Guesthouse vacation rentals near Chesapeake Bay

Guesthouse in Gloucester County

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.

Stylish Creekside Cabin w/ HotTub, Parklike 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!

4.98 out of 5 average rating, 242 reviews

Guesthouse in White Stone

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.

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.

5.0 out of 5 average rating, 319 reviews

The entrance of the guest cottage is framed by a charming picket fence, featuring a blue door and a welcoming porch. A small table with two chairs and an umbrella is situated on a wooden deck, surrounded by lush greenery.

4.9 out of 5 average rating, 363 reviews

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

4.95 out of 5 average rating, 187 reviews

A welcoming covered porch features two white chairs at the entrance of a pink home. Well-maintained shrubs and seasonal flowers border the porch area, while natural light streams through large windows, enhancing the cheerful exterior surrounded by greenery.

Guesthouse in Galesville

Nautical Charm and Relaxing Waterview!

Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still in close proximity to Washington DC, Annapolis and Baltimore! Situated in a charming waterfront and sailing community, this separate and private unit has: parking, 1 bath, queen bed, kitchenette (limited-no range), TV, high speed WiFi and Bluetooth speaker. Wake up to the cluck cluck of our four resident chickens who are tucked away in their attractive coop. Sit on the porch and take in the view!

4.99 out of 5 average rating, 144 reviews

A cozy living area features a spacious sectional couch adorned with patterned cushions. A wooden coffee table sits centrally, with a decorative rug beneath. A brick fireplace is present, flanked by windows allowing natural light, and a green door leads to the exterior.

Guesthouse in Cambridge

Rosses Chance Guest House

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

4.99 out of 5 average rating, 657 reviews

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.

Guesthouse in Easton

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.

4.94 out of 5 average rating, 186 reviews

A view from the property shows a grassy area leading to the water. A screened porch is visible, providing a tranquil space. The river reflects the blue sky and fluffy clouds, with trees lining the opposite bank. A wooden dock extends into the water.

Guesthouse in Bushwood

Little House by the water

Serenity - Privacy - Beauty - This little house by the water has it all. New Sealy queen size mattress, well equipped kitchen, Cuisinart coffee maker, full oven, glass topped stove, new refrigerator, and fully screened porch with water view. Perfect for 1 or 2 adults looking to get off the grid and recharge. In St. Mary's County,MD, just 90 minutes south of Washington DC. However, the space is small and it is really a studio apartment as I think the pictures make evident.

Guesthouse in Stevensville

The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.

Waterfront-View of Bay from your Bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

4.99 out of 5 average rating, 364 reviews

4.99 out of 5 average rating, 119 reviews

A red barn-style building is positioned on a lush green lawn, surrounded by trees and residential structures. A porch is visible on the upper level, and a colorful wheel mural decorates the front. A gravel path leads to the entrance.

Guesthouse in Cambridge

The Loft at Sailor's Retreat. Waterfront Apartment

Romantic waterfront loft for couples in a charming barn. Relax in a cozy king bed, enjoy a full bath, and cook in a well-equipped country kitchen. Sip wine or coffee on your private balcony overlooking the water, or explore the creek with kayaks and paddleboards. Share the pool (Apr–Oct), lawn games, and game room with one other unit. Perfect for a peaceful getaway to unwind and reconnect. Designed as an adults-only retreat—no children please.

5.0 out of 5 average rating, 201 reviews

Guesthouse in Gloucester

Cozy Fall Retreat - Creek Views & Fire Pits

A cozy waterfront escape tucked into 10 wooded acres above Bland Creek. Perfect for crisp fall days and peaceful evenings. - Elevated screened porch with colorful water and wooded views - Creekside fire pits for crisp fall nights - Dock, kayaks, fishing, and direct water access - Outdoor dining and hammocks beneath the trees - Immaculately clean and thoughtfully stocked for a seamless stay - Just 15 minutes from downtown Gloucester

4.94 out of 5 average rating, 587 reviews

A rustic cabin is surrounded by lush trees, with a welcoming porch showcasing seating. The exterior features wooden panels and large windows, allowing natural light to fill the interior while maintaining privacy. A gravel path leads to the entrance, enhancing the natural landscape.

Guesthouse in Saluda

Wooded Cabin retreat on fresh water pond

If your looking for a quiet place in a wooded setting, this is it. Cabin has view of private 7.5 acre pond, deck and walking trail to the scenic Dragon Run, with canoe portage. You are welcome to bring your canoe/kayak. Bird watchers, wildflower enthusiasts will enjoy what the Dragon Run has to offer. If shopping or history is your interest, this cabin is only 45 min away from Williamsburg, and will give you a place to relax.

Guesthouse in St. Leonard

An entryway leads through tall grasses and dunes to a sandy beach covered with colorful umbrellas. The clear blue sky and calm water create a serene setting, while beachgoers enjoy the day in the distance.

