You are here

Displaying 61 - 72 of 188 results matching your search criteria
Map View
List View

Tranquility

4 Bedrooms
2 Baths & 1 Half
11 Guests
In Town
Town & Country
Pet Friendly
Gas 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.

Bayside

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

Welcome to Bayside, your next relaxation haven! This charming 3-bedroom, 2-bathroom pet friendly duplex offers the perfect blend of comfort and convenience nestled in the delightful town of Cape Charles. Whether you're in town to soak up the sun at the beach or simply unwind, this property is designed to suit every aspect of your leisurely needs!

Step inside to discover a cozy atmosphere with well-appointed spaces that promise a homely feel from the moment you walk in. The primary bedroom, a restful retreat, along with two additional amply-sized bedrooms, ensures everyone has their personal space. Entertaining? The open-concept living area present the ideal setting for creating memories with loved ones.

Forget about the hassle of street parking; this house comes with its very own off-street parking spots. And for those who can't bear to leave their furry friends behind, you'll be pleased to know this home is pet friendly!

Just a short stroll away lies Central Park, where you can enjoy everything from a peaceful morning jog to a lively afternoon picnic. Need to pick up some essentials or a quick snack? There are many conveniences in town, or the grocery store is just a little over 2 miles away—talk about convenient shopping!

Whether you're looking for a calming weekend getaway or seeking a serene place to call home for a while, this house ticks all the boxes for a laid-back yet vibrant living experience. Book your stay, pack your bags, and prepare to relax—your beachside vacation awaits!

Located right next door to this beautiful duplex is "Seaside". Larger group? Bring along your friends and family and rent both units! 

- 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 (no cats). 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.

 

Pony View

3 Bedrooms
3 Baths & 1 Half
8 Guests
East Side
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Internet

Enjoy your cup of coffee as the sun peeks over the salt marshes of Assateague Island. You can often see a herd of our famous wild ponies grazing to the right of the lighthouse from your private waterfront deck and second-floor balcony - not to mention the copious amounts of waterfowl and other wildlife in the channel. Pony View boasts three bedrooms - A master with queen bed, full bath, and balcony on second floor, as well as another bedroom with a queen on the second floor - along with another full size bath. On the third floor you will find an amazing view of the marsh with the panoramic window and four twin beds, and a beautiful bathroom with a rustic wooden sliding door. The ground floor is where you'll find the hub of the house - fully equipped kitchen with refrigerator, electric range, dishwasher, and plenty of counter space. A dining table and bar seating area, a half bath, and a cozy living area with floor-to-ceiling knockout views. Or enjoy the waterfront deck just outside the living room. Pony View is pet-friendly so your furry friend can enjoy the water view as well. Dock access along with a boat slip is available for your use. Crab and fish right from the house! A deep water boat ramp is found just at the end of the complex for you to drop in. Central air/heat will keep you comfortable year round. There is also a washer/dryer, and an outside grill for your use while you're with us. Memorial Park is just a short walk up the street for a wonderful waterfront park and playground, tennis and volleyball courts, fishing pier, picnic areas, and walking trail.

- 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.

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!

- 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. 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.

Star of the Sea

3 Bedrooms
2 Baths
8 Guests
In Town
Town & Country
Pet Friendly
Gas Grill
Internet

Introducing a charming, newly renovated house, offering a perfect blend of comfort and convenience. This single-family home features an inviting sunroom, a brand-new kitchen, four well-appointed bedrooms, including a serene primary bedroom, and two modern bathrooms, all professionally decorated with a delightful beach theme.

Designed to accommodate up to eight guests, the house boasts spacious rooms that ensure ample space for relaxation and entertainment. The living areas flow beautifully outdoors to a superb deck, ideal for enjoying your morning coffee or sunset dinners, surrounded by a spacious yard.

Nestled in a vibrant neighborhood, the property promises a vacation of ease and accessibility. It’s centrally located near the heart of the town, close to a pristine beach, restaurants, and family-friendly activities, including mini-golf and Maui Jack's Waterpark. Nature enthusiasts will appreciate the proximity to the Assateague Island National Seashore, a spectacular location for wildlife and scenic views, while the nearby Downtown Chincoteague Waterfront Park provides excellent opportunities for leisurely activities.

Experience the joy of living where every day feels like a vacation. This retreat is not just a place to stay, but a home away from home. Come and see for yourself!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- Home is pet friendly with additional pet fee. 

- 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
Oyster Bay
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.

Sunset Bay Villa 118

3 Bedrooms
2 Baths
7 Guests
Sunset Bay
Waterfront
Boat Dock
Pool
Internet

Come and sit a spell. Grab a cocktail and watch your worries sail away as you enjoy the cozy private outdoor seating area to be found at Sunset Bay Villa 118. The unit is on the ground level, providing easy access after a long day at the beach. Beautifully styled with nautical decor and special attention to detail. Situated on the edge of the bay, this villa offers a private balcony with walk-out access to the marina and a reserved 40' foot deep-water boat slip. Villa 118 at Sunset Bay boasts an en suite bedroom with king bed, private bath featuring a stand up shower AND a bathtub - along with private outdoor patio access from the bedroom. Two other bedrooms feature a king in one, and a twin in the other. Fully equipped kitchen and dining area with coffee maker, refrigerator/freezer, dishwasher, electric range, and plenty of countertop for that family seafood feast you will want to make while you're with us. Have a few friends sit at the bar while you mix up a few cocktails, then enjoy "people-watching" on the Chincoteague Channel as the evening picks up. Once the sun goes down you can retire to the cozy living area in the heart of the villa. Maybe a movie on the flat screen? Or perhaps a game of chess? No matter what you decide on, you and your guest will most certainly enjoy your stay at Sunset Bay Villa 118. Please Note: This unit includes a deep-water boat slip and use of the marina.

