
Holiday home rentals near Chesapeake Bay
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Top-rated holiday home rentals near Chesapeake Bay
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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

Northern Neck Waterfront
Relax with the whole family at this peaceful waterfront retreat. Nestled along Coles Creek and the Great Wicomico River, this 3-bedroom house is a perfect waterfront getaway with all the amenities you need for a comfortable stay. Savor the beauty of nature from our backyard, where a glistening pool takes center stage, inviting you to unwind and bask in the sun. If you're an aquatic enthusiast or simply someone in search of serenity, our house in Burgess offers an idyllic haven to vacation.

Designer apt with high end finishes and furnishing
Located in a large, historic townhouse in the Historic District near Lincoln Park and the Eastern Market this professionally decorated English basement apartment includes original artwork; designer furnishings chosen for comfort; and an open concept living/dining/kitchen accented by a rustic antique dining table that seats up to 6. Lush front garden with cafe' table and seating for 6. The new bathroom features double sinks, lighted medicine cabinets and an extra-large shower. Parking permit..

Solo/Couple's Escape in Sandbridge, Virginia Beach
Enjoy some time away in this peaceful and cozy space. This is a totally separate apartment for 1 or 2 people on the ground floor of our house. You will have a ground level private entrance with a keyless self-check-in. Located in the quiet North End of Sandbridge Beach, you will have a 5-minute walk to the beach. The apartment offers a spacious king bedroom, an upscale bathroom with a tiled shower, a kitchenette, a dinette, and a living area with a sofa and smart TV with Wi-Fi streaming.

Tranquil Beachfront Getaway on the Chesapeake Bay!
Recharge your battery and reset your mind by staying at our waterfront home. Spend time with your crew 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.

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!

Gettysburg Retreat 1853 Pre-Civil War Home
Our first priority has always been the safety of our guests! You can rest easy and trust in our high level of cleanliness standards at The Gettysburg Retreat! We invite you to stay in our Historic Pre Civil War 4 Bedroom, 2 bath home, located with-in walking distance to Restaurants, Museums and everything else that Gettysburg has to offer. We have everything to make you feel right at home! My place is good for couples, solo adventurers, business travelers, families (with kids).

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.

Spacious Garden Apartment on Delightful Street
This delightful apartment is on the ground floor of a large single family house in a charming neighborhood, just 2 blocks from the center of Takoma Park, a 15 minute walk to the Metro. With its open floor plan, you will enjoy the large living room and windowed alcove, a fully-equipped kitchen, dining room and ample-sized bedroom with wall-to-wall closets. There is a separate entrance and laundry room. The house has a large front yard, with shade trees and nice gardens.

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.

One Bedroom Guest Studio Suite
Come stay at our newly renovated guest suite in the heart of Rockville, MD. The 1-bedroom studio suite is fully furnished with a fully equipped kitchenette and bathroom. Our suite is steps away from public transportation (Route 48) which takes you to the red-line metro (Wheaton or Rockville), and a walkable distance from a shopping center featuring a grocery store, restaurants, etc. There is ample space for parking in front of the property.

Stylish modern 2BR/2BA - Free Garage Parking!
*Fully renovated 2 BR 2 full bath basement apartment - renovated in 2021! *Private access *Extremely close to the restaurants, attractions and grocery stores of H St *Short walk to Union Station, Amtrak, buses to/from NYC, and metro station. *Stainless Bosch appliances *Wine fridge. *King beds with excellent comfortable mattresses. *Spacious and comfortable with a lovesac couch *Dining area *Included secure underground garage parking!
Popular amenities for holiday home rentals near Chesapeake Bay
Family-Friendly holiday homes

Luxurious 5 Bedroom Near Beach, Amenities Galore!

House near Crystal City, Pentagon, Amazon &Museums

Quirky A-Frame in A Certified Wildlife Habitat

Waterfront Home with Chef's Kitchen and Firepit

Lovely Canal front 2 bed townhouse with a pool

The Observatory on Rose Manor

Hoopers Island 4BR Waterfront • Sunset Views

Family House St. George Island w/Pool. 1.5 hr/DC.
Holiday home rentals with a patio

Cozy, updated condo. Pool, tennis, walk to beach.

Waterfront 5 Bedroom Home Close to Annapolis

South Bethany Newly remodelled Canal Front Home!

Fun and Sun in Ocean View! 5 bedrooms 12 guests

Beach Happy-steps to the beach- 4bedrooms/9guest

Waterfront 4 bedroom home with marina facilities

Private Close to Everything One-Bedroom Apartment

Parkside South, Cape Charles
Holiday home rentals with a washing machine and dryer

VB Paradise / Private Pool, Hot Tub

Sara's Cottage

Peace & Tranquile waterfront home

Bayside Breeze in North Ocean City!

Cricket House - cozy two bedroom house in downtown

Relaxing 3-Bedroom Beach Cottage By Historic Lewes

Cheerful 3 bedroom home with a pool and sauna

Sea Colony stunner...wooded retreat by the beach!
Other holiday home rentals

Charming Beach/Bay Escape with Activities for All!

1 Block to the Beach, Indoor Pool Great 4 Kids

Beautiful Waterfront Home

Harbor View - 3 bedroom home in the heart of town.

Bright 3 bedroom vacation home near beach

Harvest of tranquillity

The Robin's Nest; Lovely 1 bd with parking

Lovely 2-bedroom 1100 sq ft Apt with free parking
Destinations to explore
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- Holiday home rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Water Country USA
- First Landing State Park
- Buckroe Beach
- Jamestown Settlement
- Cape Charles Beachfront
- Outlook Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Virginia Living History Museum
- Old Dominion University
- Colonial Williamsburg's Merchants Square
- Nauticus
- Town Point Park
- Virginia Zoological Park
- First Landing Beach
- Chrysler Hall
- USS Wisconsin (BB-64)
- Hampton University
- Neptune's Park
- Point Lookout State Park




