Chepstow Vacation Rentals from CA $111: Short-Term Rentals for 2026

Q: What are some of the best vacation home rentals in Chepstow?

6 Bed House Sleeps 13 - Private Garden : This vacation home rental near Chepstow is equipped with a garden, laundry facilities, and free WiFi to help you feel comfortable during your stay. It has 6 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

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In two weeks

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Our top choices for Chepstow vacation rentals

A hot tub in an outdoor wooden enclosure with a tiled floor and a wicker chair nearby.

1. The Honey Pot

Chepstow

CA $885 total

includes taxes & fees

Sep 17 - Sep 18

A living room with two green sofas, a wooden coffee table, and a TV on a stand.

2. The Elements Residence

Chepstow

CA $1,674 total

includes taxes & fees

Sep 8 - Sep 9

A stone wall, a patterned metal fence, and a building with a tiled roof.

3. Ferryman's Lodge

Chepstow

CA $640 total

includes taxes & fees

Sep 24 - Sep 25

A modern kitchen with white cabinets, a stainless steel oven, a sink, and a yellow toaster.

4. The Snug

Caerwent

CA $550 total

includes taxes & fees

Sep 11 - Sep 12

A modern living room with a sofa, armchair, coffee table, and a painting of red buses.

5. Bottom Lodge

Caerwent

CA $767 total

includes taxes & fees

Sep 10 - Sep 11

A hot tub with a wooden deck, outdoor seating, and a view of the countryside.

6. Top Lodge

Caerwent

CA $767 total

includes taxes & fees

Sep 14 - Sep 15

A stone wall entrance to a building with a black door and a small trash bin.

7. Beautiful 1-bed Cottage in Trellech

Trellech United

Eva

CA $169 total

includes taxes & fees

Oct 5 - Oct 6

8. A rural house on the edge of the Forest of Dean with 3 pubs within a short walk.

Alvington

Philip R.

CA $262 total

includes taxes & fees

Sep 9 - Sep 10

A narrow stone corridor with a small table and chairs, a door, and a window with a view into a room.

9. The Priory Cellars Abbots Leigh

Bristol

Le-Anne

CA $140 total

includes taxes & fees

Sep 20 - Sep 21

A wooden, arched, single-room cabin with two beds and two chairs, surrounded by grass and trees.

10. Broadstone Park Camping & Fishery

Coleford

Tina

CA $111 total

includes taxes & fees

Sep 17 - Sep 18

A spacious loft-style living area with a large wooden dining table, multiple seating options, and a large sliding glass door leading to a balcony.

11. Bilsham Meadows

Bristol

CA $2,715 total

includes taxes & fees

Sep 14 - Sep 15

A conservatory with stone arches, potted plants, and a bench.

12. The Orangery Apartment

Bristol

Patricia

CA $148 total

includes taxes & fees

Sep 20 - Sep 21

A bedroom with a brick wall, a bed with white bedding, a wooden bench, a window with curtains, and a wardrobe.

13. One Bedroom Apartment Close to MOD

Bristol

Chijioke I.

CA $219 total

includes taxes & fees

Sep 10 - Sep 11

A modern kitchen with a stainless steel sink, a round mirror, and a potted plant.

14. 526 Gloucester Flat 1 - Hopewell

Horfield

Vanessa

CA $208 total

includes taxes & fees

Sep 20 - Sep 21

A hallway with a wooden staircase, a chandelier, and a radiator.

15. The Cranbrook - Stylish Bristol Stay - 8 Guests

Bishopston

CA $309 total

includes taxes & fees

Sep 13 - Sep 14

A gravel driveway leading to a stone wall and a building with ivy-covered walls.

16. HartHill Grange Bunkhouse - Unique 1850's Rural Country Accommodation

Lydney

Samuel P.

CA $1,603 total

includes taxes & fees

Sep 9 - Sep 10

A traditional building with a sign reading "Welcome to The Olde Bull Inn" at night.

17. Lovely 1-bed Loft in Newport

Caerleon

JAYNE

CA $156 total

includes taxes & fees

Sep 17 - Sep 18

A living room with a black sofa, a glass coffee table, and a fireplace.

18. Your Stay Bristol Orchard Gate

Bristol

claire

CA $328 total

includes taxes & fees

Sep 13 - Sep 14

A modern kitchen with a built-in oven, a dining area with a round table and chairs, and large windows with a view of a bridge.

