Search best cottages in Chesapeake, VA from 100+ sites!

13 available cottage rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Chesapeake, VA cottages
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Chesapeake, VA Cottages: no available offers. Here are other great options for your stay!

Cozy Country Studio Apartment - Chesapeake, VA
9.5 38 reviews

Cozy Country Studio Apartment

house, Chesapeake
This Chesapeake studio rental is peacefully located about 45 minutes from Chesapeake Bay beaches.
The cozy unit offers a queen-size bed, kitchenette, air conditioning, parking, and accommodates two guests, perfect for exploring the Chesapeake area.
Spacious Retreat 3 Bed - Chesapeake, VA
No reviews

Spacious Retreat 3 Bed

house, Portsmouth
This spacious 3-bedroom home in Portsmouth is located 11 miles from Norfolk International Airport and within 23 miles of attractions like Norfolk Botanical Garden and Topgolf Virginia Beach.
This house accommodates up to 11 guests and offers free Wi-Fi, private parking, and a full kitchen, with non-smoking accommodations and a 10:00 AM check-out.
Walk To River & Downtown: Portsmouth Apartment! - Chesapeake, VA
No reviews

Walk To River & Downtown: Portsmouth Apartment!

house, Portsmouth
This Portsmouth apartment rental is conveniently located near the riverfront and downtown, within walking distance of local attractions and 8.7 miles from Norfolk International Airport.
The 1190-square-foot house features two bedrooms, one bathroom, and accommodates up to seven guests, offering free Wi-Fi, air conditioning, parking, and a fully equipped kitchen.
Pet-friendly Norfolk Retreat ~ 7 Mi To Beach! - Chesapeake, VA
8.0 5 reviews

Pet-friendly Norfolk Retreat ~ 7 Mi To Beach!

house, Norfolk
This Norfolk vacation rental is conveniently located just 7 miles from the beach, 2.8 miles from Topgolf Virginia Beach, and 6.3 miles from Mount Trashmore Park, making it easy to explore the area's attractions. The house is perfect for families or groups, with 3 bedrooms and 2 bathrooms, comfortably accommodating up to 6 guests in its 1700 square feet of space.
This Norfolk home offers a range of amenities and features, including a fully equipped kitchen with a dishwasher, air conditioning, a spa, parking, and free Wi-Fi. Pets are welcome, and the house is close to the Virginia Beach National Golf Club and The Virginia Beach Convention Center, offering plenty of options for entertainment and activities.

Frequently Asked Questions about cottages in Chesapeake, VA

  • When is the best time to rent a cottage in Chesapeake, VA?

    The best time to rent a cottage in Chesapeake is during the spring and fall. The weather is mild, and you'll avoid the summer crowds. Plus, the foliage is beautiful in the fall.
  • What are the best cottages in Chesapeake, VA?

    Among the cottages in Chesapeake, VA, The Cozy Cottage Two Bedroom - King Bed House, Cowbell Cottage and Farm Cottage: The Cutest Retreat are the most popular ones.

  • What are the can't-miss sights in Chesapeake, VA?

    You can't miss the Chesapeake Bay Maritime Museum, the Great Dismal Swamp National Wildlife Refuge, and the Chesapeake Arboretum. These places offer a glimpse into the local history, nature, and culture of Chesapeake.
  • What are the best pet friendly cottages in Chesapeake, VA?

    The best pet friendly cottage in Chesapeake, VA is Cowbell Cottage.

  • Why consider renting a cottage in Chesapeake, VA for your stay?

    Renting a cottage in Chesapeake offers a more relaxed and private experience than staying in a hotel. You'll have your own space and kitchen, and many cottages come with amenities like a porch or yard. It's a great way to enjoy the natural beauty of the area.
  • What are the best cottages with parking in Chesapeake, VA?

    The best cottage with parking in Chesapeake, VA is Farm Cottage: The Cutest Retreat.

  • Can you easily explore Chesapeake, VA on foot or by bike?

    While Chesapeake is a large city, you can easily explore some areas on foot or by bike. The Chesapeake Bay waterfront and the Greenbrier area are both walkable and bikeable. However, you'll need a car to reach the Great Dismal Swamp and other attractions outside the city center.
  • What are the best restaurants in Chesapeake, VA with nature views?

    The Blue Crab Restaurant and The Boathouse at Indian River are great options for dining with nature views. The Blue Crab has a deck overlooking the Chesapeake Bay, and The Boathouse offers views of the Indian River.
  • What family-friendly activities are available in Chesapeake, VA?

    Chesapeake has plenty of family-friendly activities. The Chesapeake Arboretum is a great place for a walk, and the Chesapeake Bay Maritime Museum offers interactive exhibits and boat tours. For some outdoor fun, visit the Chesapeake City Park or the Northwest River Park.

Popular destinations

©2026 cozycozy.com