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Guesthouse vacation rentals in Cape Winelands District Municipality

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Top-rated guesthouse rentals in Cape Winelands District Municipality

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

Guest favorite
Guesthouse in Riebeeck Kasteel
Obiekwa Country House
Obiekwa Country House is located in the picturesque, quaint village of Riebeek Kasteel; with its wine estates and gourmet restaurants. It is set in a quiet cul-de-sac and overlooking an adjoining vineyard. Although it is set in peaceful, rural surroundings, It is a fifteen minute walk to the village square. NO LOADSHEDDING A solar energy system is in place. Please note that advertised prices are for 2 persons sharing a bedroom. If 2 guests would like 2 bedrooms, please book for 3 people.
Jun 28 – Jul 5
$103 per night
4.83 out of 5 average rating, 106 reviews
Guest favorite
Guesthouse in Montagu
Pecan Tree Cottage
Perfect couples retreat in the beautiful village of Montagu, surrounded by breathtaking mountain scenery. Within walking distance of the town centre. Hike the nature trails right on your doorstep, or simply lap up the tranquility in our fully fitted and comfortable little cottage. Explore the amazing attractions the Langeberg area has to offer, and after a long day in the heat of the Little Karoo, relax with a glass of local wine and enjoy the African sun set from the private pool. Amazing !
May 19 – 26
$50 per night
4.99 out of 5 average rating, 138 reviews
Guest favorite
Guesthouse in Cape Town
Sunbird Cottage - Somerset West
My place is in the heart of the Cape Winelands, in the picturesque town of Somerset West. Ideally located, only a scenic 20 min drive into the tourist town of Stellenbosch. 40 min to Cape Town CBD. 10 min to the beach. 1 hour to Hermanus (whale viewing and shark diving). Plenty of wine estates for tasting /meals (Lourensford & Vergelegen only 5 minutes away). Many hiking trails & MTB trails within walking/cycling distance. My place is good for couples , adventurers, business travelers.
Nov 15 – 22
$41 per night
4.9 out of 5 average rating, 198 reviews

Popular amenities for Cape Winelands District Municipality guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Barrydale
Mr Albert’s
May 25 – Jun 1
$23 per night
5.0 out of 5 average rating, 50 reviews
Guest favorite
Guesthouse in Greyton
❀Studio Frangipani: village + nature
Apr 8 – 15
$37 per night
4.92 out of 5 average rating, 90 reviews
Superhost
Guesthouse in Cape Town
Waenhuis (Wagon Shed)
Feb 20 – 27
$56 per night
4.95 out of 5 average rating, 20 reviews
Guest favorite
Guesthouse in Franschhoek
Villa-Roux Self Catering Garden Cottage
Dec 28 – Jan 4
$78 per night
4.91 out of 5 average rating, 55 reviews
Guest favorite
Guesthouse in Somerset West
2 bedroom, 100 sqm, self catering
Oct 16 – 23
$60 per night
4.88 out of 5 average rating, 99 reviews
Superhost
Guesthouse in Robertson
Quince Cottage at Tierhoek Organic Farm
Nov 12 – 19
$103 per night
5.0 out of 5 average rating, 3 reviews
Guest favorite
Guesthouse in Cape Town
Beauty
Jul 8 – 15
$89 per night
4.98 out of 5 average rating, 42 reviews
Guesthouse in Franschhoek
Franschhoek peace & quiet | Riverstone Cottage
Aug 24 – 31
$50 per night
4.66 out of 5 average rating, 291 reviews
Guesthouse in Paarl
Waterside no 2A / Owl
Jan 4 – 11
$59 per night
4.68 out of 5 average rating, 37 reviews
Guest favorite
Guesthouse in Cape Town
Unique Vintage Boutique flat pool & sea views
Jul 27 – Aug 3
$94 per night
4.83 out of 5 average rating, 23 reviews
Guest favorite
Guesthouse in Swellendam
De Wet se huisie
Jan 3 – 10
$57 per night
5.0 out of 5 average rating, 5 reviews
Guesthouse in Stellenbosch
Double-Unit Holiday Home @ Orange-Ville Guesthouse
Feb 21 – 28
$260 per night
5.0 out of 5 average rating, 4 reviews

