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Vacation rentals in Chepstow

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Top-rated vacation rentals in Chepstow

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Cottage in Chepstow

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.

Townhouse in Chepstow

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.

Chalet in Boughspring

The Studio

A refurbished stone built, 1 bedroom detached chalet in an extremely quiet rural location close to good traffic links, long-distance footpath, Forest of Dean, Wye Valley and the National Dive Centre. Large lounge with log burner, sofa and dining table. Open plan kitchen with electric oven, induction hob, microwave, fridge and toaster. One bedroom with king size bed, ensuite shower and wc. Private patio and access to garden. 5 min drive to shops in Chepstow, 40mins to Bristol / Cardiff.

Castle in Chepstow

Welsh Gatehouse: Luxury 13th Century Medieval Home

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.

Cottage in Saint Briavels

Set in AONB & 40 Acres of Private Countryside

Perfectly situated to explore all the Wye Valley and Forest of Dean has to offer, The Apple Loft is an idyllic getaway popular with honeymooners, walkers, cyclists and those just wishing to escape the hustle and bustle of everyday life. With panoramic views across Mork Valley, guests can walk our grassy tracks, explore the old lime kilns, picnic in our fields, say ‘hello’ to the pet sheep and enjoy the sights and sounds of nature, stars and sunsets in this magical and relaxing retreat.

Bungalow in Caldicot

Yeomans Lodge - Chepstow, Newly renovated.

Located within the grounds of the owners house, Yeomans Lodge is a newly renovated, quirky, self-contained, compact bungalow. It is a perfect location if you’re looking to escape to the countryside. The historic town of Chepstow and magnificent Wye Valley is a short drive away. Please note that the airbnb is in Crick, Chepstow, on some occasions the airbnb g00gle link takes you to Yeomans Acre in Gloucester which is the wrong location. Trying to sort the issue with Airbnb.

Hut in Chepstow

Chestnut Lodges - Luxury Glamping Pod Hazel Lodge

Hazel Lodge, our Luxury Glamping Pod sleeps two (adults only). It has its own mini-kitchen, ensuite shower and toilet, TV/DVD, private seating area and heating for all year round use. All bedding and towels are included together with tea, coffee, sugar and milk. We are an adult only site and with a complimentary bottle of Prosecco, our pods are perfect for a romantic couples getaway. Hazel Lodge also has exclusive use of a Jacuzzi Hot Tub - soak, relax, enjoy!

Condo in Earlswood

Luxurious homely and cosy 1st floor apartment.

The Folly first floor apartment is part of a contemporary country house set in four acres of gardens and paddocks. Whilst being part of the main house it is self-contained, fully furnished to a high standard and private. Open plan with dual aspect, lovely views to front and rear with balcony and seating overlooking the garden. King size and single bedrooms with immaculate shower room. Perfect rural location to escape to the country to re-charge and relax.

Cottage in Chepstow

Chepstow, Forest of Dean | Sleeps 4 | Dog Friendly

This warm and cosy cottage is based on the edge of the quiet village of Tutshill (the childhood home of JK Rowling) on the English side of the Welsh border. It is the perfect location if you are looking to escape to the country and explore the beautiful Forest of Dean but still be close to amenities. Walking distance to Chepstow. *10% discount for +7 night stays* *To book 12 months ahead or more please use the Airbnb website rather than the app*

Rental unit in Gloucestershire

Idyllic Country Retreat in the Forest of Dean

Set in the grounds of a magnificent country home with far reaching stunning views over the River Severn and beyond. This is a perfect place to escape and unwind from the daily hustle and bustle of life. Near to Chepstow and with easy access to the M4 & M5 Motorways and only 2 hours drive from London, 30 minutes from Bristol and 40 minutes from Cheltenham. This cosy studio apartment has only recently been completed to an exceptionally high standard.

Cottage in Llandogo

Gorgeous Stone Cottage in the Lower 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.

Home in Whitebrook

Adjoined Stone Cottage Wye Valley (Five Springs)

Self-catering cottage in a small quiet Wye Valley village in in the hills above Monmouth. Set in 6 acres of woodland and hidden gardens. Large bedroom with comfortable king (60") & single bed, lounge with log burner, TV & WiFi. Stunning large spa room with sauna, shower, jacuzzi & small toilet room. Kitchen with induction hob, grill and fan oven, microwave, washing machine, tumble dryer and fridge freezer, separate bathroom with toilet.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Chepstow vacation rentals

Free parking on premises

Air conditioning

Stay near Chepstow's top sights

Chepstow Racecourse37 locals recommend

Whirlikidz3 locals recommend

Chepstow Museum15 locals recommend

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Quick stats about vacation rentals in Chepstow

Total rentals
20 properties
Local attractions
Panevino Italian Restaurant, Lidl Chepstow, and Coffee#1 Chepstow
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
20 properties include access to wifi
Total number of reviews
1.6K reviews
Nightly prices starting at
$10 before taxes and fees

Destinations to explore