Vacation rentals with a kayak in Chesapeake

4.95 out of 5 average rating, 125 reviews

The open-concept living space is shown, featuring a comfortable seating area with a queen sleeper sofa and two armchairs. A wood-burning fireplace is adjacent to the large TV, while a dining table is set for six. Wall-to-wall glass doors provide views of the outdoors.

Condo in Williamsburg

Kingsmill 2bd2ba Condo on Golf Course 9th Fairway!

This beautiful, 2B2Ba condo is 1400 sq.ft. in the exclusive Kingsmill neighborhood. This 1st floor unit has two master suites w/ king beds. One features a luxurious bathroom w/ a walk-in shower & dual shower heads, the other has a shower/tub combo as well as a private patio, stepping out onto the 9th Fairway. The open-concept living space has dining for 6, a queen sleeper sofa, a fully stocked kitchen, and an additional private patio. Golf course views from anywhere in the main living space!

4.99 out of 5 average rating, 183 reviews

A spacious waterfront home is showcased with a well-maintained lawn and blooming yellow flowers near the entrance. A large driveway leads to a brick facade, complemented by a garage. Clear blue skies can be seen in the background, enhancing the welcoming appearance of the property.

Home in Gloucester Point

York River Vacation Home

This lovely, spacious waterfront home is located on the York River in Gloucester County Virginia. It is the perfect get away to enjoy the relaxing sounds and sights of nature. The views are spectacular! Keep an eye out for osprey and dolphins as you enjoy watching the sunrise and set over the water. There is plenty to do! Relax in the salt water pool overlooking the water, bring a pole & fish and crab right off of the private dock, or venture out on the kayaks. 16 ton boat lift, Jet ski lifts.

Farm stay in Cape Charles

The spacious kitchen features a large island with seating for six, modern appliances, and ample counter space. A bright window above the sink offers views of the surrounding landscape, while soft lighting complements the contemporary design. Light wood flooring enhances the welcoming atmosphere.

5 out of 5 average rating, 383 reviews

Private Guesthouse on Secluded Waterfront Farm

Just 5 miles from Cape Charles and 30 minutes from Virginia Beach, our contemporary Guesthouse gives you the peace and solitude characteristic of the Eastern Shore along with the convenience of being close to town. Our twenty acre waterfront farm, home to both a Vineyard and an Oyster Farm, has plenty of nearby walking or biking and a dock on a secluded arm of the Chesapeake Bay. Our farm is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

4.9 out of 5 average rating, 136 reviews

The kitchen area features dark cabinetry and a modern design, with a large sink and stove. A microwave is mounted above the stove, and a mounted TV can be seen nearby. Marble-like countertops enhance the space, which is well-lit by natural light.

Camper/RV in Portsmouth

“Genevieve” the glam RV perfect for R & R!

Genevieve is a 30 foot stunning Design RV that is located in Parkview Portsmouth, Virginia. It provides a glamping experience and a comfortable stay while your on vacation. This beautiful modern RV provides an experience of unwinding, relaxation and style. Escape the stress of a busy schedule and experience this gem. We are situated on a private residence walking distance from the Elizabeth River. Olde Towne Portsmouth, scenic views & minutes away from restaurants, grocery shopping and more.

Guesthouse in Cape Charles

Two kayaks in green and red are stacked next to a tree along a serene lakeside. A red Adirondack chair is positioned nearby, facing the water, surrounded by lush greenery. The scene reflects a natural setting ideal for relaxation and outdoor activities.

5 out of 5 average rating, 7 reviews

Eden Guest Suite on Lake Allure

Relax and recharge in nature at this unique and peaceful getaway. Private access to one of Virginia’s best freshwater fishing lakes, with kayaks and SUP included. Just 15 minutes south of Cape Charles and 5 minutes from Kiptopeake, it’s a perfect base for exploring the Shore. Surrounded by trees and just 3 minutes’ drive to Pickett’s Harbor Farm and beach access. The guest suite is separated from the main house, with a private entrance and beautiful garden views for a truly tranquil stay.

4.91 out of 5 average rating, 394 reviews

The kitchen features modern appliances, including a stainless steel refrigerator and an oven with a cooktop. Rich wooden cabinets provide ample storage, while a large granite countertop offers space for meal preparation. A circular skylight allows natural light to enhance the inviting atmosphere.

