Search Chalets in Southampton from CA $151

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Check prices for these dates

Our top choices for Southampton chalets

1. Westcliffe chalets

Westcliffe chalets
Niton
The price is CA $186
CA $223 total
includes taxes & fees
Nov 10 - Nov 11
Westcliffe chalets

2. York Street

York Street
Cowes
10.0 out of 10, Exceptional, (8 reviews)
"It was absolutely perfect ! The house was so well looked after ."
United States
Anonymous traveller
The price is CA $1,626
CA $1,892 total
includes taxes & fees
Nov 5 - Nov 6
York Street

3. Princes Esplanade

Princes Esplanade
Gurnard
10.0 out of 10, Exceptional, (4 reviews)
"We loved the beautiful location"
United States
Susan
The price is CA $1,216
CA $1,498 total
includes taxes & fees
Nov 5 - Nov 6
Princes Esplanade

4. Dassia

Dassia
Porchfield
9.6 out of 10, Exceptional, (4 reviews)
"We stayed here over Christmas and it was perfect. Our dog loved the enclosed garden. The kitchen has everything to cook a festive dinner in. We had the log burner on for the day which was great. Would definitely stay again."
United States
Emma
The price is CA $1,277
CA $1,498 total
includes taxes & fees
Nov 5 - Nov 6
Dassia

5. Hayling Hideaway, private self contained cosy annex near to beach

Hayling Hideaway, private self contained cosy annex near to beach
Hayling Island
9.6 out of 10, Exceptional, (5 reviews)
"Very clean, great location, well-set up, ideal for two people exploring the sea front and wandering along the beaches. Recommended."
United Kingdom
Tim
The price is CA $152
CA $182 total
includes taxes & fees
Nov 9 - Nov 10
Hayling Hideaway, private self contained cosy annex near to beach

6. Creek View, Isle of Wight

Creek View, Isle of Wight
Wootton Bridge
10.0 out of 10, Exceptional, (4 reviews)
"A truly amazing stay at a wonderful location. A superb home to base an island adventure! VRBO"
United States
Benjamin Gully
The price is CA $2,408
CA $2,790 total
includes taxes & fees
Nov 5 - Nov 6
Creek View, Isle of Wight

7. Rookley Farm Lodge

Rookley Farm Lodge
Rookley
10.0 out of 10, Exceptional, (11 reviews)
"Loved the location, so peaceful and relaxing and private. Loved hearing the lambs in the field, loved the pool. House has everything you could possibly need."
United States
Sue
The price is CA $2,396
CA $2,862 total
includes taxes & fees
Nov 5 - Nov 6
Rookley Farm Lodge

8. Laurel Cottage

Laurel Cottage
Newchurch
10.0 out of 10, Exceptional, (14 reviews)
"Very nice cottage with all the comforts and well placed for visiting the Isle of Wight, near Newport and not far from the coast too."
United States
Jean-Paul
The price is CA $2,276
CA $2,983 total
includes taxes & fees
Nov 5 - Nov 6
Laurel Cottage

9. The Wing at Fox Hollow

The Wing at Fox Hollow
Whiteley Bank
10.0 out of 10, Exceptional, (17 reviews)
"Very comfy bed, good variety of cooking utencils. It was perfect. We were very happy"
United States
Colin Anthony
The price is CA $602
CA $719 total
includes taxes & fees
Nov 5 - Nov 6
The Wing at Fox Hollow

10. North Quay

North Quay
St Helens
10.0 out of 10, Exceptional, (2 reviews)
"The property is amazing thank you, perfect for our holiday, everything we needed. Great facilities and beautiful decor."
United States
Dave Matthews
The price is CA $1,770
CA $2,088 total
includes taxes & fees
Nov 5 - Nov 6
North Quay

11. No 1 Ashey

No 1 Ashey
Ryde
9.4 out of 10, Exceptional, (18 reviews)
"We stayed here for three nights and loved it! The weather was amazing so we made the most out of the pool. The house is very clean and spacious."
United States
Anonymous traveller
The price is CA $1,867
CA $2,430 total
includes taxes & fees
Nov 5 - Nov 6
No 1 Ashey

