Vacation rentals with breakfast in Chesapeake

4.77 out of 5 average rating, 13 reviews

Home in Phoebus

Welcome to Harper's Haven!

Harper's Haven is the perfect location for your stay. In this quiet family friendly neighborhood, you are centrally located to military bases, Hampton Coliseum, Norfolk Scope, Water Country USA, Busch Gardens, Hampton University, beaches and so much more with a 30-minute drive or less. Whether you're here for a business or pleasure there's something for everyone. There is plenty of shopping and dining also. This quaint cottage style home offers a clean and cozy vibe. Welcome to Harper's Haven😊

5 out of 5 average rating, 24 reviews

A charming two-story home is showcased at sunset, featuring a welcoming front porch and staircase. Lush, flowering bushes and a mature tree are positioned in the front yard, while a peaceful neighborhood street is visible in the foreground.

Home in Willoughby

Relax By the Bay; Best Rated Large Spacious Home!

You won’t find another spot like this anywhere on Willoughby! Picture your family & friends dining at a table for 10 , under glowing string lights; the breeze rustling through the trees overhead smells like the beach and bbq cooking on the grill. Or maybe you’re sitting around the fire pit sharing some laughs and drinks while the kids are having their own fun on the swings and slides of the playset. This backyard is fully fenced in; has a hot/cold outdoor shower, and that’s just the beginning!

Bed and breakfast in Williamsburg

A charming two-story cottage features red doors and a brick exterior. Large windows allow natural light to fill the interior, which is framed by neatly trimmed shrubs and greenery. A gravel pathway leads to the entrance, providing a welcoming atmosphere.

4.71 out of 5 average rating, 7 reviews

Private 2BR Cottage with Breakfast - Cedars B&B

Our charming and delightful B&B is located across the street from the College of William & Mary, and under a mile from Colonial Williamsburg and downtown Williamsburg. Breakfast is complimentary, locally sourced and seasonally themed. You'll love our home-like atmosphere where you'll be taken care of by our innkeepers who know the best places to eat, play and shop and our housekeepers who will keep your room neat and tidy. Great for couples, families, solo adventurers, and business travelers.

4.97 out of 5 average rating, 118 reviews

The three-story farmhouse-style home features a charming brick facade and a front porch with blue double doors. Lush greenery surrounds the entrance, while a path leads toward the driveway. Sunlight highlights the roof and front yard, creating a welcoming exterior.

Home in Colonial Place

Newport Nook: 5/2.5 Home in Norfolk - Sleeps 10!

5 bed / 2.5 bath - Sleeps 10! Our cozy, farmhouse-style Norfolk home is 5 min from Historic Ghent / ODU. Free Wi-Fi, parking for 4 cars. Coffee, grill, & fire pit provided. Pet-friendly! NO cleaning fee or checkout instructions! Driving Distances: ODU - 5 min Sentara Norfolk General - 5 min CHKD / EVMS - 8 min Norfolk Naval Station - 14 min Virginia Beach Oceanfront - 25 min Monthly: $4,200. Fully furnished rental with all utilities, Wi-Fi, weekly housekeeping, pest & lawn care included.

4.84 out of 5 average rating, 25 reviews

A cozy living room is showcased, featuring a tufted beige sofa and two complementary armchairs. Wooden side tables with lamps provide soft lighting, while a patterned area rug lies over the hardwood floor. A wall clock and artwork add character to the muted decor.

Home in Elizabeth City

Timeless Treasure

Welcome to this Timeless Treasure! Where you and your guest will be close to everything, when you stay at this centrally located place in Elizabeth City. Our 3 bedroom, 1 bath home is ideal for families or groups of 5 people or less. Our home includes: 2 Queen beds, one twin bed, and a dedicated work area. A cozy living room for enjoying time together. A fully equipped kitchen, complete with dining. Free wifi, washer and dryer in unit. The outdoor space you can enjoy the private backyard.

