Cottage rentals near Chesapeake Bay

4.94 out of 5 average rating, 266 reviews

A warm living area features a brown leather sofa adorned with decorative pillows. A round ottoman adds a pop of color, while a textured area rug anchors the space. Natural light filters through green curtains, complemented by stylish lighting fixtures and wall artwork.

Cottage in Heathsville

HedgeRow, Deer Haven in the NNK- Dock & Boat Ramp

We welcome you to stay at "HedgeRow" a deer haven on the Great Wicomico River, located in a hidden corner of the popular Northern Neck of Virginia. You'll be delighted in all the area and this charming listing has to offer. Located just 10 minutes from Kilmarnock, enjoy wineries, shopping and local attractions nearby. Bring your boat, kayaks, fishing rods or friends, then relax in all things that encompass river life. There is a boat ramp and fishing dock available for guests use (Adults Only).

4.95 out of 5 average rating, 165 reviews

A Victorian cottage sits on a private island, surrounded by a serene lake. The green roof contrasts with the pastel exterior, while a footbridge leads to the shore. Lush grass and scattered trees create a peaceful landscape, with distant water views enhancing the setting.

Cottage in Hacksneck

Pretty Byrd Cottage, a Victorian Bayfront Getaway!

Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

4.94 out of 5 average rating, 191 reviews

A spacious deck offers breathtaking views of the water at sunset, with a stunning orange and pink sky. Four Adirondack chairs are arranged around a brown wicker coffee table, complemented by striped cushions. The serene water reflects the evening sky, creating a tranquil atmosphere.

Cottage in Onancock

A "True" Chesapeake Bay Waterfront Experience!

Get away from it all... The Thicket Point Fish Camp is a true Chesapeake Bay waterfront property and the perfect place to escape for the best of the Eastern Shore. Located just 5 miles from downtown Onancock, VA, and everyday conveniences, this property is one of a kind! This is the "Sunset House" expanded and completely renovated in May 2018, It is complemented by our "Bayside House" - also available on Airbnb. Be ready for the smell of the salt air and to enjoy million-dollar sunsets!

4.96 out of 5 average rating, 274 reviews

Cottage in Leonardtown

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

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.

4.91 out of 5 average rating, 233 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!

4.96 out of 5 average rating, 295 reviews

Cottage in Charlestown

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

4.97 out of 5 average rating, 135 reviews

A serene view of a wooden dock extending into calm waters, reflecting hues of blue, orange, and pink from the sunset. Soft clouds drift in the sky, complementing the tranquil ambiance of the waterfront scene.

Cottage in Leonardtown

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks

Welcome to Sunset View Cottage. A spacious and bright two-level waterfront home with a private dock and beach access in Leonardtown, MD. Enjoy swimming off the dock and beach in the Potomac River. Full western views across the widest part of the river make for unbelievable sunsets. Your ideal family vacation, couples getaway, or work-from-home retreat just 90 minutes outside DC. Visit us on IG @sunsetviewcottage

4.99 out of 5 average rating, 107 reviews

Two white Adirondack chairs are positioned on a grassy area, facing a calm water view. A stone fountain stands nearby, and a wooden dock extends into the water, offering a serene atmosphere with trees lining the shore.

Cottage in Hollywood

Cottage on the Creek

The Cottage is perfectly perched alongside Cuckold Creek showcasing the beauty of Southern Maryland. Our home provides plenty of space for relaxing together with a water view everywhere you turn. Each space is set up to provide you with the comforts of home, so you can relax and enjoy being in the moment. Located in the heart of Hollywood, not too far from stores or restaurants, but still "away from it all". ✨

4.95 out of 5 average rating, 107 reviews

The charming exterior of a waterfront cottage, featuring a white picket fence and a welcoming front deck. Large windows allow for natural light, while vibrant surroundings enhance the coastal feel. The front porch is partially shaded by lush greenery, inviting relaxation and enjoyment of the outdoors.

Cottage in North Beach

Cozy Waterfront Cottage - Pet Friendly

Original waterfront cottage in North Beach is perfect for a small family or two couples. Beautiful sunrises and moonrises over the boardwalk from the front deck. Walk to restaurants and nightlife, stroll the boardwalk, chill on the beach or go to the spa or charter fishing in Chesapeake Beach. Pet friendly. Beach Passes, umbrella and chairs included. 2 bedrooms plus a twin daybed that pulls out to queen bed.

4.96 out of 5 average rating, 182 reviews

A view of the sunset over Chesapeake Bay is captured from the deck, with warm hues reflecting on the water. The scene includes a grassy area leading to the shoreline and a subtle silhouette of a dock in the background.

Cottage in Deale

Chesapeake Bay Cottage

Cottage Located directly on the Chesapeake Bay. Includes sandy beach, yard, a screened in porch and deck. Two Kayaks to enjoy. Two bedroom plus den. Two full baths. Fully equipped kitchen.Kurig coffee maker and regular available. Master bedroom -queen size mattress. Second bedroom -a full-size mattress (double) third bedroom -a twin day bed with twin pullout. Both twin size mattresses.

