Home Vacation Home Rentals By Owner In Chincoteague Island, VA

Showing 80 Of 258 Vacation Rentals
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Exceptional(67)

$274.4

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Private Vacation Home

To the Lighthouse by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

If you have ever been to Chincoteague Island, you already know what an incredibly special place it is. Those who visit our island fall madly in love with our little slice of heaven, and return year after year. Imagine finding a Vacation Home worthy of such a Vacation Experience......brbrTo the Lighthouse is just that kind of home, and has had some fabulous updates. This gorgeous 3 Bedroom/3 Full Bath Home on Eastside Road directly faces Assateague Channel and our beloved Assateague Lighthouse. While separated by a small road, this home is Waterfront and has its own Private Dock for launching your kayaks, taking in sunsets, or simply exploring. The Views from inside and outside Epiphany are no less than soul-soothing.brbrAs you enter this charming home, you will love the cozy Kitchen that will please the Chef in the family. The Well-stocked Kitchen had Brand New Countertops, Appliances, and more, plus all you need to prepare fabulous family meals, or quick breakfasts before hitting the Beach. And there are so many places to enjoy that fresh Chincoteague Seafood! Dine in the huge Dining Room just off the Kitchen, in the tranquil Screened Porch, or on the side Deck taking in those Lighthouse Views! Don't feel like cooking on vacation No problem! Enjoy dinner out at one of many fine dining establishments within a 5 minute ride of To the Lighthouse.  I know you're already craving those Famous Chincoteague Oysters!brbrAs you enter through this lovely home to the Living Area, you will be captivated by the Views staring back at you from the enormous Bay Windows that line the front of house. The large Living Area is so comfortably furnished with room for everyone to relax. Enjoy the cool Central AC, Free WiFi, and Satellite TV after a sun-sational day at our beautiful Beach. With gleaming Hardwood Floors, Beachy Blues, and Wicker Accents, this is a fabulous room to spend time in - and you will never be without a water view! Along the front of the home, just off the Living Area, French Doors will lead you to a stunning Sunroom with walls of windows and a light Pine Ceiling. Ahhh, the serenity you will find here. Just imagine sipping your morning coffee while the Herons and Egrets fish for their morning meal! Also on the first floor is a Bedroom with a Twin that leads to the Screened Porch. brbrFollow the very cool Spiral Staircase upstairs to find two more Bedrooms and TWO more Full Bathrooms! The spacious Master Bedroom has a magical feel to it with a King bed, and also has those Marsh Views that will make your jaw drop. With a large closet and Lighthouse View Sitting Area, Mom and Dad will most certainly be able to relax and rejuvenate here. Just down the hall, you will find two Full Bathrooms! Full Bath 2 has gorgeous Tropical Blue Walls and bright white accents for a crisp, fresh look, and a Tub/Shower Combo. Just across from it is Full Bath 3, also with a Tub/Shower Combo and Sunny Yellow Walls. There will be no waiting in line to grab a shower at To the Lighthouse! Finally, Bedroom 3 has a comfy Queen bed and Twin bed. There is also access to the Deck off the back of the house and a staircase leading to the lush backyard.brbrThere is so much to explore at To the Lighthouse - from chasing Lightning Bugs and frogs in the tropical feeling backyard, to the critter hunting they will do at low tide off of your own Private Dock! The biggest concern with this fabulous home is that you may never want to leave!brbrTo the Lighthouse - A Soul Soothing Chincoteague Vacation Experience!brbrSeaside Vacations does not allow group rentals to guests under age 25.  Therefore,  online bookings for group rentals will not be honored.
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Bath 3