5 out of 5 average rating, 30 reviews

A refreshing pool is visible in the foreground, surrounded by several lounge chairs in pastel colors. An orange umbrella shades a dining table with additional seating. A casual bar area is located behind the pool, offering a convenient space for relaxation and refreshments.

Cottage in Sandbridge

Coconut Cottage-Sleeps 2,Pool,Beach

Take it easy at this unique and tranquil getaway. Newly built private bungalow for two. While you’re here (mid-May through mid-October), the pool is yours! Whether you’re here with your partner or close friend, enjoy access to the beach and bay. Beautiful kitchen and bar area with many amenities. Bedroom with queen bed, full bath. Take your pick of activities whether it be a day at the beach, biking or kayaking. End your day out on the dock and enjoy the sunset in calm serene surroundings.

4.86 out of 5 average rating, 56 reviews

The exterior of a ranch-style home is shown, featuring a well-maintained lawn and neatly trimmed hedges. A covered porch with steps leads to the main entrance. The brick facade is complemented by blue window shutters, under a bright blue sky with a few white clouds.

Home in Chesapeake

The Chesapeake Guesthouse

Your group will enjoy the convenience of being centrally located in the Greenbrier area of Chesapeake in this well appointed, spacious ranch style home. This property has three well appointed bedrooms, 2.5 baths, fully equipped eat-in kitchen, dining room - and a flex space we like to call "The Green Room". There is off-street parking for up to four vehicles and a huge backyard. All located within minutes of major highways, hospitals, shopping, eateries, entertainment and military bases.

Guest suite in Thoroughgood

A spacious bedroom features a queen bed adorned with a nautical-themed quilt and decorative pillows. Natural light enters through two windows with blinds. A comfortable chair is positioned beside the bed, and a side table holds a lamp. A closet with sliding doors is visible.

4.98 out of 5 average rating, 318 reviews

Home away from home~Private,quiet, mins to bay

Home away from home is a spacious, comfortable, and private apartment with 1 Queen bedroom, full bath w/ tub, living area, work space, and fully equipped kitchen. Conveniently and centrally located in historic neighborhood: 3 mins to bay, 15 mins to oceanfront. We are within 4 miles of Norfolk Premium Outlets and IKEA, and are within 5 miles to Virginia Wesleyan and 15 miles to ODU. Walk to local favorite restaurants (New River Tap House, The Rustic Spoon, 1608 Crafthouse, Comfy Belly).

Townhouse in Virginia Beach

The living room features an open layout with a comfortable sofa and an accent chair arranged around a round wooden coffee table. A ceiling fan provides airflow, while natural light fills the space through a nearby window. Stairs lead to the upper level.

4.75 out of 5 average rating, 217 reviews

Virginia Beach/Norfolk Clean & Cozy 4Beds.3 Bath

Welcome to a slice of heaven in the center of Virginia Beach. Cozy, 3 Bed 2 full baths & a half bath, home tucked away in a safe/quiet area to relax & feel at home! ■15 Min Boardwalk/Ocean Front ■12 Min Ocean View Beach ■17 Min Ocean Breeze Water Park ■7 mins Norfolk Inter. Airport. ■10 min Dwntwn Norfolk Waterside/Ghent/ MacArthur Mall ■Centrally located of Naval Station Norfolk, Joint Exped. Little Creek Base & Oceania Airbase! ■2 min Premium Outlets, & Virginia Wesleyan College!

4.96 out of 5 average rating, 24 reviews

A cozy living area is furnished with two light-colored armchairs and matching ottomans, each adorned with decorative pillows. A small side table with a lamp is positioned beside one chair. Natural light flows in through large windows, enhancing the open and airy atmosphere.

