
Cottage holiday rentals in Chepstow
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Top-rated cottage rentals in Chepstow
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Goldcrest-Lodge-Forest-of-Dean
Take it easy at this unique and tranquil getaway. Set in the Wye Valley, an area of outstanding natural beauty. You can walk/cycle for miles without touching a road. Collect eggs, milk and delicious ice cream from the farm next door Tintern Abbey with its pubs and restaurants is a walk away (an hour); the races, music at the Castle, Clearwell Caves, Puzzlewood, steam train.. and more. Travelling with friends/family? Check our other listing within the same grounds airbnb.com/h/wyevalleydairy-uk

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.

The Old Coach House at Tintern, the Wye Valley
The old coach House is a few minutes walk from the centre of Tintern on the banks of the river Wye, where you'll find the famous abbey, as well as places to eat and drink, and shops selling local crafts. The Wye Valley Walk passes the house, and the hourly bus between Chepstow and Monmouth stops just metres away. Staying at the historic Old Coach House in Tintern, you'll experience the unique charm of an early 1800s Welsh cottage, while enjoying modern comforts in a stylish and homely setting.

Quiet grade 1 listed entire cottage in Cotswolds
A bright and recently modernised grade 1 listed Cotswold stone cottage, 100 yards from the Cotswold Way with breathtaking views down the Stroud Valley, its own parking and secluded outdoor eating. Filled with natural light, it is very peaceful and extremely comfortable with luxury bedding (super king or twin bed) and kitchen. An idyllic spot for walking, cycling, exploring the local scenery or simply escaping the city Painswick is 10 minutes from Stroud ( 87 mins hourly train to London).

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.

Vauxhall Cottage: Sunny garden, stroll to town
Vauxhall Cottage is a charming home-from-home, ideal for families & friends, yet cosy for couples. The spacious layout offers social areas & quiet nooks, with 4 comfy bedrooms, large kitchen & lounge, sunroom & an enclosed, dog-friendly garden with patio & BBQ. The modernised 1790s Welsh cottage is a short stroll to Chepstow’s historic centre, Castle & riverside, ideal for the racecourse, & to explore the Forest of Dean, Wye Valley & beyond, with easy connections to Cardiff, Bristol & M4/M5.

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

3 bedroom, peaceful, secluded, & large garden
Hidden away on the edge of the ancient Forest of Dean, in the beautiful Wye Valley, with a large secluded garden, accessed by a mile long, narrow, single track lane, hanging with ferns in summer. It's is a fabulous place for walkers and town escapees. Once a woodman’s cottage, with a cosy, spacious interior, fully equipped kitchen, log burner, very comfortable beds, all you need for a relaxing break. Not suitable for young children 1-12, the large garden has a pond and steep terracing.

Country Cottage 25% Weekly Discount, Covered Patio
The Mews House is a homely, light & spacious character cottage in the village of Llanishen, Monmouthshire, between the Wye & Usk Valleys, AONB areas. There is a variety of attractions including walks from the property and in the local area, castles, Tintern Abbey, the River Wye, Roman Caerleon, horse riding, cycling & golf. It is a 2 minute walk to the village shop & garage. The village pub is closed at the moment but there are 3 other good food pubs each just over 2 miles away.

Elm Park Barn, Chewton Keynsham, BS31 2SS
Nestled between the popular cities of Bristol and Bath, stunning views with exclusive use hot tub & large indoor heated swimming pool. 3 charming outdoor seating areas. Easy access to Bath and Bristol 'Park and Rides'. TVs in bedrooms, 65" lounge smart TV. WIFI, Bluetooth Boom Box. dishwasher, washing machine, and microwave. Not suitable for children under 18 or pets. Car essential. The base price is for 2 people. Extra guests 3 and 4 pay £65 per night per person.

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 (3 days notice required/small extra charge). In close proximity to La Villa Olli: Swimming pool with waterfall, pool table & ping pong table (Small extra charge). Located near M4/M5, making travel to/from easy. Perfect for a couple getaway or a business trip in a tranquil environment within 5 minutes access to country pubs.

Birch Cottage with woodland sauna
Birch Cottage is a charming 3-bedroom stone cottage with a secluded woodland sauna cabin and views across the Wye Valley countryside. It is located on Offas Dyke footpath on a very quiet road, so is great for anyone looking to explore the network of Wye Valley footpaths. Monmouth, Forest of Dean, Bristol, Bath and Cardiff are close enough for day visits. Whatever season you prefer, it's a wonderful place to recharge your batteries and connect with nature.
Popular amenities for cottage rentals in Chepstow
Cottage rentals with a hot tub

Stream Cottage in glorious Somerset countryside.

Cottage near Bath- private hot tub, pets welcome

The Old Dairy- Boutique Cottage at Harrys Cottages

Beautiful barn conversion/hot tub views

Coastal cottage with hot tub and sea views

Romantic cosy cottage & hottub in Forest of Dean

Romantic Idyllic Nuthatch Cottage with Hot Tub

Idyllic Waterside Cottage - Private Hot Tub
Pet-friendly cottage rentals

Traditional Country Cottage

The Old Cider Mill

PRETTY GEORGIAN COTTAGE IN A VILLAGE NEAR BATH

Idyllic Forest Retreat - Abergavenny 12 miles

Coach House Annex - Annedd Bach - Wye Valley

Mid-Century Modern Chapel Conversion

Grade II Listed Underdean Lodge

Ash Holiday Let at Pathwell Farm
Private cottage rentals

Old Barn, Dyrham, Nr Bath

Countryside Cidermaker's Cottage

A beautiful cottage set in spectacular grounds

Chew Valley Cottage (West End Cottage)

Wye View Cottage

Beautiful cottage near Bath

Minnow Cottage

Lovely Courtyard Cottage near Abergavenny
Quick stats about cottage rentals in Chepstow

Nightly prices starting at
Chepstow holiday rentals start at $115 SGD per night before taxes and fees

Verified guest reviews
Over 1,230 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chepstow rentals

4.9 Average rating
Chepstow stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Cotswolds AONB
- Principality Stadium
- Cardiff Castle
- Bannau Brycheiniog National Park
- Stonehenge
- Cheltenham Racecourse
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- Lower Mill Estate
- Bike Park Wales
- Roath Park
- Cardiff Bay
- Bath Abbey
- Zip World Tower
- Sudeley Castle
- Bute Park
- No. 1 Royal Crescent
- Puzzlewood
- Newton Beach - Porthcawl
- Dunster Castle
- Eastnor Castle
- Caerphilly Castle
- Longleat Safari Park
- Dyrham Park
- Hereford Cathedral