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$344.72

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Private Vacation Home

Surf & Turf | 3BR Island Getaway, Two Living Rooms, Near Veterans Park

Chincoteague Island, Virginia, United States

Welcome to your new coastal retreat on charming Chincoteague Island! This delightful three-bedroom, two-bathroom home offers the perfect blend of comfort and convenience for those seeking a relaxed seaside lifestyle.brbrStep inside to discover a thoughtfully updated interior that's clean, bright, and vacation ready! The home features not one, but two living room areas—because sometimes you need some extra space and a separate sanctuary for escaping when someone insists on watching that show you can't stand. Whether you're entertaining guests or simply enjoying a quiet evening, you'll appreciate the flexibility this layout provides.brbrLocated just off South Main Street, you'll enjoy easy access to everything this beloved island community has to offer. Nature and fitness enthusiasts will appreciate the proximity to Veteran's Memorial Park - perfect for morning walks, afternoon picnics or letting the kiddos expel some energy! Adventure seekers can head to Maui Jack's Waterpark for family fun, while the stunning Assateague Beach beckons with its pristine shoreline and legendary wild horses roaming freely along the sand.brbrThis modest, yet inviting, home captures the essence of coastal Virginia living without unnecessary pretense. It's comfortable, practical, and positioned in one of the most enchanting island communities on the Eastern Shore!brbr​​​​​​​- Linens and towels are included with your reservation.br- No smoking is permitted on the premises. br- No pets are permitted on the premises.br- Any reservations made for a future year (known as Advanced Reservations) are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.
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Bath 2

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Exceptional(54)

$315.4

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Private Vacation Home

Family Tides by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Family Tides - The tans may fade, but the memories last forever!br br Looking for somewhere truly special to spend your Chincoteague Island Family Vacation this year Look no further, as special doesn't even begin to describe the tranquility and beauty of waterfront Family Tides. This adorable home is located directly on Lewis Creek's deep water, so by all means, bring the boat, kayaks, jet skis, or water toy of choice! With sweeping views of the Marsh, Canal, and Chincoteague Bay, you will feel as if you have found paradise.br br Family Tides has all of the touches and charm of a historic island home that you love, plus the modern amenities you need. Located in a fabulous location on Main Street, you can walk or ride your bike almost everywhere you want to be. This adorable 3 Bedroom/1.5 Bath home comfortably sleeps 8, with more than enough room both inside and out to enjoy time together.br br As you pull into the driveway, you already know how much you're going to love sitting on the wraparound Front Porch and taking in the Island Views. And you won't have to worry about little ones on the porch, as it is gated for their safety and your peace of mind. Upon entering this delightful home, the Coastal Colors, Exposed Beam Ceiling, and charming Painted Floors will just delight you. Family Tides has a large Living Area with a wall of windows facing the water. With Free WiFi, Satellite Flat Screen TV, and brand new AC/Heat, this is a fabulous place to relax after a fun-filled day on the Beach. And you won't be sacrificing those Water Views to do it - you can take them in right from the comfort of the sofa! Little ones will find hours of enjoyment playing with the Lincoln Logs and blocks the thoughtful owners have provided. Family Tides was recently purchased by a family who fell in love with this one-of-a-kind home while staying in it as Vacationers themselves! There is also a super convenient Half Bath on the main level of this cozy cottage. br br Open the double French Doors and stroll out to your own private waterfront paradise! Family Tides has an awesome Bulkhead suitable to tie up anything from a 16 foot Skiff to a 30 foot boat, and a huge Waterfront Deck with relaxing Adirondacks for taking in those famous Chincoteague Sunsets. There is even a Picnic Table for dining Al Fresco - what a perfect spot for a Crab Feast!br The kids will have a blast fishing and crabbing, and you won't believe the wildlife you will see - everything from Herons, Egrets, and Eagles, to Dolphins, Turtles, and more! The thoughtful Owners have also provide a couple of kayaks for exploring, and some beach chairs so you don't have to pack so much!br br Family Tides has several other areas for enjoying family mealtime, as well. Just off the Living Area is an open Dining Area that seats 4-6. As you wander down the hall, you'll find a large Eat-in Kitchen with absolutely everything you need to make family dinners a bay breeze. All of the charm of painted bead-board Country Cabinets and floors, plus every gadget and convenience you could want, including that ever-treasured dishwasher! The large table seats 6, and there is even a little breakfast nook. Don't feel like cooking on vacation Take a stroll down the street to one of many awesome dining establishments and try our famous salty, sweet Chincoteague Oysters or a traditional Fried Flounder Sandwich. With any luck, you'll be having a fish-fry of your own with the Flounder you catch in your own backyard!br br Upstairs are 3 Bedrooms, each with a delightful uniqueness you will love. Turning to the left at the top of the stairs, you'll find the Library with fabulous Built-in Bookcases and lots of storage. This room opens to the enormous Master Bedroom that will take your breath away. A comfortable King Bed awaits you, and you're very own Waterfront Sitting Area with comfy Wicker Furniture and another wall of windows overlooking Lewis Creek below. Just imagine enjoying your morning coffee here before anyone else is stirring. Soaring ceilings and more Exposed Beams make this room a very special place to wake up every morning. LINENS INCLUDED, NO SMOKING, NO VAPING, NO PETS. FAMILIES ONLY AND MUST BE AT LEAST 25.
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Exceptional(19)

