
Cottage holiday rentals in Chepstow
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Top-rated cottage rentals in Chepstow
Guests agree: these cottages are highly rated for location, cleanliness and more.

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.

Romantic Idyllic Nuthatch Cottage with Hot Tub
A stunning panoramic view awaits you at Nuthatch Cottage. This gorgeous, unspoilt haven is located in Mitcheldean, the enclave of the Forest of Dean and a locals-only spot in Gloucestershire. This 2 bedrooms house was built with natural Cotswolds stone. The entire house is secluded with a hot tub and has a luxuriously charming feel. It is perfectly situated to enjoy what the picturesque local area has to offer. The local shops, restaurants, and attractions are only a five-minute drive away.

Rose Cottage, dog friendly, countryside location
Rose Cottage forms part of the old stable block of the Clanna Country Estate dating back to the 1850's and as such, they combine rustic character with modern comfort. The cottage is both family and doggy friendly. The cottage provides an ideal base for exploring the natural beauty and history of the area while offering a warm and welcoming place to return to after a day of adventure. Guests have shared access to our onsite games room, which includes Pool, darts, ping pong and so much more.

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.

Tranquil cottage Forest of Dean
Wake up to the sound of bird song and enjoy the serenity of this charming dog friendly cottage nestled in Alvington. Explore The Forest of Dean with its countless walking and cycling trails, where there is the opportunity to see wild boar, pine martens and deer. Perfectly positioned to discover Tintern Abbey, FOD Steam Railway, Symonds Yat and the stunning Wye valley. Great pubs and eateries. This is a retreat for nature lovers and adventurers rather than shoppers. Come and enjoy.

Set in 40 Acres of Private Countryside in AONB
Nestled in rolling hills with 40 acres of private tracks, fields, streams, woodland and ancient lime kilns to explore, this rural hideaway is popular with walkers, cyclists and those just wishing to escape the mass media or hustle and bustle of everyday life. Recharge your batteries and enjoy the great outdoors as you toast some marshmallows over the fire pit, say hello to the pet sheep and soak up the sights and sounds of birds, wildlife and sunsets in this peaceful relaxing retreat.

Luxurious spacious cottage with awesome views !
With commanding views over Monmouth, the Wye Valley and beyond, Wern Farm Cottage is a cosy but spacious recluse ideally situated for all that Monmouthshire has to offer. Light, airy and welcoming with zip and link beds. We can accommodate 2-4 flexible to your needs. We are in a great spot for the Forest of Dean, the Brecon Beacons, Bike Park Wales, Cannop Cycle Centre and the Offa’s Dyke Path. There are lovely walks right from the door and so much to do nearby!

Cosy Cottage | Dog Friendly | Wye Valley
Mill Cottage is a delightful stone cottage situated on a private lane in the heart of a pretty village located on the River Wye. The original cottage is over 150 years old and was the home of the sawmill manager, who ran the nearby sawmill, which has long since disappeared. It is now a lovely holiday cottage, that sleeps two couples and one well-behaved dog. It overlooks a pretty church and is very conveniently located for the village pub.

Carpenters Cottage - Central Chepstow with parking
Carpenters Cottage is a quaint cosy one bedroom cottage at the bottom of Chepstow Town. It’s 2 minutes walk to the castle, town centre or the pubs on the river wye. The cottage is fully equipped with all your necessities for a wonderful home from home stay. Recently completely refurbished to a high standard it offers comfort, style and privacy with a 4* luxury finish. We hope you enjoy your stay and want to come again.
Popular amenities for cottage rentals in Chepstow
Cottage rentals with a hot tub

The Old Dairy- Boutique Cottage at Harrys Cottages

Coastal cottage with hot tub and sea views

Romantic cosy cottage & hottub in Forest of Dean

Beautiful cottage with magnificent views

The Stables: Cozy cottage with views and a hot tub

Olli's Cottage-Terrace & Jacuzzi

Idyllic Waterside Cottage - Private Hot Tub

Home Cottage - @ House of Bread holiday cottages
Pet-friendly cottage rentals

Country cottage with private woodland and orchard.

Idyllic Forest Retreat - Abergavenny 12 miles

Coach House Annex - Annedd Bach - Wye Valley

Cotswold stay - private sunny garden & pretty view

The Covey, a Tudor cottage for two.

Grade II Listed Underdean Lodge

Stunning Barn Conversion on Cotswold Way

Perfect for couples; friendly pub; great walks
Private cottage rentals

Pet-Friendly Cottage: Private Garden, Walk to Town

Cosy and quiet coachhouse. Orchard. Private patio.

Beautiful new studio cottage with off-road parking

Unique luxury retreat with glorious views & piano

Restful rural views, alpacas, wildlife- Perry Pear

Lovely Courtyard Cottage near Abergavenny

Cosy and quiet cottage nestled in the Cotswolds

Elegant Cotswolds Retreat, Bath
Quick stats about cottage rentals in Chepstow

Nightly prices starting at
Chepstow holiday rentals start at $114 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!
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- Cotswolds AONB
- Principality Stadium
- Cardiff Castle
- Bannau Brycheiniog National Park
- Stonehenge
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- Cheltenham Racecourse
- Lower Mill Estate
- Bike Park Wales
- Roath Park
- Cardiff Bay
- Sudeley Castle
- Zip World Tower
- Bath Abbey
- Bute Park
- Newton Beach - Porthcawl
- No. 1 Royal Crescent
- Royal Porthcawl Golf Club
- Dunster Castle
- Puzzlewood
- Caerphilly Castle
- Hereford Cathedral
- Bowood House and Gardens
- National Showcaves Centre for Wales




