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Langtree

3 Bedrooms
3 Baths
10 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Screened Porch
Internet
Outdoor Shower

Your home away from home... enjoy the water views, bring your boat and use your own dock, or just relax and listen to the whispering pines. 3 Bedrooms, 2 full baths (plus another shower/bath downstairs), outside shower, washer and dryer, satellite TV, and PET FRIENDLY! Great views of Oyster Bay from the front and back decks, and there's a large screened porch for outdoor enjoyment. On the lower (first level) of the home you'll find a large open room with a Queen and 2 Twin beds, as well as a large utility room and bathroom with shower. The main living level (second level) of the home features the living room, kitchen & dining area, as well as 3 bedrooms (K/K/Q) and 2 full bathrooms. Note: This property has a 7 night minimum stay during all seasons.

-Parking only for 4-5 Cars

- 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. 

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 2. Pet Restriction: NO CATS. 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.

Shore Reflections

4 Bedrooms
2 Baths & 1 Half
12 Guests
Cape Charles
Town & Country
Internet

Now available and awaiting your next vacation adventure, this lovingly restored 4-bedroom Victorian home blends traditional charm with modern convenience. Nestled in a picturesque setting with beautiful landscaping and mature trees, you're just a 10-minute drive from the vibrant Cape Charles community. Explore and enjoy downtown Cape Charles, which features a pristine beach, delicious food offerings, eclectic shopping, ice cream treats, coffee shops and so much more!

Spanning 3,000 sq ft, this exquisite property features a layout with high ceilings and wood flooring throughout, enhancing the airy and expansive feel of each room. The main living spaces boast large windows that flood the home with natural light, creating a warm, welcoming atmosphere. Four generously sized bedrooms offer ample personal space for relaxation and rejuvenation. The home also includes 2.5 bathrooms, each maintaining the character of the house with tasteful touches.

Guests will enjoy a beautifully landscaped yard, ideal for leisurely days spent outdoors or entertaining guests in a serene environment. The kitchen, equipped with essential appliances, provides a comfortable space for culinary exploration and seamlessly caters to both casual dining and larger gatherings.

This property is perfect for those who appreciate the beauty of historic homes but expect the functionality needed for a contemporary lifestyle. Make your "home away from home" in a place where tradition meets comfort in the heart of Eastville, VA. Experience the unique charm of this Victorian beauty and the inviting community that surrounds it.

- No smoking is permitted on the premises. 

- Linens and towels are provided for your stay. 

- 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.

Diving Duck

5 Bedrooms
2 Baths & 1 Half
10 Guests
Captain's Cove
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Pool
Hot Tub
Internet
Outdoor Shower

If you're looking for the complete vacation package, look no further! This 5 bedroom home features a spacious open floor plan with wall-to-wall sliding doors and windows, allowing natural light to permeate throughout the home. Downstairs you'll find the living room and great room with access to the waterside deck, a large dining area, kitchen with all the counter space you'd ever need, a half bathroom, and the master bedroom with private bath (with custom tile shower and soaking tub). Upstairs features a landing area with sofa and foosball table, 4 more bedrooms and another full bathroom. Aptly named, 'Diving Duck' is the perfect spot for watching the ducks and wildlife pitch in the bay just out the back door. There's even a floating dock perfect for launching canoes and kayaks! And as if all of that is not enough, the Captains Cove community features swimming pools (2 outdoor, 1 indoor), a fitness center, marina club restaurant and 9-hole golf course. (Fee applies for usage of community amenities.) This rental home is approximately 20 minutes to Chincoteague/Assateague Island (the beach) and 30 minutes to Ocean City, MD (beach & boardwalk attractions). What more could you ask for? Book your stay at 'Diving Duck' today! Additional game room with wet bar and pool table, and a private hot tub. All of this in addition to interior updates and renovations!

- No smoking is permitted on the premises.

- Linens and towels are included with your reservation.

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 4. 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.

- Community amenities require passes for an additional fee. Although the rental home can accommodate up to 10 guests, only 8 guests are permitted to use the community amenities (pool, etc.) at a time.

- Additional community requirements: Each occupant must disclose their name. Vehicles must be registered; make and model of each vehicle is required. Incomplete or incorrect information will result in revocation of the use of community amenities and facilities. 

 

Charlie's Cove

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Pet Friendly
Internet

Charlie's Cove is waiting to accommodate you and your guests! Conveniently located on Ridge Road in the middle of Chincoteague Island, you will find yourself immersed in complete comfort. Upon stepping through the door you are greeted by the simple, yet welcoming décor. An oversized couch is sure to relax you after a long day in the sand, cuddle up and watch a movie or play a board game! Charlie's Cove has it all... The kitchen is perfectly designed, offering an abundance of place for the cook in your family to prepare meals. There is a private den if you'd like to spend some quiet time away from the group. This home offers 3 large bedrooms - the primary features a Queen bed and en suite bathroom with large soaking tub and stand-alone shower. The second bedroom features another Queen bed, while the third bedroom has 2 Twin beds. Bring your furry friend to run in the fenced in yard - Charlie's Cove is pet friendly!  

