Vacation Rentals By Owner In Onancock, VA

Escape the hustle and bustle and get a way from it all at the Oyster Bay Getaway! Enjoy the still of the morning or listen to the quacks of wild ducks, splash of hungry fish, or tiptoeing of blue heron. Sit on the porch, coffee in hand, and watch the local waterman put in or enjoy the best sunset you have ever seen.brbrOyster Bay is a family friendly slow down and get away from it all escape. Enjoy a cozy fireplace, fully stocked kitchen with water views, large communal table, gameroom, reading nook, large living room, screened in porch, yard games, or a late night bomb fire around the fire pit. Fish or crab at the edge of the pier and ask about some of the ideal put in locations! If you need a week away from everything, this is the place for you. brbrNote: Linens are not provided but are available upon requests. Please bring mosquito spray but spray is also provided and strongly encouraged when outside. The property is located on a well and septic and a water softener is provided. Grab firewood from the local grocery store. A grill is available. Please do not park infront of the boat ramp, turn around or dock. Please ask about adding kayaking and SuP rentals!

Family Friendly Waterfront Escape w/pier, gameroom, and fire pit!

Onancock, Virginia, United States

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Bath

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$241.59

Private First Floor of a Charming 1883 Victorian – Onancock, VAbrbrStep back in time while enjoying every modern convenience at this beautifully renovated 1883 Victorian home, nestled in the heart of Onancock on Virginia's Eastern Shore. This private garden-level retreat gives you exclusive access to the entire first floor of Serenity Manor — a grand historic home thoughtfully restored to blend 19th-century character with contemporary comfort. Ideal for couples, solo travelers, or small groups of up to 4 guests.brbrYour Private King SuitebrbrThe spacious king bedroom is a retreat in itself — high ceilings, elegant crown molding, and original hardwood floors set the tone, while modern touches ensure a restful stay. You'll sleep soundly on a memory foam mattress, and the room features its own 55 4K Roku Smart TV, a personal mini-split A/C and heating unit for perfect climate control year-round, and a cozy fireplace with a faux log heater for ambiance on cooler evenings. The en-suite full bathroom includes a tub/shower combination, and there's an additional half bath in the hallway for guests' convenience.brbrMultiple Living Areas — All YoursbrbrOne of the things that makes this space truly special is how much room you have to spread out. The entire first floor is yours, and it feels nothing like a typical one-bedroom rental.brCozy up in the family room with its 65 4K Roku TV — the perfect spot for movie nights, lazy mornings, or catching up on your favorite shows. Admire the antique decor in the historically styled formal living room, which has been carefully preserved and decorated to reflect the home's 1883 origins. Start your day in the bright morning room, a sunny and inviting space that's ideal for coffee and conversation.brbrA futon and sleeper sofa provide flexible additional sleeping for extra guests, so you have options if friends or family join you.brbrFor those who need to stay connected or work remotely, a dedicated workspace is set up with a monitor, power outlets, and USB-A and USB-C charging ports — everything you need to be productive while enjoying a change of scenery.brbrA Full Kitchen for Real CookingbrbrThis isn't a kitchenette — it's a full kitchen equipped with a refrigerator, stove, oven, microwave, toaster, coffee maker, and all the dishes, silverware, and cooking basics you need to prepare meals just like home. Enjoy your meals at the main dining table or gather more casually at the kitchen seating area. Whether you're cooking a full dinner with local seafood from the market or just making morning coffee, you'll have everything at hand.brbrThe Outdoor Spaces — A True HighlightbrbrStep outside and discover one of the best parts of this property. The screened porch is the kind of space you'll find yourself returning to again and again — perfect for morning coffee, afternoon reading, or evening conversation without a single mosquito to interrupt. Beyond the porch, you have full access to the expansive backyard, a patio with seating, a charcoal grill for outdoor cooking, and a fire pit that's ideal for winding down under the stars on a quiet Eastern Shore evening.brbrThe yard is spacious, open, and private — a rare find for a rental in a walkable downtown setting. It's great for kids to play, for pets to stretch their legs, or simply for enjoying the slower pace that makes this part of Virginia so special.brbrPet-FriendlybrbrWe know your dog is part of the family. Pets are welcome at Serenity Manor, and the large backyard gives them plenty of room to enjoy the stay as much as you do. A vacuum with a pet hair attachment is provided for easy cleanup before checkout.brbrKeyless Entry & In-Unit LaundrybrbrArrival is simple — the front door features a smart lock with a keypad code, so there are no keys to worry about picking up, losing, or returning. The home also has side and rear entrances accessible from the inside. An in-unit washer and dryer adds everyday convenience, especially for longer stays or families with kids.brbrA Note on PrivacybrbrSerenity Manor also has an attached apartment available for separate rental. The two spaces are connected by a hallway with double doors that are locked from both sides, ensuring complete privacy and sound insulation. The only shared space is the driveway — please avoid blocking the circular drive to keep things easy for everyone.brbrExploring Onancock & BeyondbrbrLocation is one of this property's great strengths. From the front door, it's just a 10-minute walk along sidewalks to the heart of downtown Onancock — one of the oldest continuously occupied English settlements in North America, dating to 1680. You'll find locally owned restaurants, boutique shops, art galleries, and the scenic Onancock Wharf all within easy reach.brbrThe Wharf is a favorite gathering spot for visitors and locals alike. Enjoy waterside dining, rent a kayak or bicycle, or catch the seasonal ferry to Tangier Island — a tiny, one-of-a-kind Chesapeake Bay community accessible only by boat or small plane. It's an experience that stays with you long after you leave. (Be sure to call ahead to see if it is running.)brbrFor day trips, the Eastern Shore delivers in every direction. Head north about 45 minutes to Assateague Island National Seashore to catch a glimpse of the famous wild ponies roaming the beach. Drive south about 45 minutes to Cape Charles Beach for beautiful bay swimming, or explore Kiptopeke State Park for hiking and world-class birding. The entire Shore is ideal for cycling, fishing, and slowing down.brbrIf you're a history buff, don't miss Kerr Place — a beautifully preserved Federal-style mansion from 1799 that serves as a local history museum, just a short walk from the house. Onancock's streets are full of well-preserved historic architecture, and simply walking the town is a pleasure.brModern Comforts ThroughoutbrbrTo recap, here's what you'll enjoy throughout the first floor: high-speed Wi-Fi, 4K Roku Smart TVs in the bedroom and family room, individual climate control, a full kitchen, washer and dryer, dedicated workspace, screened porch, fire pit, charcoal grill, expansive yard, and keyless smart-lock entry.brbrYour HostbrbrI'm Steve, and I purchased this home in 2023 and spent nearly two years bringing it back to life. I'm reachable by phone, text, or messaging through the booking platform and am happy to answer questions, share local recommendations, or help with anything during your stay. Whether you're here for a romantic getaway, a family visit, or simply a peaceful escape, my goal is to make your time here exceptional.brbrWelcome to Serenity Manor. Enjoy the screened in porch, the fire pit, the backyard — and the serenity.