4.99 out of 5 average rating, 264 reviews

An aerial view highlights Rumbley Cottage's proximity to the shoreline and wetlands. The landscape features a mix of sandy beach, shallow waters, and expansive marshlands under a clear blue sky, offering a serene setting with natural beauty and tranquility.

Cottage in Westover

Rumbley Cottage on the Tangier Sound-Private Beach

Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. Many amenities: WE PROVIDE THE FIREWOOD AND STARTERS, kayaks, paddle boards, MB toiletries.

4.83 out of 5 average rating, 201 reviews

Cottage in Deale

Waterfront Cottage@ChesapeakeParadise Hot Tub/Dogs

Savor our three-bedroom Cottage in this peaceful western shore spot, enjoy two acres of green space, the pier, kayaks, swings, fire pit, shady lawns & sun-drenched loungers, local waterfront dining or eat in, close to Washington, D.C., Annapolis, & Baltimore at this honeymoon-worthy country-like micro-resort.

Popular amenities for cottage rentals near Chesapeake Bay

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.93 out of 5 average rating, 148 reviews

Cottage in Heathsville

Waterfront Cottage w Water Access, Sauna, Hot Tub

4.94 out of 5 average rating, 196 reviews

A tranquil beach scene presents soft sand leading to calm water, framed by an open sky dotted with clouds. A weathered log rests on the shoreline, while distant rocky formations add interest to the horizon.

Cottage in St. Leonard

Cozy Cottage, Hot Tub, BlockToBeach, 1hr to DC

Superhost

A shaded outdoor seating area is positioned on a wooden deck, facing the water. Comfortable blue cushioned chairs surround a matching sofa, with a white coffee table in the center. Lush greenery and a calm river view create a serene environment.

Cottage in Elkton

Sunset River Shack -amazing waterfront view

4.9 out of 5 average rating, 109 reviews

4.96 out of 5 average rating, 162 reviews

An aerial view captures the spacious backyard featuring a rectangular swimming pool surrounded by a concrete deck. Lounge chairs are placed by the poolside, with a well-maintained lawn and shrubs in the background. The two-story cottage is shown with a screened porch and a shaded area nearby.

Cottage in Chesapeake

The Cottage @ Captain Genes - Secluded Waterfront

4.97 out of 5 average rating, 381 reviews

Cottage in North Beach

Waterfront Cottage Near Herrington and North Beach

4.93 out of 5 average rating, 130 reviews

A serene private dock overlooks a calm cove, with vibrant kayaks stacked nearby. A simple bench provides seating, surrounded by lush greenery and mist rising from the water's surface, inviting relaxation and peaceful reflections.

Cottage in Montross

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach

4.87 out of 5 average rating, 116 reviews

A screened porch features a hanging bench swing with cushions in shades of blue and nautical motifs. A small chair stands nearby, adorned with a decorative pillow. Tall curtains frame the space, providing a relaxed and inviting atmosphere surrounded by greenery.

Cottage in Annapolis

Charming City Oasis. Walk to harbor, eateries.USNA

4.84 out of 5 average rating, 175 reviews

Cottage in Norfolk

902C Coastal King Retreat Steps from Beach + Sauna

Pet-friendly cottage rentals

Superhost

A sandy beach stretches along the water's edge, with a house featuring large windows nestled among green shrubs. A lighted pier extends into the water, where two children are playing. The clear sky and surrounding trees create a serene backdrop.

Cottage in Deltaville

Stunning Beachfront Cottage on the Chesapeake

4.78 out of 5 average rating, 164 reviews

4.92 out of 5 average rating, 119 reviews

The cottage is framed by a large flowering tree and surrounded by lush greenery. A spacious screened porch is visible in front, providing a cozy outdoor space. Daffodils bloom in the foreground, enhancing the rural setting on a peaceful landscape.

Cottage in Lottsburg

Charming Waterfront Home with Expansive Views

4.97 out of 5 average rating, 470 reviews

A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.

Cottage in Annapolis

Relaxing Water Views - Mill Creek Cottage

4.91 out of 5 average rating, 125 reviews

A serene sunset is captured over calm waters, with hues of orange and gold reflecting on the surface. Silhouettes of trees frame the scene, while a dock extends into the bay, creating a tranquil coastal atmosphere.

Cottage in Painter

Cottage by the bay location1/2 blockto the bay

4.93 out of 5 average rating, 116 reviews

An aerial view captures the farmhouse situated along the banks of Henry's Creek, surrounded by lush greenery. A dock extends into the water, providing access for outdoor activities. The rural landscape and nearby road are visible, emphasizing the peaceful setting.

Cottage in Kilmarnock

Creeks End Farmhouse

4.99 out of 5 average rating, 134 reviews

The view from the entrance displays a spacious deck leading to the water, framed by sturdy wooden supports. Two large doors provide access and natural light, highlighting the inviting outdoor space with chairs positioned for relaxation.

