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Homestead

3 Bedrooms
2 Baths
5 Guests
Chincoteague Island
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Set back across the street from Chincoteague Bay, Homestead sits on 30 acres of basically pristine land. A cozy cottage, originally built in 1890, had been updated but the owners kept the original charm of yesterday but with the comfort of today. Now that charm and comfort has been expanded. A new addition offers a great room with a modern kitchen, dining area and room to stretch out and relax. The design includes oversized windows, sliding doors and a sky light. The house now has 2 screen porches and a balcony that lets you feel as though you are living in in a nature preserve! Homestead sleeps 5 but best suited for 4 adults. There are now 2 full sized bathrooms. Amenities include bikes, beach chairs and umbrellas: games, crayons and colored paper and good parking. And as part of the property, you'll vacation alongside the oldest home on the island, The Captain Timothy Hill House, listed on the National Register of Historic Places. With a tidal pond in front and unspoiled woods in back, Homestead is private, quiet and with lots of room outside. A perfect retreat! So relax on one of the porches, feel the breeze from the bay, watch the animals and birds that come by or take an outside shower under the stars. The Homestead that so many have come to love is still the same just more to love!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets permitted on the premises.

- 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.

Charlie's Bayside Retreat

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

This is it! Are you looking for your perfect vacation getaway spot? Look no further. 'Charlie's Bayside Retreat' is everything you'll need for your home away from home, at the beach! The first main level features an open floor plan with a living room that opens up to a wonderful screened porch with comfortable outdoor dining furniture. The open living area also features a large Smart TV with cable and an electric fireplace. A modern kitchen that is fully stocked with everything you could possibly need, also has new appliances and a Keurig coffee maker, breakfast bar, open dining area, and powder room complete the first-floor living space. On the second floor, you'll find two bedrooms, one with a Queen bed and Smart TV and the other with 2 Twins & a Full - both with balconies and a shared full bathroom with dual sinks. The entire third floor is a spacious, private primary oasis with a Queen bed, and a luxurious en suite featuring a deep jetted tub and dual sinks. This bedroom is also equipped with a Smart TV and a balcony with amazing views & Adirondack chairs making it perfect for relaxing or sunbathing. Additional features of this fabulous vacation home include your own private boat slip (#7), pier for fishing and crabbing, fish cleaning station, covered parking area, grill, picnic table, and tons of extras! There's an outdoor shower, and beach gear including beach chairs, beach toys, and an umbrella. Not to mention you're conveniently located on South Main Street - walk to the downtown area (including Ropewalk for food and drinks) or to the annual Fireman's Carnival. The possibilities are endless. Some of the most gorgeous sunsets ever witnessed are from this spot on South Main Street & it is the perfect spot to watch rocket launches from Wallops. It doesn't get much better than this!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- 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. 

- 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.

Avalon

4 Bedrooms
2 Baths & 1 Half
10 Guests
Chincoteague Island
Waterfront
Screened Porch
Internet
Outdoor Shower

Avalon is a charming 4 bedroom, 2.5 bathroom home situated on a bulkheaded waterfront lot on Oyster Bay! There is a large great room that boasts two family rooms, a dining area and large kitchen. From the gas fireplace, to the 16' cathedral knotted pine ceilings, this home is bright, warm and inviting. Avalon offers two queen bedrooms with screened porch access (one private) and two twin bedrooms. Offering over 600 sq. ft. of screened porch - you could live outdoors! The first level also offers a full size futon and 1/2 bath. Avalon is one of our most popular offerings; it books quickly! 

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- No pets are permitted on the premises. 

- 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.

Misty's Thicket

2 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Water Access
Charcoal Grill
Screened Porch
Internet

Located on South Ridge Road, this lovely town-home features a private pier, central air conditioning, and galley style kitchen complete with a dining area and all necessary appliances. The cozy living room leads you onto one of two screened in porches perfect for unwinding with family and friends. Upstairs, you find a great master bedroom with en-suite, a full bathroom off the hallway, and a second bedroom that features a bunk bed and a queen size bed that looks out onto the second-level screened in porch affording amazing Chincoteague Island views.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- Pets are not permitted on the premises.

- 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.

