50 Best Berkshire Apartments on Holiday Lettings - Vacation rentals

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Windsor and Maidenhead
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141 Vacation rentals

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(14) Excellent 

40

Vacation home in Windsor

Windsor and Maidenhead / Windsor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
This charming detached Grade ll listed 16th Century cottage offers an abundance of beautiful character features. Nestled behind secure gates, in mature gardens in this charming Buckinghamshire village. It retains its original character combined with 21st century facili  …see more

from $153 / night

$1068 / week

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from $153 / night

(1)  

10

Vacation home in Finchampstead

Wokingham / Finchampstead

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
We have luxury 3 bedroom chalets set in the beautiful village of Finchampstead. This woodland park is situated on the 100 acre estate of California Country Park. Within the estate you will find the magnificent Longmoor Lake which runs parallel to the park. Beautiful wal  …see more

from $116 / night

$787 - $974 / week

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from $116 / night

(31) Excellent 

28

Vacation cottage in Windsor

Windsor and Maidenhead / Windsor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
This beautiful unique 18th century cottage retains its original character combined with 21st century facilities and five star amenities. An open plan ground floor style makes it ideal for families and entertaining. The kitchen leads onto a secure rear garden with outs  …see more

from $129 / night

$897 / week

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from $129 / night

(8) Very Good 

24

Eton Vacation apartment rental

Windsor / Eton

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
A charming and characterful period two bedroom apartment on Eton High Street. 3 minutes walk to Windsor & Eton train station and fantastic shops, cafes restaurants gallerys and antique shops all within very easy reach. This lovely apartment matches modern living wi  …see more

from $196 / night

$1367 / week

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from $196 / night

20

Old Windsor Vacation cottage rental

Windsor / Old Windsor

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
The Cottage is set on a quiet country road, directly opposite the magnificent Windsor Great Park, with spectacular views of Windsor Castle. It's a super warm, super cosy cottage, with a lovely garden in a unique location, on a quiet and private estate of four hou  …see more

from $232 / night

$1922 / week

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from $232 / night

(11) Excellent 

25

Wokingham Vacation home rental

Berkshire / Wokingham

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 120 mi
  • Car not necessary
Kings House is a newly renovated Grade II listed building located in the heart of Wokingham and only a short walk from the station with direct rail links to London, Gatwick and Reading. The property is a two-storey, spacious town house with a new, well equipped kitchen  …see more

from $171 / night

$976 - $1318 / week

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from $171 / night

(4) Very Good 

26

Old Windsor Vacation cottage rental

Windsor / Old Windsor

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The old wharf cottage is a beautiful riverside retreat nestled between two islands on the picturesque banks of the River Thames. Situated minutes from the historic town of Windsor and Eton as well as 40 minutes from the attractions of central London. Watch the river go  …see more

from $549 / night

$3660 - $3904 / week

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from $549 / night

(7) Very Good 

13

Vacation apartment accommodation

Windsor and Maidenhead / Windsor

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary
My lovely apartment is advertised for short term lettings (maximum one month stay) and features: - Car parking space - Sofa bed for an additional 2 adults - Sky TV & Wifi - Less than 1 minute walk to the town centre - 5 minutes drive to Legoland The apartment has  …see more

from $110 / night

$732 - $818 / week

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from $110 / night

(2) Very Good 

9

Vacation home in Eton

Berkshire / Eton

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Car not necessary
  • Private garden
Two bedroom cottage with garden just off Eton High Street just a short walk to Windsor and Eton Bridge and nearby restaurants and shops plus the train station. One double and one twin bedroom, one bathroom and lovely open plan kitchen / dining room with separate galley  …see more

from $153 / night

$836 - $958 / week

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from $153 / night

(7) Excellent 

16

Windsor Vacation apartment rental

Windsor and Maidenhead / Windsor

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
Superb, bright, modern, spacious 2 bedroom, 2 bathroom apartment with parking in gated development a short walk from Windsor town centre. Large entrance hall, modern luxury kitchen with built in dishwasher and washing machine, spacious lounge/diner with double doors  …see more

from $153 / night

$975 - $1556 / week

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from $153 / night

(1) Excellent 

17

Eton Vacation townhouse rental

Berkshire / Eton

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
A three storey town house in the popular Kingstable Street development with private off road parking for one car. This location is superb - literally three minutes walk to Windsor & Eton Bridge and the train station at Riverside. This property has three good size do  …see more