Home in Elizabeth City

Main Street Stay - 2 BR House with 2 full baths

Welcome to Main Street Stay, nestled close to the heart of downtown Elizabeth City! Within walking distance of shops, restaurants, and attractions, this cozy duplex house offers the perfect blend of comfort and convenience. After a day of adventure, unwind in the comfort of your small town getaway, complete with all new finishes and stylishly decorated for your pleasure. Whether you're here for business or leisure, Main Street Stay is the perfect home base for your Elizabeth City stay.

4.8 out of 5 average rating, 168 reviews

The entrance features a light-colored door adorned with a welcoming wreath. To the right, a sign displays the property name 'All4One' alongside the Virginia shape. The brick facade showcases a warm, inviting exterior, complemented by a traditional lantern mounted beside the door.

Home in Virginia Beach

All 4 One | Beach Living

Come enjoy time at the beach in our seaside oasis! All4One is located on the semi-private beach of Croatan in Virginia Beach. This means that although you are but a bike ride away from the hustle and bustle of the Boardwalk, you also have the beach to yourself in a quiet neighborhood setting- best of both worlds right? We certainly think so! My grandma built this home in the 1960's and my husband and have called it home for over a decade. Come enjoy your stay at the beach at our home!

Apartment in Elizabeth City

A spacious bedroom features a large bed with a patterned comforter and blue accent pillows. Two lamps provide soft lighting on either side. Rich teal walls are complemented by gold curtains, and a television sits atop a dark wood dresser. A decorative piece hangs on the wall.

5 out of 5 average rating, 15 reviews

1st floor suite at the Blue Ruby

Stay in the oldest home in Elizabeth City - a beautifully preserved gem located in the heart of the downtown historic district. This first floor suite at the Blue Ruby Inn blends old-world charm with modern amenities, just steps from local restaurants, coffee shops, breweries, and the waterfront. Whether you're exploring Elizabeth City for business or leisure, you'll be surrounded by history, convenience, and character. Book your stay at this iconic Elizabeth City home today!

Popular amenities for Chesapeake breakfast rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with breakfast

A serene waterfront view captures calm water reflecting the sky. Lush greenery lines the banks, creating a natural backdrop. A wooden dock extends into the water, providing a space for relaxation and observation of the tranquil surroundings.

4.9 out of 5 average rating, 214 reviews

Three Little Birds-Kayak, fish, bike, enjoy!

A spacious deck area is adorned with string lights, creating a warm ambiance. Comfortable seating is arranged around a fire pit, surrounded by decorative planters with colorful flowers. In the background, a pool reflects the soft glow of the sunset, enhancing the tranquil atmosphere.

Home in Currituck

4.54 out of 5 average rating, 35 reviews

Bells Island, w/pool on the water.

Home in Norfolk

4.75 out of 5 average rating, 4 reviews

- The Evergreen House -

A charming blue house features a welcoming front porch with large windows, allowing natural light to fill the space. The well-maintained lawn is surrounded by trees, creating a pleasant outdoor atmosphere. The brick steps lead to the main entrance, providing easy access.

Home in Virginia Beach

4.78 out of 5 average rating, 96 reviews

Big Fun Beach House

4.86 out of 5 average rating, 21 reviews

A spacious four-bedroom home is showcased, featuring a blend of architectural styles. The exterior showcases light-colored siding, multiple balconies, and expansive windows that invite natural light. The property is surrounded by trees, creating a serene outdoor environment.

Home in Corolla

Dog Friendly 4 bedroom Home!

A spacious bedroom is depicted, featuring a large king bed with decorative pillows. Two windows allow natural light to illuminate the room, while a 52-inch TV is mounted on a stand across from the bed. Ceiling fan and neutral-toned curtains contribute to the room's calm ambiance.

5 out of 5 average rating, 19 reviews

Lake Retreat

A well-lit guest room features a spacious bed adorned with decorative pillows and a soft throw. A nightstand and lamp sit next to the bed, while a large closet is available in the room. A plush rug enhances the warm wood flooring.

4.79 out of 5 average rating, 97 reviews

COZY Private room with a private entrance!

