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Chincoteague Island Rentals

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Seaside Vacations & Sales

Chincoteague Island

We cannot think of a better place to begin this new dawn than at Newly Renovated ‘Island Sunset’ on beautiful Chincoteague Island. This one-of-a-kind home not only sits on South Main Street - home of THE most spectacular Sunsets - it features a Private Pier and Brand New Floating Dock! Fishing, Crabbing, Kayaking - all right in your own backyard!

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

We all yearn to find that wonderful place that makes the real world feel oh, so far away. A place to kick back, relax, and forget all about your worries. For so many of us, the Beach IS our happy place - the sun on your skin, salt in your hair - no problems on your mind. ‘My Happy Place’ is just that - an escape from the rush of the day to day - a wonderfully whimsical Vacation Getaway. My Happy Place, Happy Places, The Real World, Wonderful Places, Vacation, Escape

Wonderful Places

We all yearn to find that wonderful place that makes the real world feel oh, so far away. A place to kick back, relax, and forget all about your worries. For so many of us, the Beach IS our happy place - the sun on your skin, salt in your hair - no problems on your mind. ‘My Happy Place’ is just that - an escape from the rush of the day to day - a wonderfully whimsical Vacation Getaway.

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

Welcome to Whelks on Willow - a lovely Coastal Cape Cod tucked away on Willow Street - close to everywhere you want to be, yet a million miles away from the worries of the real world. Featuring a refreshing Private Pool, Whelks on Willow is truly a Vacation Destination that sleeps 8 in comfort and style. Willow Street, Private Pool, Vacation Destinations, Cape Cod, Sectional Couch

Vacation Destinations

Sectional Couch

Welcome to Whelks on Willow - a lovely Coastal Cape Cod tucked away on Willow Street - close to everywhere you want to be, yet a million miles away from the worries of the real world. Featuring a refreshing Private Pool, Whelks on Willow is truly a Vacation Destination that sleeps 8 in comfort and style.

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

There's only one thing more precious than our time, and that is who we spend it on. Life is busy - just getting the family together can be such a challenge in today's world, but nothing is more important than doing just that. Clear the calendar, grab those you love, and head to Chincoteague Island to make Memories that you'll treasure forever. Sidewalk, World, Building, Landmarks, Happy, Calendar

There's only one thing more precious than our time, and that is who we spend it on. Life is busy - just getting the family together can be such a challenge in today's world, but nothing is more important than doing just that. Clear the calendar, grab those you love, and head to Chincoteague Island to make Memories that you'll treasure forever.

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

The best things in Life are the people we love, the places we've been, and the Memories we've made along the way. Welcome to Teague Time on beautiful Chincoteague Island - the perfect place to relax, rejuvenate, and reconnect with those who matter most. Board Game Room, Most Visited National Parks, Tub Shower Combo, Relaxing Day, Outdoor Living, Outdoor Decor, Beach Combing, Heating And Air Conditioning

Board Game Room

Most Visited National Parks

Tub Shower Combo

Heating And Air Conditioning

The best things in Life are the people we love, the places we've been, and the Memories we've made along the way. Welcome to Teague Time on beautiful Chincoteague Island - the perfect place to relax, rejuvenate, and reconnect with those who matter most.

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

Pure Paradise! This gorgeous condo sits directly on the Bay with stunning Views of the Bay, Drawbridge, and the best Sunsets to be found. Lounge by the Bayfront Pool and watch Herons and Egrets frolic over the water. Try your hand at crabbing or fishing from the Community Dock - or wander down the street to shop and dine in the Historic District. Sunset Bay Villa 313 offers the Luxury you want, the Amenities you need, all at a family-friendly price! Best Sunset, Beautiful Sunset, Drawbridge, Condo, Villa, Bay

Beautiful Sunset

Pure Paradise! This gorgeous condo sits directly on the Bay with stunning Views of the Bay, Drawbridge, and the best Sunsets to be found. Lounge by the Bayfront Pool and watch Herons and Egrets frolic over the water. Try your hand at crabbing or fishing from the Community Dock - or wander down the street to shop and dine in the Historic District. Sunset Bay Villa 313 offers the Luxury you want, the Amenities you need, all at a family-friendly price!

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

Sunset Bay 307 - Sometimes you just have to go with the Waves….. Welcome to Sunset Bay 307 - Picasso - at fabulous Sunset Bay Villas on the Chincoteague Bay - truly a work of Art! Picasso, Villas, Table

Sunset Bay 307 - Sometimes you just have to go with the Waves….. Welcome to Sunset Bay 307 - Picasso - at fabulous Sunset Bay Villas on the Chincoteague Bay - truly a work of Art!