Private First Floor of Historic Victorian–King Bed, Full Kitchen, Screened Porch

Onancock, Virginia, United States

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Bath

Sleeps

$448.93

Charming 1883 Victorian Home – 3 King Bedrooms in the Heart of OnancockbrbrStep back in time while enjoying every modern convenience at this beautifully renovated 1883 Victorian home, nestled in the heart of Onancock on Virginia's Eastern Shore. This spacious historic gem combines classic charm with luxurious, contemporary amenities, making it the perfect retreat for families, couples traveling together, or small groups of up to 6 guests.brbrThree Spacious King BedroomsbrbrThe home features three thoughtfully appointed king bedrooms, each with its own distinct character. Each bedroom boasts high ceilings, elegant crown molding, and original wood floors — exuding old-world elegance you simply can't find in newer construction. You'll sleep soundly on memory foam mattresses, and every bedroom is equipped with a 55 4K Roku Smart TV, a personal mini-split A/C and heating unit for individualized climate control, and a cozy fireplace with a faux log heater for that perfect ambiance year-round.brbrTwo of the three king bedrooms have private en-suite bathrooms for ultimate convenience and privacy. The third king bedroom uses a beautifully appointed full hall bathroom just steps away, plus there's an additional half bath on the first floor for everyday convenience. With 3.5 bathrooms total, there's never a wait.brbrMultiple Living Areas — Room to Spread OutbrbrOne of the things that makes this home truly special is how much space you have to relax and unwind. Spread out across three distinct living areas, each with its own character.brCozy up in the family room with its 65 4K Roku TV — perfect for movie nights, lazy mornings, or catching up on your favorite shows together. Admire the antique decor in the historically styled formal living room, carefully curated to reflect the home's 1883 origins, where you can enjoy a quiet conversation or simply soak in the period charm. Start your day in the bright morning room, a sunny and inviting space that's ideal for coffee, journaling, or planning the day's adventures.brbrA futon and sleeper sofa in the common areas provide flexible additional sleeping for occasional extra guests, kids, or anyone who prefers a couch nap.brbrFor those who need to stay connected or work remotely, a dedicated workspace is set up with a monitor, power outlets, and USB-A and USB-C charging ports — everything you need to be productive while enjoying a change of scenery. High-speed Wi-Fi covers the entire home.brbrA Full Kitchen Built for Real CookingbrbrThis isn't a kitchenette or token kitchen — it's a full, well-equipped kitchen ready for serious cooking and gathering. The kitchen features a refrigerator, stove, oven, microwave, toaster, coffee maker, and a comprehensive set of dishes, glassware, silverware, pots, pans, and cooking essentials. Whether you're preparing a feast with fresh local seafood from the Onancock market or just brewing morning coffee, you'll have everything at hand.brbrDining & EntertainingbrbrWhether you're hosting a formal dinner in the elegant dining room or gathering more casually around the kitchen seating area, this home offers plenty of space for shared meals. The dining room comfortably seats up to 10, leaving room for larger get-togethers, holiday meals, or just spreading out with the family.brbrOutside, the back patio invites you to enjoy meals from the charcoal grill or simply relax in the fresh Eastern Shore air.brbrThe Outdoor Spaces — A True HighlightbrbrStep outside and discover what may be the property's most beloved feature. The screened porch is the kind of space you'll find yourself returning to again and again — perfect for morning coffee, afternoon reading, or evening conversation without a single mosquito to interrupt. It's a quintessential Eastern Shore experience.brbrBeyond the porch, you have full access to the expansive private backyard, a patio with seating, a charcoal grill for outdoor cooking, and a fire pit that's ideal for winding down under the stars. The yard is spacious, open, and surprisingly private — a rare find