You are here

Displaying 25 - 36 of 85 results matching your search criteria
Map View
List View

Grandma's House

4 Bedrooms
3 Baths
12 Guests
Chincoteague Island
Gas Grill
Screened Porch
Internet
Outdoor Shower

Introducing a charming and newly renovated home on Chincoteague Island!  Grandma's House is a delightful residence, boasting four cozy bedrooms, including two primary bedrooms conveniently located on the first floor, each designed for comfort and ease. With three well-appointed bathrooms, including a walk-in shower, the home is designed to cater to your relaxation and convenience needs. Grandma's House also has a handicap ramp for your convenience!

Step into the culinary paradise of a beautifully kitchen, complete with a sleek tiled backsplash, where both seasoned and aspiring chefs can whip up delectable dishes. Connected seamlessly to the dining area, this kitchen is perfect for gatherings and feasts.

Family fun is never in short supply thanks to the inviting den, complete with an air hockey table and darts for a bit of friendly competition. The screened porch offers a breezy retreat for evenings, while the spacious patio is set with both a gas grill and smoker for those sunny weekend barbecues. The heart of this home is undoubtedly its wide-open outdoor space, complete with a basketball hoop for the sports enthusiast and a front deck that invites you to enjoy your coffee while the morning breeze gently brushes against your face.

Whether you're entertaining guests or enjoying a quiet afternoon, this home ensures you can make the most of every moment. So come by and see why this isn't just any house — it's a vibrant living space waiting to be called 'home'! Here's a fun bonus — this home is attached to a charming apartment affectionately known as "Grandpa's Cottage," which is available as a separate rental. Rent them together for a larger group!

- 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.

Shady Grove

4 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Water View
Screened Porch
Internet

Come and relax at this fabulous beach home that is tucked away on the quiet northern end of Chincoteague Island! Aptly named, "Shady Grove" is situated in a natural marshland grove in the Richardson's Landing community. Features include 4 bedrooms, 2 bathrooms, numerous updates and remodeling and a bright, open floor plan. 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. 

- 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.

Utter East

4 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Gas Grill
Screened Porch
Internet
Outdoor Shower

We're pleased to offer you 'Utter East'! Tucked off of a quiet side street in the middle of the island, this home features everything you'd need for a wonderful, relaxing vacation. If you love outdoor space, you'll love the huge screened porch, expansive decks, and beautifully landscaped fire pit sitting area on the pond. Inside the home, downstairs you'll find the living room, an additional den/family room, eat-in kitchen, dining room, two bedrooms and a full bathroom. Upstairs features two more bedrooms and another full bathroom. Don't delay; this home will book quickly! "Where sky and water meet, Where the waves grow sweet, Doubt not, Reepicheep, To find all you seek, There is the UTTER EAST." - From "The Chronicles of Narnia" by C.S. Lewis

- Linens and towels are included with your reservation.

- No smoking/vaping is permitted on the premises, including porches and outdoor areas.

- 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.

Wildflower

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

Beautiful waterfront home with shared pier plus floating dock on deep water!! Ground level is a large screened patio perfect for those summer time seafood feasts. The first level is great room boasting reclaimed barn board walls and wide plank pine floors with a separate den and full bath. There is a second screened porch overlooking that water from the great room. The second level has a large waterfront master suite with a private balcony, two more bedrooms and another full bath. Close to Memorial Park right across the street from a family restaurant! (Spiral staircase in home, may not be suitable for small children.) For larger groups for family reunions, check out nearby Moon Rising or Herbie's Hideaway!

- 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.

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.

