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Places to stay near Outlook Beach

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Top-rated vacation rentals near Outlook Beach

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.

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!

Top guest favorite
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.
Farm stay in Cape Charles
5 out of 5 average rating, 429 reviews

Guesthouse at Vessel Farm & Winery, Waterfront

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.

Guest favorite
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!

Guest favorite
A spacious bedroom features a king size bed dressed in white linens and accented with colored pillows. Two bedside lamps illuminate the room, complemented by a ceiling fan. A comfortable bench sits at the foot of the bed, with a vibrant throw blanket draped across.
Townhouse in Hampton
4.98 out of 5 average rating, 111 reviews

*Beautiful Water Views* King Bed*Fast WIFI

Do you desire Peace, Quiet & Tranquility? This townhome is the PERFECT getaway! It's RIGHT on the water and features the following: *Newer Furnishings! *Blazing Fast Panoramic WIFI & Dedicated Workspace *Bedroom 1: KING size bed overlooking the water. Not a bad way to wake up?!? *Gourmet Kit w/Granite Countertops, Stainless Steel Appliances, complete w/a Convection Oven & Coffee Maker & Creamers * Smart TVs w/Adjustable Wall Mounts for your view preference, in Each Bedroom & Living Room.

Guest favorite
An inviting living area showcases two comfortable couches arranged around a glass coffee table. A large television is mounted on the wall opposite. The dining area, featuring a modern table and chairs, can be seen in the background, enhancing the open floor plan.
Apartment in Hampton
4.9 out of 5 average rating, 122 reviews

Comfy 3 Bedroom Hideaway Minutes From H.U. & Beach

Welcome To Our Place! Ideal For Family Trips, Traveling For Business, Staycations Or Baecations In The Downtown Hampton Area. The Home (Unit A) Is Equipped With Complimentary WiFi, 65” Smart TV, Fully Stocked Kitchen, Coffee Bar, Washer & Dryer! Walking Distance To Restaurants & Nightlife! 5 Min: Buckroe Beach Fort Monroe Hampton University 15 Min: Norfolk International Airport Norfolk Premium Outlets 25 Min: Busch Gardens Williamsburg Water Country USA Virginia Beach Oceanfront

Guest favorite
A charming studio entrance is framed by lush greenery and flowering plants. A yellow exterior is complemented by a welcoming front porch adorned with climbing vines. A brick pathway leads to the door, inviting guests into a cozy retreat.
Guest suite in Hampton
4.96 out of 5 average rating, 593 reviews

Storybook Cottage

Beautiful studio within walking distance to downtown Hampton waterfront, marinas, shopping, dining, microbreweries, arts & museum district. Short drive to beaches, NASA/Langley AFB, Hampton U., and Ft. Monroe. Centrally located off I-64 between Williamsburg and Va. Beach. Quiet and cozy. Has private front and rear entrances and covered private back porch. Perfect for couples & business travelers. Complimentary coffee, tea , water, etc. No 3rd party reservations. Self check in after 3 pm.

Top guest favorite
Loft in Poquoson
4.97 out of 5 average rating, 104 reviews

Bull Island Getaway - Cozy Suite Near Yorktown

Escape to Bull Island Getaway, a private and comfortable guest suite nestled in the peaceful waterfront town of Poquoson, Virginia. Whether you're here to visit family, explore the Chesapeake Bay, enjoy local history, or travel for work, you'll have everything you need for a relaxing stay. Our suite offers the privacy of your own space while keeping you just minutes from Yorktown, Hampton, Ft. Monroe, Newport News, Langley Air Force Base, NASA, Buckroe Beach, and Colonial Williamsburg

Top guest favorite
A sandy beach stretches into the distance, bordered by gentle dunes and green grasses. A wooden walkway leads to the shore, where several figures can be seen walking. The calm ocean reflects the blue sky, dotted with fluffy white clouds.
Home in Virginia Beach
4.99 out of 5 average rating, 233 reviews

Play by the Bay 1 MIN TO WATER

LESS THAN 1 MIN WALK TO WATERS EDGE. Fantastic beach home with 3 bdrms, 3 baths, Living room-dining rm combo with vaulted ceilings, kitchen, TV in 4 rooms, Wi-Fi, large deck with natural gas Weber grill, Washer-dryer. Great water views while you are relaxing on the deck. Many amenities! Just bring your bathing suit. Our guests have all said they love this place! Very close to many wedding venues, restaurants, state park, oceanfront boardwalk is closeby, military bases, etc.

