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Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

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!

9.0 out of 10, Wonderful, (2)
"We enjoyed 4 days and 3 nights at this cute home. The house was just perfect for our family and we throughly enjoyed the porch and back yard which is where we spent most of our time. The house had everything we needed and more. The walk down to the beach was beautiful and it felt like we had our own private beach. If you are looking to get away from the hustle and bustle this is a great place. Neighbors are close in proximity, but we never really saw anyone and it was all quiet. We did meet one...
Your own private beach with this charming 3-bedroom beachfront house!
Brand NEW POOL for 2025 pool season ~Oceanfront Home “Sea Watch”
Outdoor dining

Brand NEW POOL for 2025 pool season ~Oceanfront Home “Sea Watch”

2.0 star property
10.0 out of 10, Exceptional, (4)
"The house was as advertised and the property manager was very responsive when we had a couple of questions. Will be booking this one again in the future."
Brand NEW POOL for 2025 pool season ~Oceanfront Home “Sea Watch”
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, (27)
"We had a great time. Second stay at this property."
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

10.0 out of 10, Exceptional, (2)
"great visit... we will be back."
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, (22)
"The property was so much better than we expected! It was hard to want to leave. I did not have a single complaint"
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, (70)
"Had a great stay at the art door! Property was super clean and would definitely stay here again. "
The price is SAR 417
SAR 918 total
includes taxes & fees
17 Apr - 18 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 642
SAR 1,522 total
includes taxes & fees
21 Apr - 22 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 1,202 total
includes taxes & fees
22 Apr - 23 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

7.8 out of 10, Good, (20)
"Spot on with description. Great spot, plan to return when we have more than 3 days. It was just myself and my fiancee, however plenty of room, could accommodate many! "
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 1,310
SAR 2,536 total
includes taxes & fees
1 May - 2 May
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, (50)
"Ladies get together."
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!
On the beach, sun loungers

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

9.0 out of 10, Wonderful, (59)
"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 372
SAR 844 total
includes taxes & fees
21 Apr - 22 Apr
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

9.2 out of 10, Wonderful, (30)
"Everything was so niceThe only problem was the WiFi Couldn’t watch a lot on tv it kept buffing but all else was great "
Airy Captain’s Quarters Beach Condo Near Rudee Inlet
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
On the beach

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 409
SAR 870 total
includes taxes & fees
20 Apr - 21 Apr
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

2.0 out of 10, (1)
"I actually did not stay on the property because host cancelled at the last minute and put me in another home ( his mother's house) When I arrived there was someone at the house. It was overbooked and host did not even tell me. I had to call. Left me without a place to stay. "
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

The Ocean Key Virginia Beach Resort
Indoor pool

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1311)
"Very nice pool area. Very friendly employees. And walkable to the beach and very good restaurants "
The price is SAR 375
SAR 655 total
includes taxes & fees
30 Apr - 1 May
The Ocean Key Virginia Beach Resort
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, (1035)
"Right near the freeway "
The price is SAR 417
SAR 703 total
includes taxes & fees
29 Apr - 30 Apr
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
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, (1313)
"the rooms were great. the indoor pool was cold. less then 65 degrees"
The price is SAR 303
SAR 572 total
includes taxes & fees
29 Apr - 30 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.