Cottage in Weems

The Crab Shack

4.84 out of 5 average rating, 100 reviews

The exterior of a two-story cottage is shown, featuring a blue metal roof and white siding. Blue shutters frame the windows. A small deck is visible in front, furnished with two adirondack chairs in bright green. A door centrally accesses the home.

Cottage in Wingate

Blue Crab Cottage: Remote+Nature+Fishing+Views

5.0 out of 5 average rating, 104 reviews

A modern kitchen layout is presented, featuring white cabinetry and a sleek countertop. High-end appliances, including a gas range and a refrigerator, are visible. A wooden cutting board and knife holder are positioned on the countertop, complemented by natural light filtering through a nearby window.

Cottage in Cobbs Creek

Waterfront w/Floating Dock, Kayaks~Family Home

Private cottage rentals

4.99 out of 5 average rating, 215 reviews

Cottage in Hague

Waterfront Cottage on the Potomac River

4.89 out of 5 average rating, 407 reviews

The cottage features a welcoming front porch with a flag gently waving. Lush greenery surrounds the entrance, complemented by a grassy lawn under a clear blue sky, creating an inviting approach to the home.

Cottage in White Stone

The Moore Cottage

4.98 out of 5 average rating, 164 reviews

Cottage in Annapolis

Weems Creek Cottage, Annapolis Waterfront

4.97 out of 5 average rating, 285 reviews

A welcoming cottage exterior features a covered porch with seating, light fixtures, and colorful plantings. A walkway made of stone leads to the entrance, and the surrounding landscape is highlighted by well-maintained grass and nearby neighboring homes.

Cottage in California

Cozy Little Cottage

A sandy beach borders calm waters, reflecting sunlight under a bright blue sky filled with clouds. Dark rocks and a grassy area play a role in the natural landscape, while distant structures along the shore suggest waterfront access.

4.91 out of 5 average rating, 235 reviews

Chesapeake Bay Beach Cottage

4.89 out of 5 average rating, 136 reviews

An inviting deck features a turquoise picnic table and comfortable seating with floral cushions, offering views of Cod Creek. Large windows span the cottage facade, allowing natural light to fill the interior. Surrounding trees provide a serene backdrop.

Cottage in Heathsville

Cottage with a view!

Superhost

4.93 out of 5 average rating, 161 reviews

Bull Neck Cottage

4.91 out of 5 average rating, 130 reviews

A charming cottage exterior showcases a well-maintained garden with colorful flowers lining the pathway. The front porch features a welcoming entrance, while large windows provide ample natural light. A white picket fence frames the lush greenery that surrounds the home.

Cottage in North Beach

Quiet Coastal Cottage Escape with Water Views

Luxury cottage rentals

5.0 out of 5 average rating, 125 reviews

A charming cottage is visible beside a clear pool, surrounded by well-maintained green lawns. Two shaded umbrellas stand over cushioned lounge chairs by the water's edge, creating a comfortable outdoor space for relaxation. The inviting pool reflects the bright sky, enhancing the serene atmosphere.

Cottage in Easton

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

4.98 out of 5 average rating, 200 reviews

A modern guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.

Cottage in St. Michaels

La Casita on Harris Creek, St. Michaels

4.99 out of 5 average rating, 220 reviews

A spacious kitchen with a large central island is featured, complemented by white cabinetry and stainless steel appliances. Natural light fills the room through the window, illuminating the dining area with a wooden table and blue chairs nearby, creating an inviting space for gatherings.

Cottage in Lewes

Ebb & Flow Beach House - Lewes Bay Beach Retreat

Cottage in Virginia Beach

The entrance to Unit 4 features a blue door framed by a white pergola. A shadow pattern from the structure falls across the light-colored deck, which includes several outdoor chairs. Fenced areas filled with greenery are visible in the background.

Stylish Beach Cottage w/ Pool • Walk to Boardwalk

4.87 out of 5 average rating, 160 reviews

Cottage in Rehoboth Beach

The exterior of the beach cottage features light gray siding with white trim and multiple windows. A set of steps leads to a welcoming entrance, bordered by landscaping that includes bushes and flowering plants. Sunlight brightens the scene, showcasing the cottage's inviting facade.

The Sandbar: Walk to the Boardwalk, Shops, & Sand!

4.98 out of 5 average rating, 105 reviews

5.0 out of 5 average rating, 119 reviews

The waterfront view captures a serene sunset over the canal, with soft golden light reflecting on the water. Lush grasses and reeds line the shore, enhancing the tranquil atmosphere. Nearby homes are silhouetted against the vibrant sky, creating a peaceful retreat.

Cottage in Sandbridge

Sanctuary on Sandpiper - Bayfront in Sandbridge

5.0 out of 5 average rating, 11 reviews

Cottage in Westover

Eastern Shore Private Sandy Beach & Crabbing dock!

A waterfront view features a peaceful beach with soft sand, bordered by rocky shorelines. The cottage's sunroom is visible, along with surrounding trees and other houses, creating a tranquil setting. Calm waters reflect the sky, enhancing the serene atmosphere.