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  • Shepherd Oak - (Ref. 932158)

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Shepherd Oak

Upwey near Weymouth, Dorset (Ref. 932158)



Sykes rating


  • Icon/Feature/Off-road parking Off road parking
  • Icon/Feature/Ground floor bedroom Ground floor accommodation
  • Icon/Feature/Ground floor bedroom Ground floor bedroom
  • Icon/Feature/Garden or Patio Garden / Patio
  • Icon/Feature/Baby-friendly Cot available
  • Icon/Feature/Baby-friendly Highchair available
  • Icon/Feature/Shop Pub/shop < 1 mile
  • Icon/Feature/Washing machine Washing machine
  • Icon/Feature/Dishwasher Dishwasher
  • Icon/Feature/WiFi Broadband / WiFi

Reviews & Ratings

Accuracy of the listing

21 Customer Reviews

  • "All was well the place was clean and well presented, however the lights in the entrance hall started flickering ( possible short ) also the downstairs loo the first light works but the centre one will not and the other end one will light if you keep switching it on and off."

    Having stayed here for three times the property is ready for painting, the downstairs loo door the outer finish is peeling back ( this was like it on our last visit) A positive is that Gemma phoned me on Monday to ask if everything was ok, i explained about the bathroom lights , she apologised and stated she would get someone over ? I thanked her and said do not worry. This is why i have scored 4 we will return too this property As listed on customer reviews about it not being clean , this is not the case .

    Reviewed by JoeOct 2021

  • "Lovely property in a great location."

    Very easy to book and good customer care.

    Reviewed by MartinAug 2021

  • "Given we were told that we could’ve arrive until 5pm and had to leave by 9am because of the rigour of Covid cleaning we were surprised to have to wash the cooking pots, utensils etc and avoid cobwebs."

    The dish washer was too small to accommodate a day’s meals, and not enough cutlery or crockery was available once the dishwasher was on. For four people you need eight of The downstairs bedside lamp is ripped. The kettle and toaster didn’t always work. The lay out of the house and the site as a whole was well planned with much thought going into planting to provide privacy between units. We liked it very much and would visit again if we knew cleaning had taken place. It is really not enough to expect one lot of guests to clean up after others.

    Reviewed by AnneJun 2021

  • "We really enjoyed Shepherd Oak, it had everything we needed and watching the deer in the garden was a bonus."

    The one query we had was quickly answered by Helen which was great. It's a great place to base yourselves to drive out and explore the Jurassic coast. Planning to book again in a few years time for a summer time holiday with family booking a few more of the lets neighbouring.

    Reviewed by DavidOct 2020

  • "With the Virus present it would be good to know what items are in the unit ( list ) The decor is tied and a bowl was chipped Having stayed in the same cottage before we can see the difference."

    But this did not spoil our holiday and we will more than likely book one of the other cottages.

    Reviewed by JoeSep 2020

  • "This is a very nice holiday home in a very good location for travelling in and around Devon."

    Good for families as there is a nice outside area when children can play safely. The home is a little limited in terms of kitchen equipment (which is understandable as the kitchen area is quite small). The washer/dryer machine appears to have some problems as it stops during the run and needs attention.

    Reviewed by StephenSep 2020

  • "Great location with plenty to see and do within just half an hours drive."

    Check in/out process so simple. Grounds to the property are great and perfect for families with children needing some outdoor space. A few minor areas of wear and tear but nothing that you probably wouldn't expect. Will 100% return.

    Reviewed by DaleMar 2020

  • "We started out holiday in the shepherd oak cottage, everything appeared clean and tidy, communication with the owner for key collection was great and all went well."

    Unfortunately on the second night we were disturbed by noise and in the morning found this was due to mice in the kitchen cupboards. There was a large amount of mice droppings, as we had a 1 year old with us, we contacted the owner and asked to be moved to another cottage. Within the hour we were in an adjacent cottage Bramshurst. Bramshurst was clean and tidy and perfectly adequate (no mice), however it was a less expensive cottage due to the architecture, windows and location of the property (being terraced and not semi detected, and having a view onto the other cottages, rather than open grass). The owner checked we were ok and everything was fine in the new cottage, however after checking out and requesting the difference in price to be refunded from Shepherds Oak to Bramshurst or any compensation for the move of property, this was rejected and a 10% discount offered if we booked directly with them next time, offered instead. We do not think this is acceptable and would like the difference in cottages price refunded at the least - if we had wanted to stay in the cheaper cottage we would have booked it and saved money.

