Pet-friendly holiday rentals in Chepstow

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Quick stats about holiday rentals that are pet-friendly in Chepstow

  • Nightly prices starting at

    Chepstow holiday rentals start at $225 NZD per night before taxes and fees

  • Verified guest reviews

    Over 470 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Chepstow rentals

  • 4.9 Average rating

    Chepstow stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated pet-friendly home rentals in Chepstow

Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
The exterior of a Georgian period home showcases a white facade with large windows on both levels. A private entrance is framed by greenery, while potted plants are positioned beside the door. A gravel driveway offers off-street parking, with a staircase leading to the upper level.
Holiday home in Chepstow
4.94 out of 5 average rating, 102 reviews

Spacious Chepstow home with private garden & patio

A spacious one bedroom property conveniently located for the Wye Valley, Forest of Dean and Offa's Dyke, offering magnificent walks, cycling, pubs and restaurants. Tintern Abbey is also a 10 mins drive from the property. Chepstow itself boasts a magnificent castle, charming pubs and riverside dining and drinking options. The property is located a 5 mins walk from the High Street and Bus Station, 10 mins walk from the train station with direct services to Cardiff, Newport, Gloucester and beyond

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Top Guest favourite
The traditional cottage is partially obscured by lush greenery, featuring a white exterior and prominent chimneys. A conservatory is visible, and trees frame the surroundings, creating a tranquil and inviting setting in the heart of nature.
Home in Trellech
5.0 out of 5 average rating, 134 reviews

Cute little Wye Valley cottage

Surrounded by woodland with hilltop views across the Wye Valley to Offa’s dyke, this eco friendly traditional Monmouthshire cottage is the perfect place to unwind and enjoy nature at its very best. Spend time in the garden listening to bird song and the gentle babbling of the stream or step out the gate to explore Cleddon Falls and beautiful view points along the Wye Valley walk. The medieval village of Trellech and Tintern Abbey are also within easy reach off or on road by foot, bike or car.

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Guest favourite
A hot tub is positioned on a wooden deck, surrounded by lush greenery and twinkling string lights overhead. An outdoor seating area with a picnic-style table is visible, inviting relaxation while taking in the peaceful view of the meadow and trees in the background.
Cabin in Gloucestershire
4.93 out of 5 average rating, 125 reviews

Squirrel Lodge - Hot Tub!

Squirrel Lodge is a pine scented slice of heaven in the Forest of Dean. Well equipped and situated overlooking a meadow and has direct walks into the forest and onto the Bream Heritage Walk. Also an absolute haven for fun seekers with one of the UK’s best cycle trails and downhill mountain bike course, along with abseiling, caving and canoeing. For walkers a wealth of forest trails that will guide you through the forest, take in the sculpture trail or simply take a stroll along the river Wye.

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Top Guest favourite
Cottage in Chepstow
4.97 out of 5 average rating, 114 reviews

Character cottage, stroll to town, Wye Valley base

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.

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Top Guest favourite
Cottage in Coleford
4.96 out of 5 average rating, 374 reviews

Country cottage with private woodland and orchard.

Our beautiful beamed attached cottage complete with log burner is set in over 3 acres of private ancient woodland, in the Forest of Dean near the River Wye. The garden path leads down to a secluded orchard which is a haven for birds, deer & wildlife. The cottage is located in a quiet country lane, with walks to our local pub, The Ostrich Inn and the local town. We are close to all amenities, cycle trails, river activities and the best of what the Forest of Dean and Wye Valley has to offer.

Outdoor spacesPetsCheckout

Top Guest favourite
An outdoor area is shown, featuring a patio space with modern seating and a small table. Lush green grass surrounds the stone cottage, complemented by a well-maintained plant in a pot. A gravel pathway leads alongside the property, enhancing the outdoor experience.
Cottage in Alvington
4.94 out of 5 average rating, 134 reviews

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.