for a rental in such a walkable downtown setting. Kids have room to play, dogs have room to roam, and adults have a quiet outdoor space to truly unwind.brbrPet-FriendlybrbrWe know your dog is part of the family. Pets are welcome at Serenity Manor, and the large backyard gives them plenty of room to enjoy the stay as much as you do. A vacuum with a pet hair attachment is provided for easy cleanup before checkout.brbrKeyless Entry & In-Unit LaundrybrbrArrival is simple — the front door features a smart lock with a keypad code, so there are no keys to worry about picking up, losing, or returning. Side and rear entrances are accessible from the inside as well. An in-unit washer and dryer adds everyday convenience, especially for longer stays, families with kids, or trips that involve a beach day or two.brbrA Note About the HomebrbrSerenity Manor is a 6-bedroom historic home, but for this listing only three of the king bedrooms are open and available. Other bedrooms remain closed and inaccessible to ensure your group has a curated, comfortable experience without paying for space you won't use. You'll have full and exclusive access to the entire first floor (kitchen, dining room, living rooms, morning room, screened porch, and yard) plus the three king bedrooms upstairs and their bathrooms.brbrModern Comforts ThroughoutbrbrTo recap, here's what you'll enjoy throughout your stay: 3 king memory foam beds, 4K Roku Smart TVs in every bedroom plus the family room, individual mini-split climate control in every bedroom, fireplaces in every bedroom, high-speed Wi-Fi, full kitchen, formal dining for 10, washer and dryer, dedicated workspace, screened porch, fire pit, charcoal grill, expansive yard, and keyless smart-lock entry.brbrExploring Onancock & BeyondbrbrLocation is one of this property's great strengths. From the front door, it's just a 10-minute walk along sidewalks to the heart of downtown Onancock — one of the oldest continuously occupied English settlements in North America, dating to 1680. You'll find locally owned restaurants, boutique shops, art galleries, and the scenic Onancock Wharf all within easy reach.brbrThe Wharf is a favorite gathering spot for visitors and locals alike. Enjoy waterfront dining at Mallard's, rent a kayak or bicycle, or catch the seasonal ferry to Tangier Island — a one-of-a-kind Chesapeake Bay community accessible only by boat or small plane. It's an experience that stays with you long after you leave. (Make sure to call before booking to ensure availability)brbrFor day trips, the Eastern Shore delivers in every direction. Head north about 45 minutes to Assateague Island National Seashore to catch a glimpse of the famous wild ponies roaming the beach. Drive south about 45 minutes to Cape Charles Beach for beautiful Chesapeake Bay swimming, or explore Kiptopeke State Park for hiking and world-class birding. The entire Shore is ideal for cycling, fishing, kayaking, and slowing down to enjoy life at a more deliberate pace.brbrIf you're a history buff, don't miss Kerr Place — a beautifully preserved Federal-style mansion from 1799 that serves as a local history museum, just a short walk from the house. Onancock's streets are full of well-preserved historic architecture, and simply walking the town is a pleasure in itself.brbrPerfect ForbrbrThis home is ideally suited for multi-generational family gatherings, couples traveling together (girls' weekends, guys' weekends, friend trips), small reunions or milestone celebrations, romantic getaways with extended family or friends, quiet retreats away from the bustle of city life, and Eastern Shore explorers who want a comfortable home base.brbrYour HostbrbrI'm Steve, and I purchased this home in 2023 and spent nearly two years bringing it back to its full glory. I'm reachable by phone, text, or messaging through the booking platform and am happy to answer questions, share local recommendations, or help with anything during your stay. Whether you're here for a romantic getaway, a family reunion, or simply a peaceful escape, my goal is to make your time here exceptional.brbrBook NowbrbrWelcome to Serenity Manor. Enjoy the unhurried pace that makes the Eastern Shore so special. We can't wait to host you.

