
House rentals near Chesapeake Bay
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Top-rated house rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

Charming coastal home w/ outdoor area and river views
Tucked away at the end of a quiet road, our home welcomes you. This spacious, thoughtfully designed 1 BR/1.5 BA home on 4 acres is ideal for those looking to relax and get away from it all while still being just minutes away from some of the areas best dining and attractions. Whether you want to watch the sun rise over the York River, spend the day exploring the Williamsburg historic triangle (Busch Gardens), or just take it easy around the house and enjoy the outdoor area, the choice is yours.

Soul Oasis - home on the Chesapeake Bay
Listen to the waves of the Chesapeake Bay from the trex deck. There are 2 private community beaches in the neighborhood where you can find fossils and sharks teeth. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer around the house! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.

Sunset Breezes - quiet waterfront retreat
Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. Gather with family and friends around the fire pit. Take in the beautiful water sights while paddling in a kayak, canoe, or paddleboard. Laugh with family and friends while playing corn hole, croquet, or bocce ball waterside. Photograph abundant wildlife - bald eagles, blue herons, osprey, deer, turkey and numerous waterfowl. Dine on the deck while enjoying beautiful sunsets.

"Bee-Z Haven" Waterfront Cottage on the Ware River
Curious about what makes Gloucester so wonderful? Live like a local at this Upscale Waterfront Retreat and find out for yourself why renters say "Enjoy the Breath Taking Views". Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our area is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

Sunkissed Cottage-private, natural waterfront home
Want a cozy, private getaway surrounded by nature, lush trees, beautiful sunsets on the Little Wicomico? Sunkissed Cottage is cheerful home full of wonderful amenities! Enjoy drinking coffee on the porch watching the deer and birds. Take a 2 minute walk down our path through the woods to our waterfront where you can enjoy the water. Our home has high speed internet, smart tvs in every bedroom, corn hole boards, firepit and gas grill. The kitchen is well stocked for all your culinary needs.

25-50% Off~Private Beach~Hot Tub~Fire Table~
Welcome to our Chesapeake Bay Cottage on Kent Island, Maryland! This unique 3 bed 2 bath home with luxurious amenities is a perfect getaway for families or friends looking to create unforgettable memories and experience all the Bay area offers. Escape the hustle and bustle with an easy commute from Annapolis, Washington and Baltimore. The Naval Academy is right across the Chesapeake Bay Bridge. Adventure and relaxation are within easy reach from any mid-Atlantic and northeastern location.

Peaceful Historic House Near Water, with Hot Tub!
Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces
A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l dates**

Living on Island Time
Relax with the whole family and spend life on Island Time. Full bar set up with ice maker and wine refrigerator. Private pier, paddle boards and firepit. Unwind on St Goerge Island or head out to one of the local eateries for some southern Maryland faire. Inside you have 2 spacious rooms, 2 bathrooms. A massive island for cooking, card playing or just great conversations with endless views. Crabbing, fishing. The Neighbors have 2 Great Danes and a cat that you may see occasionally

White Point Cottage -- Quiet Waterfront Getaway
Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. More on IG @whitepointcottage, and be sure to visit our sister property, Water's Edge Cottage.

1891 Coastal Charmer: fully renovated farmhouse
Built in 1891, this farmhouse has been totally renovated by a professional designer. The Cottage is filled with coastal colors and accessories so it feels fun and updated but still retains the feeling of walking into a well loved family beach cottage. We are pet friendly as any beach cottage should be and love seeing our guests and their pets enjoying the cottage. Follow the cottage on social media @ BlueOysterCottage for more pictures, design ideas and local places to visit.

Spacious Gorgeous Waterfront Home with Sunset View
Dreamy weekends on the water, the perfect getaway for the entire family and friends in the southern tip of St Mary’s peninsula. This gorgeous newly remodeled house with 5 Bedroom 3.5 Bath sleeps 10 very comfortably. Wake up with amazing water views and access to the water with your own private pier. Spend your day crabbing, fishing, kayaking, or paddle boarding. Amazing beaches at Point Lookout State Park, just a few minutes away. High speed internet, WiFi, and cable.
Popular amenities for house rentals near Chesapeake Bay
House rentals with a pool

Waterfront Retreat w/Gameroom, Firepit, Dogs+EV OK

The Glebe

Blue Heron WaterSide

Gunpowder Retreat

The Rosé Retreat: Fireplace-Screened Porch-RELAX

Beach Please! River cottage w/private beach & dock

Seas the Day Getaway ~ Pool ~ ONLY 3 mi to BEACH

Waterfront Cottage Getaway Views/Kayaks/Fire Pit
Weekly house rentals

Waterfront FamilyFriendly Home Improved for 2023

Cove Point Beach Cabin

Private Country Beach Retreat

Luxe Winter Retreat- 5 Star

Urban Loft Hideaway near DC, Tysons, Georgetown

Upper Chesapeake Getaway

The Little House on Back Creek

Chesapeake Waterfront-Fire Pit- Hot Tub-Pier
Private house rentals

Pet Friendly,Fence, Waterfront 'Rivah Dog Cottage'

New Private Beachfront panoramic view every window

Wellness Retreat | Sauna, Ice Bath, Hot Tub & Spa

Mid-Century Modern: Direct Private Beach Access

Kent Island Escape

Erica's Place Wonderful Winter Waterfront sleeps 8

Waterfront Getaway with Game Room, Kayaks, Perfect

Summer Breeze waterfront new home-Private Beach
Pet-friendly house rentals

Waterfront Getaway with Dock

Church Creek Charm (close to Blackwater Refuge)

* Beautiful Oasis w/ No Detail Spared

The Hideaway at Mill Creek

Cozy 2 bedroom home on wooded private lane

Cozy Riverside Cottage in the Woods

Tranquil Shores - Nature Inspired Relaxation!

New Hotel Chic
Quick stats about house rentals near Chesapeake Bay

Total holiday rentals
Explore 3,910 holiday rentals in Chesapeake Bay

Verified guest reviews
Over 146,620 verified reviews to help you choose

Family-friendly holiday rentals
3,190 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 1,500 rentals that welcome pets

Holiday rentals with a pool
420 properties feature pools

Rentals with dedicated workspaces
2,270 properties have a dedicated workspace

Wifi availability
3,840 of Chesapeake Bay holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesapeake Bay rentals

4.9 Average rating
Chesapeake Bay stays are highly rated by guests – averaging 4.9 out of 5!
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- House rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Buckroe Beach
- Outlook Beach
- Norfolk Botanical Garden
- Cape Charles Beachfront
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Nauticus
- First Landing Beach
- The NorVa
- Chrysler Hall
- Virginia Living History Museum
- Old Dominion University
- Colonial Williamsburg's Merchants Square
- Hampton University
- Harbor Park
- Town Point Park
- USS Wisconsin (BB-64)
- Virginia Zoological Park




