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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Top guest favorite
A modern dining area features a round table set with plates and flowers, surrounded by four black chairs. A cozy sofa is positioned nearby, with a soft color palette complementing the overall design. Light enters through an opening to the kitchen area.
Home in Rainham Mark
4.97 out of 5 average rating, 137 reviews

Modern 2 Bed House in Rainham, Kent

Welcome to this modern home from home in Rainham. Perfect for any stay - leisure, work, visiting family/friends & local attractions. Conveniently situated close to local amenities, 5-minute walk to train station and town centre, restaurants, pubs, bars, shops & more. Including 2 spacious bedrooms with double & king size bed, new luxury bathroom & open lounge with all Virgin TV channels including Sky Sports & Netflix, fully equipped modern kitchen, large garden & a parking space for your stay.

Top guest favorite
The exterior of the annex is showcased, featuring vertical wooden slats and a glass-paneled door. A small window is visible, allowing natural light into the space. The entrance is set on a paved path, surrounded by greenery and a water storage tank nearby.
Guesthouse in Sittingbourne
4.94 out of 5 average rating, 266 reviews

Self-contained annex, with off-road parking.

Self-contained annex in Sittingbourne, perfect if you are visiting the area for work or leisure. Everything you need for a comfortable stay in your own completely private place, with driveway parking and fast WiFi. The accommodation comprises a bedroom /lounge /working room, kitchen and bathroom. The annex, especially the bedroom, is very quiet and peaceful. Located conveniently for the motorway and also easy access to the town centre, train station, shops, takeaways, restaurants and pubs.

Guest favorite
A bright entrance corridor is visible, featuring wooden flooring and white walls. The front door has a glass panel design, while a round mirror is mounted on the wall. A welcome mat lies on the floor, and warm light fixtures create a welcoming ambiance.
Home in Medway
4.92 out of 5 average rating, 188 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!!!

Top guest favorite
Cabin in Rochester
4.96 out of 5 average rating, 449 reviews

Cosy Rural Retreat with Log Burner

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 

Superhost
A well-maintained exterior features a brick building with large glass doors leading to a private lawn. Colorful flower beds in the foreground display a mixture of vibrant red, pink, and purple blooms, enhancing the serene atmosphere of the outdoor space.
Farm stay in Medway
4.8 out of 5 average rating, 252 reviews

Sandown - West Street

Newly refurbished - Sandown, like its twin Ascot, has an ample sized, well equipped kitchen with a table and four chairs and a comfy sofa that turns down into a bed in seconds. The kitchen has a electric hob and oven, a fridge and a washing -dryer machine is in the adjoing outhouse. A TV is included in the kitchen. The French windows look out over your private lawn onto farmland. From the Entrance lobby turn right straight into the kitchen or left into the ensuite bedroom with TV.

Top guest favorite
An exterior view of a barn features a neatly maintained lawn, framed by a stone structure. Double glass doors lead into the barn. Two small chairs are positioned on a paved patio area near the entrance, inviting relaxation. Surrounding greenery adds a natural touch.
Guesthouse in Boughton Monchelsea
4.97 out of 5 average rating, 307 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.

Guest favorite
A spacious garden area is showcased, featuring a manicured lawn bordered by vibrant greenery. A stone path leads to a charming detached apartment, complemented by seating arrangements and a wooden table under the clear sky, promoting relaxation in a serene outdoor environment.
Cottage in Walderslade
4.92 out of 5 average rating, 479 reviews

PJ's @ Willow Cottage

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

Guest favorite
The exterior of the annex is presented, featuring a white picket fence and a gravel area. A vintage lamppost stands near the entrance, complemented by two outdoor chairs positioned on the patio. The structure showcases a pitched roof, rustic siding, and several windows, providing ample natural light.
Cottage in Boughton Monchelsea
4.9 out of 5 average rating, 811 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.

