Cottage vacation rentals 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.

Traditional Country Cottage

1 Gloucester Cottages is nestled in the quaint mining village of Stanton Drew in the Chew Valley, Somerset, The village is home of the prehistoric Stanton Drew stone circles, the second largest stone circle in Britain after Avebury. The cottage is great for families and couples, it has a fully equipped kitchen and is furnished through out, a king sized bed and double with all linen included. We have fast wifi, parking and an open working fireplace for those cosy nights in with a bottle of red.

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.

Spacious 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.

Mini MackHouse: magical escape to Gloucestershire

Welcome to our slice of magic, the CoachHouse on our family home just outside Stroud in Gloucestershire. Whether it’s the award winning market that you’ve come to experience, the culture or events of Cheltenham, Bath, Gloucester or Bristol, or the beautiful countryside, Stroud (recently voted best place to live in the UK by The Times) has something for everyone. Set in a south facing bowl, surrounded by a magical garden, Mini MackHouse is incredibly well equipped and beautifully appointed.

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.

Fuesli Lodge - Boutique Cottage at Harrys Cottages

{Hot tub is available at extra cost. Please message to check availability.} Exclusive rural retreat. Open plan living area, woodburner, underfloor heating, oak beams, quality furnishings, fully equipped country kitchen, bifold doors onto patio/private garden. Superfast Fibre Wifi. Nestled on the edge of the AONB in tranquil, private location. Countryside views. Perfect base for outdoor enthusiasts. If your desired date is not available, check out the Old Dairy and the Bentra Annex.

The Annex Cottage - A country hideaway

Beautiful , private accommodation in part of our home with stunning views. The main bedroom has a king-size bed and a queen sized bed in the second . The bathroom has both a bath & a shower. The cosy sitting room has a log burning stove and a door to the shared garden. We provide a loaf of home made bread and marmalade plus butter, home made marmalade & jam, milk, tea and coffee. The Hall Inn pub is just 200 yards away and a short drive to Usk and Raglan and the Brecon Beacons

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.

Stone Cottage with a splendid Wye Valley View

This 200 year old stone cottage tucked into the hillside yet set perfectly overlooking the beautiful Wye,has a wealth of period features,original stone fireplace and beamed ceiling and has been lovingly updated and furnished with mainly vintage finds. The cottage is ideally situated for walking and exploring Tintern the Wye Valley and Offas Dyke paths. the views and the balcony to enjoy them makes this cottage very special.