Studio on the Bay.

This studio apartment is in walking or driving distance to three private beaches in our community. There is 1 bedroom with a queen size bed, spacious bathroom and closet. The living room has a pull out full size bed and a kitchenette. Coffee, teas, beach chairs, are provided. Wanna fish??? Ask Joey about Fish Taxi! Fifteen minutes from Solomons Island (home of the Tiki Bar). An hour or so from DC, Annapolis and Waldorf.

4.97 out of 5 average rating, 125 reviews

Popular amenities for guesthouse rentals near Chesapeake Bay

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

4.93 out of 5 average rating, 121 reviews

A serene river view is captured at sunset, showcasing vibrant hues of orange, pink, and purple across the sky. A wooden pier extends into the water, backed by silhouetted trees. The calm surface reflects the colorful sky, creating a tranquil atmosphere.

Guesthouse in Gloucester

Clay Bank River Front Cottage

Superhost

The interior of the cottage features a vaulted wooden ceiling with beams, creating an open atmosphere. A spacious sectional sofa faces a wood-burning stove. The kitchen is equipped with modern appliances, while light streams through large windows draped in sheer curtains.

Guesthouse in National Harbor

Urban Cottage, MD minutes from DC/National Harbor

4.92 out of 5 average rating, 775 reviews

Guesthouse in Stevensville

The side view of a historic brick house is shown, featuring a gabled roof with multiple chimneys. The whitewashed brick exterior contrasts with the green trim around the windows and door. The well-maintained lawn surrounds the structure, complemented by mature trees in the background.

Circa 1700 Chesapeake Colonial Home

4.92 out of 5 average rating, 195 reviews

4.93 out of 5 average rating, 275 reviews

A white stairway leads to the entrance of the guest house, surrounded by trees and natural landscaping. The calm waters of Onancock Creek are visible in the background, with a glimpse of moored boats and the shoreline beyond.

Guesthouse in Onancock

Waterfront Getaway

4.96 out of 5 average rating, 112 reviews

A dock extends over the water, illuminated by blue lights on the posts. The calm bay reflects the night sky, while distant city lights create a soft glow on the horizon. Rocks line the base of the dock, enhancing the natural setting.

Guesthouse in Hampton

Fantastic Getaway

Guesthouse in Gloucester Point

A warm living area is captured, featuring a comfortable leather couch and a cozy yellow chair. A bottle of wine and two glasses are placed on the counter next to a sign inviting guests, while soft lighting creates a welcoming ambiance.

BlueBird Nest

4.95 out of 5 average rating, 174 reviews

4.85 out of 5 average rating, 157 reviews

An open-concept guesthouse space is observed, featuring a spacious bed with crisp white linens and a decorative sign reading 'SWEET TEA' on the wall. A cozy seating area includes a sofa and side table. A small kitchen area is visible, equipped with basic amenities.

Guesthouse in Oxford

Bonfield Bungalow

4.96 out of 5 average rating, 181 reviews

Guesthouse in Arlington

Little Green Guesthouse

Guest house rentals with a patio

Guesthouse in Pocomoke City

A comfortable living area features a spacious sectional sofa with decorative pillows, paired with two accent chairs. Light-colored walls and carpeting create a neutral backdrop, while a television rests on a wooden stand opposite the seating. Natural light is offered through nearby windows.

2 Bedroom Apartment

4.94 out of 5 average rating, 189 reviews

4.99 out of 5 average rating, 315 reviews

A charming stone cottage features a red front door with black shutters framing the windows. A friendly dog stands on the stone path, surrounded by lush greenery. The staircase leading to the studio is visible on the right side, along with decorative elements of the owner's residence.

Guesthouse in Towson

Cute cottage studio with full kitchen and laundry

4.96 out of 5 average rating, 343 reviews

The spacious studio features a queen-sized bed adorned with yellow accents, surrounded by lush greenery. Natural light streams through multiple windows, illuminating modern furnishings, including a kitchenette and a coffee station. A cozy rug lies below, enhancing the inviting atmosphere of the room.

Guesthouse in Richmond

Funky, Private Guesthouse Near Richmond Food Scene

Guesthouse in Catonsville

An outdoor seating area features two vibrant red chairs placed on a mulch bed. A small table stands between the chairs, surrounded by greenery and decorative plants. A bright red door provides an inviting entrance, while a vintage wrought iron fence encloses the area for privacy.

Fox Cottage *Pet Friendly*

4.95 out of 5 average rating, 354 reviews

4.9 out of 5 average rating, 212 reviews

The studio features a spacious layout with a queen-size bed adorned in vibrant teal bedding. A twin bed is positioned nearby, complemented by decorative pillows. Natural light fills the room, accentuated by large windows on either side. A comfortable couch and side tables complete the inviting setting.