Historic Victorian Home–3 King Bedrooms w/554KTVs, Full Kitchen, Screened Porch

Onancock, Virginia, United States

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Bath

Sleeps

Exceptional(1)

$411.87

Welcome to beautiful Onancock, Virginia on the Eastern shore. This vacation home is nestled in the private East Point community. The property has its own access to the water and is also next to the community’s private beach.brbrYou can spend the day relaxing, walking out into the water, and will also have the use of kayaks (2), paddle boards (2), and outdoor yard games. For those with a boat, there is a boat ramp nearby in downtown Onancock which provides access out to the Chesapeake Bay where the fishing and sunsets are amazing. Keep your eyes open for our resident Bald Eagle family that live in the surrounding trees.brbrDowntown Onancock is just about 10-15 minutes away with plenty of bar/restaurants with live entertainment, dining, shopping and sight-seeing. At the waterfront you can catch the ferry to Tangier Island. From the home, you can take day trips to Chincoteague and Cape Charles, and everywhere else in between. The Eastern Shore provides endless outdoor opportunities to explore. A Food Lion grocery store and Walmart are also just 10-15 minutes away.brbrYou will have access to the entire main part of the home. There are four bedrooms, and two bathrooms. One bedroom with a king bed, two with a queen bed, and one with a bunk bed that has a single above a full size bed. The large family room, and sitting room have all been updated with new furniture, and the kitchen has all new stainless steel appliances. The home does not have cable, but has high speed internet, and Smart tv’s are provided in all the bedrooms and living room so don’t forget your favorite entertainment sign on. Instructions will be provided for logging onto the Internet, and how to set up so all your credentials are deleted when your vacation ends.brbrThere is no washer and dryer, but a laundry mat is near by. The kitchen is fully stocked with dishes, cookware, serving ware, a Keurig, a regular coffee pot, crock pot, and microwave. There is also a gas grill. Bath towels and bed linens are provided, but you can also bring your own if you prefer. Please bring your own beach towels.brbrWe are a dog friendly home. If you’d like to bring any other pets please let us know before booking to discuss. We understand not all pets are alike, and can have anxiety, so if necessary, please bring any pet crates in case you aren’t able to leave your pets unattended if you go out for the day. We’d also like to limit it to two but can also discuss if you have the need to bring more. We’re flexible.brbrThere is absolutely no smoking allowed inside the home. Any drug use will also result in you being asked to leave. This includes marijuana.brbrOnce here, you’ll never want to leave.brbrIf interested in shorter 4-5 night stays outside of the dates between Memorial Day and Labor Day, message us.

Leave Your Paw Prints by the Bay

Onancock, Virginia, United States

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Exceptional(5)

$478.63

Discover this superb 3-bedroom waterfront gem in Onancock. This tranquil house features exquisite sunset views from covered porches on two levels of this 3 story home with lots of outdoor space. Enjoy the privacy of this Chesconessex Creek property while being just 8 minutes from the historic and fun Town of Onancock. Explore Virginia’s Eastern Shore as we are mid way between Chincoteague and Cape Charles. Exercise in the endless pool, or practice your pickleball skills on a mini practice court or in the enclosed garage; 13 foot net, paddles and balls included! The primary and guest (ensuite) bedrooms are on level 1, with the laundry area and access to the pool deck while the 3rd bedroom with twin beds in the “crow’s nest” on level 3. Kitchen, living and dining areas, and the half bath, are located on level 2. Two wraparound porches and a pool deck on the back of the house complete this lovely home with lots of outdoor spaces to enjoy! A mini pickleball court, complete with paddles and balls, is in the garage. Backyard area is fenced for convenience of bringing approved pets. We are available to answer any questions about the home, area or Eastern Shore before or during your stay at the Harbor Master!

Harbor Master-Waterfront 3 bedroom home with endless pool pickleball fenced yard

Onancock, Virginia, United States

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$930.93

Camp Chesapeake House, a private 6 bedroom vacation home nestled on 6 acres of waterfront seclusion just 3 hours from DC and Richmond. The spacious house sleeps up to 16 and includes kayaks, hot tub, movie room, private sunrise dock, kids treehouse, games and more. Bring the whole family to this great place with lots of room for fun.

Camp Chesapeake 6 bedroom Private Waterfront - Dock, Hot Tub, Family Friendly

Onancock, Virginia, United States

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Exceptional(176)

$347.45

The Parsonage on King, built in 1836, serves as the perfect place to base yourself for any visit to the Eastern Shore! brbrThe homes sleeps 8 people comfortably with 3 bedrooms and 3 full baths including 1 BR and bath on the first floor. Additional sleeping accommodations include a loft perfect for kids with 2 twin beds as well as a pullout couch in the downstairs sunroom. brbrThe main level of the house includes a living room with smart TV, Bluetooth connected stereo, couch, puzzles and books. The fully equipped kitchen opens to the dining room/sunroom and the back porch with gas grill. brbrThe Town Wharf is only steps away where you can launch a boat at the public ramp or rent kayaks, paddle boards and bikes. The passenger ferry to Tangier Island also departs from there. Onancock is home many small, locally run business included restaurants, shops, galleries, movie theater, coffee shop and a bakery that residents come from miles around to visit...all of this within walking distance from the Parsonage! brbrThe town of Chincoteague and Assateague National Park are a fun day trip where you can swim or surf at a guarded beach, hike or bike, see wild horses and visit a brewery or water park. brbrAdditional fun side trips include a winery, The Barrier Islands Center, the town of Cape Charles, Savage Neck Dunes and the town of Wachapreague which is home to a popular restaurant with outstanding water views. Also out of Wachapreague you can charter a boat to take you fishing, birding, shell collecting or just exploring on the undeveloped barrier islands.

