
Townhome holiday rentals in Chesapeake
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Top-rated townhouse rentals in Chesapeake
Guests agree: these townhouse rentals are highly rated for location, cleanliness and more.

Walk to the Beach, Surf Park, and ViBe District!
Experience Virginia Beach the local’s way in this spacious, newly renovated 2br townhouse. Centrally located so you can walk to the ViBe District, brand new Surf Park, boardwalk, festivals, and the best coffee and restaurants in town! Enjoy the free parking, beach gear, and smart TV with YoutubeTV included. Easy access to the interstate for a quick drive to Town Center or Norfolk. Vibe district 0.3 mi Atlantic Surf Park 0.6 mi Boardwalk 0.6 mi Convention center 0.5 mi Atlantic fun park 0.7 mi

*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.

Spacious 3BR | 1-mile to the Oceanfront & The Dome
Welcome to your home away from home about 1 mile from the Virginia Beach Oceanfront and The Dome and within walking distance to the VA Beach sports center! Perfect for groups up to 9, our home offers ultra-fast 1Gbps internet, 2 dedicated workspaces, and delightful amenities including FREE Parking (up to 4 vehicles). Enjoy the outdoors with our outdoor dining area and a BBQ grill. With numerous local restaurants activities nearby, it’s the ideal getaway for both relaxation and adventure.

A Walk to Beach and Sports Center & Dogs Welcome!
Perfectly located near the Convention Center and the Sports Complex this listing offers 2 bedrooms, a full kitchen and full bath with tub. Private patio with grill and seating and 2 bikes and beach chairs included. 8 blocks to the oceanfront and the ViBe arts district. Perfect for traveling families that want the amenities of a house without having to pay for an exorbitant hotel room(s). Walking distance to great dining and bars. Perfect for cheer contests, races, sporting events.

Sparkling Clean Family & Dog Friendly
Charming 2 bedroom, 1.5 bath townhouse located 1 mile/20 min walk from the oceanfront. Close enough to the oceanfront to enjoy it but also tucked away from all the hustle and bustle. Several restaurants are within walking distance. The oceanfront is easily accessible with plenty of parking available, or walk/ bike ride using the two provided bicycles. All necessities stocked as well as many extras. 65 inch TV with Cox Cable Tv in the living room for relaxing after the beach.

Oceanfront-Dome/Wavegarden-VIBE Restaurants/Beach
Cozy townhouse by the beach, short walk to the sand and 5 min walk to Wavegarden at Atlantic Park Surf Park! Enjoy self check-in, 2 free bikes, surfboards, full kitchen, 65” TV, fast Wi-Fi. Sleeps 8 (6 beds). Central to Virginia Beach & Norfolk; stroll to cafes & fun. Ask about discount for months stay. Free parking, washer/dryer, beach chairs, beach cart, and a quiet patio. Walk to the boardwalk & dining. Family-friendly; & starter coffee provided. Book your beach getaway

Family friendly townhouse
A perfect place to stay when you can't be at home!Townhouse located in lovely family friendly neighborhood. Only a 20-30 min drive to NOB, Portsmouth Naval Shipyard and Oceana. Bright open kitchen with everything you need. Large living room with new comfortable couch and large Smart TV to hang out and watch tv. Privacy fenced back yard to sit and enjoy the evening or a morning cup of coffee. Large primary bedroom with private bathroom and shower. Washer and dryer in t

*No Cleaning Fee*The Pirate's Cove~Lux Furnishings
Welcome to Pirate’s Cove! Just over the bridge from the home of The Pirates of the illustrious HAMPTON UNIVERSITY! *Great walk-able location to all of downtown's restaurants & features the following: *Brand New Carpet* Fresh paint* Premium Luxury Furnishings/Bedding *2 Designated work spaces/desks on each level w/Super Fast WIFI Internet *Fully Equipped Eat In Kit w/Seating for 6-8 *A Coffee/Tea Bar Note:King Bed can also be a single(2 Twin Mattresses)

Beach Livin' by the Chesapeake Bay - VA Beach
Beach livin' just a few short blocks to the Chesapeake Bay, Beach & great restaurants.. Tastefully decorated - all the amenities. 6 person farmhouse table. Deck has table & chairs, grill. Privacy fenced backyard. Beachcart, chairs, towels, umbrella & sand toys. 2 queen beds & 2 bunk beds. Cozy livingrm w/loveseat, wicker chair, wicker swivel rocker, barstools, smart tv with basic cable. Base Rate includes 9% VA Beach occupancy tax and Lodging room tax

956 Neptune's Beach House walk 2 Oceanfront, CCTR
Welcome to Virginia Beach! We are located less than a mile to the Beach, Convention Center & Boardwalk. This spacious townhouse has 2 bedrooms & 1.5 bathrooms. There is parking on site spacious enough to accommodate 2 vehicles. We are located minutes from oceanfront, 20 minutes from Amphitheater, 25 minutes from Downtown Norfolk, 45 minutes to Busch Gardens. The oceanfront resort area has great dining, attractions, & concerts. Vacation like a local!

