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Cottage holiday rentals in Chepstow

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Top-rated cottage rentals in Chepstow

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Cottage in Chepstow

4.84 out of 5 average rating, 357 reviews

Pineapple Cottage - Chepstow Town Centre (Wales)

17th Century cottage in the heart of Chepstow, close to Offa's Dyke & the Wye Valley. Tucked down a little cobbled street in the town centre, it’s a small but perfectly formed cottage ideal for a couple or a young family. There’s a secret door leading to the second bedroom, where you’ll even get a glimpse of Chepstow Castle from the window. It’s an ideal base for weddings at St Tewdrics (we’ve even hosted the bride and groom!) or for walking and cycling in the Forest of Dean and Wye Valley.

17–24 Jan

$185 NZD per night

Guest favourite

Cottage in Blakeney

4.86 out of 5 average rating, 443 reviews

Grade II Listed Underdean Lodge

Underdean Lodge is a lovingly restored 2 double bedroom Georgian lodge on the edge of the Forest of Dean and is the perfect base for exploring both the Forest and the Wye Valley. The lodge includes beautiful period features and a wood burning stove. Dogs welcome. Footpaths lead to the Forest from the front door. The Lodge is located adjacent to the A48 for convenient access to Gloucester, Monmouth and Chepstow which are all about 25 minutes away. View 'The Space' for Covid-19 measures taken.

6–13 Feb

$216 NZD per night

Guest favourite

Cottage in Upper Redbrook

4.95 out of 5 average rating, 298 reviews

Country cottage in the Wye Valley & Forest of Dean

A detached, romantic country retreat in the heart of the Wye Valley on the edge of the Forest of Dean. An ideal base for exploring all the fantastic activities and sites that the local area has to offer. Whether you enjoy mountain biking, rambling, canoeing, or soaking up some English and Welsh heritage - the Wye Valley and the Forest of Dean really do have something for everyone. We will happily answer any questions you have about the local area to ensure you get the most out of your stay.

8–15 Mar

$188 NZD per night

Guest favourite

Cottage in Monmouthshire

4.98 out of 5 average rating, 126 reviews

Peaceful Stone Cottage among fabulous gardens

The Garden House is a peaceful stone cottage set in the historic gardens of High Glanau Manor, the home of H. Avray Tipping (1855-1933) the Architectural Editor of Country Life Magazine from 1907. High Glanau Manor is an important Arts & Crafts house set in 12 acres of gardens designed in 1922. The gardens retain many original features including formal terraces, octagonal pool, glasshouse, pergola and 100 ft long double herbaceous borders. There are spectacular views to the Brecon Beacons

19–26 Jan

$284 NZD per night

Guest favourite

Cottage in South Gloucestershire

4.97 out of 5 average rating, 282 reviews

Beautiful Cider House Village Getaway Sleeps 4

The Cider House is a spacious and comfortable home opposite the Village Green in Cromhall, near to Wotton-under-Edge on the southern fringe of the Cotswolds in Gloucestershire. The village is conveniently located for the M5, with J14 approx. 10 mins by car, and the A38 a similar distance. Easy access to local market towns of Thornbury and Wotton-under-Edge, as well as to Bristol and Bath. The barn is next door to our home but entirely self-contained and private with parking for two cars.

14–21 Oct

$272 NZD per night

Guest favourite

Cottage in Penallt

4.98 out of 5 average rating, 184 reviews

Coach House Annex - Annedd Bach - Wye Valley

Finished to a high standard, Annedd Bach makes a comfortable base to explore the Wye Valley - walking, cycling or on the river. Set in 28 acres, the spacious accommodation benefits from underfloor heating, enjoys superb views over the Wye Valley and offers privacy with a secluded patio and garden - a true tranquil hideaway to escape the crowds. Located 4 miles from Monmouth the Cottage is approached through an historic arboretum with several giant redwoods amongst other specimen trees.

