Holiday rentals with breakfast in Chesapeake

4.86 out of 5 average rating, 21 reviews

Home in Phoebus

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!

4.97 out of 5 average rating, 124 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.

4.86 out of 5 average rating, 7 reviews

Home in Norfolk

- The Evergreen House -

Welcome! 🙂‍↕️ Enjoy relaxing and quality time with your family & friends at The Evergreen House. Quiet tree lined street in a peaceful neighborhood with a private driveway and nice fenced yard. It's perfectly situated just a few minutes from the airport, VB Town Center, top convention centers & venues, 20 mts from Ocean Front, Ocean View, Botanical Garden, Aquarium, Museums, restaurants, shopping & more. Easy access to 264, I-64 and military bases. A central location for all Hampton Roads.

Superhost

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

4.84 out of 5 average rating, 25 reviews

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.

4.86 out of 5 average rating, 57 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, 319 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).

Superhost

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.

Townhouse in Virginia Beach

4.75 out of 5 average rating, 218 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!

4.94 out of 5 average rating, 135 reviews

A sunset casts warm hues over the calm waters of the bay, with silhouettes of a shaded gazebo and a hammock. Weathered pilings and a single bird in flight can be seen against the vibrant sky, enhancing the tranquil atmosphere.

Home in Knotts Island

Island Lotus Yoga & Spa

A nature lover’s dream! Waterfront, ample natural light, serene beauty, and privacy can be all yours at our charming ranch right on the bay. The bay faces east, giving you the most breathtaking views of the sunrise and moonrise. Relax in the spa, adventure on kayaks, and chill and grill over the fire-pit. You’ll also local fresh eggs, and a private yoga class. Check us out on insta @islandlotusyoga! PS we’re not actually an island. Reach us by driving through Virginia Beach!

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, 12 reviews

Stay downtown 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. The master 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 Holiday Accommodation with Breakfast

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday 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.

4.89 out of 5 average rating, 219 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.

The cozy living area features a light-colored sofa adorned with striped cushions, complemented by a wooden coffee table. A decorative sculpture sits in front of a radiant window, surrounded by green plants. The space includes a dark television mounted above a fireplace against a rich red wall.

Private room in Newport News

4.67 out of 5 average rating, 3 reviews

Lee Hall

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 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

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 master bedroom is presented, featuring an orange accent wall and a spacious bed with light linens. A mirror reflects the room's décor, while two bedside lamps provide soft illumination. A cozy seating area includes a sofa, and a desk is positioned near the window.

4.89 out of 5 average rating, 154 reviews

BEST beaches & history n the East!

A light-filled space features a dark couch positioned near large windows adorned with sheer white curtains. Two decorative placemats and a candle holder are set on the countertop, complemented by an overhead light fixture. The clean lines and neutral colors create a modern look.

Private room in Portsmouth

Comfort & Simple Overnight stays

Bed and breakfast rentals with breakfast

An inviting attic room features a spacious bed adorned with a light quilt. Wood paneling creates a warm ambiance, while a ceiling fan provides comfort. Seating options include two patterned armchairs and a small table, complemented by a floor lamp and a window with soft curtains.

4.83 out of 5 average rating, 29 reviews

The Culpepper Inn Premium Room II

4.98 out of 5 average rating, 268 reviews

Private room in Norfolk

Military - Active/Retired/Family at Cape Defoe B&B

An elegant brick house is framed by large trees, with rows of white chairs adorned with orange and black sashes arranged on a grassy area. Small pumpkins are placed decoratively throughout, creating a festive atmosphere for an outdoor gathering.

4.86 out of 5 average rating, 81 reviews

The Culpepper Inn III

Private room in Elizabeth City

4.99 out of 5 average rating, 221 reviews

The Pepperberry Inn

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

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

Private room in Sunbury

4.71 out of 5 average rating, 7 reviews

King, breakfast and Private bathroom

Other holiday rentals with breakfast

A well-appointed bedroom features a spacious bed with a wooden headboard and soft linens. Wall-mounted bedside sconces provide subtle lighting. A flat-screen television is mounted on the wall, while a small refrigerator is located near the bed. Natural light illuminates the room, highlighting the warm wood flooring.

4.84 out of 5 average rating, 43 reviews

Breakers 204 Inn and Old Beach

A spacious bedroom features a large bed with a wooden headboard and decorative pillows. Light wood flooring complements the natural light streaming in from multiple windows. A bedside table sits beside the bed, while sliding doors lead to an outdoor seating area.

4.94 out of 5 average rating, 85 reviews

Avamere 206 Inn at Old Beach

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.

4.93 out of 5 average rating, 27 reviews

Hilltop 104 Inn at Old Beach

A well-appointed bedroom features a spacious bed with white linens and green accent pillows. An art piece with bright flowers is displayed above the bed. The room is adorned with patterned wallpaper and includes a cozy armchair, a lamp on each bedside table, and a decorative fireplace.

Hotel room in Downtown Norfolk

5 out of 5 average rating, 16 reviews

Freemason Suite at Four Eleven York

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.

4.88 out of 5 average rating, 43 reviews

The Waverly 100 Inn at Old Beach