
Cottage vacation rentals in Winterton
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Top-rated cottage rentals in Winterton
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Winterton cottage rentals
Cottage rentals with a hot tub

Chelsea Cottage, Otters Den Self Catering
Great view, swimming in the river was wonderful. Very easy check in and out. Spotless accommodation. We will return for sure. Tx Dawn

Tugela River Lodge: Hot Tub Hideaway
Tugela river lodge is the perfect blend of nature and comfort. Highly recommend for anyone looking to disconnect and recharge!

Luxurious self-catering Midlands Cottage
Had a wonderfully peaceful stay. Beautiful landscape and loads to do. The cottage has everything that one needs. We will definitely be back for a longer stay.

Ama Casa - Hoopoe Cottage - 2 sleeper
What an absolutely wonderful place to stay. We felt so at home. Had such a restful holiday. The view from the cottage is just breathtaking. Wake up to the view of the mountains. The host is so helpful and friendly. Would love to return and spend longer.
Pet-friendly cottage rentals

Wild Hare: Aloe self-catering, Midlands Meander
A beautiful and tranquil place. Debbie was great to communicate with. Check in and out were both easy. The cottage is lovely and very well appointed. Highly recommended!

Caversham Woods farm cottage 2B - 2 bedroom
Staying in this little cottage felt like being in a hug - comfortable and snug. We could not get enough of the view from the lounge. The decor is both stylish and invitingly cozy. We have a new Midlands-fave. An extra is the fact that this gem is so close to many of our family favourite foodie places….. PS: we loved how Fortunate switched on the heaters for our later than planned arrival.

GUM TREE GLEN Wrinkly Tin Cottage
Peta is an amazing host. She gave us excellent recommendations and took us on a lovely walk. She really went out of her way to ensure that we had a good stay and that we did. The beds were very comfortable and warm, the house was cozy and we had stunning views over farmland. It was like living in a story book. She left us delicious bread, butter and we even had tea, coffee and rusks. The sherry was a lovely little touch. We will definitely be back to this hidden gem

Hum Lilly Lake House
We loved our stay at Hum Lilly - even allowed to bring our little pooch which was an added bonus. Very private setting. Road is a bit of a challenge when it rains but doable (we have sedans and it was fine, just very muddy). The place has a lovely feel to it. It's basic in terms of supplies as it's self catering so make sure you bring things, as it's not like you can just pop to the shops if you run out (like we did!). We wouldn't hesitate to book there again. Loved the fire place in the lounge, the beds were SUPER comfy and all in all, I would recommend it. Certainly worth staying at :)

The Goodland Honey Cottage - Newly Renovated
Absolutely loved staying here. My girlfriends and I needed time away from the city, to relax and have a mini staycation and the honey cottage allowed us to have that experience! Definitely coming back

Tugela River Lodge: Rapids Cottage with Hot Tub
The chalet is part of the beautiful and spacious lodge. The environment is nice and quiet. Perfect place to disconnect and relax. We found everything as described, communication and check-in were easy. Definitely a recommendation, probably worthwhile spending even more time here 🙂

Far Away Place (Nguni Cottage) Midlands Meander
Certainly a paradise that’s far far away from any form of distraction or noise. A safe-haven and special spot to recover, rejuvenate, and renew. Loved the complimentary fresh fruit, tea, and rusks. Morning walks were special on the property, and I spent the entire day outside writing and breathing in the fresh air. What a gem!

Thistledown Cottage
Thank you for sharing your place with us Steve. We had an amazing holiday. The peaceful surroundings and the Mearns dam made our stay more memorable. Steve was so helpful and assisted us throughout our trip. We appreciated all the free goodies that welcomed us into the cottage. We highly recommend your place and we will definitely visit again.
Private cottage rentals

Paddock Cottage Beautiful old Farmhouse
Beautiful & tranquil place. Really enjoyed our stay & our son loved seeing the cows & horses. Such a relaxing environment

Garden Cottage
Daniel was an amazing host, very open and supportive! Very happy for me to chosen this house. Its cozy, very beautiful and absolutely lovely. Daniel, thank you very much! Highly recommend and hopefully will return to this place)

Bergview Cottage with views!
Amazing location, and access to Drakensurg Sun facilities is a bonus. Plenty of activities to do - hiking, swimming, horse riding, canoeing, abseiling, all right on your doorstep

Drakensberg Bungalow
The place was spotless, fully furnished and equipped with a gas heater, electric blankets, an amazing kitchen with even an egg boiler! Large bathroom with a shower and built in cupboard with enough space. Beautiful tranquil spot and I loved the privacy and separate own entrance that my host respected. Plenty of walking trials around. All the basic groceries were provided like tea, coffee, sugar, milk, cooking oil, salt, pepper … the list just goes on. I enjoyed my stay and had a good rest as well. Television is provided with DSTV channels. The weather: don’t believe the weather predictions … I packed completely wrong. Take clothes for hot summer as well as cold winter days. Thank you for a lovely and comfortable stay. Highly recommended.

Nguni Cottage - 6 Sleeper Midlands Break Away
Even more beautiful than in the pictures! The lake is absolutely stunning, with cows peacefully roaming around and breathtaking surroundings in every direction. It truly feels like a hidden gem. Unfortunately, it had rained quite a bit before we arrived, and our bus got stuck going up the driveway—but it was still 100% worth it. Would definitely come again!

Mill Cottage - Garden Cottage
Lovely clean and comfortable stay. Beds and pillows were comfy and shower was really nice. Thanks Janice.

Montusi Self-catering Cottages
What a beautiful place to stay in the most picturesque valley. The accommodations were comfortable and cozy after a long day of hiking!
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