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per nightMrs Lydia Pedrick - Verified booking
The house was very clean and the rooms were really good sized for my family of four. The two bathrooms were very handy. The bed linen was fresh and crisp and the beds were very comfortable to sleep in. There was a little desk and chair upstairs which was good for reading, my son enjoyed sitting there to look at his laptop and handy for drying my hair as there is a big mirror on the wall! The garden was pretty, and even though it is to the front of the property it has well established shrubs and lavender that made it private from the road, and a nice little bistro set to enjoy the fresh air. Private parking right to the front of the house which was great, and a must for my husband. A short drive from southwold beach (5 mins). We had an amazing stay at The Headmasters House and hope to return next year. Thank you for having us
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Mrs Rees - Verified booking
We loved this quirky cottage and its position. The bed is amazing - huge and comfortable. All the plumbing is new and high quality. The kitchen is mostly well equipped and the electric goods are excellent. A perfect hideaway very close to the beach and bakery, restaurants etc. and very quiet. If you have mobility problems this cottage might not be for you as access to the first and second floor is via very narrow steep and winding stairs. We would describe this cottage as stylish, characterful, well positioned and cosy.
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Mrs Prosser - Verified booking
The cottage was perfect for us and our dog. Good central location - perfect for the town and beach. You can’t park outside the cottage but we had no problems parking nearby. The cottage was clean and tidy on arrival and was well equipped. We really appreciated the flowers, welcome gifts other touches which made the cottage cosy and welcoming. One thing to note is that the stairs are very steep so may not suit everyone. We would definitely recommend to anyone looking to stay in Southwold.
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Mrs Joyes - Verified booking
Beautifully furnished cottage, which also smells amazing in every room. The bed and pillows are fitting for a 5 star hotel. As the first to stay after refurbishment everything was perfect in every room. The kitchen seemed to have lots of utensils to cook most things and the dishwasher and washing machine are a bonus: Some teething issues with heating were resolved and we enjoyed our stay. The stairs are narrow and steep, especially to the loft room, but manageable.
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Mrs Barnwell - Verified booking
I would highly recommend a stay at the Headmasters House. The accommodation is both spacious and compact making for a very comfortable stay and it is very well equipped. The cottage is ideally located for walking into Southwold or just to the Randolph for a drink or Sunday lunch. Being able to park right outside the cottage is very handy. Having a separate bathroom for each bedroom is fantastic. Altogether a perfect base for exploring this part of Suffolk.
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