from $214 / night

$1458 - $1647 / week

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from $214 / night

(1) Very Good 

13

Vacation home in Windsor

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Car not necessary
  • Private garden
Charming two bedroom holiday cottage in Windsor with one double bedroom and second bed room with twin beds (pull out). Two sofas (one is a sofa bed) and dining table with four chairs.One bathroom with shower and tub very close to town centre yet tucked away in t  …see more

from $146 / night

$854 - $1037 / week

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from $146 / night

(12) Excellent 

24

Vacation cottage in Windsor

Windsor and Maidenhead / Windsor

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Private garden
Willow Cottage is a beautiful and unique self catered holiday cottage set in a rural village but only minutes away from Windsor in Berkshire and 15 minutes from Heathrow airport. The cottage is perfect for a couple wanting to spend a peaceful few days away or a family n  …see more

from $177 / night

$1367 - $1458 / week

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from $177 / night

(1) Excellent 

9

Vacation apartment in Slough

Berkshire / Slough

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
Brand new, modern and spacious two bedroom, two bathroom apartment situated within walking distance of Slough train and bus station and the high street. The apartment is fully furnished, and has all the kitchen and bathroom amenities you would need and is serviced on a  …see more

from $141 / night

$940 / week

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from $141 / night

(26) Excellent 

20

Vacation cottage in Waltham St Lawrence

Berkshire / Waltham St Lawrence

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 0 mi
  • Child friendly
This beautifully restored Wheelwrights has been transformed into a contemporary 2 bedroom, (one kingsize bed. One twin beds) 2 bathroom cottage with all the luxuries of a modern home, and yet maintaining its original oak beams, vaulted ceilings and light gallery. Rela  …see more

from $196 / night

$1159 / week

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from $196 / night

(3) Excellent 

16

Windsor Vacation home rental

Windsor and Maidenhead / Windsor

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Child friendly
  • Car not necessary
  • Private garden
Town Centre Location with allocated parking. Beautiful secluded one-bedroom character cottage situated just a stone's throw from Windsor town centre shops & restaurants. Quiet mews area incorporating communal lawn area. The property has been totally modernise  …see more

from $104 / night

$726 - $806 / week

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from $104 / night

(16) Excellent 

18

Vacation cottage rental

Newbury / Enborne

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets
Attached single storey cottage in very quiet rural position only 2 miles from town centre Two bedrooms each with power showers, one twin, one double Central heating throughout. Sitting room with dining area and fully equipped kitchen. Patio overlooking the courtyard Mi  …see more

from $80 / night

$537 / week

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from $80 / night

(1) Excellent 

8

Maidenhead Riverside Vacation cottage rental

Maidenhead / Maidenhead Riverside

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Child friendly
  • Pet friendly
Modern, comfortable fully equipped one bedroom cottage. Suitable for short to medium term lets. Sleeps 2, (plus child on sofa bed). Tastefully converted stable, looking out onto fields and lakes. Off street parking, free wifi, laundry. Weekly service included in price.  …see more

from $92 / night

$641 - $1281 / week

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from $92 / night

(4) Excellent 

18

Vacation home in Windsor

Windsor and Maidenhead / Windsor

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Private garden
Eton/Windsor In the heart of Eton High Street, 2 minutes walk to Windsor Castle or Eton College. A unique opportunity to holiday in a 400 year old, grade 2 listed cottage, exposed beams. Boutique accommodation. Bespoke fitted kitchen, Neff appliances and double oven B  …see more

from $183 / night

$1281 / week

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from $183 / night

(12) Very Good 

45

Vacation apartment in Windsor

Windsor and Maidenhead / Windsor

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets
The Clockhouse is full of charm and character. There is a large bedroom/living room which features a double bed and an extra bed can be arranged if required. The comfortable bedroom has ample wardrobe space. There is a shower room on the ground floor, featuring a shower  …see more

from $147 / night

$1025 - $1281 / week

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from $147 / night

(3) Very Good 

28

Newbury Vacation apartment rental

Berkshire / Newbury

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary
Beautifully furnished with spacious living room with lot of natural light, to make yourself at home away from home. Featuring a fully equipped kitchen and furnished throughout, this apartment offer an ideal living space for professionals and families. This executive a  …see more

from $141 / night

$824 / week

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from $141 / night

15

Vacation home in Windsor

Windsor and Maidenhead / Windsor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
Lovely two bedroom cottage in the centre of Windsor with private off-road parking. Two bedrooms (one double one twin), new bathroom with shower over bath tub, combined living/dining room with leather sofas and flat screen TV. Small enclosed outside patio space a  …see more

