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Places to stay near Chepstow Racecourse

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Top-rated vacation rentals near Chepstow Racecourse

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

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Top guest favorite
Apartment in Monmouthshire
4.91 out of 5 average rating, 138 reviews

Cromwell House, Central Chepstow

Flat 1 is a cosy first floor flat in Cromwell House steeped in history and named after Oliver Cromwell having stayed here when invading the famous Chepstow Castle. We have recently refurbished the property to create a warm and welcoming place to enjoy all that Chepstow and the surrounding areas has to offer. This special place is close to everything and central to Chepstow making it easy to plan your visit. The flat is fully equipped with every thing you would need for your stay along with Wi-Fi

Top guest favorite
The exterior of Pineapple Cottage is shown, featuring a gray facade and a teal front door. Two potted plants sit beside the doorway. A cobbled street leads upward, lined with traditional buildings and a lantern light adding a touch of character to the scene.
Cottage in Chepstow
4.88 out of 5 average rating, 531 reviews

Pineapple Cottage - Chepstow Town Centre (Wales)

17th Century cottage in the heart of Chepstow, close to Offa's Dyke & the Wye Valley. Tucked down a little cobbled street in the town centre, it’s a small but perfectly formed cottage ideal for a couple or a young family. There’s a secret door leading to the second bedroom, where you’ll even get a glimpse of Chepstow Castle from the window. It’s an ideal base for weddings at St Tewdrics (we’ve even hosted the bride and groom!) or for walking and cycling in the Forest of Dean and Wye Valley.

Top guest favorite
A row of colorful terraced houses is showcased, featuring distinct facades in shades of white, gray, green, and yellow. A bright pink door is prominent, complemented by a charming window with lace curtains. The scene captures the character of the street in Chepstow.
Townhouse in Chepstow
4.95 out of 5 average rating, 293 reviews

Chepstow Town. Welsh Cottage.

The house is in the centre of the beautiful old market town of Chepstow. Nestled on the Welsh / English border. We are just a stone's throw from the ancient castle and the impressive Priory Church of St Mary. Within walking distance of the Chepstow Racecourse and a stroll from the railway and bus stations. 300yds from the River Wye and central to all restaurants and cafes etc. Situated near the AONB Wye Valley and Forest of Dean. Please note the property has a Jack & Jill bathroom upstairs.

Top guest favorite
A feature arched window frames panoramic views of rolling hills and fields, with sunlight illuminating the stone wall and wooden shutters. A vase of fresh flowers sits on a round table, enhancing the inviting atmosphere of the open living space.
Cottage in Saint Briavels
5 out of 5 average rating, 359 reviews

Wye Valley Escape. Romantic Loft on 40-Acre Estate

Romantic luxury loft for two on a 40-acre private estate in the Wye Valley National Landscape. Perfect for honeymooners, stargazers, proposals, anniversaries, or milestone moments. Enjoy panoramic Mork Valley views through the feature arched window, vaulted oak beams, and a cozy fire pit (logs & marshmallows incl.). Includes a generous welcome hamper and exclusive access to our dark skies, meadows, stream, and woodland. A peaceful, magical retreat with high-end, curated experiences available.

Top guest favorite
A quaint stone cottage is framed by lush greenery, featuring a large window that invites natural light inside. The well-maintained lawn includes neatly trimmed hedges and a comfortable seating area, creating a serene outdoor environment.
Cottage in Monmouthshire
4.97 out of 5 average rating, 207 reviews

Peaceful Stone Cottage among fabulous gardens

The Garden House is a peaceful stone cottage set in the historic gardens of High Glanau Manor, the home of H. Avray Tipping (1855-1933) the Architectural Editor of Country Life Magazine from 1907. High Glanau Manor is an important Arts & Crafts house set in 12 acres of gardens designed in 1922. The gardens retain many original features including formal terraces, octagonal pool, glasshouse, pergola and 100 ft long double herbaceous borders. There are spectacular views to the Brecon Beacons

Top guest favorite
The open-plan sleeping area features a spacious bed with soft linens, illuminated by gentle lighting from bedside lamps. A rustic stone ceiling adds character, while a wooden wardrobe provides storage. A plush chair is partially visible, inviting relaxation in the cozy ambiance.
Condo in Bristol City
4.99 out of 5 average rating, 152 reviews

The Vault

The Vault is a really special space, which we hope you can see from the photographs. It is a basement studio apartment with its own private entrance. It is quiet and cosy with underfloor heating and an ambient temperature all year round. This property is very central, making it easy to plan your visit. We are very close to the harbour and the property is on the famous Georgian Square, Queen Square. It feels like you have stepped into a film from Jane Austen as you come out of the building.