Oyster Catcher

4 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Screened Porch
Internet

Welcome to Oyster Catcher! This home offers a prime location, beautiful views and a deep water dock (6 feet at low tide)!  We encourage you to sit and relax on the large screened porch and enjoy all nature has to offer. Upon entering the home from the side door, you'll be greeted by the the fully equipped kitchen that provides all the essentials for meals at home, while overlooking some of the most beautiful views the Island has to offer. The living room does not lack views either- sit and relax while opening one, or all four, of the large panoramic folding doors that span across the kitchen and living area. Enjoy the sounds of nature or feel the cool salt air breeze. There is a first floor bedroom, with a full size bed and a separate full bath (tub/shower combo) - you have your own access to the screened porch from the first floor room.  The living room also has a queen sleep sofa.  Upstairs you will find two more bedrooms, one with two twins and another with a full. All bedrooms showcase breathtaking views of Deep Creek. Venture outside to the private guest cottage that holds much history from one of the Islands most plentiful seafood shacks. The guest cottage features a queen bed and full bathroom with shower, as well as a floating twin bed. Drop a line or a crab pot at the end of your private dock- maybe you will even get to enjoy a fresh catch for dinner! Oyster Catcher offers a private setting with bountiful plants and greenery, plenty of yard for whole family including your fur babies!  Other amenities include a gas grill and WIFI.

- 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.

 

Shady Side

4 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Water Access
Gas Grill
Screened Porch
Internet

Shady Side is located in Piney Island, which is among the closest communities to the beach. There is community water access, suitable for a kayak or canoe. The house features two queen bedrooms and a full bath downstairs. Upstairs you'll find two additional bedrooms, one has two twins and the other has a queen bed. There is also a full bath on the second floor. The loft features a futon with a full mattress. The large back porch is equipped with a gas grill and picnic table for your cookouts and crab feasts! 

- 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.

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. 

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.

Poole's Cove

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

Nestled just off Main Street with the water as your backdrop, Poole's Cove is a lovingly curated escape that feels inspired and inviting. Every detail of this thoughtfully decorated home invites you to slow down, breathe deeply, and truly settle in.

The layout is designed for both togetherness and solitude. The primary bedroom suite anchors the main house, while a breezeway connects you to a separate wing with two additional bedrooms and bathrooms — perfect for families or couples who want space to gather and space to retreat.

Step into a large screened-in deck and up to the rooftop deck, where water views, golden sunsets, open skies, and unforgettable stargazing await. When you're ready to unwind indoors, the upstairs office and library is a wonderful place to lose yourself in a good book.

And the best part? Poole's Cove has just undergone a complete top-to-bottom renovation. Brand new kitchen, floors, bedrooms, bathrooms, and furnishings throughout — plus significant exterior updates. The Poole's Cove you've always loved is now better than ever.

This isn't just a place to stay. It's an experience.

---

Please note: Due to this home's unique floor plan and open deck railings, it may not be suitable for young children. This is a non-smoking, pet-free property. Linens and towels are available.

- 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.

Pony Dreams

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Town & Country
Gas Grill
Screened Porch
Internet

Welcome to your perfect Chincoteague Island retreat! This brand-new three bedroom, two bathroom house offers the ideal blend of comfort and coastal charm for your vacation getaway. The open floor plan creates a seamless flow between living spaces, making it perfect for gathering with family and friends after days spent exploring this beautiful, picturesque island.

The heart of this home is its fully stocked kitchen, equipped with everything you need to prepare memorable meals using fresh local seafood. Step outside to discover your own screened "crab shack" gazebo – a delightful covered space where you can enjoy meals while staying protected from the elements. Fire up the gas grill for outdoor cooking adventures, whether you're preparing the day's catch or hosting a casual barbecue. 

Location is everything, and this property delivers. Situated close to Maddox Boulevard, you'll have easy access to the island's main thoroughfare leading to pristine beaches. The nearby Bay to Beach Trail access point offers scenic walking and biking opportunities just minutes from your door. Families will appreciate the proximity to Maui Jack's Waterpark for splash-filled fun, while nature lovers can venture to the renowned Assateague Beach to spot wild ponies and enjoy miles of unspoiled coastline.

This thoughtfully designed home provides modern amenities in a relaxed vacation setting. There's plenty of parking, including a space for your boat/trailer (up to 21'). Whether you're planning beach picnics with provisions from your well-appointed kitchen, or simply unwinding after adventures in the comfortable living spaces, every detail has been considered for your enjoyment. Experience the magic of Chincoteague Island living in this exceptional rental home.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises. 

- Linens and towels are included with your reservation.

- 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.

Pages