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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 1441 Vacation Homes in Chesapeake with updated reviews, rates, and availability.

Your own private beach with this charming 3-bedroom beachfront house!
Interior

Your own private beach with this charming 3-bedroom beachfront house!

Your own private beach with this charming 3-bedroom beachfront house!
Brand NEW POOL for 2025~Oceanfront Home “Sea Watch”~REDUCED RATES APRIL AND MAY~
Outdoor dining

Brand NEW POOL for 2025~Oceanfront Home “Sea Watch”~REDUCED RATES APRIL AND MAY~

2.0 star property
10.0 out of 10, Exceptional, (3)
"This house was perfect for our three families to spread out but also let the kids bunk up and enjoy downstairs all to themselves! We loved going down to the park, going to the market for donuts, walking the beach and enjoying the beautiful views. We can’t wait to stay here again next year. The house was well stocked, comfortable, and the host was very responsive to any questions.we loved it! "
Brand NEW POOL for 2025~Oceanfront Home “Sea Watch”~REDUCED RATES APRIL AND MAY~
Super close to beaches, the historic triangle, and bush gardens!
Fridge, microwave, oven, stovetop

Super close to beaches, the historic triangle, and bush gardens!

8.4 out of 10, Very Good, (26)
"Really enjoyed staying here definitely going back"
Super close to beaches, the historic triangle, and bush gardens!
Spacious oceanfront house w/beach access, decks, grill & free WIFI
Outdoor dining

Spacious oceanfront house w/beach access, decks, grill & free WIFI

Spacious oceanfront house w/beach access, decks, grill & free WIFI
Dog-friendly home with private pool, fenced yard, ocean view, nice deck & WiFi
Fridge, microwave, oven, stovetop

Dog-friendly home with private pool, fenced yard, ocean view, nice deck & WiFi

7.0 out of 10, Good, (20)
"Our family (10 members total) stayed for 1 week in this house. We loved the location to the beach and the public beach access. House was very clean and plenty of space. Only suggestion/change was to have outside lighting under the deck by the pool. We wanted to sit outside by the pool and swim at night but were unable to due to no lighting, it would be if they could improve/fix this, so others could swim and sit by the pool at night. Other than that it was a great stay and experience, we will be...
Dog-friendly home with private pool, fenced yard, ocean view, nice deck & WiFi
The Art Door only minutes from beach
Property grounds

The Art Door only minutes from beach

9.6 out of 10, Exceptional, (65)
"Cozy and clean half of duplex. Walkable neighborhood was a bit noisy with lots of jet traffic from nearby base. Very convenient with lots of attractions, shops and restaurants minutes away. Pet friendly with fenced in yard. Check in was very easy. Host asked how stay was going and allowed a late checkout which was much appreciated."
The price is SAR 416
SAR 922 total
includes taxes & fees
1 Apr - 2 Apr
The Art Door only minutes from beach
Oceanside beach home private outdoor pool, fast WiFi & W/D - dog-friendly
TV, DVD player, books

Oceanside beach home private outdoor pool, fast WiFi & W/D - dog-friendly

8.4 out of 10, Very Good, (25)
"We came into town for our wedding reception, and stayed at this spot which was absolutely perfect! It exceeded our expectations. Extremely spacious and the walkway to the beach was wonderful. 10/10 would stay again."
Oceanside beach home private outdoor pool, fast WiFi & W/D - dog-friendly
Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.
Property grounds

Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.

9.4 out of 10, Exceptional, (13)
"Great location and views. Property needs some updates and fixes. Good connectivity, TV's etc. We enjoyed our stay. "
Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Fridge, microwave, oven, stovetop

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

9.2 out of 10, Wonderful, (27)
"I’mi liked my stay ; everything was fine and the host communicated well with me…"
The price is SAR 567
SAR 1,418 total
includes taxes & fees
31 Mar - 1 Apr
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Tis The Season! It's Timeeee...
Fridge, microwave, oven, stovetop

Tis The Season! It's Timeeee...

2.0 star property
Tis The Season! It's Timeeee...
Beach Family Time Enjoy The Backyard Pool And Sunroom
Fridge, microwave, oven, stovetop

Beach Family Time Enjoy The Backyard Pool And Sunroom

8.6 out of 10, Excellent, (33)
"This is a good place to stay - the house is great and the location is perfect. However, the check in ptocess was very frustrating. The VRBO listing gives the wrong address, so when we arrived we pulled into a neighbor's driveway by accident. This apparently happens a lot because the neighbor (who was home) immediately pointed us to the correct house. Then the check in instructions gave the wrong key code for the front door, so we had to call and message the host multiple times just to get...
Beach Family Time Enjoy The Backyard Pool And Sunroom
Laid-Back Lakefront Luxury Near Bay & Beach: Welcome To Wiseacre!
Property grounds

Laid-Back Lakefront Luxury Near Bay & Beach: Welcome To Wiseacre!