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Guest favourite
The historic Welsh Gatehouse features an imposing stone exterior with two prominent towers. Architectural details include ancient windows and a large, arched entrance. Surrounding greenery adds to the charm of this medieval structure, set against a clear blue sky.
Castle in Chepstow
4.93 out of 5 average rating, 202 reviews

Welsh Gatehouse: Historical Castle with EV Charger

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.

WalkabilityOutdoor spacesDecor

Top Guest favourite
Barn in Oldbury-on-Severn
4.99 out of 5 average rating, 108 reviews

Kingfisher Barn

New eco-friendly two bed barn in beautiful Oldbury-on-Severn. 50m to the famous Anchor Inn. Direct access to footpaths with stunning countryside and riverside walks. 32 solar panels and electric car charging. Luxury bedrooms with king-sized doubles and dressing tables. Living space with sofa bed, recliner chairs/footstools and dining table. Kitchen fully equipped with oven, hob, microwave, washing machine. Unique wildlife photography throughout. South facing patio with table and chairs.

WalkabilityOutdoor spacesBarbecue

Guest favourite
The exterior of the barn conversion is showcased, highlighting the blend of natural stone and wood elements. A spacious patio area with large glass windows offers views of the enclosed garden, which is surrounded by lush greenery.
Barn in Leighterton
4.97 out of 5 average rating, 494 reviews

Luxury Barn conversion Cotswold’s with Sauna/Spa

The Barn is a 2 bedroom conversion in the picturesque Cotswold village of Leighterton,Tetbury with a rustic feel and a new spa room. The barn has two large bedrooms both with wet room en-suites, and one with a free standing bath. Each bedroom has a king bed & single love chair sofabed .Fitted with its own smart TV The Living area and bedrooms have WIFI Gigaclear300mbs Underfloor heating Well behaved dogs are welcome Enclosed garden. Strictly no parties /hens allowed

WalkabilityOutdoor spacesHot tub

Guest favourite
A spacious bedroom features a floral-patterned bedspread and two black accent pillows on a comfortable bed. Soft carpet covers the floor, complemented by bedside tables with matching lamps. A decorative mirror and a unique light fixture add contemporary charm to the room.
Home in Tutshill
4.93 out of 5 average rating, 101 reviews

Delightful 3-Bedroom cottage with log burner

1 Park View is a recently renovated 19th century cottage, located in the peaceful Gloucestershire village of Tutshill. The town of Chepstow is only a 10 minute walk away crossing over the Welsh border via the old Wye Bridge (1816). It's a great location if you're looking for a break in the countryside with plenty to explore in the Forest of Dean as well as the beautiful Wye Valley (AONB) and only a 5 minute walk from the Offa's Dyke national trail.

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Top Guest favourite
The exterior of a historic cottage is displayed, featuring a whitewashed facade with black window frames and a central door. Flower boxes are visible under the windows, while ivy is seen climbing the adjacent building, adding charm to the scene. A lamppost stands nearby.
Cottage in Chepstow
4.93 out of 5 average rating, 144 reviews

Historic cottage opposite Chepstow Castle

Directly opposite the castle, this cottage is in the perfect location for exploring Chepstow and its surrounding areas. The cottage dates back to the 17th century, but has been freshly modernised. Expect a homely yet luxurious stay. Chepstow itself is a historic town, packed with lovely restaurants, pubs, cafés and shops. Our house guide will give you plenty of recommendations to make the most of the area.

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Top Guest favourite
The exterior of the cottage is shown, featuring a two-story structure with a white facade and a pitched roof. A welcoming entrance is visible, framed by several windows. A paved driveway leads up to the entrance, along with flower pots enhancing the outdoor space.
Cottage in Saint Arvans
4.97 out of 5 average rating, 178 reviews

Cheerful 3 bedroom cottage a walkers Parìdice!

Gaer Hill cottage is situated just ten minutes from Chepstow race course and 30 minutes walk from the start of wye valley with Tintern abbey 15 mins drive. This 3 bed cottage is the perfect place to explore from or just kick back and relax. If you enjoy farm life this could be the place as you can watch cows graze from the bedroom window or even have sheep pass your front door or maybe a horse wonder by!

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Popular amenities for Chepstow pet-friendly home rentals