Chesapeake Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Chesapeake vacation rentals

Outdoor dining

River View

River View
Boomer
8.2 out of 10, Very Good, (22 reviews)
"The house was very clean. Had all the amenities that we needed to cook. Very quiet neighborhood and pretty view of the river in the morning."
United States
Lorie H.
The price is ￥17,925
￥30,363 total
includes taxes & fees
Mar 12 - Mar 13
River View
Fridge, microwave, oven, stovetop

RealTree Camo Cabin 2

RealTree Camo Cabin 2
Clendenin
8.6 out of 10, Excellent, (7 reviews)
"The place is just beautiful and the owner is great she made sure we had everything we needed and took very good care of our needs"
United States
Robin S.
The price is ￥14,028
￥19,016 total
includes taxes & fees
Mar 1 - Mar 2
RealTree Camo Cabin 2
Smart TV

Hiding Place is near Montgomery colleges, hospital, NRG, & trails

Hiding Place is near Montgomery colleges, hospital, NRG, & trails
Montgomery
8.8 out of 10, Excellent, (10 reviews)
"We loved this place!"
United States
Megan
The price is ￥16,834
￥29,570 total
includes taxes & fees
Mar 2 - Mar 3
Hiding Place is near Montgomery colleges, hospital, NRG, & trails
Smart TV, books, stereo

Cozy & Convenient - 20 Minutes to Charleston WV

Cozy & Convenient - 20 Minutes to Charleston WV
Quick
9.6 out of 10, Exceptional, (7 reviews)
"Everything about this property was amazing"
United States
Corey
The price is ￥19,484
￥25,126 total
includes taxes & fees
Mar 31 - Apr 1
Cozy & Convenient - 20 Minutes to Charleston WV
Smart TV

Charming 2-bedroom Bungalow - Close to Everything!

Charming 2-bedroom Bungalow - Close to Everything!
Charleston
9.6 out of 10, Exceptional, (29 reviews)
"Me and 2 friends stayed here for a weekend of dirtbike riding on July 4th and it was exactly what we needed "
United States
Quinn P.
The price is ￥11,924
￥27,379 total
includes taxes & fees
Mar 1 - Mar 2
Charming 2-bedroom Bungalow - Close to Everything!
Property grounds

The Boomer: sky, river, and mtn your postage stamp for a week of relaxation!

The Boomer: sky, river, and mtn your postage stamp for a week of relaxation!
Boomer
7.8 out of 10, Good, (13 reviews)
"Jim is an awesome host! The house is clean, comfortable and well equipped. We LOVE sitting around the firepit just taking in the gorgeous view!"
United States
Suzette B.
The price is ￥15,431
￥27,570 total
includes taxes & fees
Mar 2 - Mar 3
The Boomer: sky, river, and mtn your postage stamp for a week of relaxation!
Property grounds

Historical land mark Gauley Bridge 1893 train station

Historical land mark Gauley Bridge 1893 train station
Gauley Bridge
9.0 out of 10, Wonderful, (9 reviews)
"What’s great little find for a short stay. Such a cute place and plenty of room for more than just the 2 of us needed. "
United States
sara m.
The price is ￥18,258
￥22,662 total
includes taxes & fees
Mar 1 - Mar 2
Historical land mark Gauley Bridge 1893 train station
Terrace/patio

Luxurious cabin, 6 mi HM trails, 12 mi Charleston

Luxurious cabin, 6 mi HM trails, 12 mi Charleston
Alum Creek
10.0 out of 10, Exceptional, (38 reviews)
"Great location and had everything we needed. "
United States
Noah B.
The price is ￥18,117
￥35,250 total
includes taxes & fees
Mar 1 - Mar 2
Luxurious cabin, 6 mi HM trails, 12 mi Charleston
Outdoor dining

Travelers Rest slps 5 Riverview, near NRG, trails, fishing. NRG, Falls, & more.

Travelers Rest slps 5 Riverview, near NRG, trails, fishing. NRG, Falls, & more.
Boomer
7.8 out of 10, Good, (10 reviews)
"Easy check-in. Hosts are very accommodating to needs. Kitchen was adequate. "
United States
Alicia G.
The price is ￥18,704
￥31,566 total
includes taxes & fees
Mar 1 - Mar 2
Travelers Rest slps 5 Riverview, near NRG, trails, fishing. NRG, Falls, & more.
Smart TV, books

Ivy Branch Cottage - Danville

Ivy Branch Cottage - Danville
Danville
9.8 out of 10, Exceptional, (14 reviews)
"Nice, small very livable home. Close to everything shopping , dining etc"
Singapore
Shirley F.
The price is ￥19,484
￥47,254 total
includes taxes & fees
Mar 1 - Mar 2
Ivy Branch Cottage - Danville
Exterior detail

Budget Spacious townhome with Gigabit Internet

Budget Spacious townhome with Gigabit Internet
Charlton Heights
10.0 out of 10, Exceptional, (3 reviews)
"Very clean house, love the beautiful scenery. Perfect vaca house thank you 😊"
United States
Mia K.
The price is ￥19,219
￥44,648 total
includes taxes & fees
Mar 12 - Mar 13
Budget Spacious townhome with Gigabit Internet
Interior

