Holiday rentals in Chester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chester

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Flat in Chester
Chester Village 'Pied-à-terre' above art gallery
If finding a place in an ideal location w/ thoughtful design matters to you, then you've found it! Sunshine filled living room w/ high ceilings, a private bedroom in back w/ large private deck overlooking Pattaconk Brook. Our place is a gem, and set up for the comfort of our guests. Located in the heart of Chester Village, above our art gallery & boutique, and neighbor to some of the BEST restaurants, art and shopping in CT! NEW! Winter weekdays - ONE night stays are now available - message us!
12–19 FebIndividual Host,
£181 per night
4.95 out of 5 average rating, 308 reviews
Guest favourite
Home in Chester
Stunning Artisan Waterfall Escape, Walk Downtown
Rated one of the top 70 airbnb's near NYC on the online mag "Curbed". Featured on EarthxTV "House of What" series. Over 10 years of craftsmanship went into creating a work of art using more than 80% recycled materials. Known locally as "The Recycle House," this is the perfect place to stay to explore shops and galleries in downtown Chester - just steps away. When you are done shopping, come back and relax in the zen-like garden overlooking a waterfall or curl up inside by the fire place.
21–28 FebIndividual Host,
£361 per night
4.98 out of 5 average rating, 193 reviews
Guest favourite
Home in Lyme
“The Answer” Tidal River-Kayaks Fire pit Fireplace
“The Answer” is listed amongst the 15 best Airbnbs in Ct, from Travellers Worldwide 2022 and 2023. KAYAKS INCLUDED - NOTE: We have a floating dock- stored from Dec15-March1st This unique glass-front, peaceful, tidal river retreat, is privately nestled on historic Hamburg Cove. It offers gorgeous year-round, tranquil water and valley views. The scenic views of the cove are extraordinarily serene. The interior is open/spacious and bathed in light. Wake up to the many sounds of nature.
18–25 SeptIndividual Host,
£323 per night
4.97 out of 5 average rating, 184 reviews

Popular amenities for Chester holiday rentals

Stay near Chester's top sights

Gillette Castle State Park83 locals recommend
Cockaponset State Forest9 locals recommend
Gillette Castle7 locals recommend
Red House6 locals recommend
Adams Hometown Market8 locals recommend
Pattaconk 1850 Bar & Grille8 locals recommend

Other great holiday rentals in Chester

Guest favourite
Guest suite in Wallingford
Wintergreen Gardens Suite @ William Becroft House
8–15 JanIndividual Host,
£75 per night
5.0 out of 5 average rating, 492 reviews
Guest favourite
Home in Old Lyme
Modern Luxurious CT Country Home
16–23 FebIndividual Host,
£383 per night
4.94 out of 5 average rating, 256 reviews
Guest favourite
Home in Westbrook
Family-Friendly Cottage by The Shore
11–18 MayIndividual Host,
£203 per night
4.86 out of 5 average rating, 130 reviews
Guest favourite
Loft in Chester
The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK
9–16 JulIndividual Host,
£169 per night
4.99 out of 5 average rating, 82 reviews
Guest favourite
Flat in Chester
The Millhouse Downtown Chester
29 Oct – 5 NovIndividual Host,
£237 per night
4.99 out of 5 average rating, 68 reviews
Guest favourite
Flat in Chester
Gingerbread Apartment, Walk Downtown
3–10 JunIndividual Host,
£146 per night
4.92 out of 5 average rating, 39 reviews
Guest favourite
Guest house in Chester
Delightful Cottage in Charming Chester
28 Aug – 4 SeptIndividual Host,
£213 per night
5.0 out of 5 average rating, 41 reviews
Guest favourite
Home in Haddam
Cozy Comforts!
12–19 NovIndividual Host,
£115 per night
5.0 out of 5 average rating, 68 reviews
Guest favourite
Home in Chester
Tuscan Villa in Chester
12–19 JanIndividual Host,
£432 per night
4.98 out of 5 average rating, 50 reviews
Guest favourite
Guest suite in Chester
Colonial Parmelee House at Guest House Retreat
23–30 NovProfessional Host,
£130 per night
4.92 out of 5 average rating, 64 reviews
Guest favourite
Flat in Clinton
Cozy Shoreline Getaway
24–31 OctIndividual Host,
£123 per night
4.98 out of 5 average rating, 48 reviews
Guest favourite
Home in Essex
4-Bedroom Farmhouse *Comfort and Privacy*
16–23 FebIndividual Host,
£506 per night
5.0 out of 5 average rating, 47 reviews

Quick stats about holiday rentals in Chester

Total rentals

10 properties

Popular amenities

Kitchen, Wifi and Pool

Wifi availability

10 properties include access to wifi

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

2K reviews

Nightly prices starting at

£79 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Connecticut
  4. Middlesex County
  5. Chester