Places to stay near Chesapeake Bay

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Top-rated holiday rentals near Chesapeake Bay

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
The vintage A-frame home is nestled amongst trees, featuring a deck with a canopy in the foreground. A stone path leads to the entrance, where large windows allow for ample natural light. The surrounding landscape is adorned with greenery and decorative plants.
Cabin in Lusby
4.91 out of 5 average rating, 234 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Top guest favourite
A winding gravel pathway is illuminated by soft lighting, bordered by lush greenery. String lights are hung above, casting a warm glow over the area, which is surrounded by trees and plantings. A staircase leads to an elevated area in the background.
Guest house in Gloucester County
4.98 out of 5 average rating, 202 reviews

Modern Cabin w/ Hot Tub, Fire Pit, Creekside views

Escape to this beautifully remodeled guest cottage, designed for an unforgettable stay. Nestled in a serene 6.5-acre setting with private creek views, it's just minutes from shopping, breweries, and dining. Wake up to breathtaking scenery, unwind in a peaceful setting, and enjoy modern amenities. Relax by the fire pit or soak in the hot tub. Perfect for a romantic retreat or a fun-filled family getaway in the Historic Triangle. Unmatched comfort, charm, and relaxation—your perfect escape awaits!

Top guest favourite
A serene view of the water showcases the Rappahannock River and surrounding landscape. The horizon blends various shades of blue with green grass and patches of marshland, inviting a sense of tranquility. Wisps of clouds drift across the expansive sky.
Guest house in White Stone
5 out of 5 average rating, 282 reviews

Waterfront Guesthouse II on the Rappahannock

The “Beach House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has beautiful water views and includes access to our private beach & dock (with guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with large shower and a covered patio. The 2nd floor features a large loft bedroom with a queen bed.

Top guest favourite
A modern houseboat is anchored at the dock, featuring a covered deck with two lounge chairs. Large windows offer views of the waterfront and allow natural light into the interior. The structure sits on wooden stilts above calm waters, showcasing a serene boating environment.
Houseboat in Kent Narrows
4.97 out of 5 average rating, 178 reviews

Cass-N-Reel Luxury Houseboat

Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With 1 bedroom, 1 bathroom, and a gorgeous covered rear facing deck; this is the ultimate couples retreat! 9 waterfront/waterview bars/restaurants within walking distance! Get a taste of what the eastern shore has to offer. Minutes from the Chesapeake Bay Bridge and a short drive to Annapolis, D.C., St. Michaels, and Ocean City. Come stay and live like a local! NO Fishing/Crabbing on property

Top guest favourite
A wooden deck is shown overlooking a serene pond, framed by lush trees. A dining table with chairs is set for outdoor enjoyment, while soft natural light reflects off the water's surface, creating a peaceful ambiance.
Farm stay in Onancock
4.99 out of 5 average rating, 309 reviews

Private romantic pet friendly waterfront cottage

On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

Top guest favourite
A comfortable living area is framed by large windows showcasing a vibrant sunset over the water. Soft furnishings include two chairs with decorative pillows and a coffee table. Plants are positioned thoughtfully, enhancing the serene atmosphere.
Home in North Beach
5 out of 5 average rating, 164 reviews

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**

Top guest favourite
A bright sun porch features a round glass dining table surrounded by four light-colored chairs. Large windows provide views of the waterfront, allowing natural light to fill the space. A cozy seating area is visible in the background, offering a serene atmosphere.
Home in Leonardtown
5 out of 5 average rating, 143 reviews

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.

Top guest favourite
The exterior entrance of a converted corn crib features natural wood siding and a gabled roof. Large double doors framed by lantern-style lights open into a welcoming space, complemented by potted plants on either side. Lush green trees and a gravel path are visible in the surrounding landscape.
Guest house in Easton
4.99 out of 5 average rating, 635 reviews

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

Top guest favourite
Two classic white Adirondack chairs are positioned on a grassy bank overlooking the calm water of the Rappahannock River, framed by gently swaying trees. The sky displays a soft transition of colors as the sun sets, creating a serene and inviting view.
Home in Locust Hill
4.97 out of 5 average rating, 160 reviews

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.

Guest favourite
A charming two-story cottage is set on a lush green lawn, with a clear view of the Chesapeake Bay in the background. The cottage features large windows and a sloped roof, with a small wooden addition on one side, surrounded by well-maintained grass.
Tiny home in Cape Charles
4.98 out of 5 average rating, 340 reviews

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

Guest favourite
A serene view of a cove with gentle waves lapping against a sandy shore. The calm water reflects the clear blue sky and nearby greenery. Footprints are visible in the sand, leading toward the water's edge.
Cottage in Reedville
4.91 out of 5 average rating, 214 reviews

"Dragonfly" Waterfront Cottage on Chesapeake Bay

Bayfront beach vacation? Kayak out to dolphins? Breathtaking sunrises & sunsets? Yes, please! Relaxation and fun await at 'Dragonfly', a gorgeous cottage right on the Chesapeake Bay with spectacular views from every room. Nestled on acres and acres of waterfront, this magical property has its own cove for all the swimming, kayaking, SUP boarding and fishing you can manage. If you love nature, bring your water shoes and sense of adventure and we will take care of the rest!

Top guest favourite
A scenic view of a sunset over the water, with a silhouette of a person kayaking. Adjacent, a cozy seating area is set up around a fire pit, surrounded by trees. In the foreground, a table with wine and glasses is shaded by a red umbrella, beside a hot tub.
Home in Dameron
4.98 out of 5 average rating, 124 reviews

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 holiday rentals near Chesapeake Bay

Frequently Asked Questions

  • Where is Chesapeake Bay located?

    Chesapeake Bay lies along the east coast of the United States, stretching between Maryland and Virginia. The bay connects surrounding rural landscapes, waterfront communities, and historic towns to the Atlantic Ocean.

  • When is the best time to visit Chesapeake Bay?

    Late spring and early fall are often recommended for fewer crowds and comfortable temperatures around Chesapeake Bay. These periods typically bring mild weather, colorful scenery, and chances to enjoy outdoor activities or local festivals.

  • What are some things to do near Chesapeake Bay?

    Around Chesapeake Bay, you can explore historic towns, nature trails, and maritime museums, or join boating, fishing, and kayaking excursions. Local seafood spots, waterfront parks, and seasonal farmers' markets are frequently suggested for those wanting to connect with the region’s character.

  • How is the weather near Chesapeake Bay?

    Chesapeake Bay experiences chilly winters around 32–47°F (0–8°C) and warm, humid summers near 71–85°F (22–30°C), with rainfall spread throughout the year. Spring and fall usually bring mild temperatures and breezy days, making outdoor activities enjoyable in those seasons.

Quick stats about holiday rentals in Chesapeake Bay

  • Total holiday rentals

    Explore 6,840 holiday rentals in Chesapeake Bay

  • Verified guest reviews

    Over 295,140 verified reviews to help you choose

  • Family-friendly holiday rentals

    4,550 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 2,680 rentals that welcome pets

  • Holiday rentals with a pool

    790 properties feature pools

  • Rentals with dedicated workspaces

    3,800 properties have a dedicated workspace

  • Wifi availability

    6,630 of Chesapeake Bay holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chesapeake Bay rentals

  • 4.8 Average rating

    Chesapeake Bay stays are highly rated by guests – averaging 4.8 out of 5!

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