$286.97

/ Nightly
Private Vacation Home

Beautiful Chincoteague home beside Carnival Grounds by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Temenos is a Greek word used to designate a special place - a place of unique beauty - where you can go to separate yourself, to serve as a Retreat, a place for quiet Reflection, a place to recover your sacred center when the world is overwhelming. These words from the thoughtful Owners of this beautiful Home say it all - and encompass what we feel Chincoteague Island is all about.brbrLocated on South Main Street, Island Temenos in the heart of our charming Island, and close to everywhere you want to be. Take a short stroll to the Historic District for Dining and Shopping, catch one of our famous Sunsets at Robert Reed Waterfront Park, or do a little Fishing at the Community Pier. Enjoy gazing at our Wild Ponies next door at the Carnival Grounds next door as you relax on the Screened Porch, or wander next door for one of our famous Oyster Fritters while the Firemen's Carnival is there each weekend in July.brbrIsland Temenos may be in the heart of the action, but truly feels a million miles away. As you pull into the driveway, the charm of the White Picket Fence, and the Tree Swing swaying in the breeze, will let you know you're on Island Time now. This lovely Home sleeps 8 with 4 Bedrooms and 1 1/2 Baths. Entering through the huge Screened Porch, you're already thinking you'll be spending a lot of time right here - and big changes are in store for this Porch for Summer 2020 - new floors, furnishings, and more! brbrThe Chef in your family will love the newly renovated Kitchen with gleaming Granite and just the perfect combo of muted Sandy Tones and pops of Sea Glass Blues and Greens. Special touches like Barn Doors and Custom Window Treatments give a taste of yesteryear, but with the Modern Amenities you want and need.  Very well-equipped, preparing family meals will be a bay breeze. Dine in comfort in the spacious Dining Room, or Al Fresco on the Screened Porch - so many options! brbrAfter a fun-filled day exploring Assateague National Seashore, relax in the comfort of the AC and enjoy Free WiFi and Cable TV. Island Temenos has both a Living Room and a Family Room, making it ideal for your family to spread out or for 2 families to share! There are many inviting nooks to curl up with a good book, or take in lovely Water Views, just across Main Street. The serene Coastal Colors and Historic Hardwood Floors beckon you to come and sit a spell. This Home is not just a place to lay your head - it is truly a Vacation Experience. brbrDownstairs, you'll find 2 lovely Bedrooms, both with a comfy Queen Bed, and a Full Bath with Tub/Shower Combo. Each Bedroom truly has its own personality and unique Coastal Flair. There's also an Outdoor Shower for rinsing off after a day at the Beach. Wandering upstairs, you'll be greeted by a cozy Reading Nook, 2 more spacious Bedrooms and a Half Bath. Both Bedrooms have 2 Twin Beds each - making the upstairs the perfect Retreat for the kiddos! brbrIsland Temenos is all about quality time - time with family, time with friends, time for you. We can't think of a more perfect place to fall in love with Chincoteague Island. Let us help you plan a Vacation Retreat you won't soon forget.....brbrIsland Temenos - becasue the best kind of souvenir is a Memory......brbrSeaside Vacations does not allow group rentals to guests under age 25.  Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any mistakes. LINENS INCLUDED, NO SMOKING, NO VAPING, NO PETS. FAMILIES ONLY AND MUST BE AT LEAST 25.
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Exceptional(1)

$305.7

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Private Vacation Home

Lighthouse Estates #8 | Pool, Lighthouse Views, Pier & Pet Friendly East Side Retreat