Seas the Day

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Screened Porch
Pool
Internet

You will LOVE the quiet duplex community where this home is situated. Bright, open floor plan, with adjoining screened and open-air porches - perfect for sipping coffee in the morning or relaxing with a cool drink after a day at the beach. The first floor bedroom offers a private bathroom and the sweetest window nook - bring your book! Two additional bedrooms upstairs share a full bathroom and all bedrooms are tastefully decorated in their own fun personal themes! Hosting a group that requires more space? Rent Seas The Day's sister, 'Sea La Vie', just next door! **NEW FOR 2025: Kid's bunk room features a single Twin bunk bed + a Twin Trundle bed!**

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- 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.

Off Belay

4 Bedrooms
3 Baths
8 Guests
Chincoteague Island
Water View
Gas Grill
Screened Porch
Internet

Welcome! This spacious, luxurious home offers everything you need for a relaxing vacation. Located in the Smugglers Cove community, Off Belay is situated on a small creek, perfect for any nature enthusiast. Upon entering this gorgeous vacation home, you will be enamored with the thoughtful décor and tasteful furnishings. Beautiful hardwood floors lead you to the gourmet kitchen with an expansive kitchen island, including a 5 burner gas range. The living room boasts high ceilings,  plenty of seating,  a wood burning fireplace, and tv as well as access to the large screened in porch and open deck. The first floor also offers a primary queen suite with an attached bath (shower only), and a private den with tv and a queen sleeper sofa. You will also find another full bathroom, washer/dryer and utility sink just down the hall. Upstairs, there are two more bedrooms: a king room with a jack and jill bath as well as a twin room. Walk out to the large deck from the second floor and take in all the views Off Belay has to offer! There is plenty of out door space for entertaining, sitting and relaxation. 

- SPECIAL NOTE: This rental home has a 7 night minimum year 'round. 

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- 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.

Saltwater

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Welcome to ‘Saltwater', formerly known as 'Logan's Sunset.' A lovely 2 story waterfront townhouse on Chincoteague Bay with gorgeous views from both floors. Experience beautiful sunsets and NASA rocket launches from the front balcony. The screened back porch offers a great source of private outdoor entertainment as it boasts a comfortable six-person dining area. All three bedrooms have their own flat screen tv with cable. The main bedroom includes a desk perfect for working from home, virtual learning and streaming. Saltwater includes high-speed internet and free Wi-Fi. The main bedroom has it's own ensuite full bath with jetted tub/shower. The additional bedroom has a private full tub/shower. The 3rd bedroom has a bunk with two full size beds with an additional twin bed.  Guests can also enjoy the coastal outdoor shower. The private expansive 600 foot shared deep water dock provides hours of endless Saltwater fun! 

Need more space? Rent "Sunset Dreams" right next door! 

Saltwater has a fully stocked kitchen including an outdoor charcoal grill.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- 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. 

- 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.

Serenity at Deep Hole Hideaway

2 Bedrooms
1 Bath
6 Guests
Chincoteague Island
Pet Friendly
Charcoal Grill
Internet

Welcome to your blissful oasis, "Serenity at Deep Hole Hideaway!" This charming haven has been given a complete makeover to cater to all your vacation dreams. The kitchen is stacked with top-notch gadgets to whip up that perfect meal. The living room features a cozy sleeper sofa to squeeze in a few extra guests. The main bedroom boasts a luxurious queen-sized bed, while the guest room offers a snug twin daybed, providing ample space for up to six guests. Step outside and relax on the deck, indulging in a long-awaited book. And, if you're in the mood for some classic campfire fun, gather around the firepit and toast up some scrumptious S'mores and hotdogs!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- 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. 

- 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.

Trembling Bay

3 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Screened Porch
Internet

This beautifully renovated 3 bedroom, 2 bath Chincoteague cottage is nestled along the salt marshes in a natural setting on Chincoteague Bay. A few of the fine features include a private pier, a new kitchen & appliances, waterside screen porch & deck, and private master bedroom suite with a custom-designed luxurious bath. The numerous windows and over-sized sliding doors allow panoramic water views from nearly any spot in the house. The first floor is completely wheelchair accessible and features your main living areas, large master bedroom suite (K) with bathroom, and second full bathroom with shower/tub. Upstairs features the second and third bedrooms (D/2T). If relaxation is what you're seeking, look no further. This quiet, peaceful location at the water's edge will delight the senses. Come and see for yourself; you won't be disappointed!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- Pet Friendly with a fee, No cats, 2 dogs max. ($150 per pet) 

- 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.