A cozy den features a plush dark sofa, accompanied by a small table and an entertainment unit. A wall-mounted television and a decorative lamp provide soft lighting. A faux fireplace and a clock add functionality, while a door leads to the outside.

4.62 out of 5 average rating, 26 reviews

Vintage Den Rm, Private Entrance,& Space,VB Center

Bed and breakfast rentals with breakfast

A ranch-style home with blue siding and a welcoming front yard is featured. Two individuals stand in front of the entrance, flanked by well-maintained shrubs. A snowman decoration adds a festive touch beside the driveway, which leads to a two-car garage.

Private room in Elizabeth City

5 out of 5 average rating, 4 reviews

Tranquil area with a Studio apt very Clean !

Private room in Williamsburg

A cozy bedroom featuring a King size four poster bed adorned with decorative pillows. Soft lighting is provided by two bedside lamps, while windows dressed with dark curtains allow natural light. A comfortable chair and side table complete the inviting space.

4.97 out of 5 average rating, 58 reviews

Williamsburg Sampler - Lord Nelson Chamber

Private room in Elizabeth City

4.99 out of 5 average rating, 221 reviews

The Pepperberry Inn

Hotel room in Williamsburg

A room features a queen-sized bed adorned with a floral quilt and accented by two decorative pillows. Wall-mounted sconces provide soft lighting, and framed photographs add character. A small side table sits beside the bed, and a private bathroom is visible in the background.

4.99 out of 5 average rating, 78 reviews

Aldrich House B&B Lewis Room

Hotel room in Elizabeth City

Several vintage cars are parked in front of a stately brick building. The well-maintained structure features classic architectural elements, such as white columns and dark shutters, surrounded by neatly trimmed bushes and shaded by large trees.

4.94 out of 5 average rating, 129 reviews

The Culpepper Inn II

Private room in Williamsburg

The Rhododendren-King-Luxury-Ensuite with Shower

Hotel room in Elizabeth City

An inviting pool area features a clear blue swimming pool surrounded by lounge chairs and tables. Orange umbrellas provide shade, creating a welcoming outdoor space. Lush greenery and decorative lighting enhance the tranquil atmosphere, offering a place for relaxation and social gatherings.

4.94 out of 5 average rating, 144 reviews

The Culpepper Inn VI

Private room in Elizabeth City

4.97 out of 5 average rating, 169 reviews

The Pepperberry Inn II

Other vacation rentals with breakfast

Private room in Downtown Hampton

Lovely Private Room with full Bathroom and Pool!

Guesthouse in Elizabeth City

A curved navy sectional sofa is arranged in a welcoming living area, complemented by decorative cushions. A glass coffee table sits on a patterned area rug. Artwork graces the walls, and a vintage chandelier hangs from the ceiling, adding character to the space.

5 out of 5 average rating, 11 reviews

Stay downtown at the Blue Ruby

The sleeping area features two spacious beds, each adorned with a set of neutral linens. Wooden headboards add a natural touch, while wall-mounted lights provide soft illumination. Decorative pillows in shades of green and mustard yellow add warmth and a hint of color to the serene space.

4.92 out of 5 average rating, 26 reviews

Hilltop 104 Inn at Old Beach

Private room in Williamsburg

4.97 out of 5 average rating, 395 reviews

Private Room with King Bed on Mallardee Farm

The residence features a two-story exterior with a classic design in light gray and white tones. A spacious front porch is visible, flanked by landscaped areas, while neighboring homes are showcased in the background, contributing to a harmonious community aesthetic.

Home in Cape Charles

5 out of 5 average rating, 3 reviews

Sweet Bay - Chesapeake Properties

A bright and airy bedroom features a spacious bed with a light-colored duvet and accent pillows. A ceiling fan is positioned above, while a desk with two chairs is situated against the wall. Natural light fills the room through large windows adorned with white shutters.

4.87 out of 5 average rating, 39 reviews

The Waverly 100 Inn at Old Beach