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Sunset Bay Villa 116

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Waterfront
Pool
Internet

A beautiful ground-floor villa with walk out to marina. Luxurious master bedroom with private bath includes both a roomy tiled shower and whirlpool bath. Villa 116 will sleep 8 (beds for 6 plus a queen size air mattress), and includes a full laundry, all appliances, a gourmet kitchen, and more. There's also a pool and fitness room for your enjoyment! Tastefully furnished, you can relax, enjoy and entertain your family and friends in style. | NOTE: This unit does not have a boat slip, however, use of the marina is included.

- 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.

Capeville Cottage

3 Bedrooms
2 Baths & 1 Half
8 Guests
Cape Charles
Town & Country
Pet Friendly
Gas Grill
Screened Porch
Internet
Outdoor Shower

Welcome to Capeville Cottage in the heart of Capeville, VA - just 5 miles North of the Chesapeake Bay Bridge Tunnel. The Capeville Cottage is a charming 1700 sq.ft., 2 story home featuring 3 bedrooms and 2.5 baths. Upon pulling into the private driveway, there is a west facing front porch, great for watching the gorgeous Eastern Shore sunsets and relaxing after an active day.  You are welcomed by a large living area, high ceilings, and spacious kitchen with plenty of seating, laundry and a half bath.  There is a screened porch off of the kitchen with a picnic table that seats eight. Downstairs is a large primary bedroom with a king sized bed, high ceilings, a tv, and full bath and separate stand in shower. Upstairs there are two bedrooms. One has a twin over full bunk with a separate full size bed. The 3rd bedroom has a queen bed, tv and a shared full bath. Outside in the garage, you will find a game room with a ping pong table, darts and a large refrigerator. Capeville Cottage offers a large yard with ample parking, and a boat washing station.  Come enjoy Capeville Cottage and let the tranquil lower Eastern Shore wash your worries away!

- Linens and towels are included with your reservation. 

- No smoking is permitted on the premises. 

- This property is pet friendly with an additional pet fee of $150 per pet. All pets must be disclosed prior to arrival. Limitations: 2 dogs max (cannot exceed 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.

This rental home is conveniently located:

1 mile to Stingray's Restaurant

2.5 miles to Kiptopeke State Park and boat ramp

5 miles to downtown Cape Charles and public boat ramp

5 miles South of Wise Point boat ramp

3 blocks to the scenic bike path on Capeville Road

Shore Thing On Oyster Bay

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

Enjoy some of the island's best water views overlooking Oyster Bay from nearly every room of this custom beach home! Located on a bulk-headed waterfront lot in Richardson's Landing, you can fish and crab from the backyard! A wonderful feature of this spacious home is that you'll find your bedrooms on the first level and your main living area on the second level. The great room opens to the kitchen and features wood floors throughout. And the views are spectacular! Lots of windows!! Some of the bedrooms have waterside balconies. This home has four televisions- all with cable hooked up! You'll find all the bells and whistles here! So take a look at all the pictures and then give us a call or book online. Make memories to last a lifetime!

- 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.

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.

Joint Venture

2 Bedrooms
2 Baths & 1 Half
6 Guests
Chincoteague Island
Water View
Pet Friendly
Internet

Joint Venture is the perfect townhouse for an affordable vacation! Take a short stroll to Maddox Blvd (Beach Road) and enjoy ice cream, mini golf or any of the shops & restaurants. Bike or drive to the beach! Joint Venture offers a water view of Little Oyster Bay (tidal creek) that can be enjoyed any time of year. This property offers Wi-Fi and is pet friendly! Don't miss out!

- 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.

Sunkissed Shores

4 Bedrooms
4 Baths
15 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Sunkissed Shores invites you to experience waterfront living at its finest. This expansive four‑bedroom, four‑and‑a‑half‑bathroom retreat sits directly on Chincoteague Bay, offering sweeping water views and unforgettable sunsets from every room. Each bedroom features its own private balcony and ensuite bath, including two king suites on separate levels for added privacy. A cheerful bunkroom provides flexible sleeping for families and groups, and thoughtful touches like two pack ’n plays and a highchair make traveling with little ones effortless.