Superhost
The exterior of a cheerful yellow tiny beach home is visible, showcasing a welcoming porch with a set of steps leading to a white front door. Light filters through the large windows on either side, and a small welcome mat is placed at the entrance.
Home in Hampton
4.9 out of 5 average rating, 117 reviews

Tiny Home In Buckroe Beach

Welcome to our beautiful, newly renovated Tiny Beach Home. Perfectly located just 1 block distance to the beach. Our tiny home features unique retro interior design and is equipped with all the amenities you need for a relaxing stay. With comfy home vibes and proximity to the best restaurants, bars, and tourist attractions, this condo is the perfect place to experience all that Hampton has to offer. Book today and enjoy an unforgettable stay in Buckroe Beach.

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!!!

Top guest favorite
A vibrant sunset is captured over the water, with shades of orange and pink blending into the horizon. A wooden dock stretches into the foreground, surrounded by evenly spaced posts that rise from the calm water's surface.
Guesthouse in Hampton
4.99 out of 5 average rating, 411 reviews

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.

Popular amenities for vacation rentals near Outlook Beach

KitchenWifiPoolFree parking on premisesAir conditioning

Other top sights near Outlook Beach

Outlook Beach

81 locals recommend

Fort Monroe National Monument

49 locals recommend

Casemate Museum

28 locals recommend

Condo rentals with wifi

Top guest favorite
A bright guestroom is furnished with two double beds, each featuring a light-colored quilt. Nightstands with lamps are positioned beside the beds. A large window offers views of greenery, with soft curtains complementing the decor.
Condo in Williamsburg
4.96 out of 5 average rating, 159 reviews

Comfy 1BR w pond view Kingsmill

Top guest favorite
A cozy bedroom features a king-size bed with crisp white linens and decorative pillows. A large window offers a view of a green space beyond, with a sitting area including a chair and small table. A 50" TV and coffee station are positioned on a wooden dresser.
Condo in Williamsburg
4.95 out of 5 average rating, 219 reviews

Kingsmill 1bed/1ba on Golf Course 9th Fairway

Top guest favorite
A workspace with a wooden desk and a comfortable chair is situated by large windows, offering expansive views of the ocean. Natural light streams in, highlighting the tranquility of the beach outside. The windows are framed by light-colored blinds, with a small plant placed on the desk.
Condo in Norfolk
4.99 out of 5 average rating, 111 reviews

Beachfront Getaway, Pet Friendly, Mermaid Suite

Superhost
A modern kitchen features sleek black cabinetry and stainless steel appliances, including a refrigerator and stove. Countertops provide ample workspace, and light-colored tiles add to the clean design. Soft lighting is provided by a ceiling fixture, enhancing the kitchen's inviting ambiance.
Condo in Norfolk
4.81 out of 5 average rating, 248 reviews

Best Value Condo in Downtown Norfolk

Top guest favorite
A tranquil lakeside scene captures two individuals on paddleboards gliding across calm water. Sandy shores are lined with chairs, offering a peaceful spot to relax. In the background, a spacious building features a wraparound deck, providing views of the serene landscape.
Condo in Williamsburg
4.97 out of 5 average rating, 119 reviews

Walk to beach lovely 2/2 in "Kingsmill on James"

Guest favorite
A charming private balcony offers a dining setup for two with white Adirondack chairs and a table, overlooking the beach. A stunning sunset illuminates the horizon, while the seaside view provides a serene backdrop for the table adorned with floral centerpiece and tableware.
Condo in Virginia Beach
4.88 out of 5 average rating, 269 reviews

Oceanfront Gem VaB Studio Exceptional Views

Top guest favorite
Condo in Virginia Beach
4.97 out of 5 average rating, 149 reviews

