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Holiday homes in Chesapeake You’ll Love

Top-Rated Chesapeake Holiday homes for Every Budget and Style!

Looking for a holiday home in Chesapeake (Virginia)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $50.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Chesapeake.

We found 7 Holiday-homes in Chesapeake and the surrounding area (within 60 miles)

Relax Inn Ultimate Home in Virginia Beach, USA

Relax Inn Ultimate Home

Villa in Virginia Beach near Chesapeake, Virginia , 2052 Susan Lee Lane
Relax Inn Ultimate Home is located in Virginia Beach, just 11 miles from Norfolk Botanical Garden and 16 miles from King Neptune Statue on the Boardwa...
  • Parking
  • Bar
  • Family rooms
  • Outdoor pool
  • Kids' outdoor play equipment

Fabulous 2 Reviews 9.0

from $70.00 Show details »

Mint2Stay Suite in Portsmouth, USA

Mint2Stay Suite

Holiday home in Portsmouth near Chesapeake, Virginia , 1005 Taft Drive
Mint2Stay Suite offers accommodations in Portsmouth, 14 miles from Norfolk Botanical Garden and 25 miles from King Neptune Statue on the Boardwalk.
  • Parking
  • Family rooms

Exceptional 7 Reviews 9.9

from $80.00 Show details »

4 Mi to Dtwn Home with Fenced Yard in Portsmouth! in Portsmouth, USA

4 Mi to Dtwn Home with Fenced Yard in Po...

Holiday home in Portsmouth near Chesapeake, Virginia
4 Mi to Dtwn Home with Fenced Yard in Portsmouth! offers accommodations in Portsmouth, 23 miles from King Neptune Statue on the Boardwalk and 12 miles...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Poor 1 Reviews 3.0

from $212.30 Show details »

Virginia Beach 2Story with Pool in Virginia Beach, USA

Virginia Beach 2Story with Pool

Holiday home in Virginia Beach near Chesapeake, Virginia , 1001 Lockwood Court
Virginia Beach 2Story with Pool offers accommodations in Virginia Beach, 7.5 miles from Norfolk Botanical Garden and 15 miles from King Neptune Statue...
  • Parking
  • Pets allowed
  • Swimming Pool

no reviews

from $64.00 Show details »

Cozy Portsmouth Retreat 2BR 1BA in Portsmouth, USA

Cozy Portsmouth Retreat 2BR 1BA

Holiday home in Portsmouth near Chesapeake, Virginia , 633 Mount Vernon Avenue
Cozy Portsmouth Retreat 2BR 1BA offers accommodations in Portsmouth, 22 miles from King Neptune Statue on the Boardwalk and 11 miles from Topgolf Virg...
  • Family rooms

Exceptional 7 Reviews 9.8

from $171.60 Show details »

Portsmouth 2BR 1BA Getaway in Portsmouth, USA

Portsmouth 2BR 1BA Getaway

Holiday home in Portsmouth near Chesapeake, Virginia , 631 Mount Vernon Avenue
Featuring a garden, Portsmouth 2BR 1BA Getaway features accommodations in Portsmouth.
  • Family rooms

Good 3 Reviews 7.0

from $187.04 Show details »

Econo Lodge Chesapeake Route 13 and I-464 in Chesapeake, USA

Econo Lodge Chesapeake Route 13 and I-46...

Lodge in Chesapeake, Virginia , 2222 South Military Highway
The Econo Lodge hotel is located off Interstate 64 and is convenient to downtown Chesapeake and Norfolk.
  • Parking

Passable 93 Reviews 5.2

from $81.49 Show details »

Number of Holiday homes in Chesapeake 7
Number of guest ratings 9,671
Average price per night $397.00
Lowest price per night $50,00
Highest price per night $4.471,11

Top 10 Cheapest Holiday-homes in Chesapeake

Discover the Cheapest Holiday-homes in Chesapeake – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Chesapeake

Check out the Most Booked Holiday-homes in Chesapeake – Based on Guest Popularity.

Holiday homes in Chesapeake (Virginia), comfortable and familiar

Staying in a holiday or vacation home in Chesapeake can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Chesapeake for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Chesapeake should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com