Spacious home centrally located in the quaint waterfront town of Onancock

Onancock, Virginia, United States

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Exceptional(51)

$766.59

Gorgeous waterfront property directly overlooking expansive Cedar Creek, (off of Onancock Creek largest of the Chesapeake Bay tributaries, AND only one block from the adorable town of Onancock. No wonder Budget Magazine recently voted Onancock 'The Coolest Small Town in America!' I will add a more details about the house in the coming days. In the interim please google Onancock VA for an overview of the sites, activities, restaurants, and an historical overview of the town.

Waterfront Paradise Located on Virginia's Beautiful Eastern Shore (boat slip)

Onancock, Virginia, United States

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$302.96

Waterfront 1930s Retreat with Stunning Sunsets – OnancockbrbrWake up to water views and end your day with unforgettable sunsets at this charming 3BR/2BA 1930s home on the shore. Updated for comfort, it features a tastefully decorated living room, sunroom, spacious deck, outdoor shower, and a cozy kitchen/family room combo. Enjoy peaceful moments in every room with waterfront vistas, plus a cook’s kitchen with recipes. Sleeps 6 (2 queens, 2 twins). A serene, sunset-filled escape in historic Onancock stocked with local finds from around the coast.

Waterfront property- Point Nautica

Onancock, Virginia, United States

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Exceptional(11)

$178.14

Comfy and Quiet. An Intimate bedroom with blackout curtains adjoins a simple but clean and upgraded bathroom and shower. Prepare your food in the kitchen with full size fridge and stove, or work from a TV tray at the couch with high-speed internet via fiber to the property. There's a new 55 Roku TV in the living room for lounging around, but the area if so full of options, you will likely want to spend your time out and about! That could be touring the quaint town of Onancock and its many shops, waking a short distance to historical sites like Kerr Place, having lunch at the waterside restaurant at the Wharf .8 miles away, or a ride over to Tangier Island on a ferry leaving from the wharf, or many other day trips like seeing the ponies at Assateague Island and beach, 30 miles away, and many others! You'll love the slower pace of a small town, while having access to modern amenities and shopping. (5 minute drive to a Walmart!) Come join us and enjoy a little serenity.

Apartment

A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore

Onancock, Virginia, United States

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$435.69

Welcome to beautiful East Point! Take in spectacular sunsets from the wrap-around porches or from the community's private beach. Set out in the kayaks or just walk into the serene waters where Onancock Creek meets the Chesapeake Bay. Tour the neighborhood by foot or bike and enjoy views of the peaceful woods, beaches and private marina. The charming town of Onancock is just 10 minutes away with plenty of dining, shopping and sight-seeing. There is so much for the whole family to enjoy!

The Quarter Deck// Spacious Home with Water views!

Onancock, Virginia, United States

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Bath

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Sleeps

$347.45

Spacious home centrally located in the quaint waterfront town of Onancock

Onancock, Virginia, United States

Bed

Bath

Sleeps

$411.87

Leave Your Paw Prints by the Bay

Onancock, Virginia, United States

Bed

Bath

Sleeps

$435.69

The Quarter Deck// Spacious Home with Water views!

Onancock, Virginia, United States

Bed

Bath

Sleeps

$618.82

Timeless Elegance with Modern Luxury: Historic 6-Bedroom Home

Onancock, Virginia, United States

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Bath

Sleeps

$478.63