***4150 Grumpy's Lane*** Charming cottage located on a quiet, private lane. Close to town. Spacious sunroom addition! Newly added outside shower!*** Bed Sizes: 1 Queen, 1 Double Sleep Sofa*** Prime Season Rates: $550 weekly/$110 per night. Off Season Rates: $400 weekly/$80 per night. Additional...

***5421 Deep Hole Road -downstairs apt*** Secluded, quiet location with lots of yard for a pet. Pet Friendly!*** Bed Sizes: 1 Queen, 1 Double, 1 Sleep Sofa*** Prime Season Rates: $550 weekly/$110 per night. Off Season Rates: $400 weekly/$80 per night. Shoulder Season Rates: $475 weekly/$95 per...

Quaint and charming island cottage with all the amenities! Located on the southern end of the island, Daisey Cottage offers everything you'll need for an enjoyable vacation - central a/c, dishwasher, WiFi, washer/dryer and more. And it's even pet friendly! Additional amenities include: bedding 1,...

Stay the nights of August 26-29-$95/Night Now renting fall of 2018. There are few dates left in September. Pets Considered: $100/wk. for first pet; $50/wk. for second ***Please note pets are not allowed on Assateague National Seashore ( the beach)*** Sweet Retreat, a popular vacation...

Duck's Delight is our home in America's Happiest Seaside Town (2014 Coastal Living)! Entire home updated/renovated for the 2015 booking season! 4 bedroom (3 queen sized beds and 2 sets of bunkbeds), 2 bath Cape Cod in Chincoteague, VA., home of the Assateague ponies. Small fishing town on the...

An old Chincoteague favorite, the Blue Hen, not only has a new name (Jay's Retreat), but it has been remolded and redecorated and is awaiting your great review. We are pleased to add this home as one of our owner managed properties. Jay's Retreat offers 3 bedrooms, 1½ baths, waterfront home,...

This delightful townhome features beach living at it's best. The Master Bedroom offers a private balcony with sunset views. Snow goose also offers (shared) dock access to a tidal canal that is full of wildlife. Additional amenities include: bedding 1, bedding 2, budget, family, historic, laundry,...

Affordable waterfront accommodations! We are pleased to be able to offer you this modest Chincoteague cottage located on Main Street just south of town. An unbeatable deal - waterfront location at a non-waterfront price - you won't find it anywhere else. Book early; this one goes fast! NOTE: This...

Located very close to town, Bay Breeze will remind you of summer vacations as a child. This 3 bedroom, 2 bath homes sleeps 6 and has a washer & dryer, window a/c, and a ton of charm! Comfortable and affordable - this may be your spot at the beach! Additional amenities include: bedding 1, bedding 2,...

Peaceful 3 bedroom/2 bathroom home located directly on Eel Creek. Appreciate the natural beauty of Chincoteague Island with gorgeous nature views from both the lower level screened in porch as well as the balcony off of the master suite. Enjoy relaxing mornings with the sunrise and breeze filled...

***7203 Bunting Road*** Bright and open townhouse with private patio area and gas grill!! Offers nice wetland views. Close by is Island Escape and in walking distance to Firemans Carnival.*** Bed Sizes: 1 Queen, 1 Double, 1 Bunk (2 Twins), 1 Queen Sleep Sofa.*** Prime Season Rates: $625...

This modest, pet friendly cottage may be perfect for your island getaway. Located just a few blocks from downtown Main Street and a few blocks from Maddox Blvd, this house is conveniently located in walking distance to most of the shops and restaurants. The large screened porch allows you to enjoy...

Do you need a vacation rental where you can park your boat and bring your pet? You've found it! Sea Tag #23 is a great two bedroom unit (upper level) that overlooks beautiful Assateague Island. Enjoy relaxing on the covered porch after a day of fishing. The views of Assateague are fantastic and...

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. Piney Island offers community water access great for launching kayaks/canoes. To top it all off, Tall...

Come enjoy this 2-bedroom, 2.5 bath townhouse in the Lighthouse Estates community off East Side Drive. There is a community pool as well as water access and a dock (shared) to fish and crab from. This unit features a washer/dryer, wireless internet, central air conditioning and all the other...