19. Quay Apartments Clarence House

St Julians

Andrew

CA $125 total

includes taxes & fees

Sep 10 - Sep 11

A bedroom with a wooden headboard, a bed with a gray blanket, a pillow with a floral design, and a cat on the bed.

20. Higgihaus 26 Clare Street Aparthotel

Bristol City Centre

Tracey

CA $287 total

includes taxes & fees

Sep 27 - Sep 28

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Top Chepstow Hotel Reviews

The Coach & Horses Hotel

10/10 Excellent

"Absolutely lovely hotel, possibly 1of the best we’ve ever stayed in, from checking in to checking out, nothing was too much trouble. Emma on reception was so friendly, helpful and chatty, really made us feel welcome. The room was spotless. We had food in the restaurant in the evening, then breakfast the following morning. Food was absolutely delicious and again all the staff were so friendly and helpful. Definitely be back ."

Park Plaza Cardiff

8/10 Good

"I’ve been staying at this hotel since 2010, and it’s always been our go‑to place when visiting Cardiff. We’ve loved it for so long that even our now 11 year old looks forward to staying here. The staff are consistently helpful, the location is ideal, and the facilities have always contributed to a really enjoyable stay. However, this is the first visit where I’ve felt the hotel is overdue for a refurbishment. The rooms and bathrooms are showing their age, and the spa facilities in particular need attention. The changing rooms look very tired, and the rainfall shower experience is barely functioning. One additional point, although not the hotel’s fault, is the walk from the city centre. The area now has a large number of homeless individuals, and while I understand the complexity of the issue, it did make the walk back feel uncomfortable when I was alone with my son in the late evening."

Find out more about Chepstow

Everything you need to know about Chepstow vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chepstow vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chepstow vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chepstow vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chepstow. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chepstow vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chepstow vacation rentals we have selected for you start as low as CA $111 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chepstow rentals

At Expedia, we put the best Chepstow vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chepstow rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chepstow vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chepstow. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Chepstow?

Yes, there are vacation rentals in Chepstow close to Chepstow Leisure Centre, or you can choose a secluded option if you'd like a relaxing place to stay. Visitors like the top-notch restaurants and spas in Chepstow. Allow lots of time to check out the riverfront and bars during your visit.

What are some of the best vacation home rentals in Chepstow?

6 Bed House Sleeps 13 - Private Garden: This vacation home rental near Chepstow is equipped with a garden, laundry facilities, and free WiFi to help you feel comfortable during your stay. It has 6 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Chepstow?

Choose from 13 Expedia vacation rentals in Chepstow for a memorable vacation.

What’s there to see and do in Chepstow?

Wye Valley and River Wye are a couple of scenic spots to enjoy the outdoors, whereas Chepstow Museum is one of the cultural attractions. Chepstow Racecourse and St. Pierre Country Club are other places to visit while you're in town.

What’s a vacation rental in Chepstow like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Chepstow. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for families.

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Check prices for these dates

Our top choices for Chepstow vacation rentals

1. The Honey Pot

2. The Elements Residence

3. Ferryman's Lodge

4. The Snug

5. Bottom Lodge

6. Top Lodge

7. Beautiful 1-bed Cottage in Trellech

8. A rural house on the edge of the Forest of Dean with 3 pubs within a short walk.

9. The Priory Cellars Abbots Leigh

10. Broadstone Park Camping & Fishery

11. Bilsham Meadows

12. The Orangery Apartment

13. One Bedroom Apartment Close to MOD

14. 526 Gloucester Flat 1 - Hopewell

15. The Cranbrook - Stylish Bristol Stay - 8 Guests

16. HartHill Grange Bunkhouse - Unique 1850's Rural Country Accommodation

17. Lovely 1-bed Loft in Newport

18. Your Stay Bristol Orchard Gate

19. Quay Apartments Clarence House

20. Higgihaus 26 Clare Street Aparthotel

Find vacation rentals that suit your style

Top Chepstow Hotel Reviews

The Coach & Horses Hotel

Moxy Bristol

Park Plaza Cardiff

The Manor House At Celtic Manor

The Bristol Hotel

Village Hotel Bristol

Delta Hotels by Marriott Bristol City Centre

Majestic Hotels Bristol

Delta Hotels by Marriott St. Pierre Country Club

Find out more about Chepstow

Frequently asked questions

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