
House rentals near Chesapeake Bay
Find and book unique houses on Airbnb
Top-rated house rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

Spacious 3-BR near DC • Lotus Pond • Free Parking
Wake up to birdsong beside a tranquil lotus pond, just 20 minutes to downtown DC. Spacious 3-bed retreat offers on-site parking, fast WIFI, a home gym, steam shower, yoga space, EV charger, and five decks. Walk to organic markets, restaurants, and scenic trails in peaceful Takoma Park. Recently renovated from top to bottom. Plan your adventures by day, relax by the pond at night. Book your stay today!! Superhost service to top it off. Montgomery County Registration # STR24-00107

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, Peleton
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**

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.

Waterfront Cottage Getaway Views/Kayaks/Fire Pit
A timeless cottage on a quiet property on the Rappahannock River with charming rose garden, relaxing pool, and quintessentially Virginia feel. Find us on IG @rosehilllcottagerappahannock! Explore nearby towns of Urbanna, White Stone, and Irvington, or stay close to home to enjoy sweeping views, waterfront adirondack chairs, and kayaks — perfect for a cocktail or coffee, or take a dip in the river or pool. With open living spaces and thoughtful decor, this is your waterfront retreat.

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.

Peace Point - Waterfront, Secluded, Home w/hot tub
Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

The Llama House
Located half-way between Mathews and Gloucester on the beautiful North River with views of the Mobjack Bay, New Point Comfort Lighthouse and Gloucester Point. The ideal spot for anyone needing to reconnect with someone, nature, or themselves. Enjoy fishing, crabbing, kayaking, playing corn hole, birdwatching, napping in a hammock, sipping wine, grilling out, amazing sunsets, listening to old records, playing the ukulele, and other simple pleasures of days gone by.
Popular amenities for house rentals near Chesapeake Bay
House rentals with a pool

The Glebe

Gorgeous, Waterfront Home Is Fabulous in Winter!

Relax in Urbanna, @ The Blue Tango!

Blue Heron WaterSide

Gunpowder Retreat

Beach Please! River cottage w/private beach & dock

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

Beautiful Waterfront Home-Private, Clean, Relaxing
Weekly house rentals

Mid-Century Modern: Direct Private Beach Access

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

Cove Point Beach Cabin

Historic Apothecary | 2 Master Suites | Old Town

Private Country Beach Retreat

1891 Coastal Charmer: fully renovated farmhouse

Upper Chesapeake Getaway

The Little House on Back Creek
Private house rentals

Waterfront Studio | Bikes & Kayaks | Beach Access

Pet Friendly,Fence, Waterfront 'Rivah Dog Cottage'

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

Spacious waterfront family retreat. Dogs welcome!

Madison Bay Club House

Away at the Bay: New Home on the Chesapeake Bay!

The Haven On The Chesapeake Bay

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

Waterfront Getaway with Dock

The Hideaway at Mill Creek

Cozy 2 bedroom home on wooded private lane

Cozy Riverside Cottage in the Woods

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Luxe Winter Retreat- 5 Star

Chesapeake Waterfront-Fire Pit- Hot Tub-Pier

Luxury Modern Home on Water+Hotub- Annapolis 25min
Quick stats about house rentals near Chesapeake Bay

Total vacation rentals
Explore 3,870 vacation rentals in Chesapeake Bay

Verified guest reviews
Over 141,530 verified reviews to help you choose

Family-friendly vacation rentals
3,150 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 1,470 rentals that welcome pets

Vacation rentals with a pool
420 properties feature pools

Rentals with dedicated workspaces
2,250 properties have a dedicated workspace

Wi-Fi availability
3,800 of Chesapeake Bay vacation rentals include wi-fi 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!
Destinations to explore
- Beach house rentals Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- RV rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Condo rentals Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guesthouse rentals Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Rentals with a fire pit Chesapeake Bay
- Rentals with a washer and dryer Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farmstay rentals Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Vacation home rentals Chesapeake Bay
- Beach condo rentals Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Rentals with a home theater Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Boat rentals Chesapeake Bay
- Loft rentals Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Villa rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Hotel rooms Chesapeake Bay
- Rentals with an accessible height bed Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Boutique hotels Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Campsite rentals Chesapeake Bay
- Rentals with an accessible height toilet Chesapeake Bay
- Rentals with pools Chesapeake Bay
- House rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Assateague Beach
- Haven Beach
- Buckroe Beach
- Jamestown Settlement
- Grandview Beach
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Piney Point Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Cape Charles Beachfront
- Wilkins Beach
- James River Country Club
- Little Creek Beach
- Wallops Beach
- Sarah Constant Beach Park




