Holiday rentals with breakfast in Chesapeake

4.86 out of 5 average rating, 22 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, 128 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.

4.9 out of 5 average rating, 10 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.

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.

4.86 out of 5 average rating, 58 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).

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.

4.74 out of 5 average rating, 221 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!

4.93 out of 5 average rating, 137 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, 13 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

5 out of 5 average rating, 8 reviews

Home in Ocean View

New, Walk to Beach, Fire Pit, Game Room, King Beds

4.98 out of 5 average rating, 268 reviews

A well-appointed bedroom features a queen-sized bed adorned with decorative pillows and a floral comforter. The walls are decorated with wine-themed art, and bedside tables hold lamps and personal touches. Natural light enters through the window dressed with sheer curtains, enhancing the cozy atmosphere.

Private room in Norfolk

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

Private room in Virginia Beach

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, 222 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

4.56 out of 5 average rating, 36 reviews

Bells Island, w/pool on the water.

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 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.

Private room in Green Run

4.8 out of 5 average rating, 99 reviews

COZY Private room with a private entrance!

Home in Cape Charles

5 out of 5 average rating, 3 reviews

Sweet Bay - Chesapeake Properties

Private room in Virginia Beach

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!

Apartment rentals with breakfast

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, 16 reviews

1st floor suite at the Blue Ruby

Apartment in Williamsburg

4.5 out of 5 average rating, 4 reviews

Kingsmill on the James Resort

The Ocean Beach Club Hotel is depicted at dusk, showcasing its modern architecture with numerous windows reflecting the evening sky. The beach can be seen in the background, complementing the hotel’s seaside location. The surrounding area is well-lit, enhancing the welcoming feel of the resort.

Apartment in Virginia Beach

4.63 out of 5 average rating, 16 reviews

Luxury Suite in Beach Front Resort

A private balcony features a railing that frames a view of the ocean and beach. White chairs are positioned on the balcony, overlooking sandy shores and the expanse of water, while colorful beach umbrellas dot the landscape below.

Apartment in Virginia Beach

4.5 out of 5 average rating, 4 reviews

Oceanfront at Barclay Towers

The image showcases a welcoming entryway, featuring a vibrant turquoise wall. Two woven chairs are positioned near an arched doorway that leads to a bathroom and bedroom area. A colorful rug adds texture to the space, while a fan complements the decor.

Apartment in Norfolk

3 out of 5 average rating, 5 reviews

Beach Side Studio #5 - Pet Friendly Wi-Fi, Parking

Bed and breakfast rentals with breakfast

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

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, 80 reviews

Aldrich House B&B Lewis Room

A spacious room features a queen size bed covered in floral bedding. A decorative writing desk and an antique dresser are situated next to the bed. Soft lighting is provided by bedside lamps, and a window alcove with floral curtains allows natural light to enter.

5 out of 5 average rating, 4 reviews

Sunny Queen Room with Breakfast - Cedars B&B

Colonial Gardens B&B - Azalea Suite (2nd Floor)

A serene bedroom features a king size sleigh bed with white linens, flanked by lamps on wooden nightstands. Two comfortable chairs are positioned near a window, adorned with drapes. Soft green walls complement the decor, creating a relaxing ambiance.

4.83 out of 5 average rating, 6 reviews

FDR Bed Chambers - A Williamsburg White House

4.94 out of 5 average rating, 48 reviews

Williamsburg Sampler - Eliza Reynolds Chamber

A well-furnished bedroom is highlighted by a cozy Queen size bed, draped in a floral-patterned coverlet. Two bedside lamps provide soft lighting, and large windows dressed with sheer curtains invite natural light. A dark area rug adds contrast to the light-colored walls.

Private room in Sunbury

4.71 out of 5 average rating, 7 reviews

King, breakfast and Private bathroom