    Thank you for your feedback We appreciate you reporting the issue with the mouse. The cottage is in a countryside location where field mice live. We understood your concerns and moved you to a different property within the hour. This property is exactly the same as Shepherd Oak apart from the view. It’s really important to us that our Customers have a good holiday & if there are any problems we need this to be reported so we can take immediate action. Things can happen on holiday and as an owner it’s important that we listen and take action. We didn’t hear anything further from you during the holiday so had concluded that all was ok for you. As a gesture, we would like to offer you a 10% discount off a future stay with us. Property Owner

    Reviewed by JudyNov 2019

  • "Excellent accommodation."

    Very nice location. We would book it again when we go to Weymouth.

    Reviewed by HelenJul 2019

  • "What a lovely location, we have a small well behaved dog and the positioning of this cottage was perfect for us."

    With a bubbling brook close by, scenic walks and beautiful open spaces our short stay was idyllic. Positioned a couple of miles from both Weymouth and Dorchester you have the opportunity of beach and town with the ability to retire to tranquility. Loved every minute of it, lovely property, we would stay here again and have already recommended to others.

    Reviewed by MartinApr 2019

  • "The property was excellent,location and building etc."

    However the upstairs vanity mirror light would not switch of , also the main lights when on were flickering, cooker hood one light inop and the filters need cleaning ( smells ) These points did not cause a problem, damage to the bed room wall down stairs, along with 5 glasses not sure if they should be 6 ?? Apart from that we will be booking this property for next year,it was in a superb location. One other point the contact from Skye’s all the way was excellent and a positive one.

    Reviewed by JoeOct 2018

  • "What a lovely home a credit to the owners in a beautiful part of the country well worth a visit"

    Reviewed by DavMay 2018

  • "Beautiful location in the countryside, but still just a short drive from the beaches and tourist attractions in Weymouth."

    This cottage has been very cleverly and thoughtfully put together for holiday-makers - with unique classic features such as the full height living area windows looking out over the fields, but also very well appointed modern luxuries (got to love hot water on demand when you've got four tired, sandy and/or muddy people at the end of a great day out).

    Reviewed by EdwardApr 2018

  • "The cottage is lovely and very comfortable, in a great location."

    No complaints at all but considering the considerable price we paid for a 2 night stay we were a little disappointed that the experience could have been more welcoming. We have booked through holidaycottages.co.uk on a number of occasions and feel that the attention to detail is better. For example, the dvd remote did not work. Also mirror light in ensuite. Holiday cottages tend to have a small welcome pack to save an immediate shopping trip (eg. Milk, bread, jam). Basics like kitchen roll, cooking oil. Only small things but these make a difference when booking in the future. Regarding the accommodation itself, the only aspect that could be improved is to be able to prevent the dog from going up to the bedroom area.

    Reviewed by AlanMar 2018

  • "Arrived after the arrival time to find a gang of cleaners in the barn, a chap said that the previous occupants had trashed the place but give them half an hour to finish cleaning."

    We drove off to find somewhere to eat after our journey, we arrived back an hour or so later wondering what state the place would be in. It was fine just normal wear and tear but generally clean except that the fridge had been cleaned using a strong bleach which contaminated our food for three days, the extractor hood over the hob was dripping grease when the hob was in use and the kettle needed descaling of limescale. The barn was comfortable and well fitted out with good parking for the car.

    Reviewed by LindaMar 2018

  • "We were actually upgraded to the castlebridge 3 bed house 2bedrooms downstairs the master with ensuite upstairs."

    Gorgeous interior, lots of things not expected washer/dryer dishwasher etc etc

    Reviewed by NicoleMar 2018

  • "Lovely property, very clean and comfortable."

    Enjoyed our stay, owner Helen is friendly and happy to help. Really impressed had everything we needed for our baby stair gate even thaught of, bowls too.

    Reviewed by ClareNov 2017

  • "Excellent accomodation."

    Good facilities Nice quiet area but close enough to weymouth for the shops, pubs and beach.

    Reviewed by MitchellNov 2016

  • "Superb cottage, well designed with all Mod Cons - very well located in village setting, yet close to Weymouth beach, pubs and supermarkets."

    We and our dog loved the peaceful setting, the panoramic views and the local stream where he paddled most days. Alfie regularly mixed with our neighbours children who enjoyed his company throughout our stay. Overall, quite pricey for a 2 bedroom cottage in August, but I guess you do get what you pay and we were very lucky with the weather. Steve & Lorna - Aug 16

    Reviewed by StephenAug 2016

  • "Excellent accommodation and a great location for exploring the surrounding area."

