Places to stay in Kiptopeke

Farm stay in Cape Charles

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.

4.93 out of 5 average rating, 243 reviews

Loft in Cape Charles

The Cheriton Loft

Located in the heart of Cheriton, The Loft is a bright and sunny apartment. It is perfect for a couple and one child, three friends or one person. Cheriton is an up and coming village which is home to several galleries and an art center. It is less than 4 miles to the charming town and beach of Cape Charles, 3 miles to Oyster Boat Landing and 8 miles to Kiptopeke State Park. The apartment is owned and decorated by"The Sheep Lady", a local painter, illustrator and writer of children's books.

Guesthouse in White Stone

5 out of 5 average rating, 245 reviews

Waterfront Guesthouse II on the Rappahannock

The “Beach House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has beautiful water views and includes access to our private beach & dock (with guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with large shower and a covered patio. The 2nd floor features a large loft bedroom with a queen bed.

Tiny home in Cape Charles

4.98 out of 5 average rating, 317 reviews

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

4.89 out of 5 average rating, 101 reviews

"Live Life Sunnyside Up" - Minutes From The Beach!

Welcome to "Live Life Sunnyside Up" on the Shore! Take a trip off the busy beaten path and kick your feet up at our little slice of paradise. Kid friendly with plenty of amenties for you and your family. On a quiet street, less than 4 miles from the historic town of cape charles and beach, get ready to take a load off and enjoy the many treasures Cape Charles has to offer! Just 5 short minutes from the Oyster Boat Ramp, fishermen are sure to find their honey hole here!

4.96 out of 5 average rating, 175 reviews

Cabin in Cape Charles

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

4.96 out of 5 average rating, 122 reviews

Home in Gloucester Point

Charming coastal home w/ outdoor area and river views

Tucked away at the end of a quiet road, our home welcomes you. This spacious, thoughtfully designed 1 BR/1.5 BA home on 4 acres is ideal for those looking to relax and get away from it all while still being just minutes away from some of the areas best dining and attractions. Whether you want to watch the sun rise over the York River, spend the day exploring the historic triangle, or just take it easy around the house and enjoy the outdoor area, the choice is yours.

4.96 out of 5 average rating, 253 reviews

Steps to the Sea at Salt Box

Escape to The Salt Box, a charming 1915 duplex just one block from the beach in the heart of Cape Charles' Historic District. This cozy, private retreat sits on a peaceful, tree-lined street and is a short stroll to the beach, pier, shops, restaurants, and more! Check out our local Guidebooks or text us anytime—we're happy to share our favorite local spots! Looking for even more space? You can also book the other half of our duplex, Salt Box II!

Superhost

Cottage in Cape Charles

4.78 out of 5 average rating, 113 reviews

Sea Salt Cottage: Tranquil Getaway 5 min to beach

Escape to the Eastern shore! Sea Salt Cottage is your quiet, off-the-beaten path getaway in charming Cape Charles. -Peaceful, rural feel with a 5 min drive to beach, quaint shops & restaurants. -Dog & kid friendly w/ large yard to park boats, RV's, etc. -Hammock, tree swing, outdoor dining, fire pit, romantic sunsets. -2 min to groceries, 10 min to Kiptopeake State Park, 70 min to Chincoteague Island

4.99 out of 5 average rating, 347 reviews

Guesthouse in Phoebus

Sun Sea and Sand

Welcome to Sun Sea and Sand, a Caribbean theme in Hampton, Virginia. Sun, Sea and Sand is a beautiful, waterfront, second story, two-bedroom, one-bath guest house located on a private drive providing lots of privacy including your own private entrance as well as stairs leading from your private balcony directly to the waterfront. High-speed fiber-optic wifi and cable with blue ray player provided.

4.97 out of 5 average rating, 281 reviews

Guesthouse in Yorktown

Charming Yorktown Battlefield Cottage

Kick back and relax after a day of touring the historic triangle. This space was originally built as an artists studio for renowned folk artist Nancy Thomas. The amount of natural light is wonderful and there are still some paint remnants from its former days as an artists studio adding to its unique character and history.

