Chester Vacation Home Rentals from CA $123: Search Top Private Vacation Homes for Rent

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Our top choices for Chester vacation homes

A modern kitchen with a granite island, stainless steel appliances, and a bar area with bar stools.

1. Beachside Bliss w/ Game Room, Gym & Golf Green

Westbrook

Morgan M.

CA $855 total

includes taxes & fees

Dec 1 - Dec 2

A living room with a fireplace, a sofa, a coffee table, and a cabinet.

2. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Old Saybrook

Karol T.

CA $1,013 total

includes taxes & fees

Nov 20 - Nov 21

A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

3. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Saybrook Manor

Alexis L.

CA $781 total

includes taxes & fees

Nov 16 - Nov 17

A cozy living room with a sofa, a coffee table, and a dining area with chairs.

4. NEW private studio 1.1 miles to beach in East Lyme

East Lyme

CA $192 total

includes taxes & fees

Nov 16 - Nov 17

A modern living room with a large TV, white cabinetry, and a view of the outdoors.

5. Charming beach home, complete with pool & cozy guest house!

Clinton

Juliana A.

CA $1,844 total

includes taxes & fees

Nov 12 - Nov 13

A living room with a black sofa, blue armchairs, a small coffee table, and a flat-screen TV.

6. The Bay Cottage · Rocky Neck Park, Beach & Niantic

East Lyme

Sarah G.

CA $461 total

includes taxes & fees

Dec 2 - Dec 3

A modern kitchen with a central island, bar stools, and pendant lighting.

7. New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Durham

Iris F.

CA $1,549 total

includes taxes & fees

Nov 10 - Nov 11

A room with a patterned rug, a door leading to a kitchen, and a window with blinds.

8. Family Stays: Middletown, CT

Middletown

Audrey F.

CA $359 total

includes taxes & fees

Nov 16 - Nov 17

A modern kitchen with a central island, built-in appliances, and a dining area with a long table and chairs.

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

Salem

nic

CA $561 total

includes taxes & fees

Nov 17 - Nov 18

A covered patio with a glass table, white metal chairs, a green sofa, and a white metal bench.

10. Historic New England home ,Reunions Beach pass

Guilford

Dr. Maureen C.

CA $873 total

includes taxes & fees

Nov 10 - Nov 11

A modern living room with a sofa, coffee table, and a TV mounted on the wall.

11. Once the old Schools house now a newly furnished Apartment

Wallingford Center

Jeanette W.

CA $412 total

includes taxes & fees

Nov 12 - Nov 13

A living room with a dark blue sofa, a round ottoman, a coffee table, and a TV on a stand. There is a large abstract painting on the wall and a window with curtains.

12. Cozy basement apartment with private bathroom, kitchen and entrance.

Marlborough

CA $663 total

includes taxes & fees

Nov 11 - Nov 12

A modern living room with a sofa, a dining table, and a TV mounted on the wall.

13. Cozy, comfy,quiet &close to casinos

Montville

Lori G.

CA $327 total

includes taxes & fees

Nov 10 - Nov 11

A dining area with a glass table, two chairs, and a bottle of champagne. There are framed paintings on the walls and a refrigerator in the background.

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

New London

Alicia W.

CA $319 total

includes taxes & fees

Nov 10 - Nov 11

A modern living room with a large wooden dining table, a stone fireplace, a sofa, and a view of a lake through large windows.

15. Thames River Cottage · Near Casinos - USCGA

Montville

Bonnie H.

CA $439 total

includes taxes & fees

Nov 10 - Nov 11

A living room with a fireplace, a grey armchair, and a large window.

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

Waterford

Elaine A.

CA $618 total

includes taxes & fees

Nov 10 - Nov 11

A wooden deck with a round table and chairs overlooking a lake, surrounded by lush greenery.

17. Lakeside Bliss

East Lyme

Brenda M.

CA $741 total

includes taxes & fees

Nov 15 - Nov 16

A compact living room with a gray sofa, a coffee table, and a black TV stand.

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

Montville

christopher

CA $489 total

includes taxes & fees

Dec 10 - Dec 11

A stone pathway leading to a white building with a covered patio area.

19. Coastal retreat, short walk to downtown!

East Lyme

Hannah R.

CA $593 total

includes taxes & fees

Nov 30 - Dec 1

A wooden deck with a white staircase leading to a covered area with a table and chairs.

20. Winner's Getaway - 2mi to Mohegan Sun

Westside Norwich

DAVID C.

CA $755 total

includes taxes & fees

Nov 10 - Nov 11

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Learn more about Chester

Charming galleries and local shops line Main Street, where you'll find handcrafted jewellery and Connecticut River Valley artwork. Catch a performance at the Goodspeed Opera House in East Haddam or kayak Chester Creek when summer temperatures rise.

See all hotels in Chester

A calm lake surrounded by vibrant autumn foliage.

Top reviews in Chester

A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.

Clinton Motel

Clinton

10/10 Excellent

Adam

A living room with a stone fireplace, grey sofas, and a coffee table.

The Captain Stannard

Westbrook Center

10/10 Excellent

Our stay was great! My flight got in early, and the innkeeper was very kind to let me check in early. The room was clean, comfortable, and safe. The doors to the inn are locked with a keypad that every traveler has a unique code for safety. The first floor common area has a guestbook, a cabinet full of puzzles and other games, a TV, a kitchenette, and lots of seating. The kitchen has a large refrigerator that guests can access along with coffee, tea, and glassware. They also provide postcards...

Casey

A large, two-story house with a wrap-around porch and a conservatory.

Copper Beech Inn

Ivoryton

10/10 Excellent

The owner was so nice! She even helped with our bags. She went out of her way to show us things and find things to see and do in the area. The room was spotless, the bathroom was the nicest I've ever seen in a hotel. The breakfast was included..but was still full menu and service. I cannot say enough nice things about this place. The history is great, the neighborhood is wonderful and close to all Essex communities. Beautiful place!

Sonya