from $116 / night

$793 - $1007 / week

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from $116 / night

8

Vacation home in Cookham

Windsor and Maidenhead / Cookham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
Our little chocolate box cottage is newly refurbished with an open plan living room and kitchen and an open fire. Cookham is a beautiful bustling typical English village with all the amenities and many lovely pubs and restaurants and easily accessible from London Paddin  …see more

from $135 / night

$854 - $915 / week

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from $135 / night

12

Vacation apartment rental

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
Spacious apartment on the second floor of this executive apartment block. Electric gates to private parking area. Two bedrooms and two bathrooms. Master bedroom is ensuite, second bedroom has twin beds. Large kitchen with all modern appliances including washer-dryer,  …see more

from $153 / night

$731 - $1037 / week

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from $153 / night

15

Caversham Vacation apartment rental

Reading / Caversham

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
The Kennet Apartments are conveniently situated in Reading town centre. This secure residence offer's our visitors an exclusive and comfortable stay. Apartments are fully-furnished to a high standard with parking, HD TV and free Wi-Fi. The living areas are spacio  …see more

from $183 / night

$1281 / week

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from $183 / night

(1) Excellent 

14

Vacation home with tennis court in Newbury

Berkshire / Newbury

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Swimming pool
  • Child friendly
This is a stunning, designer house sleeping 13-15 guests which is available for holiday or short let rental in a wonderful setting in one of the most desirable areas of England within easy reach of London and the South West, and Cotswolds. It is perfect for any family w  …see more

from $976 / night

$4880 - $9468 / week

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from $976 / night

(3) Very Good 

18

Eton Vacation home rental

Windsor / Eton

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Car not necessary
Eton/Windsor In the heart of Eton High Street, 2 minutes walk to Windsor Castle or Eton College. A unique opportunity to holiday in a 400 year old, grade 2 listed cottage, exposed beams. Boutique accommodation. Bespoke fitted kitchen, Neff appliances and double oven B  …see more

from $183 / night

$1281 / week

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from $183 / night

11

Windsor Vacation apartment rental

Windsor and Maidenhead / Windsor

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
This beautiful character Central Windsor apartment with high ceilings and wooden floors is in a great location close to everything! ...Windsor Castle, beautiful crisp river walks, Alexandra Gardens, Eton College, train stations, bus routes and tucked away just a few min  …see more

from $121 / night

$731 - $987 / week

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from $121 / night

(12) Excellent 

16

Slough Vacation apartment rental

Berkshire / Slough

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
Rivington Apartments are in a new development in central Slough. The apartment is a 5 minute walk to the town centre with numerous shops, cafes and restaurants and Slough's Business Parks are within easy reach. The apartment is in an ideal location for comm  …see more

from $170 / night

$1097 - $1183 / week

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from $170 / night

(7) Excellent 

15

Apartment rental in Maidenhead Riverside with shared pool

Maidenhead / Maidenhead Riverside

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Suitable for children age 5+
New, spacious, sunny apartment in the leafy Riverside area of Maidenhead. Located in a quiet cul-de-sac, on the first floor, with Private Entrance and Off-street Parking. Ideal for runners and walkers, with direct access to the beautiful Thames Path. Walking distance  …see more

from $81 / night

$470 - $531 / week

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from $81 / night

(4) Very Good 

22

Vacation apartment in Windsor

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Car not necessary
9 The Courtyard is a well-appointed apartment situated in a secluded courtyard setting, with direct access to Windsor High Street. Just opposite is the Guildhall and a few steps away is the entrance to Windsor Castle, the largest castle in occupation. A short walk furth  …see more

from $104 / night

$726 - $952 / week

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from $104 / night

(37) Excellent 

24

Ascot Vacation apartment rental

Windsor and Maidenhead / Ascot

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 110 mi
  • Child friendly
  • Car not necessary
Windsor Forest Court is a small and exclusive mews development situated in leafy Ascot, on the 18 hole private Mill Ride Golf Course, (ideal for a Golfing Holiday). The gated, converted stables are truly stunning and of historical interest, being built in the early 190  …see more

from $156 / night

$1086 / week

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from $156 / night

(20) Excellent 

11

Apartment rental in Bracknell

Berkshire / Bracknell

1 3 6 nights min

  • 1 bedroom
  • Sleeps 3
  • 6 nights min
  • Beach/lakeside relaxation
  • Nearest beach 112 mi
  • Child friendly
The apartment at Palm Tree Cottage is a competitively-priced one-bedroom property, that sleeps 3, ideal for self-catering visitors and for business executives who need temporary accommodation with a super fast Wi-Fi service. Located in a quiet, pleasant resident  …see more

from $80 / night

$525 / week

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from $80 