
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.

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

Walk to the Beach, The Dome, & 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, Atlantic 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

3 Blocks to Beach, Fenced Backyard, Pet Friendly!
Welcome to Peach Haven, a newly renovated duplex in the Cape Charles historic district. Just 1 block from the park and 3 blocks from the beach, it's the ideal base for your Cape Charles escape. This pet-friendly rental sleeps five guests comfortably with a master bedroom (queen bed) and a second bedroom with a custom-made full-over-full bunkbed. The house has been thoughtfully stocked with everything you'll need for a comfortable stay. Need more space? Ask about renting the other side, too!

Rustic Beach Condo 3 blocks from the beach!
Make the most of your Virginia Beach experience at this rustic beach house in the heart of the city's ViBe creative arts district! This three-story, townhouse-style condo has all you need and more: watch the summer fireworks from the comfort of your third story balcony or enjoy a short walk to coffee shops, farmers markets, the local convention center, and the beach! If you want the best that VB has to offer just a stroll away from the ocean, look no further than the Baltic Beach House!

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)

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!

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

3bdr Williamsburg Townhouse, sleeps 8

The Williamsburg Haven

3BR Townhome Steps from Atlantic Surf Park & Dome!

Pet-Friendly 4BR Home • Near Beach • Sleeps 8

Modern Townhouse 5 min Drive to Ft. Eustis

CrabaCabana: The Heart of Corolla Beach Life

The Refresh Experience

VA Bch Oasis - ONE Block/3 Min walk to Oceanfront
Townhouse accommodation with a washing machine and dryer

3-Bedroom Norfolk Stay –Minutes from Bases and ODU

Cozy Condo in the Heart of Vibe District

4 Bedrooms, Beautiful Decor, Heart of It All | 517

Modern Luxury Townhome Rooftop Deck & Ocean Views!

Modern Cozy Retreat in the heart of VB!

3 Bd Townhome near Historic Waterfront Portsmouth

Bayside Bliss in the Heart of East Ocean View

Tush and Mane
Townhouse rentals with a patio

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

The Western Branch Professionals Townhome

B Walk to Beach and Sports Center. Dogs Welcome!

Wave Break Hideaway

Family Retreat by the Beach

Centrally-located Hidden Gem

Best Temporary Rental in Chesapeake

Cheerful 2 bedroom townhouse with fireplace
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 | £85 | £89 | £98 | £108 | £109 | £108 | £86 | £85 | £88 | £87 |
| 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
- Corolla Beach
- Carova Beach
- Water Country USA
- First Landing State Park
- Buckroe Beach
- Jamestown Settlement
- Cape Charles Beachfront
- Outlook Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Virginia Living History Museum
- Old Dominion University
- Colonial Williamsburg's Merchants Square
- Virginia Zoological Park
- Town Point Park
- Nauticus
- First Landing Beach
- Chrysler Hall
- Currituck Beach Lighthouse
- Currituck Club
- USS Wisconsin (BB-64)