- 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.

The Great Escape

5 Bedrooms
3 Baths
11 Guests
Cape Charles
Gas Grill
Screened Porch
Internet
Outdoor Shower

Discover the charm of Cape Charles in this beautifully restored 5-bedroom, 3-bathroom house, available for your next vacation adventure. Nestled in the heart of downtown, "The Great Escape" places you just minutes away from a vibrant selection of shopping, dining, and entertainment options, including local ice cream shops and mini-golf. Whether you're enjoying the bustling town scene or relaxing at home, this property offers both convenience and comfort.

Step onto the inviting open front porch where you can sip your morning coffee while soaking in the town views. Alternatively, the screened porch provides a tranquil retreat to unwind in the evenings without the pesky insects. Inside, you’ll find a clean and comfortable interior with ample living space that caters to both large and small families alike.

"The Great Escape" is ideal for those seeking a blend of small-town charm and modern amenities, all within walking distance of Cape Charles' delightful attractions. Whether you're settling down with your family or looking for a scenic change of pace, this vacation home promises a lifestyle of ease and excitement. Don’t miss out on making this house your new home away from home — book your getaway today!

- 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.

 

Changing Tide

3 Bedrooms
1 Bath
7 Guests
In Town
Charcoal Grill
Internet
Outdoor Shower

Book your stay at this quaint home, in a convenient downtown location. The updated coastal decor will bring on the beach vibes from the moment you walk thru the door. This adorable cottage offers many updates and has been beautifully cared for. Enjoy your morning coffee or tea on the enclosed porch, or relax in the cozy living quarters. Downstairs you have a full bath, and bedroom with queen sized bed as well as a twin sleeper in the enclosed porch. Upstairs you will find two additional living spaces with a queen and two twin beds. Outside you will find a large deck with a sunshade, perfect for enjoying an evening meal, or afternoon snack. There is a charcoal grill on the patio area, great for grilling a fresh catch- There is also an outdoor shower to rinse off after a long day at the beach.

- 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.

Grandview

4 Bedrooms
4 Baths
10 Guests
North Main
Waterfront
Pet Friendly
Boat Dock
Screened Porch
Internet
Outdoor Shower

Enjoy stunning sunsets from this 5 star home at water's edge. Relax with the amazing water view from the north side of the island. Every bedroom is a suite, to ensure all of the adults have the right amount of privacy and a quiet place to stow away with a book. The dining area is big enough to accommodate large family dinners and the kitchen has been newly remodeled and upgraded! With a breakfast bar and wide open living area, you can be sure to have lasting family moments together. Have your cameras ready to capture the changing tides, wildlife and those crazy family moments that are sure to happen in this lovely home. Grandview offers every amenity from a screened porch, an open deck, long pier with a dock, ceiling fans throughout, wireless internet and much much more! This home also includes the use of 2 kayaks.

- 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. 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.

Egret's Walk

2 Bedrooms
1 Bath
5 Guests
North Main
Town & Country
Pet Friendly
Gas Grill
Screened Porch
Internet
Outdoor Shower

Discover the charm of coastal living in this delightful 2-bedroom, 1-bath cottage nestled in a serene area north of Chincoteague town center. This home offers a unique blend of comfort and tranquil views of the surrounding marshland and creek. Watch the abundant wildlife from the comfort of your living room, adding a touch of nature’s television to your daily routine.

Inside, the home is accented with personal decor touches that provide a warm, inviting atmosphere. Though compact, the layout ensures efficient use of space, creating cozy yet comfortable living areas. Step outside and you're just a short drive from Assateague Beach, where wild ponies roam freely – a sight that never fails to amaze. For your everyday needs, Island Foods Great Valu is conveniently located nearby, and for a sweet treat, the Island Creamery can be reached within a few minutes' drive, offering the best ice cream on the shore.

This home is perfect for those looking for a peaceful retreat with the convenience of community features within reach. Make this cottage your own secluded getaway and enjoy the laid-back lifestyle that Chincoteague is famous for. Experience the joy of waking up to soothing water views and the melodious sounds of local wildlife every morning!

- 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.

 

zLT - 38100 Castaway Drive

4 Bedrooms
2 Baths & 1 Half
8 Guests
Captain's Cove
Water View
Pool
Internet

Welcome to your dream rental, "Charming Getaway," a newly built home perfect for both relaxation and entertainment. This pristine property features four well-appointed bedrooms, including two king-sized rooms, a queen room, and a twin room, accommodating various living arrangements comfortably.

With 2.5 modern bathrooms, the home facilitates smooth mornings and provides ample space for family and guests. The open-concept living area is a highlight, boasting smart TVs and a stylish piano, ensuring your leisure time is both musical and multimedia-friendly. You will also find a second living room area on the 2nd floor. 

Step outside onto the expansive deck and enjoy a serene backdrop to your morning coffee or evening dining. The outdoor space is fully equipped for any gathering, featuring a firepit and  perfect for year-round enjoyment.

Technology-friendly with Wi-Fi throughout, this home meets all modern needs, ensuring connectivity and convenience. Additional community amenities are available for a fee, offering more options for leisure and activities.

Located in a desirable area, this home is more than just a place to stay; it's a lifestyle upgrade. It promises tranquility with its beautiful views, along with the vibrancy of a lively community nearby.

Experience this beautiful setting and make "Charming Getaway" your next home-away-from-home!

- 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.

- 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. No Sunday check-ins or check-outs are permitted. 

Pages