Hill House

4 Bedrooms
2 Baths & 1 Half
9 Guests
Chincoteague Island
Pet Friendly
Charcoal Grill
Gas Grill
Screened Porch
Internet
Outdoor Shower

Welcome to Hill House! Wonderful traditional island home with fantastic new upgrades! The kitchen has been renovated, along with the bathrooms. Excellent in town location - walk to dinner, movie, shopping & galleries. Enjoy the beautiful Chincoteague sunsets with a beautiful water view! Hill House features 4 bedrooms and 2.5 bathrooms, with a first floor bedroom (double/twin Bunk) & 1/2 bath. Three more bedrooms on the second floor with a master suite (king) that offers a private staircase to the dining room. The third bedroom (queen) and fourth (two twins) are also located on the second floor. Enjoy the modern amenities of this lovingly restored island home, all while being in the middle of downtown Chincoteague's happenings.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- 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. 

- 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.

Daisey Cottage

2 Bedrooms
1 Bath
7 Guests
Chincoteague Island
Pet Friendly
Charcoal Grill
Internet

Come visit Chincoteague Island and stay in this adorable coastal cottage with your family. Lovingly remodeled and updated, this charmer located on Ridge Road is sure to book up fast! Close enough to hustle and bustle of carnival and downtown, but far enough away to enjoy some peace and quiet - you'll find all the comforts of home at Daisey Cottage. Upon entering you'll be greeted by a comfortable living area with television. Skylights to let in a ton of natural light, letting you bask in island sunshine. A cute kitchen featuring everything (electric range, fridge, dishwasher, coffee maker) you'll need to make a family meal, if you're heart so desires. A bright and cheery open dining area is connected to the kitchen - allowing you to chat while preparing meals or snacks. A full bathroom. A utility closet with washer and dryer. Two bedrooms - the master with a queen and television. And the second bedroom boasts a bunk that has a full on the bottom and a twin on the top - how fun is that?! Bring your bikes and ride down to Memorial Park for a little fishing or crabbing. Outside you'll find a cute patio area with sitting area, as well as a small fenced in area that is perfect for your four legged friends to enjoy while you're outside as well. Daisey Cottage is pet-friendly, all members of the family are welcome - book today!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- 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.

- 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.

Cedar Cove

3 Bedrooms
2 Baths
12 Guests
Chincoteague Island
Waterfront
Gas Grill
Internet
Outdoor Shower

Tranquility meets you at every turn at Cedar Cove, a custom-built waterfront home nestled amongst the pines in the Oyster Bay I community. The open floor plan allows for a bright and airy atmosphere in the common areas downstairs - an open living room with a gas fireplace to warm a chilly evening, and a bright and cheery fully-equipped kitchen. The primary bedroom is also found on the ground floor, with a queen bed and bath, flat-screen television, and private balcony overlooking the backyard and waterfront view. The bathroom also has an entrance from the entrance hall of the house, allowing it to act as a bathroom for guests downstairs as well. Upstairs you'll find a game loft complete with a foosball table, a futon, and plenty of board games to keep the kids busy on a rainy day. Two additional bedrooms are also upstairs, one with two full size beds and another with a queen size bed - both have televisions and balconies as well. A newly-remodeled full bath is also located upstairs off the loft area as well. Outside you'll find ample space for plenty of outdoor enjoyment with the family - a spacious deck with outdoor seating and dining areas, a firepit with comfortable Adirondack chairs, and an outdoor shower to rinse off the sand after a long day at the beach. Located in a quiet private community just off the "beaten path" - all the amenities Chincoteague has to offer are just minutes away on the bike or in the car. Bring your kayaks and launch right from the small dock located on the property, or grab a pack of chicken necks at the grocery store and catch a few crabs - round out the meal with a sack of oysters from Gary Howard's market just up the street (if all else fails he sells crabs at a reasonable price too). Then take the time to gather with family on the porch to enjoy the bounty the island has to offer - all from the comfort of Cedar Cove here on Chincoteague Island.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- No pets are permitted on the premises.

- 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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