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

Welcome to beautiful Sunset Bay Villas on the Chinoteague Bay - pure Paradise! These gorgeous condos sit directly on the Bay with stunning Views of the Bay, Drawbridge, and the best Sunsets to be found. Lounge by the Bayfront Pool and watch Herons and Egrets frolic over the water. Beautiful Islands, Pet Friendly Vacation Rentals, Beach Week, House Breaking, Bay View, Luxury Villa

Beautiful Islands

Pet Friendly Vacation Rentals

Welcome to beautiful Sunset Bay Villas on the Chinoteague Bay - pure Paradise! These gorgeous condos sit directly on the Bay with stunning Views of the Bay, Drawbridge, and the best Sunsets to be found. Lounge by the Bayfront Pool and watch Herons and Egrets frolic over the water.

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

Reach for the Stars on your next Chincoteague Island Vacation Shed, Cottage, Outdoor Structures, Beautiful, Stars

Outdoor Structures

Reach for the Stars on your next Chincoteague Island Vacation

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

Much like finding sea glass as you stroll on the Beach, it’s the little things in life that often make the biggest difference. Time with family - a lazy day on the beach, catching crabs off the Dock, telling stories around a campfire - these are the little things that amazing Vacation Memories are made of. Sea Glass is just the treasure you’ve been yearning for. Vacation Memories, Telling Stories, Campfire, Saltwater, Stroll, Sea Glass

Vacation Memories

Telling Stories

Much like finding sea glass as you stroll on the Beach, it’s the little things in life that often make the biggest difference. Time with family - a lazy day on the beach, catching crabs off the Dock, telling stories around a campfire - these are the little things that amazing Vacation Memories are made of. Sea Glass is just the treasure you’ve been yearning for.

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

Close your eyes and imagine breathing in that salty, sweet air - the sound of the Gulls, the watermen harvesting oysters - you’re beginning to relax, and you’re not even here yet! This is a feeling deep in your soul - this is Sea Breeze! Sea Breeze, Gulls, Relax, Cabin, House Styles, Salty

Close your eyes and imagine breathing in that salty, sweet air - the sound of the Gulls, the watermen harvesting oysters - you’re beginning to relax, and you’re not even here yet! This is a feeling deep in your soul - this is Sea Breeze!

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

Dream Vacations

Family Vacations

May you always have a shell in your pocket, and sand in your shoes….. Sandy Bottoms - the name alone stirs up fond memories of family vacations from long ago. This wonderful 4 Bedroom Home is brand new to the Seaside Vacations’ Family, and we couldn’t be happier - and it’s ready to make your Vacation Dreams come true!

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

Changes in Latitude, Changes in Attitude….. As Jimmy Buffet would say, welcome to One Particular Harbor! And just as his music has a way of relaxing and rejuvenating us, so does this fabulous Vacation Home in the heart of Chincoteague Island. Stuff To Do, Jimmy

Changes in Latitude, Changes in Attitude….. As Jimmy Buffet would say, welcome to One Particular Harbor! And just as his music has a way of relaxing and rejuvenating us, so does this fabulous Vacation Home in the heart of Chincoteague Island.

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

Break away from the daily grind at Marsh Madness - leave your troubles at the door, you won't be needing them here! This incredibly unique Waterfront Home truly has it all, including a waterfront Pier shared with only one other home, and is ready to make your Vacation Dreams come true. Waterfront Homes, Daily Grind, Mansions

Waterfront Homes

Break away from the daily grind at Marsh Madness - leave your troubles at the door, you won't be needing them here! This incredibly unique Waterfront Home truly has it all, including a waterfront Pier shared with only one other home, and is ready to make your Vacation Dreams come true.

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

Little Red Cottage - “My heart will always be in a Little Cottage by the Sea….” Cottage By The Sea, Red Cottage, Little Cottage, Little Red, Paths

Cottage By The Sea

Little Red Cottage - “My heart will always be in a Little Cottage by the Sea….”

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

Life is busy - too busy at times, it seems. When was the last time you grabbed those who matter most and just broke away from the daily grind? We’ve had quite a bit of “togetherness” this year, but isn’t it time for “experiences” together once again?! This is what Lighthouse Overlook was made for - kicking back, taking in that salty, sweet sea breeze, and enjoying life again. Leave your worries behind - kick off your Flip Flops and let the fun begin! Let The Fun Begin, The Last Time, Beach Day, Lighthouse

Let The Fun Begin

Life is busy - too busy at times, it seems. When was the last time you grabbed those who matter most and just broke away from the daily grind? We’ve had quite a bit of “togetherness” this year, but isn’t it time for “experiences” together once again?! This is what Lighthouse Overlook was made for - kicking back, taking in that salty, sweet sea breeze, and enjoying life again. Leave your worries behind - kick off your Flip Flops and let the fun begin!