Joint Venture is the perfect townhouse for any vacation. Take a short stroll or bike ride to ice cream, mini golf or any of the shops on Maddox Blvd. Easily bike or drive to the beach from the property! Joint Venture offers a beautiful waterview of Little Oyster Bay that can be enjoyed any time of...

Great 2 bedroom, 2.5 bath townhome in Lighthouse Estates community off East Side Drive. This home features all amenities including central air, washer/dryer and new kitchen appliances. In addition, there is a community pool as well as water access and a dock (shared) to fish and crab from. This is...

This comfortable, family friendly vacation rental is waiting for you to enjoy. This unit has pool access and dock access directly across the street for easy access for those fun family fishing and crabbing experiences. It is just a short distance to Memorial Park and Etta's Waterfront dining. The...

Leave all of your worries behind when you stay at this marvelous 3-bedroom, 2-bathroom Chincoteague Island vacation rental house! Boasting space to sleep 8 guests, water views and a secluded canalside location with private pier, this quaint trailer-style property will allow you to leave all your...

We are pleased to be able to offer you this fabulous 2nd level unit! The interior has been completely renovated, from the drywall and paint, to the furniture! You'll enjoy all modern amenities including flat-screen TVs (3), internet, washer/dryer facility and updated kitchen (appliances, cabinets,...

***5368 Main Street*** Very enjoyable and immaculate traditional home will delight you stepping inside. Pet Friendly! Newly added Fenced in Back Yard and Wi-Fi. 1 bedroom and 1 bath downstairs/1 bedroom upstairs.*** This Property accepts Dogs 35lbs and Under Only.*** Bed Sizes: 1 Queen, 3...

***4264 Pine Street*** Tucked away home close to town with large screened porch. 1 bedroom and sleeping porch area downstaris and 1 bedroom and sleep landing upstairs.*** Bed Sizes: 1 Queen, 1 Double, 4 Twin*** Prime Season Rates: $750 weekly/$150 per night. Off Season Rates: $495 weekly/$99 per...

A Getaway is a bright and cozy home nestled between pink Crape Myrtles in the private, secluded neighborhood of Oyster Bay II right off of North Main Street. This home features a 12 x 24 screened in deck that is perfect for outdoor gatherings, dinners, and making memories. With clean, functional...

Josie's Dream is a newer, more modern vacation rental that features a master bedroom suite with private bath and a great location across the street from Memorial Park. Walk to Etta's Restaurant, East Side Marina or Memorial Park. Note: parking has a two car maximum. Additional amenities include:...

Come for an old fashioned family vacation. This wonderfully maintained classic Chincoteague style home features a large screened porch and beautiful yard for those warm summer evenings and a wonderful enclosed outside shower. There is a family room with a wood stove, living room/library with lots...

Wonderful 2 bedroom townhome that features a great screened porch off the living room, large bedrooms (including master bedroom suite) and second-level screened porch off one bedroom. Full ensemble of appliances, central air, water access, private pier (shared by other units), and more! New...

Located on South Ridge Road, this lovely town-home features a private pier, central air conditioning, and galley style kitchen complete with a dining area and all necessary appliances. The cozy living room leads you onto one of two screened in porches perfect for unwinding with family and friends....

Located on the southern end of the island, Family Affair is a town home with gorgeous views of tidal canal in the backyard easily viewed from both stories, including the spacious second-level balcony. Enjoy the water access (tidal canal) and surround yourself in nature from the shared pier, just...

Catch of the Day is very comfortable and affordable duplex home that will cater to all of your vacation needs. This can be your home away from home - near the beach! The first level offers a large living room, a bedroom (D), an eat-in kitchen, 1/2 bath and very nice screened porch. There are two...

Come stay and relax at this quiet retreat. This listing is a newly remodeled home which is tastefully decorated. There are three color themed bedroom's; which have two queens and two twin sized beds. There is serenity all around you, come sit on the screened in porch and relax while listening to...

***6096 Taylor Street*** Perfect retreat for the traveler on a budget! Tastefully decorated cottage with 36 inch television and within walking distance of shops and restaurants. All bedrooms on same level.*** Bed Sizes: 1 Queen, 2 Twin, 1 Queen Futon*** Prime Season Rates: $650 weekly/$130 per...

