House holiday rentals in Weymouth and Portland District

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Popular amenities for house rentals in Weymouth and Portland District

House rentals with a pool

Top guest favourite
Home in Buckland Newton
5 out of 5 average rating, 6 reviews

Woodcutter's Cottage

PeteRating, 5 stars5 months ago
The cottage was beautiful and we loved that there were Christmas decorations up. It had everything that we needed and more. The hosts were very friendly and helpful. Would highly recommend to anyone looking for a relaxing place to stay.
Superhost
Home in Osmington
4.85 out of 5 average rating, 89 reviews

Large coastal cottage with spa and private pool

IanRating, 5 starstoday
Fabulous property great pool and hot tub would highly recommend to any families for holidays
Superhost
Home in Preston Road
4.84 out of 5 average rating, 113 reviews

Spacious Caravan near sea Weymouth Bay Haven

SuzanneRating, 5 stars5 months ago
This is our second time staying in this lovely caravan. It’s always pristine and lovely. I always felt like a home away from home there. The bedrooms are a good size and the extra full bathroom is a definite plus! I’d highly recommend staying here.
Guest favourite
Home in Crossways
4.95 out of 5 average rating, 40 reviews

Stunning Home with Roof Terrace at Silverlake

BarakRating, 5 stars3 weeks ago
Super comfortable and beautifully designed house, stocked with almost anything you can want The estate is beautiful and has tons to do So glad I found this place!
Top guest favourite
Home in Margaret Marsh
5 out of 5 average rating, 38 reviews

Charming thatched farmhouse, heated pool & cottage

LouiseRating, 5 stars1 week ago
Absolutely fabulous place to stay , i had a special birthday so got the family together . The house is so well equipped to high standard. The pool is brilliant nice temperature and big enough to feel like your doing your lengths in exercise, brilliant setting to sit round. Can't find anything bad to say about the place Nice kid's area with swings and trampoline.
Guest favourite
Home in Somerset
4.91 out of 5 average rating, 246 reviews

Country House - Pool Jacuzzi Escape Room Karaoke

MiaRating, 5 stars2 weeks ago
I booked this wonderful property for my best friend's hen do. 10 of us stayed here and hired the property for the weekend. We paid for the garden games, escape room, wine tasting and bbq use for one day. We had the most amazing weekend, we had an entire packed itinerary for almost every hour of the whole weekend from everything available on site and had the best time, we almost didn't have enough time to enjoy every amenity. Not only was the property expansive and full of activities ,even if we didn't pay for extras, but the hosts were incredibly welcoming. From taking time out of their own weekends to check we had everything we needed to setting up games, awarding prizes and giving the bride keepsakes for her wedding they couldn't have made us felt more welcome. Waking up in the morning there were horses, sausage dogs and incredible views paired with a kareoke room and a swimming pool. A site that can accommodate a plethora of activities, we would definitely revisit.
Superhost
Home in Dorset
4.88 out of 5 average rating, 8 reviews

East Creek + beach side + pool, dog Ringstead Bay

ZaraRating, 5 stars9 months ago
location was absolutely perfect for a relax and a decent walk everyday, we paddle boarded up the coast both ways and the scenery was stunning and finished most days with a swim in the pool. if you're after a close too everything place too stay this isn't the place for you but if you're looking for a break away from the world then this will tick all your boxes 🤗
Guest favourite
Home in Blandford Forum
4.98 out of 5 average rating, 55 reviews

Flint Cottage for two with indoor pool & sauna

Noelle And SamRating, 5 stars3 months ago
We had a blissful few days at Flint cottage. Wonderful kitchen to cook in, and multiple fabulous farm shops nearby. We ordered a heat and eat pie and a DIY breakfast pack for our first night, which made the start of the holiday so much more chilled out. The outdoor bath was also really special. We were so comfortable throughout we just relaxed completely. Can’t wait to come back!