Guest favorite
The historic Welsh Gatehouse features an imposing stone exterior with two prominent towers. Architectural details include ancient windows and a large, arched entrance. Surrounding greenery adds to the charm of this medieval structure, set against a clear blue sky.
Castle in Chepstow
4.92 out of 5 average rating, 197 reviews

Welsh Gatehouse: Historical Castle with EV Charger

The Welsh Gatehouse is a beautiful historic house with modern amenities. Imagine staying in a fairy tale castle built in 1270. The thick walls, ancient windows & steep spiral staircase say 'history'. Romantic log fires keep you warm you in winter, & the thick walls keep you cool in summer. Views from the top of the tower are extraordinary over the Severn Bridges and the Breacon Beacons (NB we call this the terrace in our description below). Unique, luxurious, quirky yet comfortable.

Top guest favorite
Cabin in Monmouthshire
5 out of 5 average rating, 137 reviews

Ty Nant Treehouse with covered hot tub

As you enjoy the short buggy ride down to the far end of our woodland you will be astounded when you come across our beautiful woodland cabin set in the treetops. You will immediately feel relaxed as you immerse yourself in the surrounding nature. Lounging chairs on the decking provide the perfect place for your morning coffee listening to the birds sing and soak away your stress in the wood fired hot tub then cosy up in front of the log burner and enjoy the tranquility of the woodland.

Top guest favorite
Dome in Milbury Heath
4.99 out of 5 average rating, 193 reviews

Lodge farm Woodland dome. Hot tub. luxury escape

A luxurious dome nestled in private woodland and flower garden. An ideal romantic/ family stay near the Cotswolds. Enjoy the wildlife view from your king size bed, woodburning stove, additional heating and air conditioning. Relax on the private decking area, outdoor dining with a barbeque and firepit for toasting marshmallows amongst the trees. The mattresses can be brought down from the loft area for younger children. Rest, relax and reward yourself with the glamping stay with us!

Top guest favorite
The exterior of a cozy pod is displayed, featuring a welcoming entrance with double doors. A wooden deck leads to the main door, complemented by outdoor seating and a barbecue. Surrounding greenery enhances the natural setting, providing an inviting atmosphere.
Cabin in Whitfield
4.96 out of 5 average rating, 139 reviews

Cosy Bluebell Pod - Eastwood Glamping

Bluebell Pod is our couples pod, with a double bed and pull out sofa, dining table, living space and a romantic outdoor bathtub with fantastic lake views and views of the farm. Our self catering pods have a kitchenette with induction hobs and a microwave. We also have outdoor seating and a private BBQ for an al-fresco dining experience. Each pod has luxurious décor selected with extra comfort in mind. Near Thornbury, Bristol where you will find lots shops and restaurants.

Top guest favorite
A well-maintained hot tub is situated on a stone patio, featuring a clear, inviting water surface. Surrounding natural stone walls provide a rustic backdrop, while a small set of steps leads up to the hot tub area. A window from a nearby building is visible in the background.
Home in Amberley
5 out of 5 average rating, 290 reviews

Magical cottage set within a woodland glade

Badgers Bothy is set within a woodland glade in the grounds of the 16th century Amberley Farmhouse and provides the most unique and charming country escape. Our idyllic cottage is set on the edge of Minchinhampton Common (located in an AONB) and with miles of footpaths which are perfect for those wishing to explore the Cotswolds. This beautiful cottage exudes an aura of peace and tranquillity and a haven for those wishing to escape the hustle and bustle of a busy life.

Top guest favorite
An inviting dining area features a light-colored wooden table set with tableware, complemented by a cozy yellow sofa. A decorative wall piece and a flat-screen TV enhance the rustic charm of the stone interior, while a soft light illuminates the space through an arched doorway.
Cottage in Tockington
4.97 out of 5 average rating, 187 reviews

Olli's Cottage-Terrace &Jacuzzi

Olli's cottage is situated in one of Bristol picturesque suburds, newly refurbished 700sq Ft/70 Sqm with private terrace and hot tub (£30 extra charge to be settled at the property). In close proximity you have another property called Olli’s Summer house: Swimming pool with waterfall, pool table & ping pong table (£100 extra charge and subject to availability). Located near M4/M5, making travel to/from easy. 3 minutes drive to country pubs.

Popular amenities for vacation rentals near Chepstow Racecourse

  1. Airbnb
  2. United Kingdom
  3. Wales
  4. Monmouthshire
  5. Chepstow
  6. Chepstow Racecourse