Chester Vacation Rentals from SAR 721: Search Short-Term Rentals

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Our top choices for Chester vacation rentals

A cabin surrounded by a natural forest setting with a fire pit and picnic table.

1. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

East Haddam

Kelvin

SAR 721 total

includes taxes & fees

14 Dec - 15 Dec

A white door with a window, set in a green brick wall.

2. Walk To Goodspeed Opera House!

East Haddam

Anonymous traveler

A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

3. 1-bedroom cottage with Grove Beach 🏖️ access.

Clinton

Marcy C.

SAR 950 total

includes taxes & fees

19 Nov - 20 Nov

A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a wooden countertop.

4. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Haddam

Kristy C.

SAR 949 total

includes taxes & fees

1 Dec - 2 Dec

A beach with waves, a clear sky, and a sandy shore.

5. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Westbrook Center

Mason T.

SAR 1,120 total

includes taxes & fees

16 Nov - 17 Nov

A bench by a calm lake with boats docked in the background.

6. The gardners Cottage 1 mile from long Island Sound - pet friendly

Clinton

Mary S.

SAR 1,280 total

includes taxes & fees

15 Nov - 16 Nov

A wooden boardwalk leading to a sandy beach with people sitting and standing, overlooking the ocean.

7. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Madison

Samantha D.

SAR 1,079 total

includes taxes & fees

16 Nov - 17 Nov

A hotel reception area with a receptionist, a guest, and a child.

8. Cozy 2 Full Beds|Free Parking & Wifi

Niantic

Anonymous traveler

SAR 344 total

includes taxes & fees

15 Nov - 16 Nov

A beach with clear skies and calm water.

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

Westbrook

Morgan M.

SAR 2,572 total

includes taxes & fees

14 Dec - 15 Dec

A living room with a beige sofa, a wooden coffee table, and a dining area with a small table and chairs. There is a large window with sheer curtains, a framed fish picture on the wall, and a potted plant.

10. Adorable Cottage with Cottage porch, walk to water & town

Westbrook Center

Francine F.

SAR 2,120 total

includes taxes & fees

15 Nov - 16 Nov

A covered outdoor seating area with a wicker sofa and a coffee table, surrounded by greenery.

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

Old Saybrook

Karol T.

SAR 1,706 total

includes taxes & fees

15 Nov - 16 Nov

A living room with stone walls, a fireplace, and a seating area with a sofa and armchairs.

12. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Center

SAR 1,503 total

includes taxes & fees

2 Dec - 3 Dec

A compact kitchen with stainless steel appliances, a marble countertop, and a black coffee maker.

13. 2BR Apartment Near Wesleyan 102

Washington Street Historic District

DANIEL M.

SAR 941 total

includes taxes & fees

15 Nov - 16 Nov

A porch with a blue door, white columns, and a stone floor.

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

Saybrook Manor

Alexis L.

SAR 2,057 total

includes taxes & fees

16 Nov - 17 Nov

15. 1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

Westbrook Center

Dorothy W.

SAR 1,489 total

includes taxes & fees

16 Nov - 17 Nov

16. The Stern at Soundview · Beach+Ocean+Sunrise

Old Lyme

"If you are looking for a place to sleep, this place is ok. No place to sit down or put anything down. Just a bed and an old beat up tiny side table. Refrigerator is tiny, needed to be cleaned and defrosted. Stains in the bathroom ceiling tiles and the smell of Marijuana at night. Hot plate and microwave present but did not use. The entryway and stairs were dirty and could use a coat of paint and trim. The beach was the highlight and a very short walk. Definitely not worth the $$$ we paid."

Janine

SAR 881 total

includes taxes & fees

15 Nov - 16 Nov

A pond with rocks and a dog in the background.

17. The Tiny Cottage & Mini Farm

Oakdale,

Paul

SAR 569 total

includes taxes & fees

15 Nov - 16 Nov

A lakeside house with a deck, surrounded by trees and a dock.