21–28 Nov

$291 NZD per night

Guest favourite

Cottage in Saint Briavels

5.0 out of 5 average rating, 241 reviews

Set in AONB & 40 Acres of Private Countryside

Perfectly situated to explore all the Wye Valley and Forest of Dean has to offer, The Apple Loft is an idyllic getaway popular with honeymooners, walkers, cyclists and those just wishing to escape the hustle and bustle of everyday life. With panoramic views across Mork Valley, guests can walk our grassy tracks, explore the old lime kilns, picnic in our fields, say ‘hello’ to the pet sheep and enjoy the sights and sounds of nature, stars and sunsets in this magical and relaxing retreat.

14–21 Apr

$307 NZD per night

Guest favourite

Cottage in Brockweir

4.99 out of 5 average rating, 176 reviews

Peaceful, 3 bedroom woodland cottage, large space

Hidden away on the edge of the ancient Forest of Dean, in the beautiful Wye Valley. Set in a large secluded garden, accessed by a long narrow lane. It is a fabulous place for walkers and romantic escapees. Originally a woodman’s cottage, with a cosy-but-spacious interior, fully equipped kitchen, log burner, lovely, comfortable king sized beds, everything you need for a relaxing break. The large cottage garden is not suitable for young children 1-12, it has a pond and steep terracing

2–9 Nov

$288 NZD per night

Guest favourite

Cottage in Trelleck

4.96 out of 5 average rating, 185 reviews

The Old Cider Mill

The Old Cider Mill is a beautifully converted old cider barn set in the wonderfully peaceful monmouthshire countryside. The cottage is a fabulous romantic and tranquil retreat set in one acre of meadow and adjoining spinney. Perfectly situated to explore all the wye valley, and nearby forest of dean, has to offer. This cosy cottage sleeps two guests and has an open plan living area with a woodburning stove. Outside is lovely gravelled courtyard with furniture and off road parking.

18–25 Oct

$238 NZD per night

Guest favourite

Cottage in Chepstow

4.9 out of 5 average rating, 104 reviews

Chepstow, Forest of Dean | Sleeps 4 | Dog Friendly

This warm and cosy cottage is based on the edge of the quiet village of Tutshill (the childhood home of JK Rowling) on the English side of the Welsh border. It is the perfect location if you are looking to escape to the country and explore the beautiful Forest of Dean but still be close to amenities. Walking distance to Chepstow. *10% discount for +7 night stays* *To book 12 months ahead or more please use the Airbnb website rather than the app*

10–17 Mar

$345 NZD per night

Guest favourite

Cottage in Llandogo

4.93 out of 5 average rating, 174 reviews

Gorgeous Stone Cottage in the Lower Wye Valley

Mill Cottage is a delightful stone cottage situated on a private lane in the heart of a pretty village located on the River Wye. The original cottage is over 150 years old and was the home of the sawmill manager, who ran the nearby sawmill, which has long since disappeared. It is now a lovely holiday cottage, that sleeps two couples and one well-behaved dog. It overlooks a pretty church and is very conveniently located for the village pub.

16–23 Apr

$227 NZD per night

Guest favourite

Cottage in Monmouthshire

4.88 out of 5 average rating, 360 reviews

Carpenters Cottage - Central Chepstow with parking

Carpenters Cottage is a quaint cosy one bedroom cottage at the bottom of Chepstow Town. It’s 2 minutes walk to the castle, town centre or the pubs on the river wye. The cottage is fully equipped with all your necessities for a wonderful home from home stay. Recently completely refurbished to a high standard it offers comfort, style and privacy with a 4* luxury finish. We hope you enjoy your stay and want to come again.

4–11 Apr

$175 NZD per night

Holiday rentals for every style

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Popular amenities for Chepstow cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Guest favourite

