Guest house holiday rentals near Chesapeake Bay

Guest house 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.

4.98 out of 5 average rating, 203 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!

4.94 out of 5 average rating, 140 reviews

A bright and open living space features a striped sofa with a wooden coffee table and decorative wicker baskets. A dining area with modern chairs is complemented by a patterned wall art piece. Natural light streams in from the doorway, enhancing the inviting atmosphere.

Guest house in Herndon

Modern Sugarland Apt-Metro/IAD

Welcome to our stylish basement apartment, perfect for modern travelers. Whether you're here for work or leisure, this space has you covered. Situated minutes from the Metro, Airport, and major work centers. The apartment features a desk with dual monitors, keyboard, mouse, and 1GB internet. At night, relax in the plush king-size bed. A convertible futon couch with a 65-inch TV, awaits your binge-watching sessions. A washer/dryer and full kitchen, w/refrigerator and stove complete the space.

Guest house 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.

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.

4.99 out of 5 average rating, 131 reviews

Spacious nature retreat close to city | The Bohive

Escape to The Bohive off I-95, a charming 1200 sq ft studio, conveniently located just off the interstate & minutes from downtown. On a private “nature reserve”, this is the perfect place to unwind & recharge. Inside, you'll find a comfortable king bed & kitchenette (no stove). The cozy living area has a smart TV, great for relaxing after a long day of exploring. Enjoy coffee on the private deck or immerse yourself in nature before heading out. Great spot for road trippers! STR2024-00002

4.9 out of 5 average rating, 323 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.

Guest house in Annapolis

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.

The living area features a comfortable sectional couch, surrounded by art pieces on light grey walls. A coffee table sits atop a textured area rug, while TV screens are positioned for easy viewing. Access to a private entrance is visible in the background.

4.95 out of 5 average rating, 467 reviews

Vibrant + Artsy - mins to NavyYard, CapHill, Dtown

1 bed 1 bath bright artsy basement unit with private rear (alley) entrance in colorful urban Anacostia neighborhood. Short term rental created to be your home away from home for however long you stay. Conveniently located 2 blocks to multiple bus stops, 1 mile from Anacostia Metro station, and a 10-minute ride to Downtown DC. Sleeps up to 5 but most optimal for 2 people. (Starting July 13, the space will only be available for up to 4 people as the yellow futon sofa will be removed.)

4.99 out of 5 average rating, 131 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.

Guest house 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, 636 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.

Guest house 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.

4.93 out of 5 average rating, 170 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.

Guest house 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.

4.99 out of 5 average rating, 280 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.

Guest house in Towson

Cute cottage studio with full kitchen and laundry

Warm and inviting private upstairs studio with off-street parking, full kitchen, laundry, electronic fireplace, rainhead shower and deck with tranquil garden in the Riderwood area of Towson. Studio is situated next to owner's stone cottage, and is tucked away at the back of 2.5 acres with private bridge and creek. Centrally located to shops, galleries, walking and biking trails, Lake Roland, Baltimore, DC and PA. Especially suitable for a restorative or romantic getaway.

Guest house 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.

4.87 out of 5 average rating, 342 reviews

The Winkler

The Winkler is a comfortable fully equipped 1BR / 1 BA apartment above our detached 3 garage @ The Tree House. Nestled in lush trees and landscaping in the Rehoboth Beach Country Club. Named after Henry Winkler who played the Fonz on Happy Days, (because he lived in the apt. over the Cunningham's garage). The apartment offers privacy and separation from the main house. Giving you an opportunity to make it your home away from home at the beach. Come Enjoy!!

Guest house 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.

4.99 out of 5 average rating, 318 reviews

Waterfront-View of Bay from your Bed-Steamy Sauna

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.

Popular amenities for guest house rentals near Chesapeake Bay

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

4.92 out of 5 average rating, 101 reviews

A comfortable living area features a light grey sofa and an accent chair, arranged around a wooden coffee table. A decorative wall art piece with floral designs adorns the wall. Soft lighting from a stylish chandelier enhances the welcoming atmosphere.

