Find short term rentals in Chepstow at the best prices

50 available short term rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Chepstow short term rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Short term and Weekly rentals in Chepstow

Best family friendly Chepstow Short term rentals

Among the 50 accommodations in Chepstow, here are the 4 best family friendly rentals

Exceptional Luxury At Laurel House By Stae-homes - Chepstow
No reviews

Exceptional Luxury At Laurel House By Stae-homes

apartment, Magor
This spacious rural property, a five-bedroom detached house, is located in Redwick, near Magor and Caldicot in South East Wales, offering easy access to Caldicot Castle and Country Park, approximately 4 kilometers away, and the Gwent Levels for scenic walks.
This family-friendly accommodation, suitable for up to 12 guests, features 476 square meters of floor area, a kitchen with an AGA cooker, a heated swimming pool and sauna for summer use, a games room with a snooker table, and extensive private grounds with gardens and parking.
Cottage ∙ 1 Bedroom ∙ 2 Guests - Chepstow
No reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

cottage, Brockweir
Ferryman's Lodge, an idyllic wooden lodge, is situated on the outskirts of Brockweir village, offering countryside views and direct access to walks within the Wye Valley National Landscape, with Chepstow a short drive away. This family-friendly cottage for two features an open-plan living space with a woodburning stove, a double bedroom with an en-suite, a kitchen with a fridge and microwave oven, and a garden with a raised veranda, all within easy reach of Brockweir's pubs, convenience store, and riverside.
Cosy Cottage | River Views | Dogs + Ev - Chepstow
9.7 129 reviews

Cosy Cottage | River Views | Dogs + Ev

apartment
This charming cottage is situated in the Wyedean area, just outside the village of Woolaston, with stunning views of the River Severn. It's within easy reach of the Gloucestershire Way, Offas Dyke, and the Forest of Dean, making it perfect for exploring the beautiful countryside. The cottage has consistently received excellent reviews for its location, cleanliness, and overall experience.
The property features two bedrooms and two bathrooms, comfortably accommodating up to four guests. It offers a fully equipped kitchen, a cosy woodburner, a spacious living area, a private garden, and a complimentary basket of eggs from the owner's free-range hens. Guests can also enjoy a personal training studio on-site and an afternoon tea service for special occasions.
Secluded And Self Contained "Room With A View" - Chepstow
9.7 253 reviews

Secluded And Self Contained "Room With A View"

B&B
This self-catering retreat is located just a short walk from Tintern village and the famous Tintern Abbey, set on a 15-acre property in the scenic Wye Valley. It has received excellent ratings for its location, cleanliness, and overall experience.
The accommodation offers a private entrance, a kitchenette with a fridge and microwave, a shower room, and a small patio with stunning views. Guests can enjoy a range of activities, including pizza nights, sauna sessions, woodland yoga, and forest bathing packages, as well as amenities such as a TV, table and chairs, and kitchenware.

Best Chepstow lodging with a kitchen

Peaceful Retreat With Hot Tub - Chepstow
9.2 84 reviews

Peaceful Retreat With Hot Tub

apartment
This Woodcroft holiday home boasts stunning River Severn views and is conveniently located for exploring Bristol, a short drive from the city centre.
The self-catering property offers two bedrooms sleeping four, a well-equipped kitchenette, private hot tub, large garden, pool table, piano, Netflix, NowTV, and an EV charger, perfect for a relaxing break.
Apartment 3 - Uk31658 (Uk31658) - Chepstow
9.9 120 reviews

Apartment 3 - Uk31658 (Uk31658)

apartment
This second-floor apartment in Chepstow is located just a short walk from the town centre and Chepstow Castle, offering a convenient base for exploring the area. The property has received excellent ratings for its location, cleanliness, and overall experience.
The self-catering flat has one bedroom and one bathroom, comfortably accommodating two guests. It features a modern kitchen, a living area with a Smart TV, and a shared garden with a private sitting-out area. Guests can enjoy on-site activities such as guided walks, beekeeping introductions, and a visit to the Wye Valley Meadery.
The Loft - Window On The Severn - Chepstow
9.8 137 reviews

