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Vacation rentals in Chepstow

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Top-rated vacation rentals in Chepstow

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Barn in Powys

4.98 out of 5 average rating, 441 reviews

Romantic waterfall Cabin,Tranquil Brecon Beacons

💕Romantic Waterfall Cabin 💕 idyllic serene location,wrapped in nature. sweet sounds of birdsong & lulling sound s of waterfall. Enjoy wildlife & flowers from the bedroom / balcony , otters , Herons, leaping Salmon /trout in rock pools below, colourful dragon flies and wagtails .. ultimate relaxation of nature Harmonious cosy decor encapsulating a romantic hideaway for two :-) cotton linens, arty decor, a comfy king size bed , atmospheric log burner& breakfast ! ,Arrive Relax Enjoy

Home in Holt

4.99 out of 5 average rating, 147 reviews

Artist's Retreat - Style, tennis and hot-tub for 4

Stylish modern country retreat with private hot tub and tennis court in two acres of countryside. Detached single story home with own parking. Beautiful kitchen diner with views over the terrace and green fields. Airy living room with wood burner. Bedroom 1 has kingsize bed and ensuite bathroom with luxury bath. Bedroom 2 can be arranged as 2 single beds or a kingsize, with ensuite bathroom. Luxury 5* linens. Located on historic farm, close to Bath and Bradford-on-Avon. Easy walk to pubs/cafe

Cottage in Stanton Drew

4.9 out of 5 average rating, 103 reviews

Somerset cottage - great rural location

It is the perfect cottage for family breaks or groups of friends looking for something special, in the old part of Stanton Drew in the stunning Chew Valley. A beautifully created, artistic and characterful large grade II listed cottage. It’s cozy in the winter, with wood burner stove. The cottage's gardens have a lovely aspect to the front with plenty of space to the rear for alfresco dining and places to relax and slow down. Perfect position to access the airport, Bristol, Bath and Wells.

Barn in Penarth

4.87 out of 5 average rating, 426 reviews

The Beach Barn

A unique 350 year old Beachfront Barn overlooking Sully Island and a few minutes walk from three seafront bars and restaurants. A tranquil escape from it all, with just the sound of the waves to send you to sleep. Originally a Threshing Barn, the accommodation has been lovingly restored, offering high, beamed ceilings, south facing full length glass doors and windows to large sunbathing decked area and gardens, Hot Tub, Cinema, Pool Table, King size bedroom, shower, Fridge Freezer , Microwave

Cottage in Painswick

5 out of 5 average rating, 152 reviews

Quiet grade 1 listed entire cottage in Cotswolds

A bright and recently modernised grade 1 listed Cotswold stone cottage, 100 yards from the Cotswold Way with breathtaking views down the Stroud Valley, its own parking and secluded outdoor eating. Filled with natural light, it is very peaceful and extremely comfortable with luxury bedding (super king or twin bed) and kitchen. An idyllic spot for walking, cycling, exploring the local scenery or simply escaping the city Painswick is 10 minutes from Stroud ( 87 mins hourly train to London).

Cottage in Powys

4.9 out of 5 average rating, 196 reviews

Mill Cottage, Llangynidr Perfect getaway location.

Our cosy but contemporary 4 * graded Mill Cottage is over 180 yrs old. Located in the heart of the Brecon Beacons. You will love it in this quiet, friendly village. Easy access to everything. Surrounded by Mountains, Canals, Lakes, Market Towns and Activity Centres. Two local pubs and a shop in walking distance. Great place for couples or a small family having a King Size bedroom and a Day bed on bedroom/landing. Just be aware you have to walk through this bedroom to access the main bedroom.

Cottage in Brain's Green

4.98 out of 5 average rating, 111 reviews

Countryside cottage,1 bedroom in Forest of Dean.

Take it easy at this unique and tranquil getaway with wood fired hot tub in the Forest of Dean. Enjoy nature in a peaceful location, with a direct access to the Forest. A short drive from the historic market town of Ross-on-Wye, Wye Valley and Welsh Borders. Wildlife are most likely to be seen earlier in the morning or towards the end of the day. Take advantage of the Forest activities, from miles of cycling trails to suit all abilities and the River Wye for canoeing and kayaking.