Home in Virginia Beach

Pet friendly 3 bedroom beach house

Welcome to your perfect vacation getaway! This remodeled 3-bed, 2.5-bath ranch house is just a mile away from the ocean front. It's an ideal destination for families, friends & pets. Bedrooms are equipped with comfy beds. Pet-Friendly: 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

4.99 out of 5 average rating, 134 reviews

A bright sunroom features large windows that frame views of the Chesapeake Bay and surrounding natural landscape. Light-colored furnishings complemented by a wooden coffee table and a small plant enhance the airy feel. The serene atmosphere is accentuated by sunlight streaming through the glass.

Cottage in Norfolk

Private Beach Access at The OV Beach House

Here at the OV Beach House, you have your own private access to the beach and STUNNING water views of the Chesapeake Bay. The sunrises and sunsets are incredible! My husband and I renovated the interior of the house this past year. We poured all of our love (and sweat) designing and crafting a home away from home with you in mind!! You'll find the kitchen stocked with all of the essentials. Towels, soap, shampoo, and conditioner are all provided. Can accommodate up to 8 people.

Place to stay in Virginia Beach

A spacious great room features a gray sofa and a light-colored armchair, complemented by a round coffee table. High ceilings and recessed lighting enhance the open layout, while the kitchen area with modern appliances is visible in the background, connected by a dining space for six.

5 out of 5 average rating, 49 reviews

Peninsula Suite on the Lynnhaven River

Entire 2nd floor waterfront suite in shared home overlooks Lynnhaven river in residential neighborhood. Ideal launching pt for vacation adventures; 30 mins by boat to Chesapeake Bay, 10 mins by car to VA Bch Oceanfront, Chic’s Beach or 20 mins to Norfolk Airport. Kayaks, paddleboards, beach towels/cooler included. 2 bedroom/2-bath suite sleeps up to 5 & parking for 2 cars. Open concept kitchen to great room, 14-ft ceilings & wall-to-wall windows overlooks 600 sq ft deck & water.

4.95 out of 5 average rating, 116 reviews

A sunset casts warm hues over the calm waters of the bay, with silhouettes of a shaded gazebo and a hammock. Weathered pilings and a single bird in flight can be seen against the vibrant sky, enhancing the tranquil atmosphere.

Home in Knotts Island

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!

4.79 out of 5 average rating, 144 reviews

An inviting entrance shows a white picket fence adorned with a heart-shaped wreath. Climbing white flowers create an archway over the gate, leading into a well-maintained grassy area. A covered porch is visible in the background, enhancing the outdoor charm.

Cottage in Chic's Beach

Quaint 2 Bedroom Cottage in Chicks Beach

2 bedroom 1 bathroom quaint cottage, walking distance only 2 blocks to the beach . The beach is great for families with children . This unit is connected to a 1 bedroom unit . 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. Starting June 25th 7 night min check in on Friday only !

Cottage in Gloucester Point

A serene view of a wooden dock extending into the calm waters of Sarah's Creek, surrounded by trees. Two kayaks, one green and one blue, are positioned on the grassy shore, with a charming cottage visible in the background.

4.94 out of 5 average rating, 254 reviews

The Cottage on Sarah's Creek

Nestled on the waters of Sarah's Creek, this cozy cottage is just a short drive from historic Williamsburg and Yorktown. Fully furnished with a new kitchen, dining area, 1 bedroom, 1 bathroom, and a large loft with a queen bed and a pool table. Whether spending your days relaxing on the beach, exploring historic sights, or taking a tour of a local vineyard, you can look forward to the quiet comfort this cottage has to offer during your stay.

4.94 out of 5 average rating, 35 reviews

A comfortable living area features two gray sofas and an accent chair arranged around a circular wooden coffee table. A mounted TV and fireplace are positioned against the white wall, while built-in cabinets hold decorative items. Natural light floods in through large windows.

Guesthouse in Chesapeake

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.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Chesapeake kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.9 out of 5 average rating, 92 reviews

Home in Gloucester

Severnly Pointe Cottage Waterfront Retreat

5 out of 5 average rating, 18 reviews

The exterior view of a two-story house is showcased, featuring wood siding and a staircase leading to the upper deck. A United States flag waves proudly from a flagpole. Lush greenery surrounds the property, creating a natural setting.