Guest house in Lusby

Garden Cottage - Fire Pit and Grill near Beaches

Guest house in Ocean City

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.

4.94 out of 5 average rating, 301 reviews

Cozy Private Cottage Near The Beach

Guest house in Myersville

A two-story cottage is set amidst lush greenery, featuring a large upper deck that offers views of the surrounding woods. Colorful azaleas and shrubs enhance the entrance, while a gravel drive leads to the property, surrounded by trees exhibiting signs of spring.

4.94 out of 5 average rating, 260 reviews

Spruce Run Cottage, Farm stay on Catoctin Mountain

An open dining and living area is showcased, featuring a modern white dining table with grey chairs. A large sectional sofa provides seating, accompanied by a television mounted on the wall. Natural light filters through the window, enhancing the airy ambiance of the space.

4.98 out of 5 average rating, 276 reviews

Gorgeous Two-Story Guesthouse w/ Driveway & W/D

Guest house in Chincoteague

The exterior of a cozy cottage is shown, featuring a wooden porch with a bench and an outdoor shower. Greenery surrounds the area, and a potted plant sits near the entrance. A stone path leads to the main door, inviting guests into the space.

4.96 out of 5 average rating, 114 reviews

Cozy Beach Cottage

Guest house in Fort Washington

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.

4.93 out of 5 average rating, 761 reviews

Urban Cottage, MD minutes from DC/National Harbor

4.89 out of 5 average rating, 126 reviews

Guest house in Annapolis

Cozy Retreat w/Private Beach Access

The open-layout kitchen and living area features modern appliances, including a stainless steel refrigerator and stove. Natural light floods in through a skylight, highlighting a cozy seating area with a blue sofa and decorative furniture. A dining table with pink chairs is also present.

4.99 out of 5 average rating, 129 reviews

Capitol Hill Carriage House

Guest house rentals with a patio

A bright sleeping area features a comfortable queen bed with layered pillows and a textured throw. A work desk with an ergonomic chair is positioned near a window, allowing soft natural light to illuminate the space. Bamboo shades provide privacy while windows offer views of the outdoors.

4.94 out of 5 average rating, 124 reviews

Casita Del Ray — Alexandria Studio Apartment

Guest house 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.

4.93 out of 5 average rating, 129 reviews

BlueBird Nest

Guest house in Mount Airy

An open living area features a comfortable seating arrangement with a light-colored sofa and a coffee table atop a soft rug. The kitchen is visible in the background, defined by wooden cabinetry and modern appliances, with natural light illuminating the space.

4.96 out of 5 average rating, 146 reviews

Treasured Hideaway on the Hill

A spacious bedroom featuring a comfortable bed with soft linens and a blue accent blanket. A wooden bench sits at the foot of the bed. To the side, a dedicated workspace with a chair is present, along with decorative wall art and large windows allowing natural light.

5 out of 5 average rating, 100 reviews

Central Location *Private *Wi-Fi *Free parking

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.

4.95 out of 5 average rating, 121 reviews

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

Guest house 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.

4.96 out of 5 average rating, 305 reviews

Fox Cottage *Pet Friendly*

The entrance area features a small wooden desk paired with a grey chair, positioned against a neutral-toned wall. A sleek white chair is situated nearby. A door with a window leads to the outside, complemented by a potted plant on a windowsill and a wall mirror.

4.88 out of 5 average rating, 276 reviews

Adorable English Basement on 15th St

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.

4.9 out of 5 average rating, 176 reviews

The Guest Suite

Guest house rentals with a washing machine and dryer

A spacious living area features a light gray sectional couch adorned with patterned throw pillows. A round wooden coffee table sits on a geometric rug, while two windows allow natural light to filter in, illuminating the comfortable space.

