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Guesthouse holiday rentals in Weymouth and Portland District

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Popular amenities for Weymouth and Portland District guesthouses

Family-Friendly guesthouses

Guesthouse in Bridport
4.71 out of 5 average rating, 642 reviews

Amazing private studio space

HannahRating, 5 stars1 day ago
Lovely and helpful host and we loved the board games
Top Guest favourite
Guesthouse in Salisbury
4.94 out of 5 average rating, 126 reviews

Rural Idyll for dog-lovers near the New Forest

SandraRating, 5 stars2 months ago
Alison‘s place was perfect, it has absolutely everything you need for a comfortable stay. The location is quiet and idyllic in a small village with lots of countryside walks from the door. There is a pub in the village and several not too far away if you need somewhere to eat. There is a Trout fishery in walking distance. Beds comfortable. The garden is perfect and enclosed for the dog to run around, and there is plenty of parking right outside the door of the cabin. Alison was an excellent unobtrusive host and left us initial provisions including eggs from her chickens and freshly cooked bread. What more could you ask for? We drove 25 minutes into the heart of the New Forest and hired bikes for the day. We’ll definitely be back!
Guest favourite
Guesthouse in Bridport
4.93 out of 5 average rating, 179 reviews

The Countryside Loft in stunning rural Dorset

AlisonRating, 5 stars1 month ago
the loft was in a beautiful location with views across the valley. We were able to access many great walking locations nearby then return to comfortable accommodation. there is a roomy shower and plenty of places to hang outdoors boots and walking gear etc. Emma was helpful and accommodating
Guest favourite
Guesthouse in Yeovil
4.91 out of 5 average rating, 11 reviews

Traditional coach house in rural private estate.

JoshuaRating, 5 stars1 month ago
What can I say, lovely property, lovely host! Amenities were more than adequate for a longer stay, and the host (Jeremy) and his family, have left us feeling well looked after and most of all made us feel very welcome! Thankyou for a lovely stay Jeremy!
Guest favourite
Guesthouse in Weymouth and Portland
4.88 out of 5 average rating, 78 reviews

Springfield

JasmineRating, 5 stars5 days ago
Beautiful little place, perfect location for exploring Weymouth and the surrounding area. Had everything you could ever need and Georgia and the family were super friendly! I am sure we will be back!
Superhost
Guesthouse in Langton Matravers, Swanage
4.67 out of 5 average rating, 169 reviews

The Chalet at Primrose Hill BH19 3EE

Sarah-JaneRating, 5 stars2 weeks ago
This place was perfect for what we needed it for! We were attending a wedding close by and needed somewhere local enough to the venue. This was a perfect location and perfect place for that! Barbara gave instructions to the property that was clear and easy to follow. And the property had everything we needed, exactly as described! Would recommend, location had beautiful views.
Guest favourite
Guesthouse in Dorset
4.88 out of 5 average rating, 325 reviews

The Barn Little Birch

PeterRating, 5 stars1 week ago
Beautiful and cozy place, cleaned and had everything we needed and more. Jan did absolutely everything for us to have a lovely stay.
Guesthouse in Charmouth
5 out of 5 average rating, 46 reviews

The Gatehouse - Friday change-overs only.

VickyRating, 5 stars10 months ago
We are a family of 4 with 2 young children and we all enjoyed staying at the Gatehouse, great space to explore and children loved being in nature with a huge garden, they loved the apple tree ‘den’. House had everything you could possibly need, John was on hand if needed and great location to explore, fossil hunt and walk the Golden Cap. Couldn’t have asked for more.

Guesthouses with a patio

Top Guest favourite
Guesthouse in Saint Leonards
4.99 out of 5 average rating, 106 reviews

Lucky Rabbit Retreat

BonnieRating, 5 stars1 week ago
Absolutely perfect stay!Everything you needed and more. Lucky rabbit retreat was spotlessly clean and the garden was so lovely and spacious and secure for my 6 month old granddaughter and dog Tigerlilly to play in. Karin was very thoughtful in what she left for us and very accommodating and friendly. We have stayed in lots of places in the new forest but this was by far the best and we cannot wait to come back again. Thank you Karin. Look forward to seeing you again!
Guest favourite
Guesthouse in Dorset
4.93 out of 5 average rating, 123 reviews

Character Barn in the Heart of Beaminster

SusanRating, 5 stars1 week ago
We only stayed for 3 night's as we were Attending a wedding nearby but it was a perfect little bolt hole. We felt right at home and had everything we could possibly want. Beaminster is a lovely little town only wish we'd had more time to explore.
Top Guest favourite
Guesthouse in Dorset
5 out of 5 average rating, 26 reviews

Rosie’s Place - 10mins to beach

LindaRating, 5 stars2 weeks ago
Just came back from a week stay place was very clean and everything you needed she has thought of everything so friendly and helpful was lots to do nearby restaurants near good beaches are amazing went to Nothe fort for the day highly recommend it brilliant day out . We took our dog Benny and most places are dog friendly will definitely go back and highly recommend Anna’s place to stay
Guest favourite
Guesthouse in Dorset
4.83 out of 5 average rating, 112 reviews

The Getaway: Quaint Log Cabin on Jurassic Coast

TomRating, 5 stars1 day ago
Tom & Naomi went out of their way to ensure I knew exactly what to expect both in the property, the location and amenities nearby. They offered a simple and easy contact-free check in for me as I was travelling for several hours, and I even found a powerful floorstanding fan on my arrival (temps were in the high 20s). All the consumables and essentials were provided, with a microwave snd kettle in the kitchenette (although perhaps including a plug-in induction hob would be a great addition for extra flexibility for cooking). Bathroom had a powerful shower and plenty of towels, just bear in mind there is only a small hook on the back of the door to accommodate any clothes you’ll put there and the towels (I just hung them over the cubicle, but perhaps installing a towel rail would be worthwhile). Thanks again for a lovely stay, and the local recommendations for food and places of interest!
Top Guest favourite
Guesthouse in Kilmington
4.99 out of 5 average rating, 108 reviews