Oceanfront Studio: Boardwalk, Beach, & Pool Views

Guest favorite
The living area features a light-colored sofa positioned across from a modern coffee table. A bar area with two stools is visible in the background, leading to a kitchen with white cabinetry. Natural light illuminates the space, creating a bright and open atmosphere.
Condo in Virginia Beach
4.86 out of 5 average rating, 177 reviews

Beach Bungalow on the Boardwalk

Family-friendly house rentals

Guest favorite
The exterior of the home is presented with a multi-level structure, featuring a balcony above a covered parking area illuminated by warm lights. A decorative planter stands near a pathway lined with pebbles, leading to the entrance of the home.
Home in Norfolk
4.9 out of 5 average rating, 123 reviews

*Escape to the Tangerine Dream*

Superhost
A modern living area features a comfortable sofa adorned with decorative pillows and a cozy throw. A large dining table with natural wood tones is visible in the background, contrasting against a blue accent wall decorated with serene artwork. Ample lighting brightens the space.
Home in Norfolk
4.93 out of 5 average rating, 105 reviews

Stylish Beach House, Hot Tub, Pet Friendly

Guest favorite
An aerial view of the property reveals a spacious backyard featuring a swimming pool surrounded by lounge chairs and inflatable pool toys. Lush greenery encircles the area, enhancing the sense of privacy, and the house is seen with its inviting deck and patio area.
Home in Portsmouth
4.92 out of 5 average rating, 173 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

Top guest favorite
A cozy living area features a striped sofa and two light armchairs, arranged around a soft, plush area rug. Natural light enters through two windows, and a mounted television is placed on the wall. A dining area is visible in the background, adorned with a simple floral centerpiece.
Home in Norfolk
4.93 out of 5 average rating, 274 reviews

Cozy beach cottage! One block to the beach!

Top guest favorite
Home in Hampton
4.96 out of 5 average rating, 114 reviews

Grandview Island Beach Cottage Private Fenced Yard

Guest favorite
Home in Norfolk
4.85 out of 5 average rating, 165 reviews

2 Min Walk to Beach • Fenced Yard • Parking

Guest favorite
The living area showcases a modern design with a ceiling fan and a large flat-screen TV mounted above a white brick fireplace. A cozy seating arrangement includes two armchairs and a blue sofa, centered around a round wooden coffee table adorned with greenery. Light-colored walls enhance the spaciousness.
Home in Hampton
4.95 out of 5 average rating, 102 reviews

Buckroe Beach House~Walk to Beach / Only 3 Blocks!

Top guest favorite
A two-story house featuring a welcoming porch with white railings and steps leading to the front door. The exterior is clad in light siding, complemented by well-kept landscaping and a driveway leading to a garage on the right. Trees provide a natural backdrop.
Home in Suffolk
4.85 out of 5 average rating, 115 reviews

Perfect Getaway!

Apartment rentals with air conditioning

Guest favorite
A well-lit bedroom features a spacious bed with decorative pillows and a cozy throw blanket. Natural light enters through a window, while a standing lamp and a woven basket add functional elements. A ceiling fan and light fixture enhance the room's comfort.
Apartment in Portsmouth
4.85 out of 5 average rating, 155 reviews

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Guest favorite
An open living area features a red couch and a round mirror on the wall. A kitchen with stainless steel appliances is visible, alongside a stone-topped dining table. Natural light enters through the windows, and a ceiling fan offers airflow.
Apartment in Hampton
4.91 out of 5 average rating, 112 reviews

Three blocks from the Beach 2

Superhost
A spacious bedroom is depicted, featuring a large bed with a light-colored blanket. A ceiling fan is installed above, and large windows are dressed with dark curtains. A couch and a small table with a chair are positioned to the side, contributing to the room's layout.
Apartment in Hampton
4.88 out of 5 average rating, 147 reviews

The Cottage at Sojourn: Buckroe - one bedroom

Top guest favorite
A spacious bedroom is presented with a king bed dressed in neutral bedding. Two bedside tables with lamps flank the bed, complementing the light wood furniture. A designated work space, including a desk and chair, is located nearby. Natural light enters through a window adorned with light curtains.
Apartment in Chesapeake
4.97 out of 5 average rating, 115 reviews

Entire Apartment - No Cleaning Fees!

