Title: Chesterland Cottages from CA $452 | Expedia.ca

  

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# Search Chesterland Cottage Rentals from CA $452

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## Check prices for these dates

In two weeks

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6269507&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6269507&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6269507&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6269507&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Chesterland Cottages

![Exterior detail](https://images.trvl-media.com/lodging/19000000/18980000/18970400/18970330/0a437ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18980000/18970400/18970330/07cd0af1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18970400/18970330/55ee409d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18980000/18970400/18970330/e0d2bd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Country Cottage Farm Stay at Stoneycreek Acres

Newbury

10/10

Exceptional

(69)

"Second time staying here in two years. The cottage is perfect for some relaxing, slow time with the wife. Molly is probably the best host we have had at a vrbo"

CA $265

CA $452 total

includes taxes & fees

Oct 31 - Nov 1

[](https://www.expedia.ca/Newbury-Hotels-Country-Cottage-Farm-Stay-At-Stoneycreek-Acres.h18970330.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/88000000/87130000/87125500/87125409/w474h316x3y3-292c5a59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/88000000/87130000/87125500/87125409/w1198h800x0y0-731229f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/88000000/87130000/87125500/87125409/eecda33d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/88000000/87130000/87125500/87125409/d67e2f64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Cleveland Heights Carriage House!

Cleveland Heights

9.8/10

Exceptional

(42)

"Love this place. Stayed here before and will continue when visiting Cleveland"

CA $273

CA $572 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/Cleveland-Hotels-Historic-Cleveland-Heights-Carriage-House.h87125409.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/71000000/70940000/70939500/70939415/2557916d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70940000/70939500/70939415/5e02cadd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/71000000/70940000/70939500/70939415/737a7f98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/71000000/70940000/70939500/70939415/f24ec50e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vineyard View | Walk to Wineries & River| Hot Tub

Madison

10/10

Exceptional

(62)

"Loved this property! Had everything you needed. Beautiful and so clean. We had the best time! The host was very helpful and replied very fast. "

CA $399

CA $647 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/Madison-Hotels-Vineyard-View-Walking-Distance-To-Wineries-River.h70939415.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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## Top Chesterland Hotel Reviews

![The Glidden House](//images.trvl-media.com/lodging/1000000/10000/4100/4042/a94737c8_y.jpg)

### The Glidden House

10/10 Excellent

"Yes"

[](https://expedia.ca/Cleveland-Hotels-The-Glidden-House.h4042.Hotel-Information)

![Hilton Garden Inn Cleveland Downtown](//images.trvl-media.com/lodging/1000000/870000/866100/866043/725ce971_y.jpg)

### Hilton Garden Inn Cleveland Downtown

10/10 Excellent

"Clean"

[](https://expedia.ca/Cleveland-Hotels-Hilton-Garden-Inn-Cleveland-Downtown.h866043.Hotel-Information)

![Fidelity Hotel](//images.trvl-media.com/lodging/110000000/109300000/109297700/109297621/2e6fd129_y.jpg)

### Fidelity Hotel

10/10 Excellent

"Clean room, pleasant helpful staff, gorgeous hotel. Walkable to venues and dining and the lake"

[](https://expedia.ca/Cleveland-Hotels-Fidelity-Hotel.h109297621.Hotel-Information)

![DoubleTree by Hilton Hotel Cleveland Downtown - Lakeside](//images.trvl-media.com/lodging/1000000/20000/19900/19876/c3bcd14b_y.jpg)

### DoubleTree by Hilton Hotel Cleveland Downtown - Lakeside

10/10 Excellent

"The room was clean. However, the common area of the hotel needed cleaned."

[](https://expedia.ca/Cleveland-Hotels-DoubleTree-By-Hilton-Cleveland-Downtown-Lakeside.h19876.Hotel-Information)

![Tru By Hilton Cleveland Midtown](//images.trvl-media.com/lodging/37000000/36480000/36475300/36475236/7ba1bba5_y.jpg)

### Tru By Hilton Cleveland Midtown

10/10 Excellent

"It was just what we needed after being at the hospital all day and evening awaiting a family member’s major surgery completion. I must say specifically HELEN IS AMAZING!!! I was stressed, extremely exhausted and full of anxiety and her kindness and welcoming spirit allowed me to have a sense of calmness that I really needed thank you thank you thank you Helen!! I love the welcome bag with the waters and popcorn too. The room was very clean and comfortable and I enjoyed the decor. I will definitely stay again when in the city or in a different city."