Cottage in Gloucestershire

4.94 out of 5 average rating, 181 reviews

Romantic cosy cottage & hottub in Forest of Dean

11–18 Jun

$244 NZD per night

Guest favourite

Cottage in Monmouthshire

4.91 out of 5 average rating, 184 reviews

The Old Dairy- Boutique Cottage at Harrys Cottages

24–31 Jan

$280 NZD per night

Guest favourite

Cottage in Weston super Mare

4.99 out of 5 average rating, 506 reviews

Private seaside retreat with hot tub

31 Dec – 7 Jan

$293 NZD per night

Guest favourite

Cottage in Gloucestershire

4.96 out of 5 average rating, 276 reviews

Idyllic Waterside Cottage - Hot Tub

15–22 Sep

$279 NZD per night

Guest favourite

Cottage in Powys

5.0 out of 5 average rating, 174 reviews

The Bothy: Cosy Cottage with Amazing Mountain View

14–21 Nov

$360 NZD per night

Guest favourite

Cottage in Longhope

4.96 out of 5 average rating, 354 reviews

Mill Garden Lodge Romantic Spa break in the Forest

20–27 Apr

$332 NZD per night

Guest favourite

Cottage in Uphill

4.95 out of 5 average rating, 170 reviews

Barn Conversion With Private Hot Tub Near To Beach

8–15 Sep

$347 NZD per night

Guest favourite

Cottage in Ewyas Harold

4.97 out of 5 average rating, 169 reviews

Beautiful cottage with magnificent views

22–29 Oct

$264 NZD per night

Pet-friendly cottage rentals

Guest favourite

Cottage in Kington Langley

4.98 out of 5 average rating, 159 reviews

Spinners Cottage, historic & romantic nr Cotswolds

14–21 Nov

$356 NZD per night

Guest favourite

Cottage in Broad Oak

4.96 out of 5 average rating, 195 reviews

The Covey, a Tudor cottage for two.

23–30 Sep

$240 NZD per night

Guest favourite

Cottage in Llangattock Lingoed

4.91 out of 5 average rating, 299 reviews

Perfect for couples; friendly pub; great walks

10–17 Feb

$259 NZD per night

Guest favourite

Cottage in Monmouthshire

4.97 out of 5 average rating, 168 reviews

Walkers Rest at The Hayloft - The Brecon Beacons

9–16 Jan

$266 NZD per night

Guest favourite

Cottage in New Mills

4.9 out of 5 average rating, 208 reviews

Highlands Cottage | cider orchard | Wye Valley

19–26 Apr

$150 NZD per night

Guest favourite

Cottage in Scowles

4.95 out of 5 average rating, 249 reviews

Country cottage with private woodland and orchard.

16–23 Mar

$392 NZD per night

Guest favourite

Cottage in Symonds Yat

4.95 out of 5 average rating, 223 reviews

Homely 2 bed cottage in the beautiful Wye Valley

28 Nov – 5 Dec

$254 NZD per night

Guest favourite

Cottage in Wickwar

4.91 out of 5 average rating, 148 reviews

Cosy 3 bedroom barn conversion near to Cotswolds.

15–22 May

$271 NZD per night

Private cottage rentals

Guest favourite

Cottage in France Lynch

4.97 out of 5 average rating, 434 reviews

Cotswold Summerhouse

15–20 Jun

$253 NZD per night

Guest favourite

Cottage in Gloucestershire

4.99 out of 5 average rating, 266 reviews

Restful rural views, wildlife, alpacas -Perry Pear

6–13 Oct

$207 NZD per night

Guest favourite

Cottage in Parkend

4.98 out of 5 average rating, 169 reviews

Edith's Cottage Forest of Dean

5–12 Sep

$242 NZD per night

Guest favourite

Cottage in Long Dean

4.99 out of 5 average rating, 198 reviews

Robin’s Nest - A cosy retreat in beautiful valley

13–20 Aug

$280 NZD per night

Guest favourite

Cottage in Llanarth

4.94 out of 5 average rating, 390 reviews

Cottage at Grove Court Stud Farm

26 Sep – 3 Oct

$152 NZD per night

Guest favourite

Cottage in Monmouthshire

4.94 out of 5 average rating, 101 reviews

The Old Granary Farm Cottage

14–21 Apr

$167 NZD per night

Guest favourite

Cottage in Chalford

4.97 out of 5 average rating, 231 reviews

One bedroom cottage in the heart of the Cotswolds

9–16 Jun

$301 NZD per night

Guest favourite

Cottage in Llanvapley

4.96 out of 5 average rating, 273 reviews

Lovely Courtyard Cottage near Abergavenny

7–14 Feb

$310 NZD per night

Destinations to explore