Chincoteague Island, Virginia, United States

Welcome to Lighthouse Estates #8, Formerly known as 'Natalie's Nook'! This 2 bedroom beach retreat is located in the popular Lighthouse Estates community on the East Side of Chincoteague Island. Enjoy all the amenities and features one could desire during their vacation - a pool, water & lighthouse views, a pier perfect for fishing, crabbing or kayaking, not to mention a vacation rental filled with all the comforts of home! Downstairs you'll find an open floor plan with living room, kitchen, dining area and powder room. Upstairs features 2 bedrooms (one master ensuite with private bathroom and water view balcony) and a full bathroom off the hallway. Lighthouse Estates #8 is conveniently located to The Pearl Restaurant, the waterfront Memorial Park, boat rentals, the Town public boat ramp & more! Come for a fabulous, relaxing stay! . brbr- Linens and towels are included with your reservation.br- No smoking is permitted on the premises. br- This property is pet friendly with a pet fee per pet. Pet fee is $150 per pet. All pets must be disclosed prior to arrival. Pet restriction: limited to one dog, no cats.br- Any reservations made for a future year (known as Advanced Reservations) are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.
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Sleep 6

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Exceptional(3)

$316.81

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Private Vacation Home

Almost Heaven | Waterfront w/ Private Pier & Boat Dock, Pet Friendly, Fireplace, Sunset Views

Chincoteague Island, Virginia, United States

Private pier with boat docking, Waterfront, Pet friendly, Internet, A/C, Fireplace, Charcoal grill. Vintage charm with all modern comforts!brbrWelcome to your new favorite island getaway! This charming Victorian cottage on Chincoteague's popular South Main Street offers the perfect blend of traditional character and modern comfort. With 3 bedrooms and 2 bathrooms, there's plenty of space for family and friends to unwind after a day of island exploring and adventures.brbrStep onto the open front porch and prepare to be amazed — breathtaking bayside sunsets await you nearly every evening. Pour yourself something refreshing, kick back in a rocking chair, and watch as the sky transforms into a canvas of orange and pink hues over Chincoteague Bay.brbrOne of this home's standout features is the private pier extending directly into the bay, complete with boat dockage capabilities. Imagine morning fishing sessions, dropping a crab line to try your hand at catching dinner, or evening cruises right from your rental home! No need to haul your boat to a public launch — your nautical adventures begin here.brbrTraveling with 4-legged family members No problem here - 'Almost Heaven' welcomes your pet(s)!brbrLocation Simply perfect. You're just minutes from downtown's delightful shops, restaurants, and even the downtown movie theater. Grocery runs are a breeze with Island Foods just a short drive away. For summer fun, Maui Jack's Waterpark is nearby, and the stunning Assateague Beach is waiting to capture vacation memories, and for your footprints in the sand.brbrThe primary bedroom on the first floor offers a peaceful retreat after long days exploring island trails or collecting seashells. The second floor features two more bedrooms and a full bathroom (shower only). This isn't just a rental — it's your ticket to the relaxed island lifestyle you've been dreaming about. Make it your home away from home'... at the beach! brbr- No smoking is permitted on the premises. br- Linens and towels are included with your reservation.br- This property is pet friendly with a pet fee per pet. Pet fee is $150 per pet. All pets must be disclosed prior to arrival.br- Any reservations made for a future year (known as Advanced Reservations) are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.
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$672.17

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Private Vacation Home

Poole's Cove | Waterfront Main Street Retreat Fully Renovated w/ Rooftop Lounge & Artistic Charm

Chincoteague Island, Virginia, United States

Nestled just off Main Street with the water as your backdrop, Poole's Cove is a lovingly curated escape that feels inspired and inviting. Every detail of this thoughtfully decorated home invites you to slow down, breathe deeply, and truly settle in.brThe layout is designed for both togetherness and solitude. The primary bedroom suite anchors the main house, while a breezeway connects you to a separate wing with two additional bedrooms and bathrooms — perfect for families or couples who want space to gather and space to retreat.brStep into a large screened-in deck and up to the rooftop deck, where water views, golden sunsets, open skies, and unforgettable stargazing await. When you're ready to unwind indoors, the upstairs office and library is a wonderful place to lose yourself in a good book.brAnd the best part Poole's Cove has just undergone a complete top-to-bottom renovation. Brand new kitchen, floors, bedrooms, bathrooms, and furnishings throughout — plus significant exterior updates. The Poole's Cove you've always loved is now better than ever.brThis isn't just a place to stay. It's an experience.br---brPlease note: Due to this home's unique floor plan and open deck railings, it may not be suitable for young children. This is a non-smoking, pet-free property. Linens and towels are available.brbr- Linens and towels are included with your reservation.br- No smoking is permitted on the premises.br- No pets are permitted on the premises.br- Any reservations made for a future year (known as Advanced Reservations) are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.
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Exceptional(4)

