Family-friendly vacation rentals in Chesapeake
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Top-rated family-friendly rentals in Chesapeake
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake family-friendly rentals
Family-friendly home rentals with a hot tub
Apartment in Williamsburg
4.89 out of 5 average rating, 124 reviewsHistoric Powhatan Resort- 2 bedroom condo!
Jun 1 – 6
Condo in Williamsburg
4.71 out of 5 average rating, 14 reviewsTimeshare Resort condo- 1 bdrm
May 1 – 8
Home in Virginia Beach
4.61 out of 5 average rating, 108 reviewsCroatan Beach - Big Kitchen, Hot Tub, 2 Masters
Nov 17 – 24
Apartment in Williamsburg
4.88 out of 5 average rating, 48 reviews★Colonial Wmbg/Busch Gardens 1BR★ ppr (#4)
Jul 6 – 13
Townhouse in Williamsburg
5.0 out of 5 average rating, 8 reviews4BDR in fun family resort. Best bargain in town.
Jul 7 – 14
Apartment in Williamsburg
4.92 out of 5 average rating, 75 reviews*Historic Powhatan Resort- 2 bedroom
Jun 17 – 24
Condo in Williamsburg
4.91 out of 5 average rating, 22 reviewsThe Historic Powhatan 2 bdrm
Jun 13 – 20
Home in Virginia Beach
4.85 out of 5 average rating, 81 reviewsComfortable 3 bedroom house with deck with hot tub
Oct 14 – 21
Family- and pet-friendly home rentals
Bungalow in Hampton
4.89 out of 5 average rating, 200 reviewsBungelow by The Beach 2BR 1BA CABLE-Hampton, VA
Feb 9 – 16
Cottage in Corolla
4.87 out of 5 average rating, 126 reviewsHorses-Views-Dog Friendly-4WD Area
Apr 1 – 8
Cottage in Williamsburg
4.84 out of 5 average rating, 515 reviewsThe Colonial Cottage
Jan 24 – 31
Home in Virginia Beach
4.89 out of 5 average rating, 292 reviewsLess than one mile to ocean, 3 bedrooms
Oct 23 – 30
Home in Virginia Beach
4.99 out of 5 average rating, 127 reviewsQuiet family location and close to BEACH!
Sep 3 – 10
Home in Virginia Beach
4.77 out of 5 average rating, 149 reviewsChic's Beach Retreat
Aug 27 – Sep 3
Cottage in Corolla
4.87 out of 5 average rating, 174 reviewsQuaint Beach Cottage in 4WD-OBX
Apr 18 – 25
Tiny home in Virginia Beach
4.85 out of 5 average rating, 13 reviewsSunset View/Waterfront RV Cottage Sandbridge Beach
Jun 3 – 10
Family-friendly home rentals with a pool
Home in Virginia Beach
4.83 out of 5 average rating, 105 reviewsStunning Views of Back Bay & Seconds to the Beach
Apr 22 – 29
Cottage in Suffolk
4.95 out of 5 average rating, 128 reviewsCottages on the Creek #3
Mar 1 – 8
Apartment in Virginia Beach
4.87 out of 5 average rating, 78 reviewsBeach Nut - Virginia Beach Oceanfront!
Jul 7 – 14
Guesthouse in Virginia Beach
4.66 out of 5 average rating, 80 reviewsPOOL, Pool House, Hot Tub, Grill, 2 bedroom
Home in Cape Charles
4.76 out of 5 average rating, 74 reviewsFamily Retreat, In-Ground Pool, plus Private Beach
Jan 18 – 25
Home in Virginia Beach
4.9 out of 5 average rating, 119 reviewsBeach Home, Upscale Croatan Resort + Private Pool
Feb 20 – 27
Apartment in Virginia Beach
4.69 out of 5 average rating, 154 reviewsOceanview, 2 Double Beds, Kitchenette, Balcony-C
Sep 8 – 15
Condo in Virginia Beach
4.82 out of 5 average rating, 50 reviewsSeas The Day of Virginia Beach
Oct 10 – 17
Quick stats about vacation rentals that are family-friendly in Chesapeake
Total rentals
510 properties
Wifi availability
500 properties include access to wifi
Rentals with dedicated workspaces
320 properties have a dedicated workspace
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
200 properties allow pets
Total number of reviews
14K reviews
Destinations to explore
- Outer Banks Vacation rentals
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- Family-friendly rentals United States
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- Family-friendly rentals Virginia
- Rentals with outdoor seating Chesapeake
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