
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.

Relaxing Waterfront Retreat w/Gameroom, Dog+EV OK
*Ask about our 3+ Night promotion* ☀️ Waterfront 🛶 Kayak/Paddleboard 👨🍳 Gas griddle ⛱️ 3 Community Beaches 🔥 Fire pit 🐶 Dogs OK (Max 2) 🎯 Gameroom ⚡️EV Outlet Relax - Star Gaze - Kayaks/Paddleboard - Hike - Fish - Swim - Beach & more! If you're looking to take a break or connect with nature, the Riverside Retreat in Montross, VA offers a peaceful sanctuary that is perfect for families, small groups, & couples Book your getaway today or ❤️ us for next time!

Private Waterfront Home W/ Hot Tub, Dock & Kayaks
Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

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.

"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.

Beach Please! River cottage w/private beach & dock
Come unwind at "Beach, Please!" Our renovated cottage on the river with a private beach and dock is waiting for you! What's there to do? There's boating, fishing, crabbing, bird watching, tanning, and hammock-napping. Need more? Ok, antique shops, breweries, wineries, live music, crab boils and oyster fests. Still need more? Cornhole, can jam, horseshoes, hiking, and swimming and tennis at the community pool. That's not all, so just trust us - you will LOVE your time in Montross, Virginia!

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.

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.

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.
Popular amenities for house rentals near Chesapeake Bay
House rentals with a pool

The Glebe

Gorgeous, Waterfront Home Is Fabulous in Winter!

Blue Heron WaterSide

The Rosé Retreat: Fireplace-Screened Porch-RELAX

Gunpowder Retreat

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

Magical wooded cottage pool +priv hottub walk2town

The Little Gypsy BoHome
Weekly house rentals

Private Country Beach Retreat

1891 Coastal Charmer: fully renovated farmhouse

Sunset Breezes - quiet waterfront retreat

Upper Chesapeake Getaway

Elegant & Authentic Annapolis

The Little House on Back Creek

Spacious Gorgeous Waterfront Home with Sunset View

Kent Island Waterfront Home with Amazing Sunsets
Private house rentals

Waterfront Studio | Bikes & Kayaks | Beach Access

Pet Friendly,Fence, Waterfront 'Rivah Dog Cottage'

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

Mid-Century Modern: Direct Private Beach Access

Spacious waterfront family retreat. Dogs welcome!

Madison Bay Club House

The Haven On The Chesapeake Bay

Erica's Place Wonderful Winter Waterfront sleeps 8
Pet-friendly house rentals

Water Oaks at Chic's Beach

Waterfront Getaway with Dock

Church Creek Charm (close to Blackwater Refuge)

The Hideaway at Mill Creek

Cozy 2 bedroom home on wooded private lane

Kent Island Escape

Chesapeake Waterfront-Fire Pit- Hot Tub-Pier

Waterfront Cottage in Colonial Beach at Placid Bay
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 and kid-friendly amenities

Pet-friendly accommodation
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

Wi-Fi availability
3,840 of Chesapeake Bay holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
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- First Landing State Park
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