House vacation rentals in Greenbackville

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Popular amenities for Greenbackville house rentals

House rentals with a pool

Guest favorite
A charming cottage exterior is showcased, featuring a distinctive A-frame design. The front porch is framed by wooden railings, while a path of stepping stones leads to the entrance. Surrounding trees provide a natural backdrop, enhancing the serene outdoor environment.
Home in Ocean Pines
5 out of 5 average rating, 5 reviews

Ocean Pines 2BR 1BA Cottage with Fire Pit

Chelsea and Elizabeth Rating, 5 stars1 month ago
Our family has a beach house in Ocean Pines, and we are looking to purchase our own in the coming years. We have stayed in all parts of ocean Pines and love it so much, we came across this house a couple months ago and I’m so glad we did! We spend most of the summer in Ocean Pines had different rentals and will definitely be coming back specifically to this one!! it’s perfect for our small family and pet friendly! The house was small but spacious, quiet and tranquil. 10/10 highly recommend!
Top guest favorite
A sparkling pool is surrounded by a paved deck and wooden fence. Comfortable loungers are positioned at the poolside, and colorful umbrellas provide shade. Lush trees form a natural backdrop, enhancing the serene environment.
Home in Bivalve
5 out of 5 average rating, 21 reviews

Family Retreat - Private Pool, 4 Bedroom, Fire Pit

AshleyRating, 5 stars1 week ago
Where do I start? My boyfriend and I randomly chose Ann’s place for a quick weekend getaway knowing nothing about the town or Bivalve. It was such a great trip! Very quiet little town with the nicest locals! Ann and Eddie came by and took us in the golf cart and sharing a little about the town. Ann’s space was PERFECT and CLEAN! So peaceful and relaxing. Having the pool was great for the few hot days we had. Absolutely loved and recommend visiting this quaint little town and staying at Ann’s if you get the chance!
Guest favorite
A stone bench is positioned on a paved area surrounded by lush greenery and colorful plants. The white and brown farmhouse is visible in the background, framed by vibrant foliage. Sunlight streams gently across the outdoor space, creating a serene outdoor seating area.
Home in Berlin
4.96 out of 5 average rating, 74 reviews

Private pool, waterfront, kayaks, bikes, firepits!

LenoreRating, 5 stars1 month ago
We can't wait to return to Golden Quarter Farm! Charming and expansive, the property has everything we were looking for in a place to spend a relaxing weekend with extended family. The historic house is bright and roomy with a well-appointed kitchen; the bedrooms are unique, comfortable, and private; and the living space homey and inviting -- perfect for spending time together. The beautiful views of the riverfront drew everyone outside for walks down the pier, through the fields, and down the sun-dappled forest trails. It was a bit too chilly during our April stay, but the possibilities for enjoying the river (canoe, kayay, SUP) and lovely pool were nonetheless enticing. Finally, I must mention that Evie and Mary were extraordinarily welcoming and accomodating, from communicating proactively to preparing the home for our stay and checking in to make sure everything was perfect. Highly recommend!
Guest favorite
A community pool is surrounded by concrete flooring and shaded by trees. In the background, a pavilion with picnic tables can be seen, along with mobile homes lining the area. Lifeguards are stationed under an umbrella, observing the calm waters.
Home in Berlin
4.94 out of 5 average rating, 51 reviews

Amazing 2 Bedroom home close to the beach!

MikeRating, 5 stars8 months ago
We needed a small place to stay for a few days and this was the perfect place for the two of us; it was cozy, spotless, well equipped for all that we needed and the decor was beachy which was perfect for the area. Jacob was quick and attentive to any question we had - it was so quiet and peaceful outside. It was a perfect getaway for us - we would highly recommend to anyone needing a nice, quiet place in the future. Thank you!!!
Guest favorite
A large swimming pool is surrounded by a concrete deck, with numerous white lounge chairs arranged along one side. The calm water reflects the clear blue sky, while the distant community homes are visible in the background, creating an inviting leisure space.
Home in Berlin
4.79 out of 5 average rating, 195 reviews

OC MD trip bayside, great amenities

SandraRating, 5 stars2 days ago
I arrived after dark, on a Friday, so I was thinking I’d have some challenge to find the house. I was wrong! There was a guard at the gate who was quite friendly and helpful, gave me the parking pass for my stay and a map with outlined directions to find the street and the house. I found it first time through. Keys were in the lockbox, instructions were clear and the gate pass card was in the dish on the table. I had a lovely quiet night in a very comfortable bed with no noise or distractions. After a 10 hour drive I needed that! In the morning I had a small convenience issue, which Terri and Shawn were immediately responsive to, offered me a self service solution which worked fabulously and I had no other problems during my stay for a total of 8 nights. I especially loved the water pressure in the shower! Love that the house is a short hop from both OC and Assateague! I would definitely stay here again!
Top guest favorite
Home in Selbyville
5 out of 5 average rating, 51 reviews

