Take 15% off the rental rate for any March or April reservation!
Let us help you 'Spring Forward'... Book a reservation between now and March 31st for any travel dates in March or April, and receive a 15% DISCOUNT off of the rental rate! Yes, it's even valid during Easter weekend!
Minimum stay is 2 nights and maximum stay is 7 nights. Please enter discount code SPRING15 when on the booking screen. Subject to availability. Discount may not be combined with any other specials.
Properties on Special
Waterman's Daughter
We are excited to introduce Waterman's Daughter! This stately townhome is located on a quiet lane off of East Side Drive. The first floor of the home features two bedrooms, both featuring full attached baths! A full size washer and dryer are conveniently located off the hall in between these bedrooms. As you make your way to the second floor of the home, you are greeted by a bright living space featuring a flat screen TV, fireplace, large windows, and doors that lead you out to the second floor balcony that features a table for two with a view. Right beyond the dining area of the home, you will find the fully equipped kitchen that features additional seating for three at the kitchen bar, a stove top oven, microwave, and dishwasher. The large Master bedroom is on the second floor of the home and features yet another full attached bath and wall-mounted flat screen TV. There's even a shared waterfront area - perfect for launching your kayak or canoe. This home is truly the perfect setting for your next Chincoteague Island vacation; clean, relaxing, and accommodating! Call us or book online today!
- 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.
Endless Summer
Come enjoy your stay at one of the most sought out locations on the Island. Easy, convenient access to the beach. With the large open floor plan, high ceilings, and easy one level living, you have everything you need at Endless Summer. Bring along your furry friends to make your vacation complete! This home has plenty of room for the whole family to gather. Enjoy the nice screened in porch or the large open front porch with your morning coffee and listen to the serene sounds of nature. The Piney Island Community offers convenient access to a kayak launch located on Pine Drive, just minutes from the 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. BREED RESTRICTIONS DO APPLY
- 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.
Seas the Day
You will LOVE the quiet duplex community where this home is situated. Bright, open floor plan, with adjoining screened and open-air porches - perfect for sipping coffee in the morning or relaxing with a cool drink after a day at the beach. The first floor bedroom offers a private bathroom and the sweetest window nook - bring your book! Two additional bedrooms upstairs share a full bathroom and all bedrooms are tastefully decorated in their own fun personal themes! Hosting a group that requires more space? Rent Seas The Day's sister, 'Sea La Vie', just next door! **NEW FOR 2025: Kid's bunk room features a single Twin bunk bed + a Twin Trundle bed!**
- 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.
Almost Heaven
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.
Homestead
Set back across the street from Chincoteague Bay, Homestead sits on 30 acres of basically pristine land. A cozy cottage, originally built in 1890, had been updated but the owners kept the original charm of yesterday but with the comfort of today. Now that charm and comfort has been expanded. A new addition offers a great room with a modern kitchen, dining area and room to stretch out and relax. The design includes oversized windows, sliding doors and a sky light. The house now has 2 screen porches and a balcony that lets you feel as though you are living in in a nature preserve! Homestead sleeps 5 but best suited for 4 adults. There are now 2 full sized bathrooms. Amenities include bikes, beach chairs and umbrellas: games, crayons and colored paper and good parking. And as part of the property, you'll vacation alongside the oldest home on the island, The Captain Timothy Hill House, listed on the National Register of Historic Places. With a tidal pond in front and unspoiled woods in back, Homestead is private, quiet and with lots of room outside. A perfect retreat! So relax on one of the porches, feel the breeze from the bay, watch the animals and birds that come by or take an outside shower under the stars. The Homestead that so many have come to love is still the same just more to love!
- Linens and towels are included with your reservation.
- No smoking is permitted on the premises.
- No pets 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.