The heart of the home is the stunning great room, where soaring ceilings and dramatic walls of windows bring the bay right inside. During cooler months, the seasonal fireplace transforms this space into a warm, inviting haven—perfect for watching winter sunsets or enjoying a quiet evening indoors. A fully equipped  kitchen—with generous counter space, quality cookware, and every gadget you could need—makes meal preparation and entertaining a pleasure. Just off the living area, an enclosed all‑weather gazebo opens to a large waterside deck, creating the perfect setting for crab feasts, morning coffee, or simply relaxing as the sky shifts from gold to pink each evening.

Upstairs, the game loft offers entertainment for all ages with a classic 1980s Space Invaders arcade machine, a commercial‑grade 4‑player arcade table with over 2,500 games, a 77" TV, board games, a chess/checkers table, and a giant wall‑mounted Connect 4. A queen sleeper sofa provides additional space for guests, and each upstairs bedroom sits in its own private wing for a peaceful retreat.

Step outside to your private pier, where you can fish, crab, or launch kayaks directly into the bay. The bulkheaded shoreline offers easy access to the water, and the eastern side of the property provides serene sunrise views over the marsh—giving you the rare opportunity to enjoy both sunrise and sunset from the same home. With unmatched views, thoughtful amenities, and room for everyone to unwind, Sunkissed Shores stands apart as a place where memories are made and every day ends with a sunset worth savoring.

- 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.

Blue Point

3 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Come for an old fashioned family vacation. This wonderfully maintained classic Chincoteague-style home features a large screened porch and beautiful, spacious yard for those warm summer evenings. A great enclosed outside shower comes in handy for rinsing the sand off after a long day at the beach. Downstairs there is a family room with a wood stove, living room/library with a TV and an eclectic selection of books, a formal dining room, full bath and kitchen. Upstairs there are three bedrooms and a full bathroom. Bring your kids and pets along, there is plenty of room to play!

- 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.

Blue Marlin

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

Blue Marlin is a brand new home that is now available exclusively - you will NOT want to miss your opportunity. Visitors from all around fall in love with the charm and beauty of our small town. Blue Marlin is nestled just a few short minutes from the heart of our downtown and offers everything you will need to enjoy a true Island vacation. Spectacular views are abound from just about every room of this gorgeous home. From the time you enter, become enamored with the fresh, beach-like feel of this well thought out Island Home. Blue Marlin offers first floor living, complete with a half bath off of the well-equipped kitchen, a king sized bedroom with beautiful bay views, TV, and en-suite bathroom. Upstairs you will find a spacious sitting entertainment area featuring a sleeper sofa and large TV, as well as two bedrooms. Each bedroom is tastefully decorated and comfortably furnished for a wonderful vacation stay. There are two twin beds, as well as a queen sized bed (with 40 in. TV) upstairs, along with a full bathroom. You may take notice to the many handcrafted furnishings in the home that the owners have taken great pride in creating. Blue Marlin offers front porch sitting, breathtaking sunset views, an outdoor grill, long dock with ladder, (yes, bring your boat!) - there's even extra parking for your boat trailer (behind the yellow house). Everything you need for a perfect vacation is here.. Oh, did we mention this home is pet friendly too?! 

- 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 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.

Sun Rayes

4 Bedrooms
3 Baths
8 Guests
Captain's Cove
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Pool
Internet
Outdoor Shower

We welcome "Sun Rayes"! What does this fabulous home have to offer? The question is: what doesn't it offer?! With 4 bedrooms, 3 bathrooms, 3 stories (with an elevator), a game room (ping pong, pool table, dart board, ring toss) and expansive decks - there's room for everyone! Situated on a canal in the popular Captain's Cove community, you have access to a boat ramp and you can dock your boat right outside your door! Also perfect for fishing, crabbing, kayaks, etc. Sun Rayes is packed full of fun - there are so many great spaces for entertaining and relaxing. The Captain's Cove community offers 3 pools (2 outdoor & 1 indoor), tiki bar, Marina Club and restaurant, 9-hole golf course, kids playground, dog park and more! (amenities are available for use with fee)  And you're only 20 minutes from Chincoteague & Assateague Islands (the beach), and 30 minutes from Ocean City, MD (boardwalk & amusements).

