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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 stars2 days ago
Lovely and helpful host and we loved the board games
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
Private room in West Bay

Double room-Premium-Ensuite

DarenRating, 5 stars21 months ago
Beautiful room, great location and the restaurant food was amazing would highly recommend for a visit to West Bay
Guest favourite
Guesthouse in Yeovil
4.91 out of 5 average rating, 11 reviews

Traditional coach house in rural private estate.

JoshuaRating, 5 stars2 months 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!
Top Guest favourite
Private room in Colyton
5 out of 5 average rating, 7 reviews

4 King Room with En suite includes breakfast

LukeRating, 5 stars8 months ago
Couldn’t be happier. Firstly, Steve’s response before arriving at his and his partner’s B&B was quick and very informative. When we arrived, Steve and his partner were unbelievably warm and welcoming without being overbearing. Our lovely hosts were extremely attentive during our whole stay, were happy to help with anything we need and so helpful recommending activities. The amenities were really cosy and absolutely spotless, providing any extras we may need and more including biscuits, tea, coffee and personal care items. The breakfast in the morning is without a doubt one of the best full English breakfasts me and my partner have eaten, and came with an array of different extras such as fruit, three different juices, plenty of cereal, toast and jams. Anyone looking at staying here at the white cottage, I really have nothing but positive things to say. What a wonderful experience! Thank you for having us. Luke and Devon
Guest favourite
Guesthouse in Weymouth and Portland
4.88 out of 5 average rating, 78 reviews

Springfield

JasmineRating, 5 stars6 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
4.87 out of 5 average rating, 326 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.

Guesthouses with a patio

Top Guest favourite
Guesthouse in Pulham
4.99 out of 5 average rating, 76 reviews

Old Smokey

SimonRating, 5 stars1 week ago
Such a beautiful place to stay. The house and the surrounding area and view. Avril was so accommodating and went above and beyond and even helped making my wife's birthday unforgettable. Highly recommend this place.
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 stars2 days 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.
Top Guest favourite
Guesthouse in South Cheriton
5 out of 5 average rating, 38 reviews

Stylish, Cosy, Countryside Annex + Patio/Parking

MaddieRating, 5 stars5 months ago
We loved staying at Little Townsend for New Year - Pamela and Zubair are the perfect hosts. The accommodation is clean, modern and cosy with everything you need. Location wise there’s lots to do in the local area - we visited Stourhead and Sherborne. Ate at a wonderful pub called The Old Inn about 5/10 mins drive away and also at the local pub The White Horse Inn which is walking distance. We could have easily stayed for longer and still not done everything we wanted to do! Will definitely revisit
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!

Guest house rentals with a washing machine and dryer

Guest favourite
Guesthouse in Hinton Saint Mary
4.86 out of 5 average rating, 59 reviews

Two-bedroom guest house lovely Dorset village.

MarkRating, 5 stars1 month ago
Very friendly host who greeted us on arrival. Loads of helpful supplies in the kitchen including milk, bread and marmalade. Everything was clean and tidy. Very comfy double bed. Few hundred metres walk to a fantastic pub. Great food and friendly staff
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, 58 reviews

Newly converted hilltop Chapel

NaomiRating, 5 stars2 days ago
We had a fantastic experience staying at the Chapel. The building has been beautifully refurbished to a high standard and was exactly as described—clean, comfortable, and thoughtfully decorated. The check-in process was smooth and hassle-free, and communication with the host was excellent. The location was perfect for us as we were looking for a peaceful place to relax for a long weekend with our dog. The amenities provided were top notch - a well appointed kitchen, two bathrooms and the bed was very comfy indeed! Overall, the chapel exceeded our expectations and we were so sad to leave! I would absolutely stay here again and would recommend it to anyone looking for a one of a kind place to stay in the area. Thank you for having us, Naomi, Justin and Woody
Guest favourite
Guesthouse in Piddlehinton
4.96 out of 5 average rating, 196 reviews

The Yorkshireman @ Piddlehinton

JaneRating, 5 stars6 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.
Guest favourite
Guesthouse in Kenny, Ashill
4.97 out of 5 average rating, 61 reviews

*Secluded detached Modern property with garden*

KatherineRating, 5 stars1 week ago
Jacqui's place was like a home from home, and had everything we needed for a comfortable weekend away (including our two dogs, who were very well catered for! - as were we with, biscuits and treats for all of us, plus milk). The place was spotless, water hot and bed comfortable. Jacqui was really great with communication, and the key box made our late arrival very flexible. Parking right outside was a real bonus for packing and unpacking, and the garden was just lovely and really useful with the dogs. We would absolutely recommend this lucky find, and we would love to come back again!
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!

Destinations to explore