Weekly house rentals

Top guest favourite
Home in Dorset
4.95 out of 5 average rating, 81 reviews

Cottage 5 mins walk to Harbour

DeniseRating, 5 stars1 day ago
This was our first trip to Weymouth and it won’t be the last! Jackie’s place is in a great location with its close proximity to the harbour and town. Coral Cottage is beautifully decorated with a seaside theme. It is homely and really comfortable and extremely well equipped - everything you could possibly need. The welcome pack was lovely - all local produce. Weymouth is perfect for a toddler - the sandy beach and shallow water - we struggled to get our grandson to leave it. Looking forward to a return visit. Thank you Jackie
Top guest favourite
Home in Dorset
4.95 out of 5 average rating, 43 reviews

Beachside Cottage with Panoramic views of the sea

JohnRating, 5 stars1 week ago
We stayed here in early June and loved the place. We were slightly perturbed that the sea view overlooked the Oasis Shop/Cafe small car park but in fact this was not noisy nor did it spoil the view. It is literally a 20 yard walk to the steep pebbled beach (some sand at low tide) and half an hour's walk to Weymouth pier along the promenade. There is also a frequent bus service. The accommodation is immaculate, having the living area upstairs. Everything we needed was provided - even an electric toothbrush charger in the bathroom. We spent many an hour on the balcony with drinks watching the swimmers, surfers, sailors and spotting the commercial/navy ships which often anchored in the bay. We had many a happy days out in the Weymouth area and were able to leave the car parked outside all the ten days as we used the bus services. We hope to return in the near future.
Guest favourite
Home in Dorset
4.9 out of 5 average rating, 30 reviews

Beautiful cottage with sea views & sunsets

VidyaRating, 5 stars1 month ago
We had a lovely stay at 2 Castle in Dorset. The property was full of charm, with a perfect blend of character and comfort. Everything was clean, well-maintained, and thoughtfully prepared. The kitchen was well-equipped, the beds were very comfortable, and we really appreciated the extra bed Peter put in for our little one. The location was fantastic—quiet and peaceful, yet close enough to explore the beautiful Dorset countryside and coast. Communication with Peter was smooth and responsive throughout, and check-in was easy. There was a little play area right opposite to the house and my little one enjoyed playing there. Overall, a wonderful spot for a relaxing getaway. We’d definitely stay here again and highly recommend it to others.
Guest favourite
Home in Dorset
4.9 out of 5 average rating, 71 reviews

Schooner Cottage

NatashaRating, 5 stars3 weeks ago
We had a very pleasant stay in Laura's lovely cottage, would happily book again.
Guest favourite
Home in Dorset
4.94 out of 5 average rating, 94 reviews

BEACH HOUSE: sleeps 14 right on Sea / Beach / Sand

HansaRating, 5 stars2 weeks ago
Our girls birthday weekend stay was fabulous! From the time I booked the house, check in till checkout all questions answered with quick responses from Patrick / Alison thank you 😊 we had an amazing time ! Excellent location opposite the beach and promenade walks every morning. 👍 the beach is clean, water is clear and swimming was enjoyable. Seaside activities a walk away with cafes and restaurants. Beach house is home from home with all your home comforts and so much more, also spacious loved the 2 kitchens and en-suites to all rooms 👍 very clean and tidy we had an amazing time and are looking for another occasion to go back ! Thank you Patrick for sharing your house and allowing us to stay there 😊
Top guest favourite
Home in Dorset
5 out of 5 average rating, 9 reviews

Nothe House - Exclusive home, Weymouth Harbour

CarleneRating, 5 stars1 month ago
Amazing house with fantastic views of the harbour. Great location as you can either walk to the beach or the town, or get the historic rowing ferry for a couple of quid, right at the bottom of the steps of Nothe Gardens. The house was really well equipped and had everything we needed for our stay, making it feel like a home away from home. Good size bedrooms with plenty of space downstairs for the 8 of us. The garden is a real sun trap and we enjoyed watching the sunsets in the evening. The hosts were brilliant - we couldn’t access the shed to get the BBQ and whilst we were out they had changed the lock and got it out ready for our return, amazing service! It was a lovely long weekend and we could’ve easily stayed longer - I can’t recommend Nothe House enough! Thank you so much!
Guest favourite
Home in Weymouth
4.98 out of 5 average rating, 51 reviews

Wolf Cottage - Stunning Harbourside Cottage

SamanthaRating, 5 stars3 months ago
I was actually disappointed when I first arrived. I had booked a "stunning harbourside cottage" only to discover this cottage is not by the harbour. However, the stunning part is accurate. It is a really lovely property that has been lovingly made into a home-from-home. Once you get over not being by the harbour, it is in a good location that is accessible to all Weymouth has to offer. We had a fabulous stay and would absolutely go back. Tim is a delightful and dedicated host.
Guest favourite
Home in Langton Herring
4.98 out of 5 average rating, 88 reviews

Coastguards Retreat: Luxury & Panoramic Sea Views

AllisonRating, 5 stars1 week ago
We absolutely loved this place. The home was clean and very up to date and very well done! The kitchen had everything we needed. The views were phenomenal and the fact it was so private was epic. I would 100% recommend this place to anyone interested in staying in this area. 5 stars are not enough.

