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.

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.

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.

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 or 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; 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

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

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!

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.

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.

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.