Holiday houses in Chesapeake

Small & Cozy Guest Suite w/ Private Bath & Jet-Tub

Keep it simple at this peaceful and centrally-located place in VB located by Kemps River shopping center. It’s a small guest suite w/ private bath (jetted tub) and available side entrance right off the driveway for easy entry. 20 min to beach. 10 to VB amphitheater. 10 to Greenbrier. 15 downtown Norfolk. Full size bed, mini fridge, microwave, keurig, TV w/Roku stick (u log in/hotspot) Free parking (2 spaces in gravel driveway) PLEASE READ captions on photos for additional info. No cleaning fee.

"The Ponderosa B" - Close to the Casino & Concerts

Lots of Great Concerts going on close by!! Ponderosa B, 500 Sq.Ft., One Bedroom Garage Apartment for 2 Adults, family oriented neighborhood about 1/2 mile Rivers Casino! -, Kick back and relax in this calm, stylish space. Private entrance and nice, safe, free parking for 1 vehicle. Large Sign for each Visitor Parking Space. One Bedroom w/very comfortable Queen size bed, Full size Kitchen, One full Bathroom. Only 4 miles to Downtown Portsmouth 5.9 miles to Norfolk, 22 mi to VB Oceanfront.

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Enjoy easy access to everything from this perfectly located, fully furnished home. Walk to fine dining, museums, a historic theater. Visit the waterfront where you can view the Navy ships or ride the Ferry to Norfolk to experience Waterside & MacArthur Mall. This is a great place for traveling professionals or those in town for sightseeing or local events. Virginia Beach Oceanfront is 30 minutes away. Home is located in a beautiful, historic area and only 8 minutes from the new casino!

Sweet Suite!

Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

Family friendly townhouse

A perfect place to stay when you can't be at home!Townhouse located in lovely family friendly neighborhood. Only a 20-30 min drive to NOB, Portsmouth Naval Shipyard and Oceana. Bright open kitchen with everything you need. Large living room with new comfortable couch and large Smart TV to hang out and watch tv. Privacy fenced back yard to sit and enjoy the evening or a morning cup of coffee. Large primary bedroom with private bathroom and shower. Washer and dryer in t

Blissful Nook @ Washington

This is a beautiful modern, comfortable, and cozy one bedroom apartment located on the second floor above the car garage. While relaxing or vacationing just know that this apartment is centrally located to Virginia Beach Oceanfront, Outer banks N.C. museums, Colonial Williamsburg, Busch garden, Water Country USA and many restaurant. This apartment is attached to the main home with a dedicated private entrance. This location is safe and private for our guest.

Western Branch Loft Suite

Enjoy your own space in this quiet studio located near Navy bases, hospitals, and the beach. It’s perfect for those looking for a little bit of peace while they are in the area for work or house hunting. This comfy guesthouse is in a safe neighborhood 5 minutes from grocery stores, restaurants, gyms, and highways to get around. Avoid the busiest traffic areas here while still being able to enjoy a day trip to the beach!

Panoramic river view retreat

Located in the heart of Western Branch, this 3-bedroom 2 bath 2100 square foot guesthouse is located on the 2nd floor of this lovely home nestled up to a full panoramic view of the Elizabeth River. Whether you are needing a quiet place to work, a place to reset while watching the sunset on the balcony or making smores at the firepit with your family, The Cove has something for everyone.

Comfy House! The Perfect Getaway

Bring the whole family to this great place with lots of room for fun! This spacious 3-bedroom, 2-bathroom home is the perfect blend of comfort and style, offering a relaxing escape for families, groups, or anyone looking for a peaceful retreat. Whether you're here for a short getaway or an extended stay, you'll find everything you need to make your time unforgettable.