Photo by Miguel Vasquez

Search Cottages in Chepstow

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Find holiday rentals that suit your style

Apartment image
Apartments
Apartments
apart-hotel image
Aparthotels
Aparthotels

Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Chepstow cottages

A single-story house with a tiled roof, a wooden fence, and a grassy yard.

1. The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is €535
includes taxes & fees
13 Nov - 14 Nov
The Honey Pot
A rustic building with a stone exterior and a metal roof, a gravel driveway, and a fenced area with a small red-roofed structure.

2. The Snug

The Snug
3.0 star property
Caerwent
The price is €348
includes taxes & fees
5 Dec - 6 Dec
The Snug
A small, single-story building with a red-tiled roof, a fenced outdoor area, and a view of surrounding greenery.

3. Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
The price is €485
includes taxes & fees
8 Nov - 9 Nov
Bottom Lodge
A hot tub with a wooden deck, outdoor seating, and a view of the countryside.

4. Top Lodge

Top Lodge
3.0 star property
Caerwent
The price is €485
includes taxes & fees
16 Nov - 17 Nov
Top Lodge
A stone building with a sign reading "Lion Inn" and outdoor seating.

5. Beautiful 1-bed Cottage in Trellech

Beautiful 1-bed Cottage in Trellech
3.0 star property
Trellech United
9.2 out of 10, Wonderful, (25 reviews)
"Lovely staff and great space to relax."
United Kingdom
Eva
The price is €108
includes taxes & fees
22 Nov - 23 Nov
Beautiful 1-bed Cottage in Trellech
A hot tub under a wooden pergola with a view of a green lawn and a distant building.

6. Bilsham Meadows

Bilsham Meadows
3.0 star property
Bristol
The price is €1,720
includes taxes & fees
8 Nov - 9 Nov
Bilsham Meadows
An open wooden door leading to a stone courtyard with a stone building in the background.

7. 2 bedroom accommodation in Lydney

2 bedroom accommodation in Lydney
Lydney
9.8 out of 10, Exceptional, (30 reviews)
"If you're looking for a comfortable cozy relaxed break, this is where to come.Absolutely perfect!"
United States
Lorraine Galea
The price is €236
includes taxes & fees
26 Nov - 27 Nov
2 bedroom accommodation in Lydney
A stone building with a tiled roof, a wooden door, and large windows.

8. Cider Press Barn - UK12379

Cider Press Barn - UK12379
Lydney
10.0 out of 10, Exceptional, (8 reviews)
"Ideally situated for trips into the Forest.Wonderful accommodation, well equipped and excellent hosts on hand."
United States
John Littlewood
The price is €267
includes taxes & fees
22 Nov - 23 Nov
Cider Press Barn - UK12379
A stone house with a sloped roof, multiple windows, and a small porch area.

9. 2 bedroom accommodation in Penallt, Monmouthshire

2 bedroom accommodation in Penallt, Monmouthshire
Trellech United
9.6 out of 10, Exceptional, (12 reviews)
"Lovely comfortable cottage. Very clean and well equipped. Such a lovely location, right by the river and a fabulous pub. Can't wait to return!"
United Kingdom
Kevan B.
The price is €368
includes taxes & fees
9 Nov - 10 Nov
2 bedroom accommodation in Penallt, Monmouthshire
A small, rustic building with a green door and windows, surrounded by lush greenery and a gravel path.

10. Individual Self-Contained Private cottage with garden at Dyrham Park, near Bath

Individual Self-Contained Private cottage with garden at Dyrham Park, near Bath
Dyrham
9.8 out of 10, Exceptional, (19 reviews)
"Lovely little cottage, very small but very comfortable"
United States
Bernadette W.
The price is €202
includes taxes & fees
8 Nov - 9 Nov
Individual Self-Contained Private cottage with garden at Dyrham Park, near Bath
A two-story building with a tiled roof, a gravel driveway, and a fenced yard.

11. 2 bedroom accommodation in Falfield, near Wotton-under-edge

2 bedroom accommodation in Falfield, near Wotton-under-edge
Falfield, near Wotton-under-edge
10.0 out of 10, Exceptional, (1 review)
"Quiet, rural location, handy for North of Bristol. Comfortable cottage."
United States
Carron Thorley
The price is €613
includes taxes & fees
6 Nov - 7 Nov
2 bedroom accommodation in Falfield, near Wotton-under-edge
An outdoor patio with a view of a lake, a barbecue grill, and a large bathtub.