12. Jollys

Jollys
Sandown
9.8 out of 10, Exceptional, (23 reviews)
"We had a fantastic stay at Jolly’s Holiday Home. The location is amazing—just a very short walk to the beach with beautiful views, and close to plenty of shops, restaurants, and other amenities. The house was spotlessly clean, well laid out, and had everything we needed for a comfortable stay. It’s a lovely holiday home in a perfect setting, making it easy to relax and enjoy the area. We would definitely recommend it and would happily stay here again!"
United States
Kelly
The price is CA $1,204
CA $1,645 total
includes taxes & fees
Nov 5 - Nov 6
Jollys

13. Orchard Cottage

Orchard Cottage
Ventnor
10.0 out of 10, Exceptional, (3 reviews)
"A very pleasant place to stay, within walking distance of the beach and in a central place to get round the island. Neighbour friendly and helpful."
United States
Mccormick
The price is CA $3,011
CA $3,406 total
includes taxes & fees
Nov 5 - Nov 6
Orchard Cottage

14. Littlestairs

Littlestairs
Shanklin
10.0 out of 10, Exceptional, (15 reviews)
"Fantastic accommodation in the perfect location right on the cliff tops. Accommodation was spotlessly clean. Loved it so much we are going back in a few months. Quite pricey for a weeks stay if only 3 of you, but otherwise it was faultless."
United States
Sue
The price is CA $2,119
CA $2,529 total
includes taxes & fees
Nov 5 - Nov 6
Littlestairs

15. Cherry Lodge

Cherry Lodge
Godshill
10.0 out of 10, Exceptional, (14 reviews)
"Lovely, peaceful location in a modern well equipped lodge - ideal for a relaxing break. Location on the edge of the delightful village of Godshill well placed for our favourite destinations. Simeon was a most accommodating and friendly host eager to hear feedback for continuous improvement."
United States
Gavin
The price is CA $1,084
CA $1,267 total
includes taxes & fees
Nov 5 - Nov 6
Cherry Lodge

16. Ivy Cottage

Ivy Cottage
Brading
10.0 out of 10, Exceptional, (2 reviews)
"Clean and cosy"
United States
Aman
The price is CA $795
CA $931 total
includes taxes & fees
Nov 5 - Nov 6
Ivy Cottage

17. Penderic, Isle of Wight

Penderic, Isle of Wight
Cowes
The price is CA $1,072
CA $1,301 total
includes taxes & fees
Nov 26 - Nov 27
Penderic, Isle of Wight

18. Pebble Beach - Isle of Wight

Pebble Beach - Isle of Wight
Bembridge
10.0 out of 10, Exceptional, (15 reviews)
"We had a lovely stay thank you! Great location and lovely walks."
United States
Anonymous traveller
The price is CA $963
CA $1,173 total
includes taxes & fees
Nov 9 - Nov 10
Pebble Beach - Isle of Wight

19. Superior Chalet 1 at Northlands Farm – Near Goodwood

Superior Chalet 1 at Northlands Farm – Near Goodwood
Chichester
The price is CA $270
CA $323 total
includes taxes & fees
Nov 5 - Nov 6
Superior Chalet 1 at Northlands Farm – Near Goodwood

20. Seagrass

Seagrass
Sandown
10.0 out of 10, Exceptional, (11 reviews)
"The property is excellent a great Christmas stay. Thank you so much for the lovely decorations and treats. Can’t wait to come back."
United States
Sharon
The price is CA $1,204
CA $1,325 total
includes taxes & fees
Nov 5 - Nov 6
Seagrass
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.

Learn more about Southampton

Explore the historic SeaCity Museum and stroll along Ocean Village marina where mega-yachts dock beside waterfront restaurants. Medieval city walls and the Tudor House Museum reveal Southampton's maritime past, while nearby New Forest offers cycling trails through ancient woodlands.

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