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

What is it that Jimmy Buffet always says? Of course - It's 5 O'Clock Somewhere! Leave your troubles at the door, you won't be needing them here! Outdoor Projector, Massanutten, Fall Getaways, Shenandoah National Park, Indoor Fireplace, Level Homes, Blue Ridge Mountains, Ocean City

Outdoor Projector

Shenandoah National Park

Indoor Fireplace

Blue Ridge Mountains

What is it that Jimmy Buffet always says? Of course - It's 5 O'Clock Somewhere! Leave your troubles at the door, you won't be needing them here!

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

We’re all about making memories that will last a lifetime - and Hudson House itself is a treasure trove of memories. This Historic Home was once the home of Ira Hudson - an iconic Chincoteague Carver. To this day, his workshop is on display at the Chincoteague Museum, always a ‘must-visit’ during your vacation. Hudson Homes, Breakfast Bar, Making Memories, Carver, Kitchen

Making Memories

We’re all about making memories that will last a lifetime - and Hudson House itself is a treasure trove of memories. This Historic Home was once the home of Ira Hudson - an iconic Chincoteague Carver. To this day, his workshop is on display at the Chincoteague Museum, always a ‘must-visit’ during your vacation.

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

Looking to catch a beach getaway at a family-friendly price? Then look no further than Fishhook Hideaway on Deep Hole Road - truly the catch-of-the-day! Little Island, Beach Getaways, Fish Hook, Hideaway, Full Bath

Looking to catch a beach getaway at a family-friendly price? Then look no further than Fishhook Hideaway on Deep Hole Road - truly the catch-of-the-day!

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

Ready to be charmed by your next Vacation? Welcome to Channel View Charmer on Chincoteague Island - mere steps to the Chincoteague Bay and Memorial Park! Family Channel, Memorial Park, Dog Friends, Golf Courses

Ready to be charmed by your next Vacation? Welcome to Channel View Charmer on Chincoteague Island - mere steps to the Chincoteague Bay and Memorial Park!

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

'Breakaway' to wild and wonderful Chincoteague Island! This lovely 2 Bedroom Townhome has captivating Views of the Assateague Channel, a Pier, and a Private Boat Slip! Bay Breeze, Boat Slip, Bayside, Water Views, Water Park

'Breakaway' to wild and wonderful Chincoteague Island! This lovely 2 Bedroom Townhome has captivating Views of the Assateague Channel, a Pier, and a Private Boat Slip!

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

You know that feeling you get when you step onto the Beach for the first time each Summer? That first deep breath - the saltiness of the Sea, the scent of Coppertone, the sound of the Gulls - this is life at Barefoot Breeze on Chincoteague Island. It’s not just a Vacation Rental, it’s a Destination, an Experience, if you will. Shower Tub, Electric Car Charger, Coppertone, Open Layout, Screened In Porch, Ocean Breeze, Walk In Shower

Electric Car Charger

Screened In Porch

You know that feeling you get when you step onto the Beach for the first time each Summer? That first deep breath - the saltiness of the Sea, the scent of Coppertone, the sound of the Gulls - this is life at Barefoot Breeze on Chincoteague Island. It’s not just a Vacation Rental, it’s a Destination, an Experience, if you will.

Seaside Vacations & Sales

Seaside Vacations & Sales

Chincoteague Island Rentals

Chincoteague House Rental Congaree National Park, Smoky Mountain National Park, Outdoor Retreat, Outdoor Fire, Assateague Island National Seashore, Swampland, New Smyrna Beach

Congaree National Park

Smoky Mountain National Park

Outdoor Retreat

Assateague Island National Seashore

New Smyrna Beach

Chincoteague House Rental

Looking for the perfect Home Base for your next Chincoteague Island Adventure? Look no further than fabulous Eastwinds 18, located in the very heart of Chincoteague Island. Townhouse, Retreat, 18th, Adventure

Looking for the perfect Home Base for your next Chincoteague Island Adventure? Look no further than fabulous Eastwinds 18, located in the very heart of Chincoteague Island.

Isn't it time for a new romance.....with Life?! A visit to fabulous Seaside Rendezvous is certainly the place to begin. Bedroom Size, Community Pool, Rendezvous, House Rental, Beach House, Fireplace

Isn't it time for a new romance.....with Life?! A visit to fabulous Seaside Rendezvous is certainly the place to begin.