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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 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.

Ms. Kitty's Bayside Bungalow

2 Bedrooms
1 Bath
6 Guests
Chincoteague Island
Pet Friendly
Gas Grill
Internet
Outdoor Shower

Welcome to Ms Kitty's Bayside Bungalow!  A charmingly remodeled home now available for rent on Eastside Drive. This delightful two-bedroom house offers comfortable living with modern amenities in a serene bayside setting. Each bedroom is furnished with a plush double bed, ensuring a restful night's sleep, and for additional guests, a queen air mattress is also available.

As you step inside, you'll be welcomed by a fresh, contemporary interior that has been newly updated to provide both style and function. The living area is equipped with a Smart Tv and Roku as well as a work desk, perfect for entertainment and relaxation. The kitchen features all the necessary appliances and ample space, making it ideal for cooking and dining.

One of the highlights of this home is its expansive, fenced backyard. It’s an ideal space for pets  and for you to enjoy outdoor activities. The nice deck area offers a perfect spot for barbecues or simply soaking up the calm atmosphere of the neighborhood. Also enjoy a large firepit for smores in the evening hours!

Situated within close proximity to Memorial Park, the location offers convenience with easy access to the boat launch, fishing pier,  playgrounds, basketball and scenic views—perfect for outdoor enthusiasts and families alike.

This rental home captures the essence of convenient and laid-back bayside living. Whether you're looking for a peaceful retreat or a cozy place close to amenities, Ms Kitty's Bayside Bungalow provides an excellent choice for individuals, couples, or small families. 

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property is dog friendly with a pet fee per pet. Pet fee is $150 per pet. All pets must be disclosed prior to arrival. (No cats or certain dog breeds, please inquire.)

- 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.

Delmarva

1 Bedroom
1 Bath
2 Guests
Cape Charles
Pet Friendly
Internet

Nestled in the heart of historic Cape Charles, this exquisite one-bedroom condominium embodies coastal living at its finest. This newly constructed residence represents the pinnacle of architectural refinement, where simplicity meets sophistication in a harmonious blend of form and function.

Step into a meticulously designed living space where each detail has been thoughtfully curated. The living room features a fireplace and large TV, while the bedroom showcases a sumptuous king-sized bed, large TV and private balcony overlooking downtown - all complemented by a custom bathroom featuring splendid tile work. Truly a sanctuary of tranquility after a day of bayside adventures.

What truly distinguishes this property is its coveted upper-level position, affording the most captivating vistas of both the charming downtown area and the magnificent Chesapeake Bay beyond. As the golden light of sunset bathes the water in amber hues, you'll appreciate the privileged perspective this elevation provides.

The crown jewel of this condo is undoubtedly the rooftop terrace — an oasis where you can sip morning coffee or evening cocktails while overlooking the shimmering waters. The full wet bar sheltered beneath an elegant pergola makes entertaining a delight rather than a duty. One might say it's the perfect spot to raise a glass to coastal living without raising your stress levels!

The unparalleled location places you mere steps from Cape Charles' most coveted attractions. Stroll to boutique shops where local artisans display their crafts, savor culinary delights at nearby restaurants, or indulge in handcrafted spirits at Cape Charles Distillery. For sweeter cravings, premium ice cream awaits just around the corner.

The pristine beach, with its gentle waves and golden sands, lies just a few blocks away. No need to concern yourself with traffic. Similarly, the picturesque harbor invites leisurely promenades as boats gently rock against the backdrop of a painted sky.

This remarkable vacation home doesn't merely offer accommodations; it presents a lifestyle where luxury meets location in perfect equilibrium. Come and see for yourself!

PLEASE NOTE: 'Delmarva' is one of 5 luxury apartments offered within the 'Cape Dunes' complex. This being the case, some amenities and spaces are shared. This includes the washer & dryer, ice maker and roof top terrace. Parking is on-street and not reserved. 