Home in Corolla

Lazy Palm Carova 4x4 Beach

5 out of 5 average rating, 4 reviews

The blue, three-story house is viewed from the side, showcasing multiple windows with white trim. A well-maintained path lined with stones leads to the entrance. Two individuals walk towards the house, and a cart is positioned neatly beside plants in the foreground.

Home in Norfolk

Beachfront Getaway, pet friendly

4.89 out of 5 average rating, 9 reviews

A spacious living area features a large sectional couch, a coffee table, and a massage chair. Natural light floods the space through sliding glass doors, illuminating the wood flooring. The open layout connects to a kitchen and dining area, enhancing the communal feel.

Home in Cape Charles

Hot Tub - Massage Chair - Golf Cart - Beach Gear

5 out of 5 average rating, 26 reviews

The exterior of a two-story beach house is shown, featuring a light blue facade and a staircase leading to the upper level. Surrounding green foliage and a wooden privacy fence create a relaxed atmosphere. A paved driveway leads to the house, with open lawn space in the foreground.

Home in Corolla

Beach Dream Inn

4.78 out of 5 average rating, 37 reviews

Two wooden Adirondack chairs are positioned on a sandy area beside the calm water. Lush green plants surround the chairs, while a bridge and boats can be seen in the distance reflecting on the water's surface.

Home in Norfolk

Wil-O-Bay Getaway

4.78 out of 5 average rating, 9 reviews

A newly built coastal home stands elevated on stilts, featuring a spacious lower deck with a pool and hot tub enclosed by a wooden fence. Multiple balconies extend from the upper floors, inviting views of the surrounding natural landscape.

Home in Corolla

Milk 'N' Honey at the 4X4 Carova Beach

4.95 out of 5 average rating, 144 reviews

A classic brick duplex features a large front porch supported by white columns. A ceiling fan hangs in the shaded area, while steps lead up to the entrance. Lush greenery lines the porch, and a clear blue sky complements the welcoming design.

Home in Cape Charles

Harbor View- (Sun - Sun rental June- Aug.)

Show all

Cottage rentals with a kayak

4.96 out of 5 average rating, 50 reviews

The cottage is positioned atop a riverbank, surrounded by greenery. Stairs lead down to a sandy beach along the James River. The home’s exterior features a simple design, and the area displays a mixture of natural vegetation and the beach below.

Cottage in Surry

Riverfront Oasis | Kayaks, Private Beach, & More

4.95 out of 5 average rating, 132 reviews

An aerial view captures the spacious backyard featuring a rectangular swimming pool surrounded by a concrete deck. Lounge chairs are placed by the poolside, with a well-maintained lawn and shrubs in the background. The two-story cottage is shown with a screened porch and a shaded area nearby.

Cottage in Chesapeake

The Cottage @ Captain Genes - Secluded Waterfront

A well-kept garden is framed by flowering hydrangeas in shades of pink and blue. The cottage features large windows with colorful accents, providing a view of the water and nearby pier. Lush greenery complements the serene waterfront setting.

Cottage in Surry

5 out of 5 average rating, 3 reviews

James River Beach Cottage - Private Beach & Pier!

A wooden pier extends into calm waters, leading toward a distant marina. A sandy beach lies in the foreground, inviting relaxation. Soft clouds float above a clear blue sky, creating a serene atmosphere that emphasizes the natural beauty of the waterfront setting.

Cottage in Surry

4.78 out of 5 average rating, 9 reviews

James River Beach Retreat - Private Beach & Pier

Cottage in Norfolk

4.8 out of 5 average rating, 143 reviews

Beach Cottage - On Beach with Wrap Around Porch

Cottage in Norfolk

4.79 out of 5 average rating, 119 reviews

Beach Cottage-Bay Views Loft on Beach & Veranda

5 out of 5 average rating, 21 reviews

A tranquil scene of a wooden dock at sunset, showcasing two white chairs facing the water. The sky is painted in warm orange and purple hues, while a kayak rests nearby, hinting at the outdoor activities available for guests.

Cottage in Sandbridge

Epic Sunsets | Waterfront Cottage | Pet Friendly