Home in Herefordshire

4.99 out of 5 average rating, 129 reviews

Old Forge Cottage, town house with character

Beautifully renovated period , grade II listed property in the charming market town of Ross on Wye, A comfortable town house with good sized bedrooms, kitchen diner, lounge with fireplace and a cosy snug. The courtyard garden is a real sun trap. Short stroll to the riverside, restaurants and shops. Ideally situated for exploring the Wye Valley, an area of outstanding natural beauty, The Forest of Dean and Symonds Yat, walking the Malvern hills and canoeing the river Wye.

Home in Cardiff

4.87 out of 5 average rating, 125 reviews

Detached Coach House near Principality Stadium

A beautiful converted detached Coach House in the heart of Cardiff City Centre being very close to the Principality Stadium, the Tramshed, BBC Studios, shopping, restaurants, bars, cinemas, Bute Park, Cardiff Castle, Cardiff Central Train Station and more. The Coach House comes with complimentary WIFI, tea, coffee, toiletries, towels, bed linen and NETFLIX. Parking is off-street for one small to medium car on the court yard.

Cabin in Monmouthshire

4.88 out of 5 average rating, 25 reviews

Unique 5 star rated lake side cabin.

Situated in the stunning Wye Valley, in Monmouthshire, The Lake House is a private holiday home where you will find everything you expect from a modern house. This wonderful property is nestled in a private corner of the valley, with a stunning lakeside view which makes for the perfect place for a getaway. The stunning natural surroundings allow you to slow down, relax and appreciate the simple things in life.

Guesthouse in Cardiff

4.87 out of 5 average rating, 356 reviews

The Lakeside Lodge

Our outhouse at the back of our garden has been lovingly transformed into a cosy, modern studio apartment. With underfloor heating, large sofa's & kitchen /breakfast area it has everything you want for a short or long stay! Separate entrance also makes it private so you can come and go as you wish. If you do want to go ahead and book, please check out our house rules first.

Rental unit in Gloucester

4.89 out of 5 average rating, 222 reviews

Unique styling with balcony views and parking

This south facing with balcony access this lovely regency period property in one of the best locations in Gloucester. Lovely high ceilings and floor to ceiling windows in the living room. This apartment is a real treat to stay in. Once home to circuit court Judges more than a century ago. Fitted kitchen with all facilities and two bathrooms.

Vacation rentals for every style

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Cottages

Quaint homes, peaceful surroundings

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Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Chepstow vacation rentals

Free parking on premises

Air conditioning

Stay near Chepstow's top sights

Chepstow Castle112 locals recommend

Chepstow Racecourse37 locals recommend

Panevino Italian Restaurant18 locals recommend

Stone Rock Pizza15 locals recommend

Chepstow Museum15 locals recommend

The Riverside Wine Bar13 locals recommend

Other great vacation rentals in Chepstow

Cottage in Monmouthshire

5 out of 5 average rating, 4 reviews

Delightful 3 bedroom cottage on the edge of a farm

Guesthouse in Ross-on-Wye

4.93 out of 5 average rating, 44 reviews

"The Jam Pot", Gorsley, Ross-on-Wye. Entire home

Home in Bristol City

4.83 out of 5 average rating, 6 reviews

Eco Home for Large Groups w/ FREE Parking & Wi-Fi

Cottage in Bristol

4.85 out of 5 average rating, 26 reviews

Hideaway Cottage - clean and cosy 2 bedroom home.

Cottage in Monmouthshire

4.87 out of 5 average rating, 95 reviews

Sugarloaf cottage - stylish elegant with hot tub

Home in Gilwern

4.97 out of 5 average rating, 60 reviews

The Cwtch

Cabin in Henllys

4.93 out of 5 average rating, 120 reviews

Rustic cabin

Condo in Kingsdown

4.85 out of 5 average rating, 75 reviews

Garden Flat with Garage for one car

Quick stats about vacation rentals in Chepstow

Total rentals
30 properties
Nightly prices starting at
R362 ZAR before taxes and fees
Total number of reviews
2.1K reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

Frequently Asked Questions

Where should I stay in Chepstow?
Make yourself at home in Chepstow by choosing from our most frequently booked neighborhoods. We have over 60 vacation rentals in Pwllmeyric, and over 60 vacation rentals in Chepstow.
Are there family-friendly vacation rentals in Chepstow?
Chepstow has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Chepstow have wifi?
Absolutely! We offer over 10 house rentals with wifi in Chepstow. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Chepstow?
Experience the best of Chepstow with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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