We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Chepstow, Wales

Redo Search in Map
See more hotels in your map view
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    Show Prices
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 10 Rentals in Chepstow
    loading...
    Chepstow is popular with travelers just like you. Don’t let them get your perfect place first—book today!
    Sort by
    From
    $125
    / Night
    Payment Protection
    View Details
    1 / 18
    4.5 of 5 stars (11) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Reviews (11) Make Inquiry
    From
    $81
    / Night
    Payment Protection
    View Details
    1 / 24
    5 of 5 stars (5) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
    Overview Reviews (5) Make Inquiry
    From
    $117
    / Night
    Payment Protection
    View Details
    1 / 4
    5 of 5 stars (22) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
    Overview Reviews (22) Make Inquiry
    From
    $117
    / Night
    Payment Protection
    View Details
    1 / 19
    5 of 5 stars (56) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    traveler have booked this property
    Overview Reviews (56) Make Inquiry
    Amenities & Details
    • Stereo System
    • Washer
    • Internet Access
    • Patio
    • Grill
    • DVD Player
    • Central Heating
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Detached 2 bed-roomed cottage sleeps up to 4 set in its own delightful lovingly tended garden with fabulous views to the surrounding Welsh countryside. Perfectly placed for exploring Wye Valley, Vale of Usk, Royal Forest of Dean and yet only 3 miles from the popular border town of Chepstow which... View all property information
    Make Inquiry
    Location Information
    Chepstow, Monmouthshire NP16 6BX
    5 of 5 stars Reviewed August 8, 2014
    Friendly and warm welcome. Cottage was very clean throughout and very well equipped. The garden was superb, my boys (aged 5 and 2) loved the secure, well kept garden and...
    5 of 5 stars Reviewed July 26, 2014
    had a great time at this cottage has everything you need and more we had a most relaxing stay going out and about to many wonderful places Monmouth and the wye valley meet lots of...
    See all reviews
    From
    $679
    / Week
    View Details
    1 / 12
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Linens Provided
    • Highchair
    • Private Yard
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    STYLISH DETACHED BARN WITH PRIVATE GARDEN AND HOT TUB This newly converted barn is situated in beautiful countryside between the Wye Valley and the Forest of Dean, overlooking the river Severn, and just over 2 miles from Chepstow, adjacent to the A48. Nestling in the southwest corner of... View all property information
    Make Inquiry
    Location Information
    Chepstow, Monmouthshire NP16 7LJ
    From
    $908
    / Week
    View Details
    1 / 16
    4.5 of 5 stars (9) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Reviews (9) Make Inquiry
    Amenities & Details
    • Watersports Nearby
    • Swingset
    • Game Room
    • Hot Tub
    • Wi-Fi
    • Ping Pong Table
    • TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Maes y Felin is a Holiday Cottage with a shared hot tub and is located on a working farm set in 126 acres of beautiful open meadows, woodland and rolling hills. There is a large playground and games room. It is the perfect location to explore the attractions and sights on offer in the area or for... View all property information
    Make Inquiry
    Location Information
    Chepstow, Monmouthshire
    4 of 5 stars Reviewed May 5, 2015
    Kids just loved the animals ! Within minutes of arriving they my 3yr old got to collect eggs! Which we then had for breakfast! Yum. my girls played on the swing/slide set just...
    5 of 5 stars Reviewed September 23, 2014
    We have just had our third stay at the cottage and I'm just as happy with it as we were the first time. Its fast becoming our favourite diver's retreat.
    See all reviews
    From
    $465
    / Week
    View Details
    1 / 7
    4 of 5 stars (1) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Towels Provided
    • TV
    • Linens Provided
    • Dishwasher
    • Refrigerator
    • Washer
    • Highchair
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Sleeping four people in two bedrooms, this quality ground floor apartment is next to the owners country pub/restaurant in the small village of Llanishen, 7 miles from Chepstow. Oak Cottage is a luxurious ground floor apartment in Llanishen village, next to the owners country pub/restaurant, 7... View all property information
    Make Inquiry
    Location Information
    Chepstow, Monmouthshire
    From
    $908
    / Week
    View Details
    1 / 17
    5 of 5 stars (11) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (11) Make Inquiry
    Amenities & Details
    • Ping Pong Table
    • Hot Tub
    • Stereo System
    • Watersports Nearby
    • Wi-Fi
    • Game Room
    • Swingset
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Set in 126 acres of beautiful open meadows, woodland and rolling hills on a working farm, Maes y Gwy Holiday Cottage in Monmouthshire has a hot tub (shared with one other cottage), large play area and games room. It is the perfect location to explore the attractions and sights on offer in the area... View all property information
    Make Inquiry
    Location Information
    Chepstow, Monmouthshire
    5 of 5 stars Reviewed April 8, 2015
    We had a wonderful holiday at the Maes-y-Gwy over Easter. Enjoyed every minute of it. The location is central (20 min from everything), it was peaceful, the kids playground was a...
    5 of 5 stars Reviewed January 6, 2015
    We stayed for a few days just after new year to chill out and that's exactly what we did. The cottage was lovely and the owners were great, they let our kids collect eggs and...
    See all reviews
    From
    $585
    / Week
    View Details
    1 / 11
    3 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Inquiry
    Amenities & Details
    • Stove
    • Central Heating
    • Linens Provided
    • Fireplace
    • Refrigerator
    • Internet Access
    • TV
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Chateau Terrace, a traditional house sleeping up to 5 people, has all you could want from a town centre property. Set over four floors there is a cosy sitting room, a kitchen/diner with decking looking over Chepstow Castle, three bedrooms, a bathroom and a shower room. Characterful with antique... View all property information
    Make Inquiry
    Location Information
    Chepstow, Monmouthshire NP16 5EY
    Inquire for rates
    1 / 14
    5 of 5 stars (1) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
    traveler have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • TV
    • Private Fishing...
    • Washer
    • Central Heating
    • Wi-Fi
    • Swingset
    • Shared Outdoor Pool...
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    1 bedroom dog friendly cottage with a private balcony and wonderful views overlooking the grounds and countryside beyond. It has a cosy open plan kitchen/lounge dining room and a large superking or twin bedroom with French Doors leading to the balcony. The bathroom has bath and shower over. The... View all property information
    Make Inquiry
    Location Information
    Chepstow, Monmouthshire NP16 6RD
    5 of 5 stars Reviewed April 19, 2015
    Parsons Grove is a beautiful spot to stay in. The view of the hills, woods and fields from our balcony was just lovely. The cottage gave us everything we needed for the week and...
    See all reviews
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing