Chester, CT Cottage Rentals from $152

A calm river with boats, wooden docks, and buildings along the shore.

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Our top choices for Chester cottages

A small single-story house with a front porch, a potted plant, and two Adirondack chairs.

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

Clinton

Marcy C.

$222 nightly

Nov 19 - Nov 20

Total with taxes and fees

A white cottage with a front door, a garage, and a small porch with a potted plant.

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

Clinton

Mary S.

$300 nightly

Nov 15 - Nov 16

Total with taxes and fees

A two-story house with a porch, a mailbox, and a lawn.

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

Madison

Samantha D.

$253 nightly

Nov 17 - Nov 18

Total with taxes and fees

A two-story house with a porch, multiple windows, and a front door.

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

Westbrook Center

Francine F.

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

5. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Center

$293 nightly

Nov 18 - Nov 19

Total with taxes and fees

A small white house with black shutters, a porch, and a red barn in the background.

6. The Tiny Cottage & Mini Farm

Oakdale,

Paul

$134 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

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

Old Lyme

Jessica H.

$403 nightly

Nov 20 - Nov 21

Total with taxes and fees

A dining area with a round wooden table surrounded by six white chairs with dark cushions. A potted plant with green foliage and pink flowers is placed in the center.

8. Privet Farm cottage with AC and Deck in charming Salem Connecticut

Salem

Kellie

$273 nightly

Nov 15 - Nov 16

Total with taxes and fees

A small, single-story house with a white porch and a wooden front door.

9. Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Waterford

Jenna K.

$278 nightly

Dec 9 - Dec 10

Total with taxes and fees

A covered outdoor area with a stone patio, a grill, and Adirondack chairs overlooking a forested landscape.

10. Montville Retreat Near Mohegan Sun: 2-home Bundle!

Montville

$897 nightly

Nov 29 - Nov 30

Total with taxes and fees

A small white house with a green door, two wicker chairs with red cushions, and a welcome mat.

11. 115 Rose Cottage with 2 bedroom walk to Groton Bay

Groton

Meredith

$340 nightly

Dec 14 - Dec 15

Total with taxes and fees

A wooden house with a porch, stone steps, and a gravel pathway.

12. Large Family-Friendly Cottage

Waterford

Henry B.

A modern living room with wicker furniture, a blue sofa, and a flat-screen TV.

13. Sun-Filled Private Large Cottage

Waterford

$503 nightly

Nov 28 - Nov 29

Total with taxes and fees

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Top Chester Hotel Reviews

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

10/10 Excellent

"The hotel stay was great.The staff were very friendly and helpful.A great experience from start to end.We would definitely stay there again."

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."

Find out more about Chester

Chester Cottages information

Number of reviews	108
Accommodation	135 Cottages
Lowest Price	$152
Highest Price	$1,031

Frequently asked questions

How much do cottages in Chester cost?

You can expect to pay between $152 and $1,031 per night for cottages in Chester. No matter your budget, an epic stay is only a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many cottages are there in Chester?

Enjoy reconnecting with nature in one of the 135 cottages located in Chester. To help you find your ideal place, use our handy filter tool to search for must-have amenities.

Why book your cottage in Chester with Expedia?

We think that a vacay should be simple, so if you're after cottages in Chester at a great price, Expedia delivers. Stick to the budget and go for a wallet-friendly option far from the hustle and bustle, or book a luxury cottage to spoil your favorite people.

How can I find cheap cottages in Chester?

With Expedia's filter tool, scoring cheap cottages in Chester has never been simpler. To view properties that'll make your bank balance smile, refine your search by amenities, budget and star rating.

What is there to do in Chester near my cottage?

If you're eager to discover the best of Chester, find your way to Norma Terris Theater. It's a winner with locals and tourists alike.

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Things to do in Groton

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OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Chester cottages

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

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

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

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