
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.

Charming 2BR Close to HU & Waterfront
*SAFE/WALKABLE GREAT LOCATION📍* Stay here and enjoy ALL the pleasantries of Downtown Hampton's quaint waterfront. WALKABLE* to the marina, many restaurants, pubs, IMAX theater, museums+ Historic Post Office* Hampton U* Mill Point Park* City Hall* Phoebus/Ft Monroe-5 min Hampton Coliseum/Convention Aquaplex-7min Buckroe Beach-8min Boo Williams Sports -11min Langley AFB/Newport News-15min Norfolk/ODU-23min Busch Gardens/Williamsburg-28min Portsmouth-29min Virginia Beach-40min ⭐️⭐️⭐️⭐️⭐️📍

Bike to Beach! Dog Friendly and Sparkling Clean
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. There are several restaurants and a brewery within walking distance. There are many parking options at the oceanfront or you can walk or pedal your way there on the 2 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.

*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.

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

NEW! Walk or Bike to the Beach & 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, boardwalk, festivals, and the best coffee shops and restaurants in town! Enjoy the free parking, beach gear, and smart TV with YoutubeTV and Netflix included. Easy access to the interstate for a quick drive to Town Center or Norfolk. Vibe district 0.3 mi Boardwalk 0.6 mi Convention center 0.5 mi Atlantic fun park 0.7 mi

*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)

940 Poseidon'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.

Fast WiFi! King! Tree House bed! Arcade! SMRT TVs
“Guest Favorite”. Open and inviting 2 bedroom townhouse in the heart of Virginia Beach. 5 minutes to the Virginia Beach Amphitheater, Farmers Market, Mall, Movie Theater and Restaurant. 10 Minutes to town center. 15 minutes to the ocean front, convention center and Norfolk. Kids will love our treehouse style bunk beds with tent feature! Stand up Arcade with 12 games including PacMan, Galaga, Dig-Dug, Ms PacMan and more!

Chicks Beach Getaway large yard 500 yards to Beach
4 bedroom 3 bath duplex with a large yard, screened porch & large deck This home is in the Chicks Beach area of Virginia Beach or Chesapeake Beaches. less than 500 yards walk to the beach. Nice back yard and screen porch. $125 for 1 pet and $75 for second. 2 pet max. PLEASE NOTE: Saturday check in and 7 night stay required starting June 4th 2026. Check out 10am checkin is 3:30pm 4 car max

Lakefront Oasis with Fenced Yard
Escape to our peaceful 3-BR lakefront townhouse in Hampton Roads! Comfortably sleeping 7, this family-friendly retreat offers a fully equipped kitchen, dedicated workspace, and a private fenced backyard with serene water views. Enjoy easy access to beaches and local attractions from this quiet, centrally located home. Perfect for families or groups seeking a relaxing getaway.
Popular amenities for townhouse rentals in Chesapeake
Family-friendly townhouse rentals

Chesapeake Bay Beach House" Chix Beach"

Jefferson Abbey II

Just 1-1/2 block from the Beach w/Private Garage!

3bdr Williamsburg Townhouse, sleeps 8

The Williamsburg Haven

3BR Townhome Steps from Atlantic Surf Park & Dome!

Congo Craze!

Beach TownHome near Boardwalk
Townhouse accommodation with a washing machine and dryer

Beach Borough Bliss: Stylish, Remodeled Townhome

Red House on Lake James

Cozy Condo in the Heart of Vibe District

3 Bd Townhome near Historic Waterfront Portsmouth

Doctors Orders - 4 bdrm hot tub walk to beach

CrabaCabana: The Heart of Corolla Beach Life

Tush and Mane

Lux Landing 3br/3bth Spacious Getaway!
Townhouse rentals with a patio

A Walk to Beach and Sports Center & Dogs Welcome!

Spacious 3BR|1 mile to the Oceanfront & The Dome

The Western Branch Professionals Townhome

Cozy Oasis-Spacious 4 Bedroom Condo!

Wave Break Hideaway

Family Retreat by the Beach

Centrally-located Hidden Gem

Best Temporary Rental in Chesapeake
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £77 | £79 | £86 | £89 | £98 | £108 | £109 | £108 | £86 | £92 | £86 | £88 |
| 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 80 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at £15 per night before taxes and fees

Verified guest reviews
Over 3,220 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 Cinemark Chesapeake Square
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- Townhouse rentals Virginia
- Townhouse rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Carova Beach
- Corolla Beach
- Water Country USA
- First Landing State Park
- Buckroe Beach
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
- Cape Charles Beachfront
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- The NorVa
- Currituck Beach
- Currituck Beach Lighthouse
- Nauticus
- Old Dominion University
- First Landing Beach
- Colonial Williamsburg's Merchants Square
- Hampton University
- Regent University
- Currituck Club
- USS Wisconsin (BB-64)