Guesthouse in Alexandria

The Guest Suite

4.96 out of 5 average rating, 100 reviews

Guesthouse in Frederick

Private Woodland Retreat | Near Downtown Frederick

4.95 out of 5 average rating, 132 reviews

A two-story accessory dwelling unit features a combination of brick and siding exterior, with large windows allowing natural light. A set of stairs leads to the entrance, and the surrounding area is shaded by trees, contributing to a tranquil outdoor setting.

Guesthouse in Brookland

DC Treehouse - Charming, private 1-bdrm ADU in DC

4.99 out of 5 average rating, 163 reviews

Guesthouse in Richmond

Spacious, pet-friendly nature retreat | The Bohive

Guest house rentals with a washer and dryer

A spiral staircase leads to a lofted sleeping area in a well-lit living space. Warm wood tones are present in the furniture and flooring. A small kitchen area is visible, along with a dining table set for four. Lighting fixtures enhance the modern feel.

4.99 out of 5 average rating, 165 reviews

Garden View, 1 Bedroom and a Loft.

4.95 out of 5 average rating, 138 reviews

Guesthouse in Lewes

Crow’s Nest • 1 BR Lewes Guest Apt – Bike to Beach

Guesthouse in Cape St. Claire

A single-story home is positioned at the end of a paved driveway, surrounded by greenery. The exterior features a brown roof, light-colored siding, and multiple windows. A white bench is located in front of the house, offering a place to relax in the garden-like setting.

"L'auberge du Cape Saint Claire"

4.84 out of 5 average rating, 231 reviews

The exterior of the remodeled guest cottage is shown, featuring a brick façade with two symmetrical entries. Each entry is framed by white columns and topped with a maroon awning. Large windows with white trim offer views into the interior, while a gravel parking area is visible in the foreground.

4.92 out of 5 average rating, 133 reviews

Private Cottage on gated estate

Guesthouse in Southwest Washington

A modern kitchen is equipped with stainless steel appliances and navy blue cabinetry. White countertops provide a clean look, while two pendant lights hang over the island. Natural light floods in from the adjacent space, revealing glimpses of the outdoor area through large sliding doors.

Walk to museums and restaurants. Free Parking.

4.96 out of 5 average rating, 340 reviews

The exterior of a charming carriage house apartment is presented, featuring a well-maintained garden, stone pathway, and illuminated by string lights. Two adirondack chairs and a fire pit enhance the inviting outdoor space, with lush grass and mature trees providing a natural backdrop.

4.95 out of 5 average rating, 118 reviews

Carriage House near Navy Stadium, parking, pets

Guesthouse in Rehoboth Beach

The structure features a modern design with a wooden exterior and large glass windows. A spacious deck is accessible from the upper level, surrounded by lush greenery. The ground floor includes a stone facade with garage doors, creating a harmonious blend with the natural surroundings.

The Winkler

4.88 out of 5 average rating, 372 reviews

A modern kitchen area is displayed, featuring light cabinetry and sleek stainless-steel appliances. A dining table with two stools is positioned in front of the kitchen, complemented by a potted plant. Natural light illuminates the open space, highlighting the wood flooring and inviting design.

4.88 out of 5 average rating, 217 reviews

Annapolis Guesthouse - Completely Separate Space

Other guesthouse vacation rentals

A spacious living area features a large leather sofa facing a flat-screen TV and a coffee table. A decorative guitar rests beside the couch. A bar stool adds seating, while a window introduces natural light, highlighting the contemporary decor.

4.97 out of 5 average rating, 267 reviews

Comfortable Cottage Near Downtown Annapolis

4.95 out of 5 average rating, 319 reviews

A cozy cottage guesthouse is surrounded by trees, featuring a welcoming entrance with a wooden door. Large windows with grid patterns allow natural light to illuminate the exterior, and a small stone pathway leads to the door, framed by a landscaped yard.

Guesthouse in Ocean City

Cozy Private Cottage Near The Beach

The image illustrates a charming tiny home nestled among trees, featuring a spacious bluestone patio with outdoor seating and a fire pit. In the background, a gas grill is positioned nearby. Lush green grass surrounds the area, creating a serene and inviting setting.

4.95 out of 5 average rating, 210 reviews

Lil’ House - A Serene Tiny Home Experience

4.96 out of 5 average rating, 28 reviews

Guesthouse in Hague

Bell House

Superhost

Guesthouse in Cape Charles

Eden Guest Suite on Lake Allure

4.97 out of 5 average rating, 68 reviews

Superhost

Guesthouse in Solomons

Sunrise Veranda Back Creek Villa with Sunroom

4.94 out of 5 average rating, 32 reviews

Guesthouse in Stevensville

Private Guesthouse | 7-acres | Near wedding venues

5.0 out of 5 average rating, 25 reviews