Luxury Delaware Retreat II 6 BR II 6 BT II Views

AidaRating, 5 stars1 week ago
We had an absolutely amazing stay! The location was very convenient to the beach, great local restaurants and shops. The house itself was spotless, beautifully decorated, and had everything we needed for a comfortable and relaxing vacation. We traveled with young kids and they felt very comfortable in this home. Ron, our host, was incredibly responsive and thoughtful, providing clear check-in instructions and great local recommendations. It’s clear he really cares about creating a welcoming and enjoyable experience. If you're looking for a peaceful and memorable vacation home, this is the place. We can’t wait to come back!
Superhost
Home in Berlin
4.8 out of 5 average rating, 110 reviews

Mosaic Life Escapes -Bayfront Million Dollar Views

PaulRating, 5 stars6 months ago
Stayed for the weekend after Thanksgiving and it was a great experience. The house was cozy, the beds were comfortable, and the bathroom shower was awesome. The best part of the house is the view out over the bay. It’s really peaceful and a great spot to have coffee and watch the sunrise. We will definitely stay here again!
Guest favorite
A blue water slide is displayed adjacent to a large indoor swimming pool. Brightly colored bunting decorations hang along the poolside. Nearby, lifeguard chairs and railings are positioned for safety, complementing the spacious and well-maintained aquatic environment.
Home in Ocean Pines
4.88 out of 5 average rating, 145 reviews

Tortuga Cottage: Your All- Season Getaway

MariaRating, 5 stars2 weeks ago
This was our second stay at Tortuga Cottage. As spacious and clean for my husband, me, and our two young boys plus our Labrador retriever as we remembered it from 2 years ago. It is nestled in a friendly, shaded neighborhood that felt safe and welcoming to walk our dog around and explore the local restaurants, trails, and stores. Only 15 minutes from the beach with accessible parking and locker rooms. Kristy was great at communicating before, during, and leading up to departing from our stay. If you’re on the fence about booking this place, just do it! You’ll be overjoyed that you did.

Weekly house rentals

Guest favorite
A circular fire pit area is surrounded by four blue Adirondack chairs on a gravel surface. The setting features a serene waterfront view, framed by trees, with a vibrant sunset reflecting on the water's surface.
Home in Reedville
4.95 out of 5 average rating, 42 reviews

Sunnybank Getaway - Waterfront w/Pier & Kayaks

SandyRating, 5 stars4 weeks ago
We love our stay here! The house had everything we needed and more. It was easy to find, and the views were amazing. We spent the whole time outside in the nature, and we loved how quiet it was. Kevin was easy to reach for any questions we had, and we appreciated his help. We would definitely come back here in the future.
Top guest favorite
The ranch-style house is situated on a spacious green lawn, surrounded by trees. Soft outdoor lighting highlights the front of the home as dusk approaches. A secondary building is visible to the right, with a clear area for parking and landscaping enhancing the natural setting.
Home in Snow Hill
5 out of 5 average rating, 19 reviews

The Puskar’s Landing

CandaceRating, 5 stars3 weeks ago
Such a beautiful home! It also was very cozy and peaceful. The beach and pier is a nice walk away and the hot tub was perfect for relaxing. Host was very friendly and responsive if we needed anything. I will most definitely be staying here again!
Top guest favorite
White Adirondack chairs are positioned around a black outdoor fire pit, surrounded by trees that provide shade. A tranquil view of the river is visible in the background, reflecting the clear blue sky and scattered clouds.
Home in Snow Hill
4.98 out of 5 average rating, 63 reviews

Riverfront Retreat-Kayaking/Fishing/Nearby Beaches

NatalieRating, 5 stars1 day ago
Comfortable accommodations in a beautiful, peaceful spot to enjoy with family. Loved looking out the windows at the Pocomoke River at different times of the day and night! :-)
Superhost
A historic red farmhouse is set against a twilight sky, highlighting its charming exterior and expansive lawn. The structure features various gabled roofs and a screened porch, creating a spacious atmosphere for relaxation and connectivity with nature.
Home in Snow Hill
5 out of 5 average rating, 4 reviews

