaurants and having the golf cart is also a fun bonus to get everyone down to the pool/beach. Thank you Molly for another awesome stay!!
Guest favorite
A private inground pool is surrounded by a wooden fence, creating an enclosed space. The pool features a concrete deck with steps leading in, and several trees provide a natural shading. The area is well-maintained, highlighting a tranquil setting within the backyard.
Villa in Norfolk
4.97 out of 5 average rating, 36 reviews

4 Bedroom house with POOL, 5 mins. walk to BEACH!

LaToyaRating, 5 stars4 months ago
We had an absolutely wonderful stay at Roshana's place! From the moment we arrived, Roshana made us feel incredibly welcome. The accommodation was exactly as described, if not better. The space was spotless, well-decorated, and equipped with everything we needed for a comfortable stay. Roshana went above and beyond to ensure we had a great experience. The location was perfect, close to all the attractions and restaurants, yet in a quiet and peaceful neighborhood. Communication with Roshana was seamless. She was always quick to respond and very helpful with any questions I had. I truly appreciated her hospitality and attention to detail. I highly recommend staying at Roshana's place if you're visiting Norfolk. I would definitely stay here again on my next trip!
A private retreat is visible with two houses positioned along a sandy beach. A wooden pier extends toward the water. Lush green trees frame the property, providing a serene atmosphere. The main house features a spacious facade, while the guest house presents a charming design, both overlooking the waterfront.
Villa in Princess Anne
4.82 out of 5 average rating, 138 reviews

Waterfront Retreat & Guest House

LaurenRating, 5 stars3 months 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.
Guest favorite
A vibrant red kayak is positioned in calm waters, facing a stunning sunset. The sky is painted with soft hues of orange and yellow, reflecting on the water's surface. Small droplets of water rest on the kayak, capturing a moment of tranquility in nature.
Villa in Fort Washington
4.91 out of 5 average rating, 67 reviews

Waterfront Villa with kayaks/hot-tub! 25 min to DC

MaiRating, 5 stars2 weeks ago
We had a really wonderful experience at Sean and Angelica's place. The house is very beautiful, peaceful, and has an amazing view. Sean and Angelica were super responsive, friendly, helpful and hospitable. We highly recommend this great place.

Villa rentals with a pool

Superhost
A light blue two-story building features white railings and a spacious deck. Large windows provide natural light, while air conditioning units are positioned for comfort. A gravel area surrounds the property, enhancing accessibility and outdoor space.
Villa in Chincoteague
4.63 out of 5 average rating, 8 reviews

Sol Villa

ArmandoRating, 5 stars5 months ago
loved the place....went to work nasa ...quite...neat...perfect...clean.....didn't have any problems...
Guest favorite
Villa in Millville
4.88 out of 5 average rating, 51 reviews

Spacious Villa 3 miles to Bethany Beach Water Acc

JenniferRating, 5 stars8 months ago
We stayed here for our annual trip to Bethany Beach. It was just far enough to get out of the crowd of tourists and close enough to ride bikes to the beach with our children 9yrs-13yrs. The villa was spacious and comfortable. Any concerns we could have had, April was there to assist and in a timely manner. We would def recommend this house to anyone especially with children. The house accommodated to everyone’s needs . Thank you guys for your hospitality!
The living area features a dark blue sofa adorned with plaid and nautical-themed cushions. A matching upholstered chair is present, along with a decorative ottoman. Wall art depicting coastal scenes is mounted above, flanked by oars. Two lamps provide ambient lighting beside the sofa.
Villa in Bethany Beach
4.88 out of 5 average rating, 34 reviews

Sea Colony West-Summer Breeze, villa 2bdrm/2bth(8)

AnntoinetteRating, 5 stars9 months ago
Absolutely awesome place very close and convenient to all activities- bigger than I expected and 💯 delighted- I could not have been more pleased - very grateful!!
A comfortable living area is furnished with two light-colored sofas facing each other, accompanied by a textured area rug. Wall art depicting serene coastal scenes is displayed above the sofas. A ceiling fan provides gentle illumination in the softly colored room.
Villa in Dagsboro
4.63 out of 5 average rating, 59 reviews

Dagsboro Retreat Beautiful 4 Bed and 1 Bath Villa

RyanRating, 5 stars8 months ago
Gerald was great, exactly what we were expecting as we were in town for a baseball tournament.
Superhost
A fully equipped kitchen is presented with white cabinetry and a clean countertop. A stainless steel sink is flanked by a coffee maker and toaster. An electric stove with a white finish features four burners, providing essential cooking space for guests.
Villa in Chincoteague
4.7 out of 5 average rating, 10 reviews

Sand Dollar Villa

AudreyRating, 5 stars12 months ago
We ended up staying at the Reef because our original plans had us staying at a place that was just awful. I’m so glad this space was available; we felt totally at home. It was clean, comfortable, and convenient to any destination we had. I messaged the host asking if we could check in earlier in the day and she responded right away; we were able to do so and that was so accommodating to our timeframe. We are so pleased that we stayed at the Reef. The amenities were great: grills and picnic tables outside were a nice touch and the indoor pool was open as well.
Villa in Ocean View
4.5 out of 5 average rating, 6 reviews

3BR dog-friendly resort community stay, water view

TrindaRating, 5 stars16 months ago
Beautiful condo and community. Went for an off-season getaway and was very happy they are dog friendly. The condo was clean and spacious. There were LOTS of steps to the second floor. Not a problem for us, just something to be aware of. We did not use any of the resort amenities but the community was quiet and a great place to walk the dog. Since it was a winter getaway, was hoping to cozy up by the fire however there was a tag on the mantel saying the gas was off due to a valve leak. It was dated 2021, so I guess they aren’t concerned with getting it fixed. I would stay here again.
Villa in Sussex County
4.93 out of 5 average rating, 15 reviews

Luxury Bishop's Landing Villa Near Bethany Beach

JimRating, 5 stars32 months ago
Great townhouse, lots of space, good location near the pool. Amenities were good and as advertised - BBQ, full nice kitchen, living room, dining room area, three large bedrooms. Scott was always quick to respond and check-in/check-out was easy. Thanks again!
An outdoor tennis court is depicted with vibrant blue and green surfaces, encased in a protective chain-link fence. Nearby, a white bench is positioned for seating. The surrounding greenery enhances the recreational atmosphere, providing a spacious area for guests to enjoy.
Villa in Sussex County
5 out of 5 average rating, 3 reviews

2 miles to Bethany Beach! Linens & towels included

JosephRating, 5 stars8 months ago
Mark’s home was absolutely amazing! Super clean! So spacious. Beautifully decorated. It was just as described. There are so many restaurant and recreational options nearby. The pool was so much fun. Parking was great, right out front with overflow parking. The arcade set up was so fun for my son. Huge TVs in every room. So amazingly clean and the beds were so comfortable! Neighborhood was private, quiet and safe. Will definitely stay again.

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