Vacation rentals in Isle of Wight

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Top-rated vacation rentals in Isle of Wight

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A well-appointed bedroom features a spacious bed with a textured white cover. Colorful accent pillows add depth to the decor. A wooden dresser stands against one wall, while a bedside lamp illuminates the space. Natural light filters through a window adorned with light curtains.

Home in Smithfield

4.97 out of 5 average rating, 326 reviews

Mason Manor - Downtown Smithfield next to WCP

Historic Smithfield 233 S Mason Street 2 Bedrooms 1 Bath Located in the heart of historic Smithfield boasts old world charm and character with a touch of today’s conveniences. The living room has gas fireplace for cool evenings & leads to dining area & updated fully equipped kitchen. The full bath is updated with jetted tub. Front porch swing for relaxing and back deck for entertainment. Windsor Castle Park just steps away. Located just around the corner from restaurants, shopping & more.

FamilyLocationGetting around

Top guest favorite

A winding gravel pathway is illuminated by soft lighting, bordered by lush greenery. String lights are hung above, casting a warm glow over the area, which is surrounded by trees and plantings. A staircase leads to an elevated area in the background.

Guesthouse in Gloucester County

4.97 out of 5 average rating, 238 reviews

Stylish Creekside Cabin w/ HotTub, Parklike views.

Escape to this beautifully remodeled guest cottage, designed for an unforgettable stay. Nestled in a serene 6.5-acre setting with private creek views, it's just minutes from shopping, breweries, and dining. Wake up to breathtaking scenery, unwind in a peaceful setting, and enjoy modern amenities. Relax by the fire pit or soak in the hot tub. Perfect for a romantic retreat or a fun-filled family getaway in the Historic Triangle. Unmatched comfort, charm, and relaxation—your perfect escape awaits!

LocationFamilyWifi

Top guest favorite

A serene cottage, surrounded by lush greenery, features a welcoming front porch with chairs and warm lighting. A gravel pathway leads to the entrance, highlighting the harmony between the home and its natural surroundings.

Farm stay in Smithfield

5 out of 5 average rating, 186 reviews

Cozy Farm Cottage with Horses, Fire Pit, & Trails

Escape to Timberline Ranch, a 30-acre horse farm near historic Smithfield. Horses and goats are visible from multiple windows. Your bedroom is cozy with room-darkening drapes, plenty of blankets and pillows. The kitchen is well stocked. Coffee station stocked and to-go cups. Bathroom has a ceiling heater, towel warmer, essentials. W/D with detergent. Step out to the front porch rocking chairs, fire pit (wood incl), and picnic table. Explore trails, follow the creek, and hunt for hidden gnomes.

FamilyLocationWalkability

Superhost

A couple relaxes on the deck of the sailboat, enjoying drinks against a vibrant sunset backdrop of pink and purple hues. Soft blankets and a cozy atmosphere are present, with the marina and boats gently reflected in the calm water.

Boat in Norfolk

4.91 out of 5 average rating, 140 reviews

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!

LocationFamilyLayout

Top guest favorite

The exterior of a two-story colonial home is framed by large trees and a manicured lawn. White wooden siding complements the grey metal roof. A white picket fence encircles the front yard, highlighting the entrance adorned with double doors and several windows with green shutters.

Home in Smithfield

4.98 out of 5 average rating, 66 reviews

Oak Level Acres

Welcome to Oak Level! This beautiful house built in 1768 sits on 10 acres of land surrounded by over 1000 acres of farmland. Inside you'll discover unique artifacts preserved from the property's rich history. This restored colonial home sleeps 13 people comfortably with 4 bedrooms & 2.5 bathrooms. Fully stocked with fresh linens, towels, cookware, & other essentials. Only a 30min drive from Colonial Williamsburg. It is the perfect place for a family getaway, company retreat, or special event.

LocationFamilyAmenities

Top guest favorite

A charming two-story house features a covered front porch adorned with white railings and light landscaping. The exterior is painted in soft yellow, complemented by white trim. A gravel pathway leads to the entrance, with a well-maintained grassy yard on either side.

