Holiday rentals with a kayak in Chesapeake

1-Bedroom Home Near Christopher Newport University

Sip a bourbon while you listen to a record on the vintage player. Create your CD playlist to pop in the 90s 5 disk changer while you cook on a seasoned cast iron on the new stove. Check out the coffee bar for home roasted beans. Soak in the hot tub, or get a high score on Dig Dug. Centrally located in Newport News near CNU. 25-30 minute drive to Busch Gardens, Water Country, and Colonial Williamsburg. 45 minute drive to the ocean front. Great neighborhood with sidewalks for running and walking.

Exclusive Beachfront Home w/ 180° Views & Hot Tub!

If you enjoy majestic ocean views from almost every room & your own exclusive beach just steps below, Bay Bliss is for you! The panoramic views from this luxury home are unmatched & sure to relax you! Sip coffee from the grand deck or take a soak in the hot tub w/ breathtaking views. Cook/eat in the high-end chef's kitchen or watch a movie on a 75" TV all with stunning views! Wake up in the plush, king-sized bed and enjoy views of the water without having to get up. Your bliss at the bay awaits!

The Great River Escape *Hot Tub!

Welcome to the River Escape, where the sun is hot and river breezes are cool! Located on the Hampton River, on a big fenced lot, with easy river access and just a 10 minute drive to sandy toes and the sound of crashing waves, this fantastic river house is made for the best family vacations around. It is furnished to comfortably sleep 6, featuring a spacious, well-stocked kitchen, private in-ground pool, hot tuband a gas grill in the backyard! Just add family, and you've got instant vacation fun!

3 bedroom 3 bathroom beach house pets welcome

Welcome to your vacation getaway! This remodeled 3-bedroom, 2.5-bath ranch house is just a mile away from the ocean front. It's an ideal destination for families, friends & pets. All bedrooms have queen beds and smart tvs. Pet-Friendly (fee)The spacious backyard and deck are perfect for playtime and relaxation. Great location close to shopping and restaurants. You’ll feel right at home in this safe neighborhood. Please note: No parties. Only 9 people are allowed at the house at any time

The Sportman's Lodge

The Sportsman’s Lodge is a rustic and relaxing modern getaway with all the conveniences you are accustomed to but surrounded by the gorgeous Back Bay Wildlife Refuge. Enjoy the relaxing countryside at this waterfront property, while still being only a short drive away from Sand Bridge Beach. If you are looking to get away from the standard Virginia Beach Boardwalk tourist experience and get back to nature, this is the place for you. Free kayaking to Back Bay, access to fishing and crabbing.

Waterfront Cottage w/ Dock/Kayaks + Dog Friendly

Sea La Vie Sandbridge is a boutique beach cottage tucked between the ocean and Back Bay. Designed for couples and small groups, it includes bikes, kayaks, beach gear, and cozy outdoor seating. Walk to the beach or explore wildlife trails. Inside, enjoy a fully equipped kitchen, plush beds, and smart features. Thoughtfully curated for rest and connection—no chores, just effortless, memorable stays. smooth, memorable experience. ***Pool is open from Memorial day until End of September ***

On Beach 3BD+Loft: Sauna|HotTub|Billard|FencedDeck

Located right on the beach and overlooking the scenic Chesapeake Bay, this beachfront home is the perfect place for a family retreat, romantic getaway or friends seeking adventure. Marvel at the panoramic views and dramatic colors from sunrise to sunset. Go for a swim or relax, soak up the sun & let the gentle sea breeze wash your worries away! You’ll love the direct private beach access, hot tub, sauna, chef’s kitchen, game room with pool table, bar areas, large deck and more!!

Quaint 2 Bedroom Cottage in Chicks Beach

This 2 bedroom 1 bathroom quaint cottage is the perfect small family getaway. Located 2 residential blocks to the beach. The beach is great for families with children. This unit is connected to a 1 bedroom rental. Back yard has a single detached unit also . Great for small families. There is a fenced in front yard Back yard and laundry area is shared with guest suite next door. 2 Car max allowed $100 pet fee with pre approval. ***Summer 2026 check in on Friday only ****

Jen n John's Mini Mansion.

Welcome to Surfside at Sandbridge!!! Sandbridge is the northern most portion of the OBX!!! Location location location. this tiny home is 3 years old and was previously a vacation property. This will be it's first year on airbnb. there is a queen adjustable bed in the master and two twins in the loft. There is room for a air mattress in the loft also. This unit comes fully stocked for everything you'd need for a beach vacation. Towels..chairs..beach canopy..boogie boards..ect.

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!

Bayfront Pool Retreat, Walk to Beach

Experience one of Sandbridge’s most unique waterfront retreats, featuring a private pool overlooking Back Bay, plus a private dock and boat ramp right on the property. Just a short walk from the beach, you’ll enjoy the rare combination of bay and ocean access in one location. Newly refreshed on the exterior, this spacious 6-bedroom home is perfect for boating, fishing, kayaking, relaxing poolside, and taking in spectacular sunsets and sunrises.

Oceanfront Cozy Beach Duplex

Wake up to stunning ocean views in this beachfront duplex in East Ocean View, Norfolk! Each 2BR unit offers cozy comfort, a full kitchen, fast Wi-Fi, and direct beach access just steps from your door. Perfect for family vacations, couples, or group getaways. Enjoy sunrise views from the bedroom, sandy strolls, and easy access to local dining. Free parking, smart TV, and self check-in included. Perfect spot for a family vacation.