Top guest favorite
A garden area is showcased, featuring vibrant pink flowers in the foreground. Lush green grass and hedges frame the view, which extends to a peaceful waterfront scene with trees lining the shoreline. Natural light enhances the serene outdoor atmosphere.
Apartment in Yorktown
4.99 out of 5 average rating, 150 reviews

Yorktown on the Waterfront

Top guest favorite
A wooden deck is showcased, surrounded by lush greenery. The railing is made of wood with black metal accents. The space offers an inviting outdoor area, nestled in a tranquil environment with a view of trees and a fenced yard.
Apartment in Virginia Beach
4.92 out of 5 average rating, 601 reviews

Private apartment only 3 blocks from the Beach

Top guest favorite
A spacious studio apartment features a queen-size bed adorned with a colorful coral-themed quilt. Nearby, a small seating area is visible, alongside a well-equipped kitchen. Warm wood flooring enhances the inviting atmosphere, complemented by a modern ceiling fan and natural light entering through the window.
Apartment in Newport News
4.98 out of 5 average rating, 253 reviews

Centrally Located Sleek Studio Apartment

Guest favorite
A modern kitchen area is equipped with sleek cabinetry and stainless steel appliances, including a microwave. A dining table with two black chairs is positioned next to a gray sofa adorned with patterned cushions. A minimalistic coffee table is placed in front, enhancing the open layout.
Apartment in Norfolk
4.83 out of 5 average rating, 103 reviews

The Rosalie Suite 4, Steps from Norfolks Hospitals

Other great vacation rentals near Outlook Beach

Top guest favorite
The beachfront home is positioned within a serene neighborhood, featuring a spacious deck and elegant exterior. Bright lights glow from multiple windows, indicating a welcoming interior. Lush greenery surrounds the property, enhancing the sense of tranquility in this coastal setting.
Townhouse in Norfolk
5 out of 5 average rating, 60 reviews

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

Guest favorite
Guesthouse in Norfolk
4.96 out of 5 average rating, 23 reviews

The garden house

Guest favorite
A welcoming living area features a comfortable brown leather sofa adorned with colorful accent pillows. Two small potted plants are placed on a light blue table, complemented by decorative trays showcasing vibrant patterns. A mounted television and a floor lamp are visible in the background.
Home in Hampton
4.94 out of 5 average rating, 149 reviews

Fully Furnished Home in Hampton 5mins from H Uni

Top guest favorite
A charming two-story home is seen from the street, featuring a welcoming front porch with white railing. Large windows allow natural light to fill the space. The yard is well-maintained and bordered by a sidewalk, surrounded by trees that provide shade.
Home in Norfolk
4.99 out of 5 average rating, 160 reviews

Ghent on the Corner: Cozy 3 bed 2.5 bath home

Top guest favorite
Two comfortable white Adirondack chairs are positioned on a wooden deck, facing the peaceful expanse of the Chesapeake Bay. The scene includes soft grass in the foreground and a clear sky above, creating a serene viewing spot for enjoying the beach.
Guest suite in Norfolk
4.93 out of 5 average rating, 669 reviews

Beachfront Exclusive Bay front Suite

Top guest favorite
Home in Norfolk
4.95 out of 5 average rating, 78 reviews

Beach Bungalow • Navy Base • Quiet St • Dogs OK

Guest favorite
A spacious home is depicted with a welcoming front porch featuring a gentle ramp for accessibility. Lush greenery surrounds the exterior, and the peaceful atmosphere is enhanced by the colorful sunset sky. The house showcases a combination of brick and siding with large windows.
Home in Hampton
4.86 out of 5 average rating, 416 reviews

Family Holiday House. Events and Beaches Nearby

Guest favorite
Large windows provide stunning views of the lake, reflecting vibrant colors of the sunset. A small potted plant sits on a table beside a white chair, while light from the setting sun casts a warm glow across the interior space.
Home in Norfolk
4.94 out of 5 average rating, 137 reviews

THE POINT! Private waterfront Oasis!