**While this home will accommodate up to 8 guests, there is only sleeping space for 6 (2 Queen beds and 2 Twin beds). Please feel free to bring an air mattress or cot. 

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 3. 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.

Hailey's Round House

3 Bedrooms
2 Baths
9 Guests
Chincoteague Island
Water Access
Screened Porch
Internet

Check out Chincoteague’s newest Piney Island vacation rental! Hailey’s Round House is in a prime location on Chincoteague, in a quiet development road but just a short walk to the bridge to Assateague and the Maddox Boulevard shops and restaurants!  You could take a bicycle or short drive to the Assateague beach and access to all of the bicycle trails around Chincoteague and Assateague to enjoy the wild ponies or many of the restaurants on Chincoteague.   

Hailey's Round House is a recently renovated, beautiful 3 bedroom home with 2 bathrooms. The luxury porcelain floors throughout will leave you feeling entranced from the moment you walk through the door. Spacious, thoughtful, aesthetically pleasing, and comfortable are just a few words to describe what you will experience at Hailey's Round House. This home offers first floor living, a huge screened porch, quartz countertops, ample deck space, seclusion as well convenience. On the first floor, you will find a full bath with walk in tiled shower, as well as a complete living room, and bedroom featuring a full sized bed.  You can reach the second floor by a private exterior entrance, or from the winding spiral staircase located inside. Upstairs you will find a second living room as well as two more bedrooms and another full bathroom with a tub. One bedroom features a full sized bed and the third is perfect for the kids, offering a twin as well as a full. While there are many focal points of this fabulous home, we are certain most of your time will be spent on the expansive deck, enjoying the sounds of nature and the deer who frequently visit the yard or downstairs in the screened porch. Hailey's Round House is located in one of the Island's most desired locations of Piney Island! It is close to the beach and ready to host your vacation stay! 

- 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.

Three Little Sandpipers

3 Bedrooms
2 Baths
8 Guests
Cape Charles
Pool
Internet

Tucked inside the gated Bay Creek community, this inviting three-bedroom, two-bathroom condo located on the second floor offers an easygoing rhythm of life that's hard to wonder too far from. From the moment you cross the threshold, the open floor plan unfolds with a relaxed, sociable flow that suits both quiet evenings and lively gatherings.

The comfortable living room steals the spotlight, anchored by a fireplace that promises cozy cooler nights and double doors that swing open to a private patio. Slip outside with your morning coffee or evening glass of wine, and let the salty Eastern Shore breeze do the rest. Three well-proportioned bedrooms give everyone room to spread out, while the primary bedroom serves as a restful retreat after sun-filled days.

When you're craving a little activity, historic downtown Cape Charles is just minutes away, brimming with restaurants, charming shops, a movie theater, and a beautiful beachfront for sunset chasing. The 6-seat golf cart is perfect for galavanting around town! Grocery runs to Food Lion are refreshingly quick, and the Chesapeake Bay Bridge-Tunnel keeps wider adventures within easy reach.

Comfortable, convenient, and surrounded by natural beauty — this is coastal vacationing without the fuss. Book your vacation today and come see for yourself!

- 6-seater golf cart is available with an additional fee of $80 per day required

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly. An additional fee of $150 will apply. Pet restriction: One small dog under 35 lbs. NO CATS. All pets must be disclosed prior to arrival.  

- Bay Creek Community amenities are not available with this rental home. 

- 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.

Stella della Baia

2 Bedrooms
1 Bath
5 Guests
Chincoteague Island
Charcoal Grill

Welcome to 'Stella della Baia'! This is the perfect little getaway spot if you're looking for something simple, comfortable, clean and affordable. Everything is BRAND NEW and waiting for you! Located just south of downtown, Stella della Baia is conveniently located to the Fireman's Carnival, movie theater, downtown restaurants & shopping, and more. If you're traveling with a larger group but like the separate of "your own place", check out 'Stella del Mare'! Book both homes and receive a 5% discount off of each! 

- 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.

Farmhouse Sunset

3 Bedrooms
2 Baths
8 Guests
Cape Charles
Town & Country
Gas Grill
Internet

New vacation home listing! Completely renovated and ready to impress, this inviting lower-level three-bedroom, two-bath duplex rental offers comfort, flexibility, and a location that makes everyday living refreshingly convenient. Designed with boaters and coastal enthusiasts in mind, the home sits just minutes from the Chesapeake Bay, giving you quick access to the water without turning every outing into a full expedition.

Inside, the residence feels fresh and updated, with renovations that bring a clean, polished look throughout. The layout is well-suited for a variety of living arrangements, and the duplex configuration adds versatility for those needing extra room. For larger groups or extended stays, there is even the opportunity to rent both the upper and lower portions, creating a practical setup with space to spread out.