10.0 out of 10, Exceptional, (33)
"The house was a shock in how great it was. The host Chuck is also super nice and accommodating."
The price is SAR 784
SAR 1,167 total
includes taxes & fees
21 Apr - 22 Apr
Laid-Back Lakefront Luxury Near Bay & Beach: Welcome To Wiseacre!
Oceanfront home w/ocean views, WiFi, central AC, balcony, deck, washer/dryer
Property grounds

Oceanfront home w/ocean views, WiFi, central AC, balcony, deck, washer/dryer

7.6 out of 10, Good, (19)
"Overall this property is nice. It is an older home with charm but also with general wear and age being by the ocean. The property could use a sprucing up and the kitchen ware is older. There is a musty smell but it is not over powering and expected with the age of the home and its location. My critical feedback is on the management side of our vacation. The company only offers one complimentary toilet paper roll, garbage bag, and paper towel roll, so if you plan to stay longer be prepared to buy...
Oceanfront home w/ocean views, WiFi, central AC, balcony, deck, washer/dryer
Big Beautiful Beachfront House! 5 bed/3.5 bath directly on the beach!
Exterior

Big Beautiful Beachfront House! 5 bed/3.5 bath directly on the beach!

9.4 out of 10, Exceptional, (13)
"Wonderful place to spend tbe weekend!"
The price is SAR 1,122
SAR 2,268 total
includes taxes & fees
30 Mar - 31 Mar
Big Beautiful Beachfront House! 5 bed/3.5 bath directly on the beach!
7 beds! One block from beach! Bikes included!
Aerial view

7 beds! One block from beach! Bikes included!

10.0 out of 10, Exceptional, (47)
"Friends and I had a great stay at this property. It was completely as advertised. Lots of room to spread out, and close to the beach and boardwalk. Communication was great, and everything was top notch. Would highly recommend this property!"
7 beds! One block from beach! Bikes included!
Serenity on the Bay-Complimentary Sunrise & Sunset Views
4 bedrooms, WiFi, bed sheets

Serenity on the Bay-Complimentary Sunrise & Sunset Views

9.6 out of 10, Exceptional, (31)
"Very clean and spacious. Nice and quiet. I will be coming back."
Serenity on the Bay-Complimentary Sunrise & Sunset Views
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Beach nearby, sun loungers

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

9.0 out of 10, Wonderful, (58)
"Property is clean and neat. However, a tad rundown. Very close to the beach as described and next to the Oceanview fishing pier. Communication with property owner excellent. Overall a good experience."
The price is SAR 409
SAR 883 total
includes taxes & fees
30 Mar - 31 Mar
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Airy Captain’s Quarters Beach Condo Near Rudee Inlet
Smart TV

Airy Captain’s Quarters Beach Condo Near Rudee Inlet

9.0 out of 10, Wonderful, (28)
"It was very convenient to all events, restaurants and shopping very easy to access. Wish you had an air fryer in a crockpot though, but we may do."
Airy Captain’s Quarters Beach Condo Near Rudee Inlet
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Beach nearby

Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

8.8 out of 10, Excellent, (52)
"We were not in the house much, but the time we did spend there was enjoyable."
The price is SAR 446
SAR 922 total
includes taxes & fees
30 Mar - 31 Mar
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
NEW! Big Waterfront House w/ Amazing View and Swim Deck
Terrace/patio

NEW! Big Waterfront House w/ Amazing View and Swim Deck

The price is SAR 1,643
SAR 2,771 total
includes taxes & fees
10 Apr - 11 Apr
NEW! Big Waterfront House w/ Amazing View and Swim Deck
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.
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Other property types in Chesapeake

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Exterior

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.0 out of 10, Very Good, (1158)
"I appreciated the space in my room, namely the refrigerator, cooktop, microwave, coffee maker and kitchen sink, as well as the separate bedroom and two separate oceanfront balconies. I would definitely return. "
The price is SAR 334
SAR 607 total
includes taxes & fees
9 Apr - 10 Apr
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
The Ocean Key Virginia Beach Resort
Indoor pool

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1303)
"We stay in that area every time we visit Virginia Beach."
The price is SAR 334
SAR 607 total
includes taxes & fees
9 Apr - 10 Apr
The Ocean Key Virginia Beach Resort
The Atrium Resort, Virginia Beach by Vacatia
Beach nearby

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very Good, (1302)
"The room was very clean. The bathroom was a great size and very clean. We had a problem with the bath not changing to a shower and called downstairs and maintenance was up to our room less than 2 minutes later and fixed it. The front desk employees were very nice and so were the maintenance employees. The indoor pool was well maintained and great for my kids. It went up to 4ft deep so it wasn’t too deep for my 10 & 12 year old. We will definitely be back! "
The price is SAR 214
SAR 469 total
includes taxes & fees
1 Apr - 2 Apr
The Atrium Resort, Virginia Beach by Vacatia
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.