Holiday Homes in Delmarva Peninsula

Down By The Bay - Cape Charles -1st Floor Primary

🏖Come visit this updated 1930's bungalow. 5 blks to restaurants, shops & beach end of our street 🏠 1st floor Primary KING 2026, w/ large bunky upstairs sleeps up to 8 (+ pack and play & air mattress) 🛶 Take stroll/ride to the beach, hose off in outdoor shower, grill on patio & cozy up to a fire. Or relax in the clawfoot tub! 💻 Work remote? Work space ready for you! Wifi/Netflix. Updated kitchen & laundry space in your home away from home! 🐶 Dogs <50lbs (2 max) ☀️ Sunday-Sunday June - August

Teal on Teal Ave - Dog Friendly Getaway by the Bay

Kick back and relax in this calm, stylish and tech enabled cottage. Enjoy the fully fenced in yard and close proximity to Cape May’s best breweries and wineries! Your dogs will love the yard, stocked toys and designated pot filler for their water bowl. The kids who will enjoy the fire pit, close proximity to the bay and custom build bunk beds (with a TV in each bunk). Not your average beach cottage - brand new TVs / appliances. Sonos audio and customizable Philips Hue lighting throughout.

Tranquil Beachfront Getaway on the Chesapeake Bay!

Recharge your battery and reset your mind by staying at our waterfront paradise. Spend time with your tribe while relaxing in this beautiful, well appointed home featuring stunning wide water views of the Chesapeake Bay. "Almost Heaven" is located at the end of a gravel lane, amongst trees, making it the perfect getaway. The expansive patio and beachfront yard offer infinity views of your private beach. Bait a crab pot to catch your own dinner or enjoy a meal from one of the local restaurants.

Lovely Front 2 BR Cottage * Pets Considered *POOL

You'll be close to everything when you stay at this centrally-located, completely remodeled 2 unit building in beautiful Stone Harbor. Close to the beach, this 2 bedroom has a POOL (May-September) & a washer/dryer. Primary has a King sized bed, 2nd BR has 2 single beds, sofa has a Queen sleeper. YOU WILL NEED TO BRING SHEETS & TOWELS. No smoking. Check-in at 1pm, check out at 10am. Pets considered on a case by case basis, additional fees will apply. Summer Season runs Memorial Day to Sept 26.

Waterfront Home in Ventnor

LIFE IS BETTER ON THE BAY! This 5 bedroom, 3 full bath home is beautifully decorated and sits on the intercoastal canal in Ventnor, just a 3 block walk to the Beach. Swim, paddleboard or kayak right off the dock. Catch beautiful sunsets from the rooftop deck. ** GUESTS MUST BE OVER 30YRS OLD AND HAVE ALL POSITIVE REVIEWS TO BOOK THIS HOME! A GOV'T ISSUED PHOTO ID IS REQUIRED TO BE SENT TO THE HOST WITHIN 24HRS OF BOOKING. The Guest booking the home, must stay at the home. ** NO PETS

Newly Renovated 3BR Crest Cottage near EVERYTHING

Welcome to the Crest Cottage, our curated cottage in the heart of Wildwood Crest. Our newly renovated home features includes: - New kitchen and bathroom - New floors & paint throughout - New deck railings and deck - All new furniture and technology inside and out including beds and TV, Nest A/C control, Ring Security, and grill - Bunk beds for the kids !! You’ll be right near popular Wildwood attractions and restaurants & all reservations include discounts at Lakeview Docks Water Sports.

Recently Updated 2 bed -2 bath in heart of Dewey

Updated condo - bay block, block from the beach! 2 bed, 2 bath- one block from the beach, one block from bay Sleeps 4 comfortably, great for a small family, small group of friends, or two couples Stay in the heart of Dewey Beach and walk to everything. Short drive/ walk (about 1 mile) to Rehoboth Beach Half block away from the best spot to watch the sunset *Pets not allowed Playground for the kids at end of street Renters will be responsible for providing own towels and sheets

5BR | Heated Pool, Hot Tub, Elevator, Game Room

☀️ Welcome to your spacious 4,900 sqft coastal home, just 750 ft from the sand! Thoughtfully designed for gathering & relaxation, this 5-bedroom, 4.5-bath retreat offers the perfect blend of fun and comfort, featuring a heated pool, hot tub, cabana with bar, private elevator, and a game room with arcade games the whole family will love. Enjoy seamless indoor–outdoor living with multiple lounge areas, a fully equipped kitchen, and everything you need for an effortless beach getaway.

In-Law Suite in Van Ness/Cleveland Prk/free parkin

Bright new in-law suite with a separate entrance, full kitchen, washer & dryer, fast internet, pull-out couch, laptop desks, and a pack n' play for little ones. Easy access to National Mall via Van Ness metro stop four minutes away. Flexible check in and check out, no cleaning fees (though smoking, marijuana and incense are a firm no). We've been hosting people from all over the world for several years, and we're happy to help you have a great time in Washington, for leisure or work!

Spacious Vacation Home near Bethany Beach

This charming 3BR/2.5BA Bethany Beach getaway offers family-friendly fun. Relax in comfy bedrooms, game nights in the large family room, or chill in the loft office/TV area. Prepare meals in the fully-equipped kitchen & enjoy them on the outdoor living space with a peaceful pond view. Hike the Assawoman Nature Preserve, soak up the sun at Bethany or Fenwick , or marvel at wild horses roaming Assateague National Park (30 min). Create lasting memories at this tranquil retreat.

Vacay Stay-2BR/1Bath, Family Groups Only

Family friendly upstairs, garage apartment. Located on the same property as Dolores by the Sea, only 0.2 miles away from beach and boardwalk. Nestled in a quiet part of town but close to everything. This quaint apartment is perfect for small family’s looking for a relaxing beach vacation. Due to neighborhood restrictions we can only rent to family groups or individuals 25 y/o and over. This is a upstairs unit and may not be for those who have mobility restrictions.

Dog-friendly Rehoboth Oceanblock 11 Cooper Cottage

Newly Restored, charming oceanblock beach cottage w/new kitchen & bathrooms. Decor has been updated throughout w/ a timeless beach aesthetic. Fully stocked kitchen to turn out a gourmet meal. New amenities complement the classic attributes of this 1930's-era cottage. Linens, towels, beach chairs & cart provided. Gas BBQ & outdoor shower included. The beach & boardwalk are just 500 ft away, Funland 3/10 of a mile & downtown Rehoboth 4/10 of a mile.