Home in Smithfield

4.92 out of 5 average rating, 236 reviews

Pigs Inn a Blanket

Pigs Inn a Blanket is the perfect spot for your Smithfield, VA stay! In close walking distance to all of the wonderful shops, farmer's market, historic spots, restaurants, parks and more. After you have toured all the wonderful things Smithfield has to offer, enjoy time with your family in the backyard oasis, with the grill and/or the fire pit. The home features 3 bedrooms and 2 full baths with a living room, dining area, kitchen and laundry. Perfect spot for you and your family! NO SMOKING!!

LocationValueLong stay

Top guest favorite

A charming log cabin is set amidst a lush green landscape, surrounded by towering trees. A stone pathway leads to the entrance, while natural stumps serve as rustic seating. Sunlight filters through the branches, casting a warm glow across the inviting exterior.

Home in Smithfield

4.99 out of 5 average rating, 67 reviews

Serene 8ac log house W/hot tub! Spacious 4BR/2BA

Welcome to your perfect short-term rental getaway in Smithfield, Virginia! Nestled along the picturesque riverbank, this enchanting log cabin invites you to unwind in the lap of natural beauty. Immerse yourself in the serenity of the surroundings as you indulge in the charm of a gorgeous retreat. **The Cabin:** Discover the allure of rustic elegance with our stunning log cabin, providing a cozy haven for your escape. You’ll be captivated by the tranquility that defines this unique dwelling.

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Superhost

Home in Carrollton

4.82 out of 5 average rating, 11 reviews

Green Acres is the Place to Be…

Welcome to your family’s home‑away‑from‑home in beautiful Carrollton, Virginia. This bright and cozy single‑family house offers a peaceful neighborhood setting, plenty of space for kids to play, and quick access to some of Coastal Virginia’s best family attractions. You are 10 minutes away from historic downtown Smitfield (Ham Capital of the World) which features shopping and dining. Don’t forget to stop in the Isle of Wight Museum and see the World’s Oldest Edible Cured Ham.

LocationFamilyHospitality

Guest favorite

A two-story cabin made of wood stands beside a serene pond, surrounded by tall pine trees. The cabin features large windows and a spacious deck with rocking chairs, inviting peaceful moments by the water's edge.

Cabin in Cape Charles

4.96 out of 5 average rating, 254 reviews

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.

FamilyValueHiking

Top guest favorite

An outdoor area features a small red Tiny House beside a clear pool. Two shaded seating areas are provided with umbrellas, along with a picnic table and a swing. Open green space extends beyond, bordered by trees, creating a natural setting.

Tiny home in Wakefield

4.96 out of 5 average rating, 97 reviews

Cute 1-bdrm tiny house in the country w/firepits

Enjoy the sounds of nature at this Studio-style Tiny House with heat for wintry nights and air conditioning. Tiny House features a kitchenette with a mini fridge, microwave, portable electric stove, coffee pot and grill. Plus a kitchen sink and running deep well water. Relax on the porch. This sleeps 2 privately and with a full size bed and a sleeper sofa. Inside you will find a new toilet for your convenience, plus a outdoor bathroom, shower and wash station.

LocationValueCleanliness

Top guest favorite

Home in Williamsburg

5 out of 5 average rating, 12 reviews

Williamsburg's Stylish 1959 Mid-Century Modern Gem

Step back in time at this authentic Mid-Century Modern retreat in Williamsburg. Set on over an acre, this 4-bedroom, 2-bath home blends iconic '50s style with modern comfort. Spend evenings gathered on the patio, fire up the gas grill at the outdoor kitchen with its own sink and counter space, and admire several classic vehicles on display that complete the vintage atmosphere. Spacious, stylish, and unforgettable, it's a stay unlike any other.

FamilyLocationHospitality

Top guest favorite

An aerial view showcases a beach cottage with a white roof situated near a sandy shore. The beach is visible with gentle waves lapping at the coastline. Surrounding vegetation and neighboring homes are seen, enhancing the coastal ambience.

Cottage in Norfolk

4.98 out of 5 average rating, 108 reviews

Life on a Sandbar right on Chesapeake Bay

Two bedroom, two bath cottage located on Willoughby Beach right on the shore of the Chesapeake Bay. Centrally located between Williamsburg, Jamestown, Hampton, and Norfolk, Virginia Beach, and the Outer Banks. Close to Norfolk Naval Bases and Old Dominion University. Great for surf fishing or pier fishing on nearby Ocean View Fishing Pier and Restaurant. THIS PROPERTY CANNOT BE RENTED THOUGH CRAIGSLIST!!! DON'T BE SCAMMED!!!

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