    Reviewed by GaryJul 2016

  • "Had a great stay at Shepherd Oak, it was a really good base to explore Dorset."

    The cottage is excellent and the owner was really helpful from start to finish. Would highly recommend to anyone looking for a pet friendly location.

    Reviewed by SteveApr 2016

Show more

North Manor Meadow Cottages

A cluster of five impressive, architect-designed cottages nestling in a semi-rural south Dorset location, within the valley of the River Wey, on the edge of the village of Upwey, just 3.5 miles north of Weymouth. These five wonderful holiday homes are grouped around an attractive shingled courtyard and are the perfect base for couples, families or friends who wish to enjoy all that Dorset has to offer. These superb cottages have been created to offer holiday accommodation of an exceptionally high standard, featuring vaulted ceilings and en-suite facilities, and great attention to detail has been made in the choice of furnishings and equipment in each one. Each cottage has its own private patio area, as well as use of attractive shared raised lawned areas that take you up shingle paths to a seating area. With such a variety of accommodation on offer, up to 24 people can enjoy the delights of this lovely location, situated so close to the family-friendly seaside resort of Weymouth with its golden sands, attractive harbour offering diving and fishing trips and all kinds of watersports. Locally, take a visit to nearby Portland with its rugged scenery and dramatic Chesil Beach, or venture inland to the attractive bustling market town of Dorchester, Thomas Hardy’s ‘Casterbridge’, where you will find a fine selection of shops and restaurants. In fact there’s so much to see and do, a week is hardly long enough! These luxurious cottages provide an excellent and convenient base from which to explore this stunning coastal area.

The property

This superb semi-detached cottage is one of five on-site and is located on the edge of the village of Upwey, near Weymouth.

This quality cottage has been constructed and furnished to a very high standard.

Once inside this luxury cottage you will find vaulted ceilings in the open plan living area, along with floor-to-ceiling windows.

Also on the ground floor is a zip/link king-size double bedroom and a bathroom, and on the first floor is a mezzanine bedroom with en-suite facilities.

Open the doors out to the patio to your own sitting area, where you can relax with a glass of your favourite tipple.

This beautiful cottage is an ideal touring base for couples, families and friends.

Note: This property can be booked with Refs: 932157, 932159, 932160 and 932161, together they sleep 24 people.


  • Mostly ground floor
  • Two bedrooms: 1 x first floor mezzanine double with en-suite shower, basin and WC, 1 x king-size double (zip/link, can be twin on request)
  • Bathroom with bath, shower over, basin and WC
  • Open plan living area with kitchen, dining area and sitting area.
  • Gas central heating
  • Electric oven and ceramic hob, microwave, fridge, washer/dryer, dishwasher, 3 x Smart TVs with Freeview, WiFi
  • Fuel and power inc. in rent
  • Bed linen and towels inc. in rent
  • Travel cot and highchair on request
  • Off road parking for 1 car
  • Private patio with furniture, plus shared hillside garden with picnic benches
  • One well-behaved dog welcome
  • Sorry, no smoking
  • Shop and pub 10 mins walk
  • Beach 3.5 miles
  • Note: Dogs must be kept on a lead whilst outside, and nearby kennels available to rent by arrangement with owner
  • Note: Sloping ceiling in first floor bedroom.

View on map

About the location


Dorchester 4.5 miles; Weymouth 4 miles.

The picturesque village of Upwey lies just four miles north of Weymouth, nestling beneath the Dorset Ridgeway, and takes its name from the shallow chalk stream, the River Wey, which bubbles up here from an underground spring. Upwey is well-known for its Wishing Well, where George III once sought the benefits of the natural spring water. It is now a delightful tea room, serving lunches and traditional cream teas. There are a number of footpaths leading directly from the village to miles of unspoilt countryside, and close by is the market town of Dorchester, Thomas Hardy’s ’Casterbridge’. An easy drive or bus ride takes you to the popular seaside resort of Weymouth offering visitors glorious golden sandy beaches, excellent watersports facilities and a bustling harbour. An attractive village location and an ideal place to escape from the hustle and bustle of everyday life.

Region Information

This property offers the following short breaks:

  • Winter
  • Christmas
Book with confidence
If your booking can't take place due to a COVID-19 lockdown in the UK or Ireland, you can request a change of date or receive a full rental charges refund.

Owners may request any evidence that they reasonably require before making a refund. Sykes Holiday Cottages is not agreeing to pay or guarantee any refund from the Owner to you under this Book with confidence.
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