Private house rentals

Guest favourite
Home in Dorset
4.97 out of 5 average rating, 62 reviews

Our Place in Portland Cosy Cottage with a Sea View

LauraRating, 5 stars1 week ago
Fantastic stay at Joanne's. The house was cozy and had all the appliances we could need for a few days and in very good condition. All little details had been carefully thougt of, including a welcome hamper. The shower had very good pressure and the terrace was very enjoyable in the sunny mornings. Parking can be tricky to find at times but despite that we had a very pleasant stay.
Superhost
Home in Dorset
4.84 out of 5 average rating, 38 reviews

Coastal Retreat

KatherineRating, 5 starstoday
Super house! Super comfy! Highly recommend!! Rachel went out of her way to help us a few times! Massive thanks for being so helpful
Top guest favourite
Home in Winfrith Newburgh
5 out of 5 average rating, 63 reviews

Cobweb Cottage, Winfrith Newburgh

ApichatRating, 5 stars1 week ago
It was great experience staying at The Cobweb cottage as it is very beautiful, nice and clean. We enjoyed our time there. I also would like say special thanks to Celia who was very proactive and responsive to our request.
Superhost
Home in Portland, Dorset
4.88 out of 5 average rating, 51 reviews

Seaview Home w/Private Garden,BBQ,Decking,Fire Pit

KrishanRating, 5 stars3 weeks ago
We had a lovely, peaceful stay at Kilpa’s place which is perfectly situated around farmland, with coastal walks, a pub and other amenities nearby. Her comms were brilliant throughout and she couldn’t have been more accommodating. I’d happily recommend her place to anyone looking for a great getaway in Dorset.
Guest favourite
Home in Dorset
4.95 out of 5 average rating, 19 reviews

Henley House

LeeRating, 5 starstoday
Second time staying at Leigh’s. Fantastic location with a short walk into town. Spacious house with room for all the family/ groups (to all be together or room to split up). Plenty of parking and decent sized garden to relax in. Great communication and flexibility. Leigh was happy for us to drop off some food/drinks in the fridge well before check in. We took the dog for a walk and then came back to move in properly. Lots of items in the garage which can be used at home or the beach. We love Weymouth as it’s great for walking (beaches or coastal paths) with plenty of good restaurants and pubs. We particularly like the area around Brewers Quay (close to the house). Leigh’s house is a fantastic place to base yourself to explore Weymouth and the surrounding area. Give it a try, you won’t be disappointed.
Top guest favourite
Home in Dorset
4.98 out of 5 average rating, 65 reviews

Newly renovated, 3 bed, 200m from beach, parking

ElliceRating, 5 starstoday
Wow! What can I say apart from AMAZING! not only is Sarah one of the kindest most helpful human beings her holiday home is next level of beautiful. The standard of decor and amenities is at the highest level and the home is absolutely cleaned to the highest standard- almost like it was brand new and unused! Sarah was so helpful literally planned my whole weekend for me so we saw and made the most of our time and made my partners 40th birthday surprise really something else! We would definitely be back to Sarah’s place as it was local and accessible and met beyond all our needs. You should be very proud Sarah you have an amazing home ! Thank you ☺️
Top guest favourite
Home in Dorset
5 out of 5 average rating, 16 reviews

1GB Wifi | SuperKing bed | Sport TV | Washer/Dryer

LouiseRating, 5 stars2 weeks ago
Thanks so much to Barney and Imogen for an amazing stay. Their cottage is light and spacious and beautifully furnished with all of the comforts and luxuries of home. We loved all the thoughtful touches such as a shopping cart for trips to the local supermarket, phone chargers in every room, TV platforms already set up and lots of interesting books and board games. And we were pleasantly surprised by the outside space which, although quite small, was a lovely, quiet, sunny spot for morning coffee.
Guest favourite
Home in Dorset
4.92 out of 5 average rating, 86 reviews

Two bedroom family home, minutes from the beach.

LeeRating, 5 stars2 weeks ago
This is our second time at Alison's and once again the house was lovely I had forgotten about the wonderful aroma of honeysuckle that greets you in the back yard, we found that in addition to the nice walk along Roswell old tram line, there is perhaps a slightly quicker way down the hill from the end of the road that leads into Weymouth Town centre, this place has everything that anyone could ever want, there is a beach close by and bus stops close by.Alison has been excellent once again.

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