Entire Home - Close to Beach - Pet Friendly
Welcome to "The Crab Shack" located in Salt Marsh Point. This is our newly renovated home located just minutes from the oceanfront. Everything here is brand new, upscale, comfy and just waiting for you. Imagine relaxing on the front veranda in upscale patio furniture, offset umbrella, outdoor grill and privacy fence. Or take it inside to the professionally decorated beach themed setting, with everything brand new and waiting for you.

Beach condo. 1.5blocks 2 beach.Packed w/ Amenities
This private 3 story condo is nestled in the heart of Virginia Beach’s oceanfront resort area. Located less than 2 blocks from the Virginia Beach boardwalk and beach! The fully outfitted kitchen, each bedroom, and the great room have their own balconies! Enjoy the convenience of living so close to everything the resort area has to offer. Beach cruisers, grill, beach cart, and essential beach gear included. You’ll love it!
Popular amenities for townhouse rentals in Chesapeake
Family-friendly townhouse rentals

3BDR TH near history, relaxation and fun! Sleeps 8

3Bdr for 8 guests near Busch Gardens

Virginia Beach + Beats-Near VaBeach & Amphitheater

Williamsburg Getaway

3-BDR @ Historic Powhatan Resort

Luxury gated community 3Beds 3Baths Corolla OBX

Prime Downtown 2BR Near HU & Waterfront

4BDR Hilton Powhatan Resort. Sleeps 12. Pools
Townhouse accommodation with a washing machine and dryer

Spacious Beach Townhouse

Virginia Beach 4BR Townhouse 2 Living Rooms

3 Bd Townhome near Historic Waterfront Portsmouth

Bayside Bliss in the Heart of East Ocean View

Modern Townhouse 5 min Drive to Ft. Eustis

Lux Landing 3br/3bth Spacious Getaway!

VA Bch Oasis - ONE Block/3 Min walk to Oceanfront

Group‑Friendly 4BR • Prime Location
Townhouse rentals with a patio

Cozy Condo in the Heart of Vibe District

Summer 2026 Corolla Light Resort OBX 4BR/4.5Bath

The Western Branch Professionals Townhome

Cozy Oasis-Spacious 4 Bedroom Condo!

Vibe District • Near Beach • Balcony • Sleeps 6

Relaxing on the bay/Relocation Special/Close beach

Family Retreat by the Beach

Best Temporary Rental in Chesapeake
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $149 SGD | $139 SGD | $121 SGD | $153 SGD | $168 SGD | $185 SGD | $187 SGD | $185 SGD | $148 SGD | $146 SGD | $150 SGD | $149 SGD |
| Avg. temp | 6°C | 7°C | 10°C | 16°C | 20°C | 25°C | 27°C | 26°C | 23°C | 18°C | 12°C | 8°C |
Quick stats about townhouse rentals in Chesapeake

Total holiday rentals
Explore 90 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at $25 SGD per night before taxes and fees

Verified guest reviews
Over 3,110 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
80 of Chesapeake holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesapeake rentals

4.8 Average rating
Chesapeake stays are highly rated by guests – averaging 4.8 out of 5!

Nearby attractions
Chesapeake’s top spots include Chrysler Museum of Art, Nauticus and Cinema Cafe-Greenbrier Mall
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- Townhouse rentals Virginia
- Townhouse rentals United States
- Busch Gardens Williamsburg
- Virginia Beach Oceanfront
- Corolla Beach
- Carova Beach
- Buckroe Beach
- Water Country USA
- Cape Charles Beachfront
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Nauticus
- Hampton University
- First Landing Beach
- Virginia Zoological Park
- Colonial Williamsburg's Merchants Square
- Town Point Park
- Regent University
- Old Dominion University
- Virginia Living History Museum
- Currituck Club
- Currituck Beach Lighthouse