Charming 2 bed self-contained cottage with Patio

RoryRating, 5 stars3 weeks ago
We had a lovely stay at Susan's place. The property was beautifully furnished and had a very calming aura. Directions to the property were clear and the village itself is really lovely and peaceful. The view from the bathroom in the morning was stunning! The place was really clean - even though this is a dog friendly property (and we didn't bring any) Susan clearly took care to ensure the place was spotless and free from hair. We'd definitely stay again.
Guest favourite
Guesthouse in Lyme Regis
4.97 out of 5 average rating, 186 reviews

Cosy lodge, parking, beautiful setting, Lyme Regis

MarisaRating, 5 stars1 month ago
Our family had a lovely weekend at Helen's place. It was beautifully located, clean and safe for the kids (4 year old and 10 month old). It's a short walk to Uplyme and a 5 min drive to Lyme Regis. We would definitelly come back for a longer break.
Guest favourite
Guesthouse in Upton
4.91 out of 5 average rating, 204 reviews

Arne View Lodge, South facing with Hot tub.

EveRating, 5 stars2 weeks ago
Victoria and Steve’s place is just as described - clean, super cosy and the hot tub is fab. Great launch pad to explore Studland/Corke/the coastal area. Easy to get around - bus to Poole from pretty much outside the front door (Rockfish restaurant is great!) and if you don’t mind a 20/30 mins walk, there are a couple of nice pubs in walking distance. Thanks for a lovely stay!
Superhost
Guesthouse in Bere Regis
4.82 out of 5 average rating, 130 reviews

Unique Private Cabin in Purbeck Dorset Countryside

jolandaRating, 5 stars6 days ago
We enjoyed our stay. Very nice that the dog could run free in the garden. Everything was to our liking.

Guest house rentals with a washing machine and dryer

Guest favourite
Guesthouse in Fontmell Magna
4.94 out of 5 average rating, 35 reviews

A spacious home from home in North Dorset

RossRating, 5 stars1 month ago
Great communication, have booked another visit!
Guest favourite
Guesthouse in Milkwell
4.95 out of 5 average rating, 87 reviews

Milkwell’s heavenly place

SteveRating, 5 stars1 month ago
A wonderful studio to stay and enjoy the delightful countryside which is on your doorstep. I’d highly recommend staying at Poppy’s studio.
Top Guest favourite
Guesthouse in Okeford Fitzpaine
5 out of 5 average rating, 25 reviews

Delightful barn in scenic North Dorset

Nancy Rating, 5 stars3 weeks ago
Andrew and Janine were lovely hosts. They left a very generous tray of welcome goodies from local sources which I was very grateful for and Andrew gave me some great recommendations for activities while we were there. It was a beautiful and peaceful stay and we thoroughly enjoyed our time there. Thank you
Top Guest favourite
Guesthouse in Dorset
5 out of 5 average rating, 57 reviews

Newly converted hilltop Chapel

RachelRating, 5 stars4 weeks ago
We’ve just come back from a lovely long weekend staying in Gina’s beautiful converted chapel. The property is very tastefully designed and felt very much like a suite in a luxury country hotel. There are stunning walks and rolling countryside from the doorstep and Berwick St John is a very pretty little village. It was the perfect place for a relaxing weekend with our dog and truly felt like a home from home that we hope to return to again.
Guest favourite
Guesthouse in Piddlehinton
4.96 out of 5 average rating, 195 reviews

The Yorkshireman @ Piddlehinton

JaneRating, 5 stars5 days ago
A great place to stay in a pretty little village within easy reach of Dorchester and the coast. A very comfortable double bed on the mezzanine level, and like all areas immaculate. Claire has put together an informative booklet for her guests with all the information needed for a relaxing stay.
Superhost
Guesthouse in Dorset
4.89 out of 5 average rating, 18 reviews

Rural retreat in north Dorset with beautiful views

RuthRating, 5 stars5 months ago
We had a great stay and would definitely book again! It was spacious and clean. We enjoyed the views and the air hockey table!
Top Guest favourite
Guesthouse in Hambridge
5 out of 5 average rating, 24 reviews

Spacious Stables Conversion

ChloeRating, 5 stars1 month ago
Damien’s place was the perfect place for a group of 7 of us to celebrate a hen do. We wanted somewhere a bit luxurious, peaceful and secluded so we wouldn’t disturb anyone. Damien’s place covered all bases! Check in was seamless, love the fact the key is secured inside the lockbox so you never have to take it out with you and risk losing it! Loads of nice touches around the house, lots of high tech that added to the luxury, but was easy to use. Clear instructions for everything on the iPad in the kitchen. Place was spotlessly clean. We hired a private chef to come in and cook for our group, he commented on how well the kitchen was stocked and what a beautiful space it was to cook in! Highly recommend this accommodation and would stay again!
Top Guest favourite
Guesthouse in Devon
4.98 out of 5 average rating, 58 reviews

The Wheel House, Cosy Rural Getaway

hilaryRating, 5 stars5 months ago
An ideal location for local Christmas family visiting , so we didn’t have need for local pubs/restaurants, however useful info from previous guests was available. It’s a lovely little ‘cottage’ with all you need , loads of hot water , and a nice cool bottle of wine on arrival !

Destinations to explore