Piney Island Paradise
Welcome to Piney Island Paradise! This well-furnished townhouse is nestled in a secluded cul-de-sac along East Side Drive and offers some of the best views of Assateague Island and the historic lighthouse located across the channel. The channel on Eastside offers some of the calmest water for kayaking, plentiful crabbing, and great fishing. Enjoy the most beautiful sunrise views from this vacation home along with quiet solitude! This home also offers 2 kayaks for your enjoyment!
Upon entering this home, you will find a half bath, first floor bedroom with a queen-sized bed, a well-stocked kitchen, living room, and large waterfront deck with plenty of seating to relax, enjoy the wildlife, and watch the ponies grazing on Assateague Island. On the 2nd floor you will find two more bedrooms as well as the laundry area. The main suite features a king-sized bed with a full bathroom and waterfront deck to enjoy the peaceful sounds of nature and beautiful sunrise views. You will also find a 3rd bedroom that easily accommodates 5 more guests. This room features a twin over twin bunk, a twin over full bunk, and a full bathroom with walk in shower. This home also includes a nice assortment of beach chairs and a small attached garage where you can store your bicycles and kayaks. If you are looking for a home with all the amenities and want to enjoy the beauty of Chincoteague & Assateague Island, this is it!
- 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.
Serenity at Oyster Bay
Aptly named, "Serenity at Oyster Bay" is just what you'll find at this delightful vacation home. Located in the highly-demanded community of Oyster Bay I, you'll enjoy the peaceful, quiet area nestled amongst the tall pines and marsh grasses. The main living area features a fantastic open floor plan; perfect for gathering the family and entertaining. The back of the house features a bright sunroom that looks out over a natural preserve - cozy up with a cup of coffee and a nice book! This home also features 3 bedrooms, 2 full bathrooms (completely remodeled) and has undergone a lot of fresh new upgrades! There's a little sitting deck out back, a screened porch, covered picnic/game area (with cornhole boards), fish cleaning station, and so much more! And, as if that's not enough, there are water views and you're very close to the Oyster Bay Community water access! Don't delay - Serenity at Oyster Bay is sure to book quickly!
- 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.
Horseshoe Hideaway
Located in a secluded neighborhood, in the middle of town, 'Horseshoe Hideaway' is comfortably situated back off of a back road, fully enclosed by a fence, and ensconced by a generous yard and mature wooded area. With all the convenience of traveling around the island with ease, this home allows guests to drive or bike to Maddox Blvd, the beach or to the Main Street shops within minutes. Enjoy the outdoors on the fully screened in porches located on both the front and the back of the home, or take advantage of the generous back deck (accessed by a ramp or stairs) and supplied with a large gas grill, picnic table and Adirondack chairs. Inside the home features 3 bedrooms and 2 full bathrooms, a separate dining room, living room and eat in kitchen. There are several seating areas where guests can spread out or congregate as a group. The home is appointed with everything you need to enjoy a vacation at the Beach. This cute-as-a-button rancher home is waiting for your family vacation! Clean, comfortable and modest best describe the single-level home; there's an open kitchen, living and dining area that opens up to a front AND back screened porch. Enjoy all of the outdoor space from one of the 2 screened porches, or the spacious back deck and back yard! Located on a side street just off of Ridge Road, 'Horseshoe Hideaway' is conveniently located just minutes from downtown Chincoteague, as well as the "Beach Road." Come and check it out for yourself!
- 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.
Lottie's Lookout
Come stay at this Chincoteague Island Charmer, better known as Lottie's Lookout! This large spacious home features 3 levels, with 3 large bedrooms, and 3 bathrooms. The first level features a front porch, pull out sofa, large dining table for family meals, and a full bathroom. Upstairs you will find 3 twins, (one bunk) and another bedroom down the hall with a queen sized bed. There is a full bathroom on this level as well. On the third floor, you have a full sized bed and bathroom with a tub (no shower). Enjoy the outdoors in the large yard, or grill up some good food from one of the many local markets. Lottie's Lookout is in a perfect location, close to the downtown area!
- 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.
Cockleshell Cottage
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.