The Loft - Window On The Severn

apartment
The Loft is a self-contained apartment located just three miles from Stroat, offering a tranquil escape in the Forest of Dean with stunning views over the River Severn. The apartment has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for a relaxing getaway.
The apartment is situated above a garage, offering a private entrance and a sense of seclusion. It can accommodate up to three guests and features a fully equipped kitchenette, a Scandinavian wood burner, a garden, and access to the Forest of Dean's trails and attractions.
Sedbury Farm Cottages - Chepstow
8.4 125 reviews

Sedbury Farm Cottages

apartment, Chepstow
Sedbury Farm Cottages offers a self-catering apartment in Chepstow, approximately 24 kilometres from Bristol Parkway Station and 31 kilometres from Cabot Circus in Bristol, close to Chepstow town centre and its historic attractions.
This family-friendly property features a private patio, free Wi-Fi, free parking, a fully equipped kitchen with dishwasher, a comfortable seating area with flat-screen TV, and a private bathroom; a relaxing garden is also available for guest use.

Frequently Asked Questions about short term rentals in Chepstow

Popular destinations

Best Chepstow lodging with laundry available

Sedbury Farm Cottage #5 - Chepstow
9.6 9 reviews

Sedbury Farm Cottage #5

apartment
This Sedbury cottage, situated in a peaceful countryside setting near the River Wye, offers a tranquil escape within easy driving distance of Sedbury's amenities.
The one-bedroom self-catering property sleeps five, boasting a kitchen, bathroom, parking, and internet access; explore the Forest of Dean and Wye Valley from this convenient base.
Sedbury Farm Cottages #1 - Chepstow
9.0 132 reviews

Sedbury Farm Cottages #1

apartment
This two-bedroom apartment in Gloucestershire is ideally situated for exploring the Cotswolds, with easy access to attractions like the picturesque Cotswold Water Park, just 20 kilometers away. The self-catering apartment provides a comfortable and independent stay for up to five guests, with a modern interior and all the amenities you need to feel at home.
Room 1 At The Cwtch - Chepstow
No reviews

Room 1 At The Cwtch

apartment
This modern studio flat is located in Chepstow, Monmouthshire, providing direct access to the Wye Valley.
This apartment offers accommodation for two guests with one bedroom, one bathroom, and a kitchen, ideal for exploring local hiking and cycling routes.
Apartment ∙ 1 Bedroom ∙ 2 Guests - Chepstow
No reviews

Apartment ∙ 1 Bedroom ∙ 2 Guests

apartment
This studio flat is located on Welsh Street in Chepstow, a historic market town offering easy access to Chepstow Castle, just 200 metres away, and the Wye Valley Area of Outstanding Natural Beauty.
This family-friendly accommodation for two provides a cosy and contemporary studio design with an en-suite shower room, a fully equipped shared kitchen, and free Wi-Fi, ideal for exploring South Wales.

Best Chepstow lodging with air conditioning

Two Rivers, Chepstow By Marston’s Inns - Chepstow
No reviews

Two Rivers, Chepstow By Marston’s Inns

B&B, Gwent
The Two Rivers, Chepstow by Marston’s Inns guest house is located in Gwent, 24 km from the city centre, close to landmarks such as Gate House, Chepstow Museum, and Symonds Yat Rock, offering a peaceful and tranquil setting for a relaxing getaway. The guest house provides a comfortable and welcoming stay with discreet service, focusing on a home-like atmosphere.
The property features a bar and restaurant, providing a convenient option for meals and drinks. Guests can enjoy complimentary Wi-Fi access throughout the property, free parking, and a traditional English breakfast for a small fee.
©2026 cozycozy.com