18. Waterfront! Brand New Cozy Cottage in Old Lyme, CT

Old Lyme

Jessica H.

SAR 1,722 total

includes taxes & fees

20 Nov - 21 Nov

A cabin by a lake with a wooden exterior, a deck, and a small outdoor seating area.

19. Cozy Lakefront Tiny House

East Lyme

Richard R.

Two Adirondack chairs facing a lake with autumn foliage, a fire pit, and a wooden deck.

20. Lakefront Boho Tiny House

East Lyme

Linda M.

SAR 1,258 total

includes taxes & fees

29 Nov - 30 Nov

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Top Chester Hotel Reviews

Regency Inn & Suites New London, Mystic

8/10 Good

"My son & I truly enjoyed our stay, and the hotel staff are absolutely wonderful! The room and hotel are definitely clean/maintained. The indoor pool was far too cold for my little one, and I assumed it would be heated so that’s on me. The page here says there is an arcade room, but they do not have an arcade or a computer room! I was super disappointed about that because I booked here specifically for the pool and arcade. Breakfast was great and we had so many options. I also really liked the seating area, it was warm and cozy!☺️ thank you!"

Clarion Inn North Haven - New Haven North

8/10 Good

"The hotel is undergoing renovations so it's not as clean as it could be. The updated rooms are really nice but it needed a few things. 1) Rooms needs a hairdryer 2) also needs a 2nd trash can 3) Coffeemaker doesnt work right The breakfast was ok but it wasnt bad either. The bathrooms was tootier. Love the double shower heads and the toiletries. Helped with not having to pack my own. Overall I would stay here again. Hopefully it's cleaner after renovations are done. And the chemical rug smell goes away."

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"Everything was great just make sure you get there before it gets dark out. It’s relevantly hard to find the cabins in the pitch black. Overall the area was very quiet. We had neighbors but you really can’t hear anyone around you. It’s a great way to disconnect and unwind."

Frequently asked questions

Are there vacation rentals in Chester?

Yes, we offer vacation rentals close to well known sights in Chester, or you can go with a more secluded option if you'd like a relaxing place to stay. Chester is known for its waterfront and parks. Make sure you have time to check out the theaters while you're in the area.

What are some of the best vacation rentals in Chester?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This vacation home rental near Chester is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Chester?

Expedia has 3 vacation rentals for your stay in Chester.

What’s there to see and do in Chester?

Cultural attractions include Norma Terris Theater, whereas Connecticut River is a spot to enjoy nature. While here, Chester Creek Marina and Connecticut Valley Railroad State Park Trail are other places worth a visit.

What’s a vacation rental in Chester like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Chester. Vacation rentals offer extras like laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a family trip or a small group gathering.

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Check prices for these dates

Our top choices for Chester vacation rentals

1. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2. Walk To Goodspeed Opera House!

3. 1-bedroom cottage with Grove Beach 🏖️ access.

4. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

5. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

6. The gardners Cottage 1 mile from long Island Sound - pet friendly

7. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

8. Cozy 2 Full Beds|Free Parking & Wifi

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

10. Adorable Cottage with Cottage porch, walk to water & town

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

12. Westbrook Getaway-Near Beaches, Train & Shoreline

13. 2BR Apartment Near Wesleyan 102

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

15. 1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

16. The Stern at Soundview · Beach+Ocean+Sunrise

17. The Tiny Cottage & Mini Farm

18. Waterfront! Brand New Cozy Cottage in Old Lyme, CT

19. Cozy Lakefront Tiny House

20. Lakefront Boho Tiny House

Find vacation rentals that suit your style

Top Chester Hotel Reviews

Regency Inn & Suites New London, Mystic

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

Days Inn by Wyndham Berlin Meriden

Water's Edge Resort & Spa

Clarion Inn North Haven - New Haven North

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Microtel Inn & Suites by Wyndham Uncasville Casino Area

Mohegan Sun

Inn at Middletown

Frequently asked questions

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