$296.22

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Private Vacation Home

Horseshoe Hideaway | Secluded Ranch w/ Dual Screened Porches + Large Yard

Chincoteague Island, Virginia, United States

Located in a secluded neighborhood, in the middle of town, 'Horseshoe Hideaway' is comfortably situated back off of a back road, fully enclosed by a fence, and ensconced by a generous yard and mature wooded area. With all the convenience of traveling around the island with ease, this home allows guests to drive or bike to Maddox Blvd, the beach or to the Main Street shops within minutes. Enjoy the outdoors on the fully screened in porches located on both the front and the back of the home, or take advantage of the generous back deck (accessed by a ramp or stairs) and supplied with a large gas grill, picnic table and Adirondack chairs. Inside the home features 3 bedrooms and 2 full bathrooms, a separate dining room, living room and eat in kitchen. There are several seating areas where guests can spread out or congregate as a group. The home is appointed with everything you need to enjoy a vacation at the Beach. This cute-as-a-button rancher home is waiting for your family vacation! Clean, comfortable and modest best describe the single-level home; there's an open kitchen, living and dining area that opens up to a front AND back screened porch. Enjoy all of the outdoor space from one of the 2 screened porches, or the spacious back deck and back yard! Located on a side street just off of Ridge Road, 'Horseshoe Hideaway' is conveniently located just minutes from downtown Chincoteague, as well as the Beach Road. Come and check it out for yourself! brbr​​​​​​​- Linens and towels are included with your rservation.br- No smoking is permitted on the premises. br- No pets are permitted on the premises.br- Any reservations made for a future year (known as Advanced Reservations) are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.
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Exceptional(1)

$321.6

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Private Vacation Home

Blue Chair Bay | South Main Bayfront w/ 2-Level Screened Porches, Sunset Views & Shared Pier

Chincoteague Island, Virginia, United States

If you're looking for a little slice of paradise at the beach, look no further! This delightful townhome is adorned with beachy, Kenny Chesney vibes throughout! As Kenny Chesney sings, There's a blue rocking chair, Sittin' in the sand, Weathered by the storms and well oiled hands, It sways back and forth with the help of the winds, Seems to always be there, like an old trusted friend. Enjoy all of the outdoor space - from the 2 level waterside screened porches, to the covered parking area with picnic table - there's plenty of room for all to enjoy. The downstairs features the kitchen and dining area, a half bathroom, living room, and expansive screened porch. Upstairs you'll find 3 bedrooms; one of them a master suite with private bathroom. There's also another full shared bathroom off the hallway. The South Main street location offers some of the most beautiful sunsets you'll ever see. Watch the tide roll in, the boats sail by, and the dolphins play along the Chincoteague Bay. There's also a shared pier if you'd like to try your hand at fishing, or if you'd like to sit on the water and relax with a cup of coffee. Don't delay - these townhomes are very popular and book quickly! brbr- No smoking is permitted on the premises. br- Linens and towels are included with your reservation.br- No pets are permitted on the premises. br- Any reservations made for a future year (known as Advanced Reservations) are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.
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$338.0

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My Island Escape | Luxury New Home, Gourmet Kitchen, Soaking Tub, Deck Retreat Near North Main

Chincoteague Island, Virginia, United States

Tucked away on a quiet lane off of North Main is where you will find My Island Escape. This brand-new home is absolutely immaculate! Luxury finishings, tastefully appointed furniture and decor make for a flawless backdrop to your next vacation. The living room at My Island Escape features ample comfortable seating and a flat screen television, and flows into the fully equipped, gourmet, eat-in kitchen that features a large island and plenty of space for cooking, dining, and enjoying meals with the family. The master bedroom features a Queen size bed with an en suite highlighted by a large soaking tub, double vanity, and separate glass stand up shower. The two other bedrooms in the home are close by a full bathroom located off the hallway. Another bonus in this home is the spacious laundry room complete with a full-size washer and dryer, iron and an ironing board, and connects to a convenient half bath. Outside, you will find deck space with outdoor furniture, and a picnic table with umbrella for outdoor dining. If you are looking for a clean, relaxing, upscale rental with great attention to detail look no further and escape to My Island Escape! brbr​​​​​​​- Linens and towels are included with your reservation.br- No smoking is permitted on the premises. br- No pets are permitted on the premises.br- Any reservations made for a future year (known as Advanced Reservations) are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.
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Bath 2

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