Vacation rentals in Chatham

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Top-rated vacation rentals in Chatham

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

Guesthouse in Detling

4.92 out of 5 average rating, 132 reviews

Adorable 1 bed guesthouse with patio

Sit back & relax in this calm, cosy space. Set within the grounds of our gated family home in Detling located on the slope of the North Downs, 4 miles north east of Maidstone, & on the Pilgrims' Way. Whether you want a relaxing get away or want to explore many of the wonderful walks and bike trails the north downs have to offer you can be sure to find a warm and cosy place to stay at the end of the day. We have a very friendly dog who will be on hand to greet you along with 2 young children

Sep. 22 – 29

$171 CAD per night

Guest favourite

Home in Medway

4.9 out of 5 average rating, 130 reviews

2-bedroom house in historic Rochester with Parking

Dove’s Place is a 2 bedroom terraced house with addition of a conservatory space and free allocated parking space. The property is adjacent to River Medway located in Rochester and close to green spaces and guests can also enjoy river walk. It is a walking distance to Rochester Castle, Cathedral, Train Station, High Street Shops, Restaurants, Museums, Coffee Shops and Bars. Great place for Family, Professionals and Tourist. We guarantee a memorable stay with our slogan, HERE FOR YOU!!!

Jul. 14 – 21

$207 CAD per night

Guest favourite

Cottage in Chatham

4.92 out of 5 average rating, 437 reviews

PJ's @ Willow Cottage

Small but beautifully created detached one bedroom apartment with kitchen, living room/study, dining room and shower room/bathroom. Close to places of interest, train station, bus routes and M2 / M20 motorways . Superfast Wi-Fi, flat screen TV, fridge/freezer, microwave, hob, coffee/hot water machines and many extras. Double bed with Simba memory foam mattress , Chesterfield chair and settee. Off-road parking and full access to large garden area. A secure bicycle store also available.

Dec. 26 – Jan. 2

$127 CAD per night

Guest favourite

Farm stay in Oad Street

4.96 out of 5 average rating, 121 reviews

Unique Self contained lodge within stable setting

This unique stylish property is very close to junction 5 on the M2 with easy access to London. Plan your visits to Canterbury Cathedral, Leeds Castle, Whitstable, Rochester Castle and many other tourist attractions with ease from this central location. The Property is two miles from the closest shop and the nearest train station is Sittingbourne. The property is set amongst beautiful paddocks with horses in livery in the adjacent stables. There is ample secure parking and easy access.

Jun. 10 – 17

$192 CAD per night

Guest favourite

Cabin in Rochester

4.94 out of 5 average rating, 270 reviews

Countryside Cabin with Private Patio

The Snuggery is a converted outbuilding that has been set up for a cosy stay with a wood burning stove and lots of snuggly wraps to cuddle up in. The open plan interior, high vaulted ceilings and natural oak flooring create an interior which is fun, light and airy. Walking enthusiasts will enjoy walks from the back door straight on to the North Downs Way and there is a bench by the front door fitted with a heated element, perfect for warming up your walking boots. Photos by Chloe-Rae

Oct. 27 – Nov. 3

$190 CAD per night

Guest favourite

Guesthouse in Boughton Monchelsea

4.96 out of 5 average rating, 141 reviews

Adorable 1 bedroom guest barn, Boughton Monchelsea

This barn is situated in the picturesque village of Boughton Monchelsea. It has its own private garden with stunning meadow views. It has lots of local amenities to explore and is only 15 minutes drive from Leeds castle and a 15 minute drive to the train station which will take you directly into London. The exposed oak beamed barn is situated next to a traditional oast house, perfect for romantic getaways and people who want to escape the fast pace of everyday life.

Dec. 14 – 21

$178 CAD per night

Guest favourite

Cottage in Boughton Monchelsea

4.91 out of 5 average rating, 515 reviews

The Oast Cottage: Private Annex with own entrance.

We are pleased to offer our refurbished annex with double bedroom, private bathroom, own front door and a private field for dogs. Oast Cottage is a converted stables attached to the main Oast House. The Oast is set in a conservation area of Boughton Monchelsea which consists of converted farm buildings, listed houses and a 16th Century pub (directly opposite). The area boasts many places to visit (including Leeds Castle), countryside walks, as well as numerous pubs.

Dec. 29 – Jan. 5

$135 CAD per night

Guest favourite

Guest suite in Wateringbury

4.98 out of 5 average rating, 166 reviews

Peaceful apt, views, Wi-Fi, garden & sunsets

Relax or work in this stylish apartment with private courtyard garden and vintage summerhouse * First floor apartment with free parking * Rural views * Wi-Fi * Self check in * 6ft super king bed * Heating * Smart TV * Plus a summerhouse * Under 1 hour train from London * Local pub/food 10 minute walk * Close to country walks * River Medway 1 mile for boating/walks * Not suitable for pets or children * Please note EV charging is NOT permitted on the property*

Aug. 21 – 28

$196 CAD per night

Guest favourite

Home in Kent

4.93 out of 5 average rating, 216 reviews

Hermitage Cottage cosy 1-4 person accommodation.

Hermitage Cottage offers annexe accommodation. Bathed in sunshine in private garden setting. We are a commuters dream with Barming railway station at the door. London Victoria 57 minutes and Maidstone East just three minutes by rail. Fully fenced with garaging for one vehicle., entry by automatic gates. Finished to a very high standard with under floor heating and feature fire place. Your every comfort is assured. Welcome pack included.

Dec. 20 – 27

$154 CAD per night

Guest favourite

Cottage in Marden

4.99 out of 5 average rating, 479 reviews

The Lodge

**Opted in to Airbnb's enhanced cleaning protocol** Cosy barn-style accommodation nestled in the heart of the Kent countryside. Located close to National Trust sites and country walks. The Lodge is the perfect country getaway and romantic retreat. Please note this is strictly a NO SMOKING property inside the Lodge, the garden and surrounding field. The property is also NOT SUITABLE for infants, children or pets. Two adults only.

Dec. 23 – 30

$160 CAD per night

Guest favourite

Apartment in The Precinct

4.9 out of 5 average rating, 128 reviews

Cosy 18th Century Undercroft

Tucked away between the Medieval Castle and Cathedral, the Undercroft belongs to the impressive Georgian Townhouse above and has been professionally restored to retain the opulence and integrity one would expect. With its great views of the Cathedral, free parking, two-minute proximity to both the High Street and High Speed train station, the Undercroft is one of the most desirable addresses in Rochester.

Jun. 28 – Jul. 5

$150 CAD per night

Guest favourite

Apartment in Medway

4.91 out of 5 average rating, 213 reviews

Ascot - West Street

Newly refurbished - Ascot, like its twin Sandown, has an ample sized, well equipped kitchen with a table and four chairs and a comfy sofa that turns down to a bed in seconds. A TV is included in the kitchen. The French windows look out over your small private lawn onto farmland From the kitchen you go past the entrance lobby into a twin bedded bedroom with TV. A large modern bathroom adjoins the bedroom.

Dec. 18 – 25

$112 CAD per night