Best Cottages in Chester in 2026

A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

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Our top choices for Chester cottages

1. Terrific 3-bedroom cottage with AC in charming Cavendish

Cavendish

Mark G.

includes taxes & fees

30 Aug - 31 Aug

2. Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Walpole

Kelly

includes taxes & fees

30 Aug - 31 Aug

3. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Ludlow

includes taxes & fees

30 Aug - 31 Aug

4. Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont

Stratton

includes taxes & fees

9 Sept - 10 Sept

5. 3 Mi to Mount Snow: Spacious West Dover Home

West Dover

includes taxes & fees

30 Aug - 31 Aug

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Top Chester Hotel Reviews

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent

"Nice room and property. With was down."

On The River Inn

10/10 Excellent

"This was one of the nicest hotels I have ever stayed in! We had a river view room with rocking chairs on the balcony, s’mores kits were offered every night (pick up by the front desk) and 2 fire pits to choose from. Game room was cute (although the air hockey table’s fan wasn’t strong on one side), library was absolutely gorgeous. Loved having water refilling stations on 2 of the 3 floors and 24/7 coffee/tea stations, too. Queen beds were very comfy, and the room was so spacious. I’d love another piece of furniture with drawers to keep our stuff though - we lived out of our suitcases because there was only an armoire with 3 half drawers. And maybe another towel bar or hooks in the bathroom to hang the towels to dry, especially if you have 4 people in a room. Breakfast buffet (included with our Expedia stay but extra for others) was always hot & fresh. We had 4 breakfasts: French toast, pancakes, waffles, french toast again. There was always fresh homemade pastries and muffins, yogurt, and oatmeal. I would have loved some fresh fruit like berries to go with the yogurt instead of apples and oranges. Staff was always so nice and helpful, especially at breakfast. Housekeeping forgot twice to give us the 4 fresh towels (gave 3 instead) but we got replacements when we asked at the desk."

The Shire Woodstock

8/10 Good

"We enjoyed our stay very much. We found our stay to very quiet. The back of the property was so peaceful and relaxing sitting by the river, listening to the birds and the gurgling of the river as it moves along. The room was comfortable with a fridge and freezer for snacks/fruit etc. I'd like to see another chair in the room so that 2 people can sit by the window and experience the view although this wasn't a game changer."

Find out more about Chester

Chester Cottages information

Number of reviews	11
Accommodation	176 Cottages
Lowest Price	£248
Highest Price	£1,439

Frequently asked questions

Why book your cottage in Chester with Expedia?

We think that travelling should be a walk in the park, so if you're on the lookout for cottages in Chester at a competitive price, Expedia has you covered. Stick to the budget and choose a cheap option far from the hustle and bustle, or splurge on an upscale cottage to pamper your loved ones.

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Expedia can help you look for cheap cottages in Chester. To reserve a superb stay in a few quick clicks, try out our handy filter tool to refine your search by amenities, star rating and budget.

What is there to do in Chester near my cottage?

Once you've unpacked your suitcases, venture out and discover the incredible things Chester has on offer. DaVallia Art & Accents is a top attraction to add to your must-do list.

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester cottages

1. Terrific 3-bedroom cottage with AC in charming Cavendish

2. Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

3. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

4. Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont

5. 3 Mi to Mount Snow: Spacious West Dover Home

Find holiday rentals that suit your style

Top Chester Hotel Reviews

The Palmer House Resort, an Ascend Collection Hotel

Latchis Hotel

The Equinox Golf Resort And Spa

On The River Inn

Days Inn by Wyndham Keene NH

Keene Elm City Hotel, an Ascend Collection Hotel

The Shire Woodstock

Hampton Inn and Suites Manchester

Hampton Inn Brattleboro

Find out more about Chester

Chester Cottages information

Frequently asked questions

Explore a world of travel with Expedia

Search Chester Cottages

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester cottages

1. Terrific 3-bedroom cottage with AC in charming Cavendish

2. Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

3. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

4. Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont

5. 3 Mi to Mount Snow: Spacious West Dover Home

Find holiday rentals that suit your style

Top Chester Hotel Reviews

The Palmer House Resort, an Ascend Collection Hotel

Find out more about Chester

Chester Cottages information

Frequently asked questions

Explore a world of travel with Expedia