
House vacation rentals in Greenbackville
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Top-rated house rentals in Greenbackville
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Popular amenities for Greenbackville house rentals
House rentals with a pool

Ocean Pines 2BR 1BA Cottage with Fire Pit
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!

Family Retreat - Private Pool, 4 Bedroom, Fire Pit
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!

Private pool, waterfront, kayaks, bikes, firepits!
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!

Amazing 2 Bedroom home close to the beach!
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!!!

OC MD trip bayside, great amenities
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!

Luxury Delaware Retreat II 6 BR II 6 BT II Views
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!

Mosaic Life Escapes -Bayfront Million Dollar Views
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!

Tortuga Cottage: Your All- Season Getaway
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

Sunnybank Getaway - Waterfront w/Pier & Kayaks
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.

The Puskar’s Landing
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!

Riverfront Retreat-Kayaking/Fishing/Nearby Beaches
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! :-)

"Tweedy" Bird House
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!

SpaciousCondo nearOcean City|Winery|Golf on 5Acres
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!

Leave your paw prints by the bay
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.

countryside home in Princess Anne
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!

Chesapeake Bay Retreat | Private Dock + Beach
Eastview is beautiful, the home and the surroundings. There’s plenty of room if you are traveling with a large group.
Private house rentals

The Shell Hunter
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!

Serene Waterfront Metompkin Retreat - Entire Home
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.

Quiet country getaway
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!

Magnolia House ~Linens Included~
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!

Marshall’s Retreat Chesapeake small town getaway
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.

Rusty Anchor
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.

Island Jewell Near Chincoteague
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!

Eagles Nest- (Water View)
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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- Ocean City Beach
- Assateague Island National Seashore
- Ocean City Boardwalk
- Jolly Roger Amusement Park
- Towers Beach
- Northside Park
- Assateague Beach
- Bayside Resort Golf Club
- Jolly Roger at the Pier
- Delaware Seashore State Park
- Snead Beach
- Peninsula Golf & Country Club
- Heritage Shores
- Plantation Lakes Golf and Country Club
- Baywood Greens Golf Maintenance
- Bear Trap Dunes
- Wallops Beach
- Trimper Rides of Ocean City
- Coin Beach
- Fenwick Island State Park Beach
- Bow Beach
- Assateague State Park
- Parramore Beach
- Gargathy Beach