Search Chessington Cottage Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11
In one month
Jan 23 - Jan 25
In two months
Feb 20 - Feb 22

Our top choices for Chessington cottages

Outdoor dining
Cosy city retreat in Belgravia. Pet-Friendly!

Cosy city retreat in Belgravia. Pet-Friendly!

Cosy city retreat in Belgravia. Pet-Friendly!
2.0 star property
London City Centre
The price is ￥113,242
￥172,012 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Cosy city retreat in Belgravia. Pet-Friendly!
Exterior
Blackwood - Peaceful cottage surround by woodlands

Blackwood - Peaceful cottage surround by woodlands

Blackwood - Peaceful cottage surround by woodlands
2.0 star property
Cobham
The price is ￥33,703
￥52,661 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Blackwood - Peaceful cottage surround by woodlands
Cottage | Terrace/patio
Dreamwood Lodge

Dreamwood Lodge

Dreamwood Lodge
3.0 star property
Bromley Common and Keston
The price is ￥158,278
￥189,934 total
includes taxes & fees
Dec 29 - Dec 30
Dreamwood Lodge
Property grounds
1 Bed Cottage-Museum View-Garden-Free Parking

1 Bed Cottage-Museum View-Garden-Free Parking

1 Bed Cottage-Museum View-Garden-Free Parking
Weybridge
10.0 out of 10, Exceptional, (1)
"Xanthe was the consumate host. She brought us wonderful treats and her beautiful welcoming smile. We walked to the Brooklands museum. A must if you are into planes,buses, and automobiles. Love this place.Suzanne "
United States
Suzanne D.
The price is ￥28,858
￥34,124 total
includes taxes & fees
Dec 28 - Dec 29
1 Bed Cottage-Museum View-Garden-Free Parking
Property grounds
Cozy en-suite with exclusive private entrance

Cozy en-suite with exclusive private entrance

Cozy en-suite with exclusive private entrance
2.0 star property
Great Bookham
The price is ￥15,166
￥21,696 total
includes taxes & fees
Dec 27 - Dec 28
Cozy en-suite with exclusive private entrance
Property grounds
Charming Cottage within Ancient Woodland Forest

Charming Cottage within Ancient Woodland Forest

Charming Cottage within Ancient Woodland Forest
Cobham
10.0 out of 10, Exceptional, (1)
"Thoroughly enjoyed our stay at this beautiful, cozy, warm Ariel cottage. Woodland area for walks nearby golf course, dogs welcome although we did not take any pets but so suitable for your furry friends.Jake very welcoming, thankyou so much"
United Kingdom
Heidi C.
The price is ￥22,939
￥40,422 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Charming Cottage within Ancient Woodland Forest
Interior
Inviting 2-Bed Cottage in Windsor

Inviting 2-Bed Cottage in Windsor

Inviting 2-Bed Cottage in Windsor
Windsor City Centre
7.0 out of 10, Good, (7)
"Everything you could need for a break away in beautiful Windsor"
United Kingdom
Gemma W.
The price is ￥28,858
￥39,390 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Inviting 2-Bed Cottage in Windsor
Exterior
2 bedroom accommodation in Godstone

2 bedroom accommodation in Godstone

2 bedroom accommodation in Godstone
Godstone
8.8 out of 10, Excellent, (3)
"Great place to stay. Very spacious"
United States
Anne Lauritsen
The price is ￥57,085
￥57,085 total
includes taxes & fees
Jan 5 - Jan 6, 2026
2 bedroom accommodation in Godstone
Property grounds
The Lakehouse Apartment by inspirestays-com - a home sleeping 2 guests in 1 bedroom

The Lakehouse Apartment by inspirestays-com - a home sleeping 2 guests in 1 bedroom

