Vacation rentals with a kayak in Chesapeake

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!

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.

The Green Bean Bungalow

Kick back and relax at The Green Bean Bungalow (400 sq ft) with peaceful waterfront views of Back Bay Sandbridge. This tiny home comes with full bay access (paddleboard provided), community pools (seasonal), tennis/pickleball court, basketball court, playground, a short distance to the beach (beach chairs & beach/pool towels included) and local restaurants. We are a part of the Surfside RV Resort in Sandbridge. You’ll be foot steps away from family fun and relaxation! *Please read all info below

902 CH Carriage House 20 Steps to Beach & Specials

902 CH Historic Carriage House 20 Steps to Beach + Hot Tub, Beachfront Grilling. Specials - Free Kayaks/Paddle-Boards/Beach Chair & Beach Umbrellas starting September 8 Step back in time at the Historic Carriage House, a beautifully restored 120-year-old gem just 20 feet from the Chesapeake Bay. Once home to horses and rowboats in the early 1900s, this 1-bedroom, 1-bath carriage house now blends timeless charm with modern comfort — offering guests a truly unique and peaceful bayfront getaway.

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 ****

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.

7BR Bayfront|Pool, Hot Tub|EV|3 Kings|Sleeps 19

Spacious Bayfront Getaway! New listing for 2026 ✨ Rare Sandbridge short stays available! 🌅 Bayfront sunsets • kayaks & dock 🏖️ 5-min walk to Beach 🔥 Pool + hot tub • fire pit • outdoor shower • multiple decks 🛌 Sleeps 19 • 7BR / 8BA (all ensuite) • 3 King suites 🍽️ 2 kitchens • 2 living areas • seating for 20 🎮 Arcade + game room 🚗 Parking for 7+ • EV charger (bring your cable) 🏡 4,500 sq ft • open & built for gathering

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.

Jen n John's Mini Mansion.

Welcome to Surfside at Sandbridge!!! Sandbridge is the northern most portion of the OBX!!! Location location location. There is a queen adjustable bed in the downstairs bedroom, and two twin mattresses in the loft. This unit comes fully stocked for everything you'd need for a beach vacation. Towels..chairs..beach canopy..boogie boards.. Wheeleez beach cart.. kayak…pedal boat… beach cruisers.. etc.

New! Luxe Sandbridge Beach, Pool, Hot Tub

Sandbridge Beach Retreat | Pool • Hot Tub • 5BR Sandbridge Escape Welcome to your luxury Sandbridge retreat, where Coastal Virginia Beach living meets entertainment and adventure. This spacious 5-bedroom, 3.5-bathroom coastal home offers everything you need for the perfect beach vacation, private pool, hot tub, multi-level decks for sunrise coffee and sunset wine overlooking the Atlantic Ocean.