Guest house rentals with a patio

Guest favorite
Guesthouse in Villiersdorp
Kliprivier Cottage
Sep 5 – 12
$52 per night
5.0 out of 5 average rating, 29 reviews
Guest favorite
Guesthouse in Cape Town
The Rigel Retreat
Aug 5 – 12
$26 per night
4.76 out of 5 average rating, 96 reviews
Guest favorite
Guesthouse in McGregor
Kothuis Frangipani - Adorable cottage with pool
Oct 31 – Nov 7
$49 per night
4.94 out of 5 average rating, 35 reviews
Guest favorite
Guesthouse in Riebeek-Kasteel
Silky Oaks Couples Retreat
Jan 6 – 13
$65 per night
4.88 out of 5 average rating, 17 reviews
Guest favorite
Guesthouse in Swellendam
Granny Kitsch Cottage, Swellendam Historic Distric
Apr 2 – 9
$41 per night
4.96 out of 5 average rating, 27 reviews
Guest favorite
Guesthouse in Tulbagh Road
Le Florival
Oct 27 – Nov 3
$40 per night
4.89 out of 5 average rating, 28 reviews
Guest favorite
Guesthouse in Cape Town
Stellendal River Cottage - serene & central
Jun 18 – 25
$124 per night
4.92 out of 5 average rating, 13 reviews
Guest favorite
Guesthouse in Stellenbosch
Luxury 2-bedroom cottage with patio & safe parking
Nov 14 – 21
$75 per night
4.94 out of 5 average rating, 32 reviews
Guest favorite
Guesthouse in Stellenbosch
Modern Private Flat, Aircon, Secure Parking
Dec 5 – 12
$59 per night
4.81 out of 5 average rating, 26 reviews
Guest favorite
Guesthouse in Cape Town
Charming 2 Roomed Garden Cottage own patio, pool
Feb 9 – 16
$35 per night
4.82 out of 5 average rating, 33 reviews
Superhost
Guesthouse in Paarl, Drakenstein
La Damon 2
Nov 12 – 19
$51 per night
New place to stay
Guesthouse in Citrusdal
Weavers Cottage on Waterfall Farm (sleeps 4)
May 1 – 8
$117 per night
New place to stay

Guest house rentals with a washer and dryer

Guest favorite
Guesthouse in Somerset West
Beautiful GreenWood Cottage|Hydrogen & Ozone Sauna
Dec 24 – 31
$126 per night
4.93 out of 5 average rating, 125 reviews
Guest favorite
Guesthouse in Franschhoek
Upmarket cottage exclusively for a couple
Nov 3 – 10
$176 per night
5.0 out of 5 average rating, 22 reviews
Guest favorite
Guesthouse in Swellendam
Swellendam Guesthouse - Bukkenburg
Aug 27 – Sep 3
$91 per night
4.94 out of 5 average rating, 48 reviews
Guest favorite
Guesthouse in Franschhoek
Mayflower Cottage
Feb 24 – Mar 3
$135 per night
4.96 out of 5 average rating, 334 reviews
Guest favorite
Guesthouse in McGregor
Jubilee Cottage
Mar 26 – Apr 2
$35 per night
4.76 out of 5 average rating, 55 reviews
Guest favorite
Guesthouse in Stellenbosch
Stellenbosch Garden Apartment
Jun 17 – 24
$62 per night
4.9 out of 5 average rating, 87 reviews
Guest favorite
Guesthouse in Somerset West
Cottage in security Estate with tennis court
Apr 7 – 14
$93 per night
4.77 out of 5 average rating, 13 reviews
Guest favorite
Guesthouse in Cape Town
Cottage@Somerset
Jun 30 – Jul 7
$56 per night
5.0 out of 5 average rating, 12 reviews
Guesthouse in Greyton
Toad Hall sleeps 12 to 20 people with largest pool
Oct 4 – 11
$467 per night
New place to stay
Guesthouse in Cape Winelands
Bloekomsrus Farm
Oct 23 – 30
$40 per night
3.6 out of 5 average rating, 10 reviews
Guesthouse in Cape Town
Brookwood Studio
Dec 7 – 14
$53 per night
New place to stay
Guest favorite
Guesthouse in Wellington
Hanna
Aug 29 – Sep 5
$41 per night
4.98 out of 5 average rating, 203 reviews

Destinations to explore