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property is pet friendly with an additional fee of $150.  All pets must be disclosed prior to arrival. Only 1 small dog is permitted, less than 50 lbs. NO CATS. 

- 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.

Poole's Cove

3 Bedrooms
3 Baths
6 Guests
Chincoteague Island
Waterfront
Gas Grill
Screened Porch
Internet
Outdoor Shower

Poole's Cove manages to be tucked away right on Main Street. This home has been decorated with an artists' eye and poet's heart. The set up of this home offers plenty of room for the whole family, but enough distance for quiet moments to yourself. The Master bedroom suite is located in the main part of the house. Just a few steps through a breezeway brings you to the second part of the home with 2 more bedrooms and bathrooms. The outside stairs will bring you up to a rooftop lounging area to catch some relaxing rays. Also upstairs is an office with the perfect reading nook to curl up and catch up on some reading. This house doesn't just offer you a stay it offers you the full experience. Poole's Cove has undergone a COMPLETE renovation! The entire interior - kitchen, floors, bedrooms, bathrooms, furniture, everything - is all BRAND NEW! The Poole's Cove you've come to know, and love is even better than before. **IMPORTANT NOTE: Because of this home's unique floor plan and railing-less decks, it may not be suitable for younger children.**

- 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.

Belle of the Bay

4 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Screened Porch
Internet
Outdoor Shower

Truly the "Belle of the Bay", this beautiful custom waterfront home is tucked away at the very tip of one of Chincoteague's most popular residential communities - Oyster Bay I. This means you'll enjoy unobstructed 360 degree water and marshland views from nearly every space in the home. The decor and local art collection alone will "wow" you! Watch the sun rise as you sip your morning coffee from the balcony or screened porch. Enjoy the quiet and privacy as you watch the wildlife that surrounds this fabulous property. The main house features 3 bedrooms, 2 full bathrooms, and an additional loft sleeping area (twin trundle bed). The detached garage features another living area/bedroom (2 Twin beds) that is available for guest use (lower level garage is not accessible by guests). NOTE: Living room fireplace is not functional. 

- 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.

Beach Haven

3 Bedrooms
2 Baths & 1 Half
9 Guests
Chincoteague Island
Town & Country
Charcoal Grill
Internet

If you enjoy being close to town and activities, 'Beach Haven' is most likely your perfect spot! Located on just one block off of Main Street, this lovely home is conveniently located to downtown Chincoteague Island, the movie theater, restaurants, famous Island Creamery, adventure park and more! The wrap around second-level deck is nicely furnished and inviting - it's the ideal place to relax with a cup of coffee in the morning or a cool drink after a long day at the beach. 

As you enter this fantastic modern home, you're greeted by an open floor plan. The main level features the living room, kitchen with breakfast bar, dining room and half bath/powder room. The lower level is entirely a two-car garage that is accessible by guests; it's a wonderful place to store your bikes or beach gear! Upstairs you'll find 3 bedrooms and 2 full bathrooms, one of them being a master bedroom en-suite. Two bedrooms feature a queen bed each, and the third (kid's) bedroom features a bunk bed (2 Doubles) and a Twin bed. 

Lets talk electronics! This home has been carefully and tastefully furnished for the discerning traveler. The living room and all 3 bedrooms all have large Smart TVs, and the kid's bedroom includes an HDMI cable for easily connecting gaming consoles, etc. You'll also enjoy amenities such as keyless self check-in and check-out.

Come for a week in the summer, or come for a shorter stay in the spring or fall. 'Beach Haven' is available year-round and the island is gorgeous the whole year through!

- 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.

Tall Pines

2 Bedrooms
1 Baths & 1 Half
6 Guests
Chincoteague Island
Water Access
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Located in lovely Piney Island within a short bike ride to the beach. This single story 2 bedroom, 1.5 bathroom house offers a large screened porch, fully equipped kitchen and spacious living room. Tall Pines has two bedrooms, one with a queen, and other featuring two twins. There is also an air mattress for guest use.  Piney Island offers community water access great for launching kayaks/canoes. To top it all off, Tall Pines is pet friendly with and outdoor dog run in the yard. You won't be disappointed! | | Note: Water access is a shared with the community just a short distance from the rental home.