The Lakehouse Apartment by inspirestays-com - a home sleeping 2 guests in 1 bedroom
Rudgwick
10.0 out of 10, Exceptional, (2)
"Away from all traffic with lovely views this well equipped apartment provides an ideal base for West Sussex and Surrey. The kitchen is particularly good and we much enjoyed our second stay here."
United States
Anonymous traveler
The price is ￥114,422
￥114,422 total
includes taxes & fees
Jan 8 - Jan 9, 2026
The Lakehouse Apartment by inspirestays-com - a home sleeping 2 guests in 1 bedroom
Exterior
Nr Windsor- Unique Cottage Stay for upto 14 guests

Nr Windsor- Unique Cottage Stay for upto 14 guests

Nr Windsor- Unique Cottage Stay for upto 14 guests
Dorney
10.0 out of 10, Exceptional, (2)
"Great house, really well equipped with loads of parking. Great area with loads to do with the kids. We would love to book it again! Thank you!"
United Kingdom
Laura S.
The price is ￥77,938
￥124,280 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Nr Windsor- Unique Cottage Stay for upto 14 guests
Cottage | Interior
Cozy 4-bed Cottage Garden Walk to River Thames

Cozy 4-bed Cottage Garden Walk to River Thames

Cozy 4-bed Cottage Garden Walk to River Thames
3.0 star property
Hampton
6.0 out of 10, (1)
"No Parking close by to drop off luggage. Treacherous, steep downhill path through a park to take several heavy suitcases. Incredibly poor communication from the property, who in the first instance did not respond for over a week to our request for an early check in. e repeatedly asked host for check in details,and we eventually got them on the day of check in only 15 minutes before scheduled (normal) check in time, at which time we were already at the weddding of my daughter, having travelled...
United Kingdom
Andre
The price is ￥44,867
￥44,867 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cozy 4-bed Cottage Garden Walk to River Thames
Private kitchen
1 bedroom accommodation in Carshalton

1 bedroom accommodation in Carshalton

1 bedroom accommodation in Carshalton
Carshalton South and Clockhouse
The price is ￥44,235
￥44,235 total
includes taxes & fees
Jan 2 - Jan 3, 2026
1 bedroom accommodation in Carshalton
Cottage | Terrace/patio
Coventina

Coventina

Coventina
3.0 star property
Wraysbury
The price is ￥405,185
￥486,222 total
includes taxes & fees
Dec 29 - Dec 30
Coventina
TV
4-Bed Cottage, Sleeps 8, Walk to Thames Garden

4-Bed Cottage, Sleeps 8, Walk to Thames Garden

4-Bed Cottage, Sleeps 8, Walk to Thames Garden
Hampton
2.0 out of 10, (2)
"Communication from the owners was poor right up until the day of check in. I made contact a few days before we were due to stay, to understand the process of check in. After reading my messages, they totally ignored them and we had to call the night before to make sure that our booking was actually in place. The property itself was spacious and clean, but unfortunately there was no love put into this place at all. The decor was bland and uninviting and minimal to say the least. The chest of...
United Kingdom
The T.
The price is ￥44,867
￥44,867 total
includes taxes & fees
Jan 4 - Jan 5, 2026
4-Bed Cottage, Sleeps 8, Walk to Thames Garden
Exterior
The Observatory Annexe

The Observatory Annexe

The Observatory Annexe
3.5 star property
Dorking
The price is ￥92,031
￥110,437 total
includes taxes & fees
Dec 29 - Dec 30
The Observatory Annexe
Cottage | Exterior
1 Bed Cottage-museum View-garden-free Parking

1 Bed Cottage-museum View-garden-free Parking

1 Bed Cottage-museum View-garden-free Parking
3.0 star property
Weybridge
8.8 out of 10, Excellent, (3)
"This was a perfect find. Communication great, the host is a pleasure to deal with. Great space and super-quiet. A lovely place to relax. Highly recommended "
United Kingdom
Raquel
The price is ￥28,312
￥33,578 total
includes taxes & fees
Jan 25 - Jan 26, 2026
1 Bed Cottage-museum View-garden-free Parking
Exterior
Thames Retreat

