
Holiday rentals with breakfast in Chesapeake
Find and book unique Holiday Accommodation with Breakfast on Airbnb
Top-rated Holiday Accommodation with Breakfast in Chesapeake
Guests agree: These breakfast rentals are highly rated for location, cleanliness and more.

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

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😊

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!

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.

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.

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.

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.

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).

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!

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!

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!

Perfect Getaway!
Home away from home!! Beautiful 2 story house with 3 bedrooms, 3 bathrooms, and a huge playroom over the garage. The master suite has a beautiful bathroom with a jacuzzi tub, and huge walk in shower. The fenced in backyard has plenty of space to run around, and has an awesome saltwater inground pool for fun! In addition, there is a 2 level, new deck, and patio furniture to sit and relax on. There is something for everyone to do here.. I’m positive you will love it!
Popular amenities for Chesapeake Holiday Accommodation with Breakfast
Holiday House Rentals with breakfast

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

Lee Hall

Big Fun Beach House

Dog Friendly 4 bedroom Home!

Lake Retreat

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

Sweet Bay - Chesapeake Properties

BEST beaches & history n the East!
Bed and breakfast rentals with breakfast

Williamsburg Sampler - Lord Nelson Chamber

Williamsburg Manor - Russel House Green Room

Aldrich House B&B Lewis Room

The Rhododendren-King-Luxury-Ensuite with Shower

Sunny Queen Room with Breakfast - Cedars B&B

King, breakfast and Private bathroom

Adams Bed Chamber - A Williamsburg White House

Williamsburg Manor - James Geddy Family Suite
Other holiday rentals with breakfast

Breakers 204 Inn at Old Beach

Avamere 206 Inn at Old Beach

Williamsburg Sampler - King William Suite

Hilltop 104 Inn at Old Beach

Private Room with King Bed on Mallardee Farm

Pinewood 102 Inn at Old Beach

Albermarle #202 Inn at Old Beach

Newcastle 106 Inn at Old Beach
Quick stats about holiday rentals with breakfast included in Chesapeake

Total holiday rentals
Explore 50 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at $30 AUD per night before taxes and fees

Verified guest reviews
Over 1,140 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Chesapeake holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Chesapeake rentals

4.8 Average rating
Chesapeake stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Chesapeake's top spots, include Chrysler Museum of Art, Nauticus, and Cinemark Chesapeake Square
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- Rentals with breakfast Virginia
- Rentals with breakfast United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Carova Beach
- Corolla Beach
- Water Country USA
- First Landing State Park
- Buckroe Beach
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
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- Ocean Breeze Waterpark
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- The NorVa
- Currituck Beach Lighthouse
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- Old Dominion University
- Colonial Williamsburg's Merchants Square
- The Mariners' Museum
- Virginia Living History Museum
- Sandy Bottom Nature Park
- Virginia Air & Space Sci. Center