Royal Retreat Downtown-Convention Center

Royal Retreat Downtown-Convention Center
Downtown Charleston
8.4 out of 10, Very Good, (34 reviews)
"Shops and convention center within walking distance "
United States
Smokey 2.
The price is ￥17,146
￥32,565 total
includes taxes & fees
Mar 1 - Mar 2
Royal Retreat Downtown-Convention Center
Terrace/patio

Off grid Couples Cabin in Southern West Virginia

Off grid Couples Cabin in Southern West Virginia
Charleston
8.0 out of 10, Very Good, (3 reviews)
"We had a little weekend getaway planned, and Brandon was the perfect host! It was a bit rainy and muddy when we came but Brandon was more than accommodating to make sure everything went smoothly. Would definitely recommend and stay again "
United States
Hayden M.
The price is ￥16,834
￥22,159 total
includes taxes & fees
Mar 1 - Mar 2
Off grid Couples Cabin in Southern West Virginia
Property grounds

Cozy loft in private country setting 5 mins from downtown, Pet Friendly

Cozy loft in private country setting 5 mins from downtown, Pet Friendly
Charleston
9.0 out of 10, Wonderful, (20 reviews)
"Nice people great stay"
United States
John B.
The price is ￥18,097
￥30,557 total
includes taxes & fees
Mar 2 - Mar 3
Cozy loft in private country setting 5 mins from downtown, Pet Friendly
Outdoor dining

Cozy River Cottage

Cozy River Cottage
Dunbar
9.8 out of 10, Exceptional, (17 reviews)
"It was great for a quiet get away"
United States
sallie c.
The price is ￥14,808
￥33,279 total
includes taxes & fees
Mar 15 - Mar 16
Cozy River Cottage
Dining

Walking Distance to Shawnee Soccer Complex

Walking Distance to Shawnee Soccer Complex
Dunbar
9.6 out of 10, Exceptional, (12 reviews)
"Lots of room for 6 adults to stay for a long weekend. This property was as stated, clean and nice and roomy. A few properties around it were run down."
United States
Tylee F.
The price is ￥21,042
￥45,439 total
includes taxes & fees
Mar 8 - Mar 9
Walking Distance to Shawnee Soccer Complex
1 bedroom, desk, iron/ironing board, free WiFi

Charming Apartment in CrossLanes

Charming Apartment in CrossLanes
Charleston
10.0 out of 10, Exceptional, (7 reviews)
"Great little place for 1 or 2 people. The only problem we had was the way Google maps brought us in. Once we figured out the roads in the neighborhood, we really had no issues. Our hostess was very quick to respond the one question we had. If in the area again, we would pick this spot over a hotel any time."
United States
Amy S.
The price is ￥10,911
￥24,253 total
includes taxes & fees
Mar 9 - Mar 10
Charming Apartment in CrossLanes
Property grounds

Prayer Mountain-Off Grid Farm spot#2

Prayer Mountain-Off Grid Farm spot#2
Charleston
The price is ￥17,556
￥22,971 total
includes taxes & fees
Mar 11 - Mar 12
Prayer Mountain-Off Grid Farm spot#2
Fridge, microwave, oven, stovetop

Royal Retreat for corporate & family stay in Saint Albans area

Royal Retreat for corporate & family stay in Saint Albans area
St Albans
8.0 out of 10, Very Good, (63 reviews)
"Nice property and after some communication issues all was well for the time we were there. "
United States
Kay G.
The price is ￥18,570
￥33,140 total
includes taxes & fees
Mar 22 - Mar 23
Royal Retreat for corporate & family stay in Saint Albans area
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesapeake Hotel Reviews

Sleep Inn & Suites Cross Lanes - South Charleston

Sleep Inn & Suites Cross Lanes - South Charleston

10/10 Excellent
"As always, the hotel and room were great!"
Darryl 1-night trip
Posted 2 days ago
Sleep Inn & Suites Cross Lanes - South Charleston

Find out more about Chesapeake

Search for holiday rentals in Chesapeake on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesapeake using one of the methods below:

  • View our selection of featured holiday rentals in Chesapeake
  • Use the map to find apartments and other holiday homes in the Chesapeake neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesapeake while they last

Look no further and take a look at our great range of rental properties in Chesapeake!

Frequently asked questions

Can I find a vacation rental in Chesapeake?

Yes, you can find vacation rentals close to the most popular attractions in Chesapeake, or you can select a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Chesapeake?

South Hills Charmer: This vacation home rental near Chesapeake is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

What’s there to see and do in Chesapeake?

Explore the area and family-friendly sights such as Memorial Ice Arena, or get out into nature at a spot like Kanawha State Forest. University of Charleston and West Virginia State Capitol Building are a couple of places you'll find in the larger area.

What’s a vacation rental in Chesapeake like?

A vacation rental is a private property you can stay in for several days or longer in Chesapeake. Vacation rentals offer amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a family getaway.