- 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 prior to arrival. Pet restriction: 2 pet max.

- 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. 

Almost Heaven

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

Private pier with boat docking, Waterfront, Pet friendly, Internet, A/C, Fireplace, Charcoal grill. Vintage charm with all modern comforts!

Welcome to your new favorite island getaway! This charming Victorian cottage on Chincoteague's popular South Main Street offers the perfect blend of traditional character and modern comfort. With 3 bedrooms and 2 bathrooms, there's plenty of space for family and friends to unwind after a day of island exploring and adventures.

Step onto the open front porch and prepare to be amazed — breathtaking bayside sunsets await you nearly every evening. Pour yourself something refreshing, kick back in a rocking chair, and watch as the sky transforms into a canvas of orange and pink hues over Chincoteague Bay.

One of this home's standout features is the private pier extending directly into the bay, complete with boat dockage capabilities. Imagine morning fishing sessions, dropping a crab line to try your hand at catching dinner, or evening cruises right from your rental home! No need to haul your boat to a public launch — your nautical adventures begin here.

Traveling with 4-legged family members? No problem here - 'Almost Heaven' welcomes your pet(s)!

Location? Simply perfect. You're just minutes from downtown's delightful shops, restaurants, and even the downtown movie theater. Grocery runs are a breeze with Island Foods just a short drive away. For summer fun, Maui Jack's Waterpark is nearby, and the stunning Assateague Beach is waiting to capture vacation memories, and for your footprints in the sand.

The primary bedroom on the first floor offers a peaceful retreat after long days exploring island trails or collecting seashells. The second floor features two more bedrooms and a full bathroom (shower only). This isn't just a rental — it's your ticket to the relaxed island lifestyle you've been dreaming about. Make it your "home away from home'... at the beach!

- 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 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.

Cockleshell Cottage

3 Bedrooms
3 Baths
10 Guests
Chincoteague Island
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Nestled on a quiet cul-de-sac in a private community just off North Main Street (Oyster Bay II) is where you'll find the charming Cockleshell Cottage! This modern 3 bedroom, 3 bathroom home boasts a first-floor master bedroom suite (Queen), all amenities and comfortable furnishings. Upstairs features 2 more bedrooms (Double and Double/pull-out Twin trundle), and a full bathroom. Cockleshell Cottage is handicap accessible. Relax and enjoy the breeze on the open front porch or back screened porch. Call us today; this home books fast!

- 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. Pet restriction: limited to two small dogs only.

- 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.

Twins at Bay

3 Bedrooms
2 Baths & 1 Half
7 Guests
Cape Charles
Pet Friendly
Gas Grill
Internet

Welcome to your next coastal retreat at "Twins at Bay"! This charming 3-bedroom, 2.5-bathroom house offers the perfect blend of historical allure and modern convenience. Each bedroom, situated upstairs, promises peaceful private spaces, while the welcoming front porch invites you to enjoy serene evenings or lively mornings with the convenience of the downtown area. 

Imagine stepping out to bask in the aroma of saltwater only a few short minutes away,  and spending your days exploring local attractions. Perfect for seafood enthusiasts, the area boasts some of the best dining spots where you can indulge in fresh catches daily. If you're feeling sporty, challenge your friends or family to a playful round of miniature golf nearby. For those days when you'd rather stay close to home, the property comes complete with a gas grill—ideal for those impromptu barbecues. The beach is just a heartbeat away, offering endless sand, surf, and sun for all who crave the ocean breeze.

Pet lovers rejoice! This home embraces your furry friends, making it a true family haven. The friendly neighborhood further adds to the vibrant community spirit, ensuring every occupant feels instantly part of the local fabric. Twins at Bay is newly renovated and perfect for your next vacation! 

- 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.

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