Thames Retreat

Thames Retreat
3.0 star property
Wraysbury
The price is ￥73,589
￥88,307 total
includes taxes & fees
Dec 29 - Dec 30
Thames Retreat
Cottage | Interior
Inviting 2-bed Cottage in Windsor

Inviting 2-bed Cottage in Windsor

Inviting 2-bed Cottage in Windsor
3.0 star property
Windsor City Centre
2.0 out of 10, (1)
"We had absolutely no heating. I tried several times to contact the owner by email, messenger and by phoning her. No reply. I had been in contact with her regarding check in via email and messenger, I even sent a photo of the temperature in the house. 10 degrees. I had to source 2 radiators myself, which a kind neighbour lent us. I would like a refund for our inconvenience "
United Kingdom
Anonymous traveler
The price is ￥28,601
￥39,133 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Inviting 2-bed Cottage in Windsor
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chessington Hotel Reviews

The Westminster London, Curio Collection by Hilton

The Westminster London, Curio Collection by Hilton

10/10 Excellent
"Good location, Nice restaurant Helpful staff"
Carolyn 4-night trip
Posted 22 hours ago
The Westminster London, Curio Collection by Hilton

Find out more about Chessington

Chessington Cottages information

Number of reviews
12
Accommodation
349 Cottages
Lowest Price
￥21,696
Highest Price
￥486,222

Frequently asked questions

How much do cottages in Chessington cost?
Prices for cottages in Chessington range between ￥21,696 and ￥486,222 per night. No matter your budget, you're sure to find the perfect place to soak up nature's beauty. 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.
What are the best cottages in Chessington?
A guest favorite is Bright and Spacious 5 Bedroom Family Home Near Wimbledon. Get comfortable at this 4-star stay which features a terrace and a garden. 3 Bedroom House In Central Wimbledon is another popular option to consider. Put your bags down at this 4-star cottage and take advantage of amenities such as a fireplace and a garden. You can pick from multiple cottages in Chessington with a total average guest review rating of 8.4.
How many cottages are there in Chessington?
Reconnect with nature in one of the 349 cottages located in Chessington. To help you select a stay that's right for you, take advantage of our filters to search for must-have amenities.
Are there any family-friendly cottages in Chessington?
Vacationing with your group in Chessington is simple at Bright and Spacious 5 Bedroom Family Home Near Wimbledon. With amenities like a fireplace and an oven, you'll find all the necessary comforts at this 4-star cottage. 3 Bedroom House In Central Wimbledon is another family-friendly stay where you and the rest of your squad can take time out from the hectic pace of life in the city. This cottage has a 4-star rating and conveniences including WiFi and a fireplace. After checking in and chilling out together in your home away from home, it's time to explore some of the local sights. Hampton Court Palace and Chessington World of Adventures are fun family-friendly attractions in Chessington.
Are there any 5-star cottages in Chessington?
Although you won't find any 5-star cottages in Chessington, there are 4-star options that will check all your boxes. Enjoy unhurried days in peaceful surroundings at Bright and Spacious 5 Bedroom Family Home Near Wimbledon. Located approximately 14 kilometers from the downtown area, it has a terrace and a garden. Another stylish stay is 3 Bedroom House In Central Wimbledon. It's around 11 kilometers from central Chessington and features amenities such as a terrace and a garden.
Why book your cottage in Chessington with Expedia?
We think a getaway should be a breeze, so if you're after cottages in Chessington at an affordable price, Expedia has got your back. Keep the budget under control and check in to an inexpensive option far from the rush of the city, or book an upmarket cottage to pamper your favorite people.
How can I find cheap cottages in Chessington?
A wonderful way to find cheap cottages in Chessington is with Expedia's useful filter tool. Narrow your search results by amenities, budget and star rating to discover awesome rates in just a few clicks.
What is there to do in Chessington near my cottage?
The most practical travel accessory is a well-planned to-do list. Chessington World of Adventures is a good spot to begin your sightseeing in Chessington.