Top guest favorite
An open plan living area features a circular wooden table surrounded by teal chairs and a cozy seating arrangement with a leather sofa and armchair. A television is positioned beside a decorative fireplace, while natural light filters in through windows overlooking lush greenery.
Guest suite in Wateringbury
4.99 out of 5 average rating, 268 reviews

Peaceful, country views, garden, WiFi & sunsets

Relax or work in this stylish apartment with private courtyard garden and vintage summerhouse * First floor apartment with free parking * Country 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*

Top guest favorite
A charming two-story building features a classic white-clapboard façade with a large window on the upper level. The entryway is framed by a beige curtain, while greenery is visible in front of the structure. Adjacent buildings showcase brick and painted exteriors.
Cottage in Rochester
4.95 out of 5 average rating, 312 reviews

The Old Tuck Shop (entire cottage - 1 double bed)

Ideally located for exploration of the historic Medway Towns and surrounding areas of Kent,The Old Tuck Shop is the perfect place for a relaxing getaway. The accommodation can sleep up to 3 guests, but this listing is only for two guests sharing the double room. If the second single bedroom is required please contact your host before booking or see the other listing. There is a full bathroom upstairs and an additional loo and cloakroom downstairs.

Top guest favorite
A spacious living area showcases wooden beams and an open layout. A comfortable sofa faces a wood-burning stove, with a flat-screen TV nearby. The dining table is surrounded by woven chairs, and large windows provide natural light while offering views of the entrance and surrounding nature.
Cottage in Marden
4.99 out of 5 average rating, 581 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.

Guest favorite
A charming barn conversion is depicted amidst a grassy landscape, with a gravel driveway leading to its entrance. The structure features black wooden siding and a metal roof, surrounded by rows of pear orchards and open farmland under a partly cloudy sky.
Farm stay in Medway
4.93 out of 5 average rating, 182 reviews

Unique barn conversion with beautiful marsh views

This recently converted barn is situated on the edge of the North Kent Marshes, with stunning views of the birds and wildlife on the marshes and surrounded by pear orchards to the rear. You’ll enjoy complete privacy, with no surrounding properties and a real sense of peace and tranquillity. The property is located in the middle of a working farm, with our sheep grazing the marshes and a variety of fruit grown in the orchards.

Popular amenities for Chatham vacation rentals

When is the best time to visit Chatham?

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Avg. priceR2,046 ZARR2,114 ZARR2,114 ZARR2,234 ZARR2,217 ZARR2,217 ZARR2,268 ZARR2,285 ZARR2,200 ZARR2,200 ZARR2,114 ZARR2,251 ZAR
Avg. temp5°C5°C7°C10°C13°C16°C18°C18°C15°C12°C8°C6°C

Frequently Asked Questions

  • Where should I stay in Chatham?

    Make yourself at home in Chatham by choosing from our most frequently booked neighborhoods. We have over 600 vacation rentals in Upnor, over 280 vacation rentals in Blue Bell Hill, and over 600 vacation rentals in St. Mary''s Island.

  • Are there vacation rentals with a dedicated workspace in Chatham?

    Yes! Work meets play with ease at over 200 vacation rentals in Chatham featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Chatham?

    Four-legged friends are welcome in Chatham. Choose from more than 40 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in apartment rentals in Chatham?

    Experience the best of Chatham with our apartment rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Chatham have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Chatham. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Chatham have wifi?

    Absolutely! We offer over 20 condo rentals with wifi in Chatham. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chatham have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Chatham. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chatham have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Chatham. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly apartment rentals in Chatham?

    Chatham has more than 30 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Apartment Rentals in Chatham?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 100 homes with wifi, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Chatham

  • Total vacation rentals

    Explore 460 vacation rentals in Chatham

  • Nightly prices starting at

    Chatham vacation rentals start at R341 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 5,660 verified reviews to help you choose

  • Family-friendly vacation rentals

    200 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    200 properties have a dedicated workspace

  • Wi-Fi availability

    430 of Chatham vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Chatham rentals

  • 4.6 Average rating

    Chatham stays receive an average rating of 4.6 out of 5 from guests

  1. Airbnb
  2. United Kingdom
  3. England
  4. Medway
  5. Chatham