Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
Experiences
Experiences
Services
Services
Start your search
Location
Homes in Chesapeake
Check in / Check out
Any week
Guests
Add guests
Become a host
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Type of place
Show map
Search results; Over 1,000 homes in Chesapeake
Over 1,000 homes in Chesapeake
Top guest favourite
Guest favourite
Home in Chesapeake
Quiet 3/2 beautiful Chesapeake
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
9–14 Nov
9–14 Nov
$1,654 SGD
$1,451 SGD
Show price breakdown
for 5 nights
Free cancellation
4.94 out of 5 average rating, 67 reviews
4.94 (67)
Guest favourite
Guest favourite
Townhouse in Chesapeake
Tasha's Townhouse *King, Queen, Twin*
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
30 Sept – 5 Oct
30 Sept – 5 Oct
$1,257 SGD
Show price breakdown
for 5 nights
$1,257 SGD for 5 nights
Free cancellation
4.86 out of 5 average rating, 249 reviews
4.86 (249)
Guest favourite
Guest favourite
Townhouse in Chesapeake
Waterfront Oasis: Fishing Pier, Pool, Beach Access
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
13–18 Sept
13–18 Sept
$2,892 SGD
$2,496 SGD
Show price breakdown
for 5 nights
Extended stay discount
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Guest favourite
Guest favourite
Home in Chesapeake
Simply Amazing in Chesapeake
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
28 Sept – 3 Oct
28 Sept – 3 Oct
$2,387 SGD
Show price breakdown
for 5 nights
$2,387 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 41 reviews
4.98 (41)
Guest favourite
Guest favourite
Townhouse in Chesapeake
Family friendly townhouse
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
20–25 Sept
20–25 Sept
$1,148 SGD
Show price breakdown
for 5 nights
$1,148 SGD for 5 nights
4.9 out of 5 average rating, 195 reviews
4.9 (195)
Guest favourite
Guest favourite
Home in Chesapeake
2 Master Suites, Sleeps 6-8, King bed, 2.5 baths
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
13–18 Sept
13–18 Sept
$1,552 SGD
Show price breakdown
for 5 nights
$1,552 SGD for 5 nights
4.96 out of 5 average rating, 105 reviews
4.96 (105)
Top guest favourite
Guest favourite
Flat in Chesapeake
Blissful Nook @ Washington
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
22–27 Sept
22–27 Sept
$818 SGD
Show price breakdown
for 5 nights
$818 SGD for 5 nights
4.98 out of 5 average rating, 124 reviews
4.98 (124)
Superhost
Superhost
Home in Chesapeake
Comfy House! The Perfect Getaway
4 bedrooms
4 bedrooms
,
·
4 queen beds
4 queen beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$2,323 SGD
$2,044 SGD
Show price breakdown
for 5 nights
Free cancellation
4.9 out of 5 average rating, 92 reviews
4.9 (92)
Guest favourite
Guest favourite
Guest suite in Chesapeake
Sweet Suite!
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
11–16 Oct
11–16 Oct
$659 SGD
Show price breakdown
for 5 nights
$659 SGD for 5 nights
4.94 out of 5 average rating, 681 reviews
4.94 (681)
Home in Portsmouth
Tidewater Treasurer
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,234 SGD
Show price breakdown
for 5 nights
$1,234 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Guest suite in Chesapeake
Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!
4 beds
4 beds
,
·
1 bathroom
1 bathroom
20–25 Sept
20–25 Sept
$751 SGD
$659 SGD
Show price breakdown
for 5 nights
4.97 out of 5 average rating, 394 reviews
4.97 (394)
Top guest favourite
Guest favourite
Home in Portsmouth
Hidden Gem.4/bedroom cozy home fenced in yard
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
13–18 Sept
13–18 Sept
$1,597 SGD
Show price breakdown
for 5 nights
$1,597 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 113 reviews
5.0 (113)
Guest favourite
Guest favourite
Room in Chesapeake
Green room
1 queen bed
1 queen bed
,
·
2 bathrooms
2 bathrooms
18–23 Sept
18–23 Sept
$398 SGD
Show price breakdown
for 5 nights
$398 SGD for 5 nights
Free cancellation
4.8 out of 5 average rating, 71 reviews
4.8 (71)
Top guest favourite
Guest favourite
Home in Chesapeake
Cook's Country Escape - Cozy Retreat
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
11–16 Oct
11–16 Oct
$997 SGD
Show price breakdown
for 5 nights
$997 SGD for 5 nights
4.96 out of 5 average rating, 144 reviews
4.96 (144)
Top guest favourite
Guest favourite
Guest suite in Chesapeake
Beautiful Two Bedroom King Bed Guest House
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
8–13 Sept
8–13 Sept
$2,155 SGD
Show price breakdown
for 5 nights
$2,155 SGD for 5 nights
4.99 out of 5 average rating, 187 reviews
4.99 (187)
Top guest favourite
Guest favourite
Home in Norfolk
Blessed and peaceful home
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
28 Sept – 3 Oct
28 Sept – 3 Oct
$2,689 SGD
Show price breakdown
for 5 nights
$2,689 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 45 reviews
4.96 (45)
Guest favourite
Guest favourite
Home in Portsmouth
Wooded Wonderland Miniature Golf Hot tub Pool
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$2,424 SGD
Show price breakdown
for 5 nights
$2,424 SGD for 5 nights
4.93 out of 5 average rating, 174 reviews
4.93 (174)
Guest favourite
Guest favourite
Home in Chesapeake
The Manor- Extended Stays
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
8–13 Sept
8–13 Sept
$2,288 SGD
Show price breakdown
for 5 nights
$2,288 SGD for 5 nights
5.0 out of 5 average rating, 8 reviews
5.0 (8)
1
2
3
4
…
15