12. Enjoy a romantic retreat at this luxurious shepherd’s hut.

Enjoy a romantic retreat at this luxurious shepherd’s hut.
Usk
9.8 out of 10, Exceptional, (10 reviews)
"A comfortable and relaxing stay. Very clean and well appointed shepherds hut with a great welcome pack. amazing views from the hut. Recommended to friends and family.We hope to get back again soon!!!"
United States
Gary Allworthy
The price is €320
includes taxes & fees
5 Nov - 6 Nov
Enjoy a romantic retreat at this luxurious shepherd’s hut.
A neatly made bed with white linens and a fluffy white towel, two bottles of ELSYL, a black lamp, and a patterned wallpaper.

13. The Old Dairy at Combe Lodge - Hopewell

The Old Dairy at Combe Lodge - Hopewell
North Somerset
8.4 out of 10, Very good, (11 reviews)
"Great place, Lots of kitchen equipment. Comfy and warm on a cold wintry stay."
United Kingdom
Barbara B.
The price is €137
includes taxes & fees
5 Nov - 6 Nov
The Old Dairy at Combe Lodge - Hopewell
A pathway leading to a house with a well-maintained lawn and a wooden fence on one side.

14. Tysylfaen Brecon Beacons

Tysylfaen Brecon Beacons
3.0 star property
Crickhowell
The price is €222
includes taxes & fees
16 Nov - 17 Nov
Tysylfaen Brecon Beacons
A stone house with a tiled roof, white-framed windows, and a front door.

15. Traditional Country Cottage

Traditional Country Cottage
Stanton Drew
8.8 out of 10, Excellent, (3 reviews)
"Highly recommend.We will definitely be back. The cottage and the scenery surrounding it was wonderful. Clean, comfortable ,lots of personal touches and peaceful.Was lovely to spend a few days with my teenage son just doing nothing "
United States
Rachel C.
The price is €207
includes taxes & fees
5 Nov - 6 Nov
Traditional Country Cottage
A hot tub with a view of a grassy area and wooden fences.

16. Hidden Well

Hidden Well
2.0 star property
Bristol
The price is €1,566
includes taxes & fees
16 Nov - 17 Nov
Hidden Well
A wooden front door with a small porch and steps leading up to it.

17. 3 bedroom accommodation in Abergavenny

3 bedroom accommodation in Abergavenny
Abergavenny
10.0 out of 10, Exceptional, (7 reviews)
"Great place and really enjoyed our stay. Thank you!"
United States
Nicholas Smith
The price is €339
includes taxes & fees
23 Nov - 24 Nov
3 bedroom accommodation in Abergavenny
A two-story brick house with a large glass door entrance, a chimney, and a garden with a patio area.

18. 2 bedroom accommodation in Blaenavon

2 bedroom accommodation in Blaenavon
Blaenavon
9.4 out of 10, Exceptional, (3 reviews)
"Lovely place to stay and explore the area, including the fascinating World Heritage sites and beautiful local countryside."
United Kingdom
Dean
The price is €176
includes taxes & fees
11 Nov - 12 Nov
2 bedroom accommodation in Blaenavon
A modern house with a stone facade, large glass windows, and a view of the surrounding landscape.

19. A large group retreat that sleeps 16 guests in 4 bedrooms

A large group retreat that sleeps 16 guests in 4 bedrooms
Chew Stoke
9.8 out of 10, Exceptional, (21 reviews)
"Stunning views in an excellent location, spacious accommodation with a huge garden, we absolutely loved it"
United States
sam h.
The price is €1,645
includes taxes & fees
5 Nov - 6 Nov
A large group retreat that sleeps 16 guests in 4 bedrooms
A two-story brick house with a blue front extension, a balcony, and a small garden area.

20. 4 bedroom accommodation in Newent

4 bedroom accommodation in Newent
Newent
8.8 out of 10, Excellent, (15 reviews)
"Lovely spot to base our holiday. Quiet & clean! Traveled around to Stepstow Castle, Westbury Court Gardens, Croft and Berrington Hall. Owner was very thorough with great instructions !"
United States
Douglas Jackson
The price is €387
includes taxes & fees
16 Nov - 17 Nov
4 bedroom accommodation in Newent
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Learn more about Chepstow

Towering over the River Wye, Chepstow Castle's ancient stone walls tell stories of medieval battles and royal intrigue. Hike the nearby Wye Valley Walk for spectacular views, or time your visit for the Chepstow Festival's lively music performances.

See all hotels in Chepstow
A historic stone building on a cliff overlooking a beach.
Photo by Miguel Vasquez
Open Photo by Miguel Vasquez

Explore a world of travel with Expedia