There's plenty of room for everyone here at Island Thyme! This spacious home features a living room and den, large eat-in kitchen and dining area, and a huge wrap-around deck -- perfect for enjoying the quiet, peaceful setting. The many extras include a hot tub (on back deck), and Foosball table....

Bay Dreamer is a spacious 3 bedroom duplex home with multiple porches and decks and spectacular sunset views, just minutes from downtown. When you enter the home you'll find a furnished rec room. The second floor features an open living room (queen sleeper sofa), dining area and kitchen. There is a...

****6389 Circle Drive**** Comfortable Island home packed with amenities. Sea Pines offers a nice shady yard and back screened porch in a quiet neighborhood. HD Flat Screen TV. Offers WiFi and Wired High Speed Internet and Charcoal Grill! Bathroom Newly Renovated for the 2017 season. Close to...

Looking for a fun place for a family vacation? Look no further! Blue Diamond offers all amenities: community pool, shared water access, comfortable furnishings and high speed internet (just to name a few). And if that's not enough, Blue Diamond is located on the popular East Side of the island...

***7531 Pony Cove Lane*** This is an immaculate, tucked away duplex for very quiet and peaceful setting. It offers a large sun porch,and back yard. Will be a 10 x 22 screen porch will be added for the 2010 rental season.*** Bed Sizes: 2 Queen, 1Twin Day Bed w/Trundle, 1 Queen Sleep Sofa ***...

***5454 Amrien Circle*** Enjoy marsh and bay views from the wrap around deck and screened porch. This bright and cheerful single story home was newly furnished in 2005. Tucked away in a private subdivision off North Main Street. Wi-Fi available. All bedrooms on the same level. Next door to...

***7071 Bond Street*** Tastefully decorated townhouse with many new appliances, screen porch and convenient in town location. Offers Wi-Fi. 2 bedrooms and 1 bath downstairs/1 bedroom and 1 bath upstairs.*** Bed Sizes: 1 King, 1 Double, 2 Twin, 1 Queen Sleep Sofa*** Prime Season Rates: $650...

***6703 Megan Lane*** Bright and spacious duplex located on private lane. In walking distance of many island attractions. Offers second floor master bedroom suite. 1 bedroom and 1 bath downstairs/1 bedroom and 1 bath upstairs. Nearby is Georges Retreat.***Offering WiFi*** Bed Sizes: 1 Queen, 1...

Looking for a clean, comfortable spot that's conveniently located? It's here at Eastwinds! This 2 bedroom townhome features an open floor plan downstairs, and 2 bedrooms/2 full bathrooms upstairs. You're just a few minutes from downtown - restaurants, shopping, movie theater and more. And,...

Captain's Loft has NEW OWNERS! This vacation home is located just a short walk to Maddox Blvd! Close to everything, but situated perfectly for a quiet and relaxing stay. This duplex home features three bedrooms downstairs, and two of those bedrooms have full baths. There's another full bath...

Come stay in this classic Eastern Shore Style home. Located just a few blocks from our famous downtown Main Street area, you are within walking distance to most of our shops and restaurants. Serendipity has a very nice screened porch for those memorable Chincoteague Summer evenings. This home also...

Charming 3 bedroom ranch home located in one of Chincoteague Island's finer residential communities. Nice, quiet location with a water view of Oyster Bay. 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...

A very nice waterview duplex overlooking Assateague Island and the lighthouse. Located across the street from 'Mr. Baldy's Restaurant' and within walking distance to Memorial Park park (where there is a boat ramp, a fishing pier, and play area for the kids). Enjoy the waterside screened porch....

Fantastic 2 bedroom ranch-style home with a great location on East Side! This home features central air, washer/dryer, dishwasher, fireplace and more. Public boat launch located right across the street. Marina, Memorial Park and a seafood restaurant are all within a short distance. Large yard,...

***3400 Ridge Road*** Lovely 2 Bedrooms, 1.5 Baths duplex with water views. This duplex overlooks Assateague Island with great views for the Pony Swim. This is the Best way to watch the Pony Swim and not move from your porch! Sit and enjoy the views from 2 porches. The screened porch is off of the...

Lighthouse View is located on the east side of our ialnd and includes a private community pool for your enjoyment. The 3 bedroom, 2 bath townhouse features two first floor bedrooms with full bath in the hallway and a master bedroom suite upstairs. There's water access across the street with a...