"Tweedy" Bird House

AcadiaRating, 5 stars2 weeks ago
The Tweedy Bird house is absolutely beautiful. It is clearly a well loved property, and we felt at immediately relaxed and at home. The dock is beautiful, the kitchen has everything you could possibly want for cooking, and the bedrooms are cozy. Claire was incredibly helpful when we had a few questions, and helped us arrange a seafood order. Thanks, Claire!
Top guest favorite
A barn-style exterior of the condo is showcased, featuring a metal roof and three large garage doors at ground level. The second floor includes a deck with an entrance door. Expansive green space surrounds the property, with trees visible in the background under a clear blue sky.
Home in Berlin
4.92 out of 5 average rating, 53 reviews

SpaciousCondo nearOcean City|Winery|Golf on 5Acres

JasmineRating, 5 stars5 days ago
My husband and our 2 small children had a great time. There was tons of space for them to run around and children’s beach toys for them to enjoy at the beach, just 15 minutes away!
Guest favorite
A charming vacation home is surrounded by tall trees and coastal grasses. The property features a combination of brick and shingle siding, with large windows. Adironack chairs are positioned on the lawn, inviting relaxation. A white picket fence adds to the serene atmosphere.
Home in Onancock
5 out of 5 average rating, 19 reviews

Leave your paw prints by the bay

MaryRating, 5 stars1 month ago
First of all, this house and the views are STUNNING. This was the first vacation that I have taken with my fiancé and our 2 pups, and we had the best time--it was such a sad day when we had to leave lol. We basically ordered Doordash and Walmart Pickups the entire time we were there and never left the property during our stay. The kitchen was very well stocked with all the cookware you could need, there are kayaks and paddle boards for entertainment, and plenty of floats for relaxing in the bay. There is a little private beach within 1 min walking distance from the house and there is access to the water from the backyard. It had everything we wanted for a relaxing vacation with our pups. I am already working on convincing my fiancé that we need to go back in the near future. 10/10 would recommend.
Guest favorite
A cozy living area is furnished with soft gray seating, including two recliners and a spacious sofa. A wooden coffee table centers the room, complemented by a patterned rug. Light filters in through large windows, enhancing the inviting atmosphere, while wall art adds a touch of nature.
Home in Princess Anne
4.93 out of 5 average rating, 15 reviews

countryside home in Princess Anne

ChristenRating, 5 stars4 days ago
10 stars – The Best Host & Perfect Stay! This country spot was everything we needed and more! Super clean, incredibly peaceful, and the perfect escape from the noise of everyday life. The best surprise? Not a single mosquito in sight—which is rare for the country! The host was amazing and made the whole experience even better. We even extended our stay because we didn't want to leave. Already planning our next visit. Highly recommend!
Top guest favorite
A large waterfront estate is viewed from a distance, framed by tall trees. The house features a wraparound porch with blue rocking chairs, surrounded by expansive green lawns. The soft glow of sunset casts elongated shadows on the ground, enhancing the serene atmosphere.
Home in Onancock
4.96 out of 5 average rating, 85 reviews

Chesapeake Bay Retreat | Private Dock + Beach

AdrienneRating, 5 stars8 months ago
Eastview is beautiful, the home and the surroundings. There’s plenty of room if you are traveling with a large group.

Private house rentals

Top guest favorite
The front exterior of a charming house features a peaked roof and a welcoming entrance. Large windows provide ample natural light, framed by a neutral color scheme. A stone pathway leads to the front door, surrounded by a landscaped area with decorative rocks and seasonal plants.
Home in Chincoteague
5 out of 5 average rating, 36 reviews

The Shell Hunter

BenjaminRating, 5 stars2 weeks ago
The Shell Hunter was perfect for our family of 4's fourth summer vacationing on Chincoteague. Janel's instructions for check in were clear, and everything was exactly as shown/described in the listing. The location was perfect, tucked away but still walkable to the main drag. The house itself was ideal for my wife and I and our two young children, with a great king bed upstairs and two additional private rooms downstairs. There were plenty of dishes/cookware in the spacious kitchen and we especially loved the two porches (front and back) and the outdoor shower so we didn't have to track beach sand into the house. We've stayed in a different vacation home on each of our visits to the island, but this one may have to become a repeat!
Top guest favorite
A large wooden deck features several adirondack chairs positioned to face expansive views of the marshland and water. A clear blue sky complements the serene landscape, with gentle clouds casting soft shadows over the scene.
Home in Parksley
5 out of 5 average rating, 17 reviews