Outside, plentiful parking is a standout feature, especially for tenants with multiple vehicles, a boat, or visiting guests. Convenient highway access makes commuting and weekend plans simple, while nearby essentials add to the home’s everyday appeal. The location also offers a practical route toward the Chesapeake Bay Bridge-Tunnel, helping regional travel feel a bit less complicated. Royal Farms is close by for fuel and quick stops, and Food Lion is within easy reach when it is time to stock the kitchen.

Whether you are seeking a comfortable year-round vacation spot, a well-placed coastal retreat, or a flexible rental near the bay, this home checks the boxes with ease and a little style to spare. 

- 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.

Turtle Bay

4 Bedrooms
3 Baths
8 Guests
Captain's Cove
Waterfront
Screened Porch
Pool
Internet

Treat yourself to an unforgettable stay at Turtle Bay! This brand new construction will leave you in awe. The coastal décor is everything perfect for a beautiful vacation. Immerse yourself in the plentiful views, sit and sip your morning coffee or evening beverage from the screened porch or cozy up by the fire in the living room. Cooking will be a breeze in the tastefully laid out kitchen featuring stainless steel appliances and granite countertops. Enjoy the large open floor plan and the inviting owners suite with a queen sized bed and  a walk in shower. The other 3 bedrooms also feature queen sized beds, one with a smart tv as well as two full bathrooms.

Turtle Bay is nestled in the beautiful community of Captains Cove Community features swimming pools (2 outdoor, 1 indoor), a fitness center, marina club restaurant and 9-hole golf course. (Fee applies for usage of community amenities.) This rental home is approximately 20 minutes to Chincoteague/Assateague Island (the beach) and 30 minutes to Ocean City, MD (beach & boardwalk attractions).

- 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.

- Community amenities require passes for an additional fee.

- Additional community requirements: Each occupant must disclose their name. Vehicles must be registered; make and model of each vehicle is required. Incomplete or incorrect information will result in revocation of the use of community amenities and facilities. 

Sea La Vie

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

Aptly named, "Sea la Vie" means "Sea Life" or Life at the Beach. This beautifully upgraded three bed, two and a half bath duplex home is nestled in a small, quiet community. Bright, open floor plan allows plenty of sunshine and space to socialize. Relax by the pool after a long day at the beach. Enjoy a bug-free oasis on the screened porch, or grill out on the open deck. First floor bedroom is situated as a private suite with personal full bathroom. Two additional bedrooms upstairs share a second full bathroom. Picnic area out back, community pool just steps out front, you won't run out of things to do! Hosting a group requiring even more space? Rent Sea La Vie's sister, 'Seas The Day', just next door! **NEW FOR 2025: Kid's bunk room features a single Twin bed + a Bunk bed with a Twin over Full size 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.

Teal Lighthouse

2 Bedrooms
2 Baths & 1 Half
6 Guests
Chincoteague Island
Internet

Welcome to your next island escape — "Teal Lighthouse"! This lovingly decorated two-bedroom, two-and-a-half-bathroom townhouse proves that you don't need to break the bank to live the coastal dream. Every corner of this charming retreat reflects the creative spirit of Chincoteague Island, with local artist's touches woven throughout that give each room its own personality and warmth.

The primary suite offers a private balcony and bathroom sanctuary where you can unwind after sun-soaked days exploring everything this magical island has to offer. Clean, cute, and effortlessly inviting, this townhouse strikes the perfect balance between cozy comfort and coastal style.

Speaking of exploration, the location here is truly something special. Lace up your sneakers and stroll to the nearby Bay to Beach Trail access point for morning walks surrounded by natural beauty. Feeling adventurous? Maui Jack's Waterpark is just a short distance away, delivering splashy thrills for the whole family. And when the ocean calls — because it always does — the legendary Assateague Beach awaits, complete with wild ponies and endless stretches of pristine shoreline.

Situated conveniently near Beach Road, you'll find yourself surrounded by fantastic restaurants, eclectic shopping, and the laid-back island atmosphere that makes Chincoteague Island one of Coastal Virginia's most beloved destinations.

- No smoking is permitted on the premises.

- Linens and towels are included with your reservation.

- Parking is limited to two spaces.

- 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.

Tranquility

4 Bedrooms
2 Baths & 1 Half
11 Guests
Chincoteague Island
Town & Country
Pet Friendly
Charcoal Grill
Internet

Welcome to Tranquility! This show stopper of a home is a brand new construction, featuring  2 bedrooms, 2 bonus rooms and 2.5 baths. Sleeps up to 11 with 1 king, 2 queens, 2 queen conversion sofa/sleepers and a twin fold-out sleeper chair. Deep Hole Hideaway rental properties can accommodate up to 23 people by renting all 3 units in this complex! (based upon availability)  Tranquility Great for family reunions or large gatherings! Please reach out to our office or check out "Escape at Deep Hole " and "Serenity at Deep Hole" for multi home bookings. 

 

Pet friendly, private and quiet. This property allows for entertainment and relaxation for both you and your kids! There is also outdoor seating, cornhole, a firepit, picnic tables and barbecues for additional recreation for your vacation. Book your stay today, this one won't last long! 

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum pets allowed: 4. Cats are considered on a case by case basis. 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.

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