5 out of 5 average rating, 253 reviews

Sunny, Stylish Carriage House with a View

A bright living area is highlighted by a teal sofa, paired with a low coffee table. A dining table is set with green chairs and a vase of flowers. Natural light filters through two large windows, and a bed is visible in the background, draped in neutral bedding.

5 out of 5 average rating, 134 reviews

Studio Apartment in the Heart of Union Hill

4.99 out of 5 average rating, 108 reviews

An open living area features a spacious bed with warm bedding and a comfortable pop-up sleeper sofa. Sunlight enters through large windows, illuminating the wood floor and neutral-colored walls. A cozy area rug adds texture, while a small dining table is visible in the background.

Guest house in Pomfret

Adorable Large Efficiency Getaway Retreat

A spacious living area is highlighted by a large flat-screen television and a comfortable blue couch adorned with red accent pillows. A dining island with high-backed chairs is visible, leading to a bright kitchen equipped with modern appliances and ample cabinetry.

4.97 out of 5 average rating, 106 reviews

NoVA guest house

The inviting studio features a full-size bed dressed in a vibrant yellow blanket, complemented by decorative pillows. A modern wall art piece is displayed above the nightstand, and a doorway leads to a well-appointed bathroom, visible in the background.

4.92 out of 5 average rating, 199 reviews

Charming Studio with Free Parking & Private Entry

Guest house in Williamsburg

4.98 out of 5 average rating, 409 reviews

Freedom Cottage /King Bed-Jamestown/ Busch Gardens

5 out of 5 average rating, 222 reviews

The exterior of a blue cottage is presented, featuring large glass doors that open onto a spacious lawn. Two wooden chairs are positioned on a stone patio, surrounded by green grass and trees, offering a serene outdoor setting.

Guest house in Arlington

Private Sunny Cottage with King Bed + Yard / Patio

4.99 out of 5 average rating, 152 reviews

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.

Guest house in Annapolis

Garden View, a spacious 1 bedroom with loft.

Other guest house holiday rentals

A spacious sleeping area features a wooden bed with a striped blanket, complemented by large arched windows that allow natural light. A wooden dresser is positioned against one wall, while a cozy armchair and a small side table create additional seating.

4.97 out of 5 average rating, 522 reviews

Outdoor Explorer's Dream Studio,James River Park

5 out of 5 average rating, 24 reviews

A cozy living space features a brown reclining sofa paired with a black accent chair. A wooden coffee table centers the room, and a large art print is mounted on the wall. A full kitchen showcases modern appliances and ample counter space, illuminated by overhead lighting.

Guest house in Cambridge

Cozy Guest House Near Park

Guest house in Galesville

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.

4.95 out of 5 average rating, 182 reviews

Nautical Charm and relaxing waterview!

4.99 out of 5 average rating, 75 reviews

A serene garden landscape is visible, showcasing a pond surrounded by smooth stones and lush green plants. A flag stands tall nearby, and a meandering path leads through the manicured yard, featuring various plant beds and a wooded backdrop.

Guest house in Cambridge

Camelot Cottage

A spacious room features a modern bed with soft linens, flanked by two wooden nightstands and minimalistic lamps. A desk with a brown chair sits against a white wall adorned with framed black-and-white photographs. Natural light filters through glass block windows, enhancing the clean lines of the design.

4.98 out of 5 average rating, 202 reviews

Modern Capitol Hill East guest house

4.97 out of 5 average rating, 217 reviews

The charming exterior of a white cottage is displayed, featuring a prominent front door framed by a small porch and two large windows. A landscaped garden with colorful flowers and greenery surrounds the entrance, complemented by a stone pathway and decorative gravel.

Guest house in Arlington

The Little House

4.97 out of 5 average rating, 207 reviews

A spacious common area features tall ceilings and large windows, allowing natural light to fill the room. Bookshelves line the walls, filled with a diverse collection of books. A comfortable white sofa and glass coffee table create a cozy seating area, with a TV positioned nearby.

Guest house in Milton

The Book Nook - A Private Downtown Retreat