Serene Waterfront Metompkin Retreat - Entire Home

Cynthia-DoriceRating, 5 stars8 months ago
We really enjoyed our 3 night stay! Great house on a quiet marsh. The morning sunrises were beautiful, loved being able to use the kayaks to paddle to the ocean, and great bird watching. Would love to come back.
Top guest favorite
A spacious bedroom features two large beds adorned with neutral linens. Natural light filters through two windows, illuminating the room. A vintage wardrobe and a bench provide additional storage and seating. Textured rugs enhance the room's comfort, complemented by soft lighting from bedside lamps.
Home in Willards
4.95 out of 5 average rating, 20 reviews

Quiet country getaway

AshleyRating, 5 stars1 month ago
We were in for our nieces graduation from SU and this was the perfect place to stay. It reminded me so much of home! It was peaceful and relaxing. It was so nice I wish we had been able to spend more time there! Susan was an exceptional host. She was very informative, gave us helpful tips, and was very friendly. I would recommend this place to stay to anyone. Best AIR BnB I’ve been to so far!
Top guest favorite
A spacious living area features a large sectional couch and a coffee table, surrounded by wooden flooring. A world map adorns the wall, and natural light streams in through the windows. The open layout flows into a dining area visible in the background.
Home in Chincoteague
5 out of 5 average rating, 23 reviews

Magnolia House ~Linens Included~

ErinRating, 5 stars2 weeks ago
This was our second stay at the Magnolia house! It’s a charming place with tons of character! Comfortable furniture and very clean. Great kitchen and the rain shower bathroom is amazing. Great outdoor space and convenient parking area. Lots of walkable fun things to do. Great restaurants, shopping and we even caught the local farmers market with locally made crafts, fresh produce and seafood! The beach is a short drive and saw the wild ponies on our way into the park! It was a wonderful experience! We look forward to our next trip!
Guest favorite
The exterior of a modern, single-story house features a light blue façade with contrasting dark shingles. A wooden staircase leads to the front door, while a small deck is visible to the left. A paved walkway runs along the well-maintained lawn.
Home in Crisfield
4.99 out of 5 average rating, 86 reviews

Marshall’s Retreat Chesapeake small town getaway

WillettaRating, 5 stars3 months ago
I am originally from the area and I come here occasionally. I usually stay about 45 minutes from Crisfield. This Home had everything that we needed. I always bring a special bag with cleaning supplies, toiletries, hand soap, etc. But this place has it all. I love the wall decorations and am going to use some of those for ideas for our home. Thank you for the use of your home. It was very affordable. We will definitely book again.
Top guest favorite
The two-story farmhouse is surrounded by a spacious yard, highlighted by a prominent American flag flying in front. Large windows allow natural light, while the earthy green exterior blends with the surrounding trees. A charming white bench adds to the inviting outdoor space.
Home in Deal Island Historic District
4.97 out of 5 average rating, 29 reviews

Rusty Anchor

RachelRating, 5 stars2 weeks ago
Rustic and charming, the Rusty Anchor was exactly what we hoped for. The screened porch was a favorite hang out spot. The kitchen sink was absolutely adorable. And the host had tons of family friendly amenities available like a baby bath, beach toys, coloring books, and board games. It looks just like the pictures. Her recommendations for the Washington Inn (now Sugar Water), the local beach, and the produce stand were all fantastic. We didn’t want to leave. If you are looking for a low-key, relaxing get-away, this is the perfect place.
Top guest favorite
A sunlit porch features white walls and ceiling, complemented by large windows dressed in light-filtering blinds. A cozy swing sits against one wall, while a woven chair adorned with a cushion invites relaxation. A patterned rug runs along the floor, enhancing the welcoming space.
Home in Saxis
5 out of 5 average rating, 11 reviews

Island Jewell Near Chincoteague

MichelleRating, 5 stars8 months ago
My husband and I booked a last minute anniversary trip and Denise's home was absolutely perfect. This little home was everything that you could want and more for peace and relaxation. Denise was helpful and responsive and accomodated a very late night check in with no problems!
Top guest favorite
A three-story house features a modern design with blue siding and white railings. Two balconies are visible on the front, while a welcoming entrance is marked by a circular decorative piece. The ground level is supported by brick columns, surrounded by a gravel yard.
Home in Chincoteague
4.97 out of 5 average rating, 32 reviews

Eagles Nest- (Water View)

KatieRating, 5 stars1 week ago
This is our family’s second year at Eagles Nest, and I can’t recommended highly enough! Clean, comfortable, with beautiful views from every angle. Kevin is super friendly and responsive, and really goes above and beyond for guests. A+!

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