- 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.

Southern Dream

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Water View
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Charming 3 bedroom ranch home located in one of Chincoteague Island's residential communities. Nice, quiet location with a water view of Oyster Bay. You'll enjoy the easy, one-story floor plan with open living room/kitchen/dining areas. If you love the outdoors, spend your time outside on the spacious deck or screened porch - there's plenty of room for all! Many modern amenities such as central air, high speed internet, charcoal grill and an outside shower will ensure your comfort during your 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.

Beach Bungalow

3 Bedrooms
3 Baths
11 Guests
Chincoteague Island
Waterfront
Pet Friendly
Charcoal Grill
Internet

This fabulous "Beach Bungalow" is waiting for you! Tucked away on the marshlands overlooking Oyster Bay and the East Side of the island is where you'll find this 3 bedroom cute-as-a-button cottage. There are fresh new upgrades, including a bathroom, a new laundry closet, and a new deck. The bright, natural sunlight streams into the rooms via skylights and the floor plan is open and inviting. The living room extends to the dining area, which is completely open to the kitchen. Off of the kitchen, you step down into a family room/bedroom with a full bathroom, futon fold-out bed, and a Twin pull-out sleeper chair. From the hallway off of the dining area, you'll find two more bedrooms, one with a new ensuite bathroom. There is a new washer/dryer closet and a full bathroom accessed in the hallway. The master bedroom will be your favorite spot in the house with large sliding doors on 3 sides and a fabulous, cozy sitting area overlooking the marshes and bay, it's perfect for unwinding after a day at the beach, or quietly starting your day. Conveniently located to Maddox Boulevard (Beach Road) and downtown Chincoteague Island you're only a few minutes from restaurants, shopping, movies, the beach, and more! The fabulous new deck will be another spot you will love to enjoy the beautiful views all day and night! There's room for everyone, even your pet(s)! Not to mention the fenced-in yard for your furry family member!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property is pet friendly with a pet fee per pet. Pet fee is $150 per pet. All pets must be disclosed before 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.

Hidden Treasure

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

"X" marks the spot here at Hidden Treasure. Nestled in a cove along the shoreline of the island's most exclusive neighborhood on the northern end, you'll have everything you need for a perfect family vacation. ENDLESS outdoor space in the form of a long private dock with a large sitting area at the end, huge deck off the living area overlooking the water, a screened in dining area off the deck, and a large shared balcony off of two of the bedrooms on the upper level. The spacious home offers 4 bedrooms and 3 bathrooms. On the ground level you'll find the fully-equipped kitchen with breakfast bar and dining area. The kitchen opens up to the cozy living area, with a fireplace and an unbelievable view of Chincoteague Bay. You'll find plenty of seating for your family, just around the corner is another sitting area for overflow - or if you just want to curl up with a good book alone (no judgement!). Also located on the ground level is a full bath and bedroom with two twins - ideal for putting the little ones to bed but still being able to keep an eye on them. Upstairs you'll find the other 3 bedrooms. The master suite - furnished with a king bed, bath with Jacuzzi soaking tub and shower, flat-screen, and yet another knockout view on the balcony. The balcony runs the length of the house and is shared on the other end with a bedroom with a queen. An additional full bath, and another bedroom with two twins is also found upstairs as well. Crab and fish right off the dock, and enjoy cooking and enjoying your bounty together al-fresco at the screened-in porch on the deck. Or pour yourself a nice chilled beverage and walk down to the end of the dock and wait for the sun to slip under the horizon over Chincoteague Bay - bringing the end to another day of treasured memories made at Hidden Treasure.

- *NEW FOR 2025: Level 2 EV charger!*

- 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.

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