Skip to content
HomesHomesNEWNEWExperiencesExperiences, newNEWNEWServicesServices, new
Start your search
1
Become a host

Search results; Over 1,000 places in ChesterOver 1,000 places in Chester

Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Prices include all fees
Guest favorite
Guest favorite
Apartment in Chester
Chester Village 'Pied-à-terre' above art gallery
3 beds3 beds
May 26 – 31May 26 – 31
 
R17,014 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 366 reviews4.93 (366)
Top guest favorite
Guest favorite
Loft in Chester
The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK
2 beds2 beds
May 25 – 30May 25 – 30
 
R18,271 ZAR for 5 nights
for 5 nights
4.99 out of 5 average rating, 141 reviews4.99 (141)
Guest favorite
Guest favorite
Apartment in Chester
The Little Chestnut.
3 beds3 beds
May 26 – 31May 26 – 31
 
R26,546 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 21 reviews5.0 (21)
Guest favorite
Guest favorite
166
Reviews
4.95Stars
Rating
6
Years hosting
Room in Chester
Stay with JenniferStay with JenniferProfessional artist,  · Professional artist
Comfy Artist View at Chester Village
May 20 – 25May 20 – 25
 
R15,799 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 166 reviews4.95 (166)
Top guest favorite
Guest favorite
Apartment in Chester
Charming Chester Retreat - Cottage
2 queen beds2 queen beds
May 31 – Jun 5May 31 – Jun 5
 
R24,354 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 165 reviews4.98 (165)
Guest favorite
Guest favorite
Cottage in Chester
Updated cottage "Beriozka" on Cedar Lake
3 beds3 beds
May 26 – 31May 26 – 31
 
R22,356 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 268 reviews4.97 (268)
Top guest favorite
Guest favorite
Apartment in Deep River
Lovely Garden-Level Apartment in Heart of Town
Free cancellationFree cancellation
May 26 – 31May 26 – 31
 
R18,163 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 144 reviews4.93 (144)
Top guest favorite
Guest favorite
Apartment in Chester
New, modern studio steps from downtown Chester CT
1 queen bed1 queen bed
May 26 – 31May 26 – 31
 
R23,860 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 25 reviews5.0 (25)
Guest favorite
Guest favorite
Apartment in Chester
Gingerbread Apartment, Walk Downtown
4 beds4 beds
Jun 8 – 13Jun 8 – 13
 
R18,056 ZAR for 5 nights
for 5 nights
4.85 out of 5 average rating, 61 reviews4.85 (61)
Superhost
Superhost
Tiny home in Deep River
Her tiny boat house
1 single bed1 single bed
May 20 – 25May 20 – 25
 
R5,589 ZAR for 5 nights
for 5 nights
Top guest favorite
Guest favorite
Apartment in Chester
The Millhouse Downtown Chester
2 queen beds2 queen beds
May 30 – Jun 4May 30 – Jun 4
 
R34,822 ZAR for 5 nights
for 5 nights
4.99 out of 5 average rating, 94 reviews4.99 (94)
Guest favorite
Guest favorite
Home in Chester
Stunning Artisan Waterfall Escape, Walk Downtown
3 beds3 beds
May 27 – Jun 1May 27 – Jun 1
R38,307 ZAR 
 R32,845 ZAR for 5 nights, originally R38,307 ZAR
for 5 nights
4.98 out of 5 average rating, 209 reviews4.98 (209)
Guest favorite
Guest favorite
Barn in Deep River
Zen retreat
1 bed1 bed
May 25 – 30May 25 – 30
 
R13,757 ZAR for 5 nights
for 5 nights
4.91 out of 5 average rating, 32 reviews4.91 (32)
Apartment in Chester
Spotless Riverview apartment with kayaks
Free cancellationFree cancellation
Jul 15 – 20Jul 15 – 20
 
R14,187 ZAR for 5 nights
for 5 nights
New place to stayNew
Superhost
Superhost
Cottage in Deep River
Cottage overlooking the CT river
2 beds2 beds
May 26 – 31May 26 – 31
 
R13,886 ZAR for 5 nights
for 5 nights
4.73 out of 5 average rating, 240 reviews4.73 (240)
Home in Chester
Chester Cottage Waterfall House
3 beds3 beds
May 26 – 31May 26 – 31
 
R32,243 ZAR for 5 nights
for 5 nights
4.86 out of 5 average rating, 98 reviews4.86 (98)
Top guest favorite
Guest favorite
Cottage in Deep River
Country Cottage in Private Garden Setting
2 beds2 beds
May 26 – 31May 26 – 31
 
R17,841 ZAR for 5 nights
for 5 nights
4.91 out of 5 average rating, 57 reviews4.91 (57)
Home in Chester
Chester Village Gem Spacious Retreat Near Downtown
Free cancellationFree cancellation
Aug 11 – 16Aug 11 – 16
R153,217 ZAR 
 R127,898 ZAR for 5 nights, originally R153,217 ZAR
for 5 nights
New place to stayNew
234…15

Site Footer

Support

  • Help Center
  • AirCover
  • Anti-discrimination
  • Disability support
  • Cancellation options
  • Report neighborhood concern

Hosting

  • Airbnb your home
  • AirCover for Hosts
  • Hosting resources
  • Community forum
  • Hosting responsibly
  • Join a free Hosting class
  • Find a co‑host

Airbnb

  • 2025 Summer Release
  • Newsroom
  • New features
  • Careers
  • Investors
  • Airbnb.org emergency stays
Footer section
© 2025 Airbnb, Inc.
·
  1. Privacy·
  2. ·Terms·
  3. ·Sitemap
© 2025 Airbnb, Inc.
·
  1. Privacy·
  2. ·Terms·
  3. ·Sitemap
© 2025 Airbnb, Inc.
·
  1. Privacy·
  2. ·Terms·
  3. ·Sitemap
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.
Now you’ll see one price for your trip, all fees included.