Guest suite in Machipongo

5 out of 5 average rating, 107 reviews

Peaceful Suite in Machipongo

Welcome to our soul-nourishing space perfect for your getaway! A magical place where time seems to stand still in the peace and tranquility. Nature beckons as birds fly back and forth, chimes sing in the breeze, stars glisten in the sky. Welcome to Feather Tree Retreat, a refreshing haven on the Eastern Shore of Virginia!

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Other great vacation rentals in Kiptopeke

5 out of 5 average rating, 44 reviews

Barn in Cape Charles

Coastal Red Barn Retreat

StephanieRating, 5 stars2 weeks ago

The Barn is a beautiful place to stay. The craftsmanship is impressive. The home was immaculate, and the neighborhood is peaceful. The starter kit made travel so much easier, since we didn’t have to worry about bedding, paper products, etc. The welcome book sent ahead of time was perfect to start thinking about how we would spend our time. It’s in a great location. Close to the beach, downtown, hiking, shopping, and dining. Then to come home to relax in the jacuzzi, by the fire pit, watch the sunset over the fields, or play games. Our family had a great vacation thanks to how comfortable Hunter and family made everything.

4.92 out of 5 average rating, 36 reviews

Home in Port Haywood

Anne's Beachfront Shangri-La

VickiRating, 5 stars3 days ago

We had a wonderful stay at Brandon’s place! It was private and beautiful! The house also contained everything we could possibly need from kayaks to a pack and play! We will definitely be back! Thank you!

Guest suite in Cape Charles

4.98 out of 5 average rating, 50 reviews

Chesapeake Retreat - Bay view

CathleenRating, 5 stars5 days ago

Comfortable, clean, and spacious unit. I stayed here for a wedding at the Mimosa Barn which was a 4 minute drive. Cape Charles and other activities were a 10 minute drive. Margaret provided snacks, coffee & creamer, and a bottle of prosecco for us to enjoy. The neighbor's dogs greeted us when we checked in - they are very friendly but be aware they may run in front of your car when pulling in so watch out (especially at night!). There is a private entrance. The unit is connected to the rest of the house by a set of stairs which were blocked off by a styrofoam wall and a curtain. It felt very private - we did not see the host, or even any neighbors during our stay.

4.92 out of 5 average rating, 65 reviews

Seaglass Estate

PhilipRating, 5 stars9 months ago

Nareina was a great host. We had an issue come up prior to arrival and she worked with us and helped out tremendously. She was awesome to work with, very quick responses to questions, and very Pleasant. The house was great, very comfortable and close to area attractions. Outstanding fire pit in the back with great furniture. Very peaceful location and comfortable home!

Place to stay in Machipongo

5 out of 5 average rating, 74 reviews

Smokehouse on the Chesapeake Bay

NatalieRating, 5 stars3 weeks ago

Kenneth was an exceptional host for the following reasons -provided great recommendations for food, adventure on & off the property, & everything in between -approachable when we had questions and/or curiosity -clear & prompt communication -such a cozy, welcoming restored smokehouse (smelled like cedar, oak, & pine in there..LOVED it) -very well kept & clean, his & her robes were perfect for the shower & towels, washcloths, & linens were ready & waiting - fully stocked with treats, coffees & teas -gorgeous property w/ amazing dock for casting a few & enjoying unreal sunsets - super peaceful & serene My husband & I had our mini moon here & it was a continuation of our dreamy marriage to each other. We look forward to our return <3 Love, The Sassers

Superhost

4.9 out of 5 average rating, 29 reviews

Cape Cottage B (Upstairs)

KaseyRating, 5 starstoday

Perfect for a small family. My husband and I and our two little boys throughly enjoyed our stay. It is a little too far to walk to the beach but we rented a golf cart which was great to get around Cape Charles. It was a great stay and we would definitely come back!

Cottage in Gwynn's Island

4.91 out of 5 average rating, 34 reviews

Little Gray Beach House

CorrineRating, 5 stars1 week ago

We loved our short stay at the Little Gray House. The view alone was worth the stay. The beaches are both easy walks and the area is lovely. Everything was clean and cozy and Bronwyn and Kat gave lots of information ahead of time, including some great recommendations. Would definitely recommend checking out The Hatchery and the Gwynn’s Island Museum on the island and spending some time exploring Mathews. We will be staying here again and hopefully soon!