Chester Vacation Home Rentals from CA $121: Search Top Private Vacation Homes for Rent

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Our top choices for Chester vacation homes

An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

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

Westbrook

Morgan M.

CA $742 total

includes taxes & fees

Nov 10 - Nov 11

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 $614 total

includes taxes & fees

Nov 8 - Nov 9

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 $775 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 $190 total

includes taxes & fees

Nov 9 - Nov 10

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 $1,829 total

includes taxes & fees

Nov 12 - Nov 13

A tranquil beach with stunning ocean views.

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

East Lyme

Sarah G.

CA $472 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 $1,597 total

includes taxes & fees

Nov 7 - Nov 8

8. Family Stays: Middletown, CT

Middletown

Audrey F.

CA $380 total

includes taxes & fees

Nov 17 - Nov 18

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 $550 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

Liz H.

CA $864 total

includes taxes & fees

Nov 9 - Nov 10

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 $418 total

includes taxes & fees

Nov 17 - Nov 18

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 $632 total

includes taxes & fees

Nov 9 - Nov 10

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 $314 total

includes taxes & fees

Nov 17 - Nov 18

A sandy beach with a wooden fence in the foreground and a clear sky with clouds in the background.

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

New London

Alicia W.

CA $316 total

includes taxes & fees

Nov 11 - Nov 12

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 $451 total

includes taxes & fees

Nov 9 - Nov 10

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 $582 total

includes taxes & fees

Nov 9 - Nov 10

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

17. Lakeside Bliss

East Lyme

Brenda M.

CA $733 total

includes taxes & fees

Nov 12 - Nov 13

A waterfront promenade with a concrete walkway, metal railing, and a sandy beach.

18. 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.

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

Westside Norwich

DAVID C.

CA $747 total

includes taxes & fees

Nov 15 - Nov 16

A deck with wicker furniture and a view of a lake.

20. Thames River Retreat · CT College+Casinos+USCGA

Waterford

Kristine E.

CA $966 total

includes taxes & fees

Nov 9 - Nov 10

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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 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 conservatory with a glass ceiling, wooden furniture, and large windows offering a view of the garden.

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