Search Vacation Homes in Chesapeake

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Chesapeake

Our top choices for Chesapeake vacation homes

3-bedroom home away from home in fabulous Chesapeake, Virginia.

2.0 star property
10.0 out of 10, Exceptional, (32)
"Awesome spot….. very comfortable Perfect for our stay"
3-bedroom home away from home in fabulous Chesapeake, Virginia.

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

9.4 out of 10, Exceptional, (3)
"Property is well maintained. Great AC. Perfect for a couple to get away for a week. Central location was perfect for everything we planned to do for the week. "
The price is SAR 334
SAR 1,004 total
includes taxes & fees
26 Sep - 27 Sep
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Knot Three- Balcony View of ICW- Dog Friendly!

9.6 out of 10, Exceptional, (4)
"The whole process was very easy and smooth. The property was clean and comfortable. I would definitely stay here again in the future!"
The price is SAR 409
SAR 909 total
includes taxes & fees
10 Sep - 11 Sep
Knot Three- Balcony View of ICW- Dog Friendly!

The Art Door only minutes from beach

9.8 out of 10, Exceptional, (89)
"Loved the stay! Property was very clean, quiet and easy to get to everything Virginia Beach has to offer. The property manager was very quick to respond and helpful. Will stay there again"
The Art Door only minutes from beach

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

9.0 out of 10, Wonderful, (16)
"House was clean and welcoming. Communication was great. I would stay again in a heart beat. I’m active duty military and host was very accommodating. "
The price is SAR 424
SAR 935 total
includes taxes & fees
3 Sep - 4 Sep
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Large 2 bedroom | Queen beds | Safe Area

7.8 out of 10, Good, (8)
"House looks like the pictures which makes that a hugh plus. Property waa very well maintained. "
The price is SAR 446
SAR 1,089 total
includes taxes & fees
1 Sep - 2 Sep
Large 2 bedroom | Queen beds | Safe Area

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

9.0 out of 10, Wonderful, (35)
"Property is as listed. Very clean, comfortable and had everything we needed for our trip. "
The price is SAR 589
SAR 1,427 total
includes taxes & fees
26 Sep - 27 Sep
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

10min to Ocean View: BBQ - Volleyball - Fire pit

10min to Ocean View: BBQ - Volleyball - Fire pit

$10K Off: 28BR Oceanfront Mega Estate | Sleeps 62 -6 Acres | Weddings & Retreats

10.0 out of 10, Exceptional, (2)
"We booked this house last minute as our wedding, which was originally planned for Asheville, North Carolina was canceled due to hurricane Helena. We chose the Fitzgerald as it had enough bedrooms and bathrooms to accommodate the family. The wedding was just a small internal affair, vendors or anything like that. The property owner was very communicative and helpful throughout the entire process. We had one minor issue where a pipe got backed up, but they came and took care of everything that we...
$10K Off: 28BR Oceanfront Mega Estate | Sleeps 62 -6 Acres | Weddings & Retreats

Cozy Room • Near Dam Neck Base & Beach Access

9.0 out of 10, Wonderful, (2)
"Nice and quiet, no problem checking in. Would have appreciated a few more towels for the bathroom but other than that we enjoyed our visit."
The price is SAR 443
SAR 529 total
includes taxes & fees
1 Sep - 2 Sep
Cozy Room • Near Dam Neck Base & Beach Access

Cozy Frog on the Beach! 2-bedroom Efficiency w/ Beach Access, WiFi, Smart TV

7.6 out of 10, Good, (4)
"Vrbo itself was very clean, easy access to beach. Fully equipped with kitchen gadgets, including utensils, pots and pans, silverware and coffee maker. Furnished with bath towels. Overall, a quiet, nice neighborhood."
The price is SAR 447
SAR 835 total
includes taxes & fees
1 Sep - 2 Sep
Cozy Frog on the Beach! 2-bedroom Efficiency w/ Beach Access, WiFi, Smart TV

Shipside Suite~Modern~ Fast WI-FI~Cozy

The price is SAR 274
SAR 1,273 total
includes taxes & fees
1 Sep - 2 Sep
Shipside Suite~Modern~ Fast WI-FI~Cozy

Perfect for families!

6.6 out of 10, (8)
"we enjoy the stay and we’ll book again great location located right behind the Newport police station. There’s also lots of things to do in the location. A big pond for fishing my family enjoyed."
Perfect for families!

Carrick Bend -Balcony View of ICW- Dog Friendly!

Carrick Bend -Balcony View of ICW- Dog Friendly!

Sojourn | Coastal Cottage | 3 BR

9.4 out of 10, Exceptional, (33)
"We stayed here for an extended weekend and it was such a cute place! Very clean and relaxing. The beach is just a couple minutes of walking from the house and easy to get to. "
Sojourn | Coastal Cottage | 3 BR

Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

9.0 out of 10, Wonderful, (67)
"Like the fire pit outside and so close to the beach and the pier the only downside is 1 bedroom doesn’t have AC but other than that it’s perfect We’ll stay there again "
The price is SAR 672
SAR 1,232 total
includes taxes & fees
7 Sep - 8 Sep
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

#Buckroe Bungalow ~Escape to the Beach 2mins Away!

9.0 out of 10, Wonderful, (18)
"We had a great stay. This house was very clean and very conveniently located. We were close to Buckroe Beach and the very delicious Buckroe Coffee Company. We were close to Langley AFB, Fort Monroe, Downtown Hampton. It was a perfect homebase for our trip to visit our airmen"
#Buckroe Bungalow ~Escape to the Beach 2mins Away!

Sweet home to share with the family

8.8 out of 10, Excellent, (32)
"I stayed here for my birthday to hang out with friends and we loved it. The host was super sweet and very accommodating. Even let us stay later and check in early."
The price is SAR 1,257
SAR 2,256 total
includes taxes & fees
27 Sep - 28 Sep
Sweet home to share with the family

In Virginia Beach near restaurants, the city of Virginia and the beaches.

The price is SAR 300
SAR 1,043 total
includes taxes & fees
11 Sep - 12 Sep
In Virginia Beach near restaurants, the city of Virginia and the beaches.

Comfort & Quiet in a Central location

6.0 out of 10, (1)
"It is in a nice, quiet neighborhood with a good location. The place was clean-ish, but could be more clean. There were no exhaust fans in the bathrooms, which made for a damp smell and a humid area to get ready for the day. Barely any extra amenities like linens, pillows, towels, washcloths, or toilet paper. There is a washer and drier but no laundry soap to use. An ok place to stay in a pinch, but not my first choice."
The price is SAR 413
SAR 1,437 total
includes taxes & fees
10 Sep - 11 Sep
Comfort & Quiet in a Central location
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chesapeake Hotel Reviews