Holiday Homes in Chester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Chester holiday homes

Dining

Thames River Cottage · Near Casinos - USCGA

Thames River Cottage · Near Casinos - USCGA
Montville
10.0 out of 10, Exceptional, (2 reviews)
"A lovely quick overnight."
United States
Bonnie H.
The price is €287
includes taxes & fees
20 Apr - 21 Apr
Thames River Cottage · Near Casinos - USCGA
Exterior

Winner's Getaway - 2mi to Mohegan Sun

Winner's Getaway - 2mi to Mohegan Sun
Westside Norwich
10.0 out of 10, Exceptional, (12 reviews)
"Close to casino, would recommend"
United States
Joe M.
The price is €452
includes taxes & fees
20 Apr - 21 Apr
Winner's Getaway - 2mi to Mohegan Sun
Private kitchen

Charming 2-bedroom house with WiFi, AC in lovely Waterford

Charming 2-bedroom house with WiFi, AC in lovely Waterford
Waterford
10.0 out of 10, Exceptional, (1 review)
"The home was very clean and welcoming."
United States
Michelle M.
The price is €314
includes taxes & fees
29 Apr - 30 Apr
Charming 2-bedroom house with WiFi, AC in lovely Waterford
TV

Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!

Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!
Montville
10.0 out of 10, Exceptional, (6 reviews)
"great place to stay"
United States
christopher
The price is €271
includes taxes & fees
19 Apr - 20 Apr
Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!
Smart TV

Cozy, comfy,quiet &close to casinos

Cozy, comfy,quiet &close to casinos
Montville
9.4 out of 10, Exceptional, (51 reviews)
"It was cozy, clean and very close to Mohegan sun! "
United States
Lauren K.
The price is €259
includes taxes & fees
29 Apr - 30 Apr
Cozy, comfy,quiet &close to casinos
Beach nearby

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
New London
8.0 out of 10, Very good, (18 reviews)
"Needed an inexpensive place to stay for a trade show event. This was 20 minutes from Mohegan and perfect for me and an employee. "
United States
Hippy P.
The price is €221
includes taxes & fees
21 Apr - 22 Apr
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
Interior

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Salem
9.8 out of 10, Exceptional, (10 reviews)
"Place is nice would stay again "
United States
nic
The price is €365
includes taxes & fees
21 Apr - 22 Apr
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
TV

#35 - Beautiful 3 BR Beach Haven

#35 - Beautiful 3 BR Beach Haven
Old Lyme
The price is €370
includes taxes & fees
21 Apr - 22 Apr
#35 - Beautiful 3 BR Beach Haven
Beach nearby

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (54 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
The price is €233
includes taxes & fees
29 Apr - 30 Apr
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Smart TV, books

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
The price is €450
includes taxes & fees
5 May - 6 May
Rogers Lake House (87) · CT College+Beach+USCGA
Terrace/patio

Thames River Retreat · CT College+Casinos+USCGA

Thames River Retreat · CT College+Casinos+USCGA
Waterford
10.0 out of 10, Exceptional, (21 reviews)
"Only stayed for 1 night but the house was clean and had what our group needed. Beautiful location. "
United States
Alexander L.
The price is €676
includes taxes & fees
22 Apr - 23 Apr
Thames River Retreat · CT College+Casinos+USCGA
1 bedroom, iron/ironing board, WiFi, bed sheets

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is €253
includes taxes & fees
1 May - 2 May
Once the old Schools house now a newly furnished Apartment
Microwave, oven, stovetop, dishwasher

Entire Vacation Home in Waterford Connecticut

Entire Vacation Home in Waterford Connecticut
Waterford
8.8 out of 10, Excellent, (3 reviews)
"Located so perfectly close to everything we wanted to do on vacation. The house was so clean and comfortable. Communication with the owner was A++. The neighbors were even so friendly and waving/smiling. It felt as if we were home. If we come back to that area again we hope this place will be available. "
United States
Jennifer A.
The price is €358
includes taxes & fees
19 Apr - 20 Apr
Entire Vacation Home in Waterford Connecticut
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (25 reviews)
"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"
United States
Harmony R.
The price is €193
includes taxes & fees
29 Apr - 30 Apr
Family Stays: Middletown, CT
Beach nearby

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (4 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is €346
includes taxes & fees
22 Apr - 23 Apr
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Smart TV, fireplace, books

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Waterford
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful home, we enjoyed our stay. Clean, modern and had everything there we needed. Host was very attentive to our needs and was quick to respond. Looking forward to spend another long weekend there. Highly recommend!"
United States
Brenda W.
The price is €420
includes taxes & fees
12 May - 13 May
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Terrace/patio

Tranquil Farmhouse Retreat

Tranquil Farmhouse Retreat
Montville
9.8 out of 10, Exceptional, (22 reviews)
"We had a great stay during the Thanksgiving holiday. We were able to enjoy the space of the house and the close proximity to Mohegan Sun."
United States
Allison R.
The price is €764
includes taxes & fees
19 Apr - 20 Apr
Tranquil Farmhouse Retreat
Smart TV, books

Charming 3-bedroom ranch 1 minute from Mohegan Sun.

Charming 3-bedroom ranch 1 minute from Mohegan Sun.
Montville
10.0 out of 10, Exceptional, (18 reviews)
"This really is a charming ranch. The beds were clean and comfortable. Kitchen and bath were very clean. Easy access, easy to find and great location for a casino weekend. "
United States
Jennifer F.
The price is €435
includes taxes & fees
26 Apr - 27 Apr
Charming 3-bedroom ranch 1 minute from Mohegan Sun.
Fridge, microwave, oven, stovetop

Groton Bay / Heated pool opens May 6th 2023!

Groton Bay / Heated pool opens May 6th 2023!
Groton
7.0 out of 10, Good, (11 reviews)
"We enjoyed our stay at the house especially the pool. The location was close to many attractions. The management team was very responsive to our needs. The kitchen could use to be updated and the common rooms could use new furniture. "
United States
Christina L.
Groton Bay / Heated pool opens May 6th 2023!
Fridge, microwave, oven, stovetop

Luxury, New, Quiet - King Beds, 5 minutes to Mohegan Sun

Luxury, New, Quiet - King Beds, 5 minutes to Mohegan Sun
Montville
9.8 out of 10, Exceptional, (8 reviews)
"Great location in close proximity to the casino. "
United States
Brian B.
The price is €413
includes taxes & fees
29 Apr - 30 Apr
Luxury, New, Quiet - King Beds, 5 minutes to Mohegan Sun
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

8/10 Good
"The room was clean and comfortable. The staff was very friendly and helpful. The breakfast food was only fair because they don't use warming trays and the food is cold. Otherwise it's a nice place to stay."
John 2-night trip
Posted 1 hour ago
Hyatt Place Uncasville - Casino Area

Find out more about Chester

Chester Holiday Homes information

Number of reviews
284
Accommodation
351 Holiday Homes
Lowest Price
€193
Highest Price
€764