[](https://expedia.ca/Cleveland-Hotels-Tru-By-Hilton-Cleveland-Midtown.h36475236.Hotel-Information)

![Drury Plaza Hotel Cleveland Downtown](//images.trvl-media.com/lodging/14000000/13580000/13579000/13578935/78bc1417_y.jpg)

### Drury Plaza Hotel Cleveland Downtown

10/10 Excellent

"The best historical hotel in Cleveland! The staff is always friendly. The hotel is extremely well maintenance for its age. You almost feel like you’re staying in an old museum or palace. Free dinner, free drinks, free breakfast! As a world traveler, I haven’t experienced such perks at any other hotel, from boutique to chains. The rooms are big, comfortable and quiet. It’s also in a very centralized location downtown. This would be considered a safe neighborhood."

[](https://expedia.ca/Cleveland-Hotels-Drury-Plaza-Hotel-Cleveland-Downtown.h13578935.Hotel-Information)

![Hotel Indigo Cleveland Downtown by IHG](//images.trvl-media.com/lodging/1000000/120000/119000/119000/11326ddb_y.jpg)

### Hotel Indigo Cleveland Downtown by IHG

10/10 Excellent

"Valet parking was well worth the $60 to just hand over the keys and not worry about parking in a deck somewhere. We were across the street from the entrance for Rocket fieldhouse. Walkable to plenty of bars and restaurants. I highly recommend Mabel's BBQ! The room was clean and modern. Very friendly staff. Keycard entrance after hours so no one that shouldn't be there is wandering in. Very great experience! Highly recommend!"

[](https://expedia.ca/Cleveland-Hotels-Hotel-Indigo-Cleveland-Downtown.h119000.Hotel-Information)

![Crowne Plaza Cleveland at Playhouse Square by IHG](//images.trvl-media.com/lodging/1000000/20000/17500/17461/84e209cd_y.jpg)

### Crowne Plaza Cleveland at Playhouse Square by IHG

10/10 Excellent

"Me and my partner stayed for concert in Cleveland the hotel was amazing very friendly. The staff between April, Latoya and David checked on us our entire stay. We will definitely be back soon. Thank you for a wonderful stay. "

[](https://expedia.ca/Cleveland-Hotels-Crowne-Plaza-Cleveland-At-Playhouse-Square.h17461.Hotel-Information)

![Extended Stay America Premier Suites - Cleveland - Independence](//images.trvl-media.com/lodging/1000000/50000/43400/43391/937b3534_y.jpg)

### Extended Stay America Premier Suites - Cleveland - Independence

10/10 Excellent

"Good"

[](https://expedia.ca/Cleveland-Hotels-Hyatt-Place-Independence.h43391.Hotel-Information)

## Find out more about Chesterland

## Chesterland Cottages information

| Number of reviews | 171 |
| --- | --- |
| Accommodation | 51 Cottages |
| Lowest Price | CA $452 |
| Highest Price | CA $647 |

## Frequently asked questions

### Why book your cottage in Chesterland with Expedia?

> Booking a cottage in Chesterland is as simple as entering your travel dates and choosing an ideal place for outdoor recreation and relaxation. From ritzy retreats to affordable stays and cottages that feature conveniences like a kitchen, Expedia has something for all tastes. As for unbeatable deals? We've got them as well!

### How can I find cheap cottages in Chesterland?

> The easiest way to compare cheap cottages in Chesterland is with Expedia's handy filter tool. Narrow your search by star rating, amenities and budget to snag unbeatable prices with only a few clicks.

### What is there to do in Chesterland near my cottage?

> Once you've checked in to your hotel, set out and explore the awesome things Chesterland has for you to experience. [Fowler's Mill Golf Course](https://www.expedia.ca/Fowlers-Mill-Golf-Course-Chesterland.d6269511.Vacation-Attraction) is a great attraction to add to your must-do list.

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