Holiday rentals with a patio in Chesapeake

Romantic Sailboat Experience + Seafood Restaurant

We can't adequately describe how romantic & carefree it feels to step aboard our sail boat. The perfect stay begins by treating yourselves to dinner at the marina's seafood restaurant, then snuggle up together on deck to watch the sunset turn the sky pink & purple. The marina atmosphere is simply magical & you'll love rocking with the gentle sway of calm waters. Come enjoy a weekend aboard this amazingly cozy & romantic sail boat. Convenient to Norfolk & Virginia Beach, the location is prime!

THE POINT! Private waterfront Oasis!

Enjoy breath taking views & a fully equipped home w/ many amenities. Looking for a private & intimate experience of quality time & a relaxing retreat w/ nature & ample space to spread out, this is IT! Convenient to VB Oceanfront, Downtown Norfolk, Rivers Casino, Waterside & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect family/friends group trips, 12 minutes from Carnival Cruise Port. Oh & bring your fishing poles, river is fully stocked!

Wooded Wonderland Miniature Golf Hot tub Pool

Make yourself at home! This property offers a warm and welcoming environment for guests, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!

Quiet 3/2 beautiful Chesapeake

Enjoy a peaceful stay at this lovely 3-bedroom house nestled in the Great Bridge area of Chesapeake. The bedrooms feature a King size bed, queen bed, and two twin beds, perfect for a variety of guests. With amenities like WiFi, AC, full kitchen, covered/screened-in back patio, large fenced in yard and a washer/dryer machine, your comfort is guaranteed. The two bathrooms offer convenient shower facilities. Feel at home in this fantastic property and make the most of your stay in Chesapeake.

Serene Tree House Retreat | Spacious 1br/1bth Home

Step inside a tucked-away hidden oasis surrounded by trees and waterfront views. The apt is on the 2nd floor amongst the trees. One of the trees is a 200-year-old Magnolia Tree, which is why the space is called Magnolia Tree House. The tall windows make the space bright and airy and give you a 180-degree scenic view of the treetops. To bring the outside in, we decorated the apt to feel like the trees are also inside. The cozy furnishings will make it hard to leave.

Cook's Country Escape - Cozy Retreat

Escape the everyday and enjoy this cozy countryside retreat! Nestled halfway between Virginia Beach and the Outer Banks, this home offers the charm of a cabin with the comforts of a full house. Perfect for families or friends, it’s a peaceful getaway from city life yet close to beaches, parks, and attractions. From the moment you arrive, you’ll feel the warmth and relaxation of a true country home. It’s been a great rental with great ratings.

Beachfront stay with kayaks & paddleboards

Private beach access, Chesapeake Bay views, and kayaks and paddle boards included. This waterfront home is made for slow mornings, beach days, sunset evenings, and time on the water. My husband and I renovated the interior ourselves with comfort and simplicity in mind. The kitchen is stocked with the essentials, and towels, soap, shampoo, and conditioner are provided so you can settle in easily and enjoy the bay.

Ghent on the Corner: Cozy 3 bed 2.5 bath home

My cozy, 3 bed / 2.5 bath Norfolk home has a spacious 1st floor primary suite with a full bathroom, 2 bedrooms upstairs along with a 2nd full bathroom. No cleaning fee or checkout instructions. Pet-friendly! Free Wi-Fi, parking for 4 cars, grill & gazebo. Distances: CHKD - 5 min EVMS - 5 min Sentara Norfolk General - 5 min Waterside / Downtown - 10 min Ocean View - 20 min VB Oceanfront - 25 min

Spacious 3 Bedroom Home | Near many Shops & Dining

Nestled in a prime location, this bright and inviting 3-bedroom home puts you minutes from shopping, top restaurants, beaches, golf, hospitals, and military bases. Enjoy the perfect blend of comfort and convenience, plus a huge fenced backyard ideal for relaxing, pets, or outdoor fun. Whether for a family getaway, business trip, or long-term stay, your unforgettable Chesapeake stay starts here.

Waterfront Oasis: Fishing Pier, Pool, Beach Access

Escape to our waterfront retreat in Chesapeake's premier Bryan's Cove community! This modern 3-bedroom townhome comfortably sleeps 8. Enjoy resort-style living with a community pool, pier on Deep Creek, and a dog park. Perfect for families and groups seeking a peaceful coastal getaway with modern comforts and convenient access to local attractions. Your serene Virginia vacation starts here.

Best Temporary Rental in Chesapeake

Owner is a Real Estate Agent in the State of Virginia. Comfortably and Elegantly Furnished townhome conveniently located in the Greenbrier area of Chesapeake where you'll find tons of shopping, restaurants and close proximity to the interstate. Two reserved parking spaces right at your front door. Quiet location, comfortable beds, super clean! Welcome to your home away from home.

Comfy House! The Perfect Getaway

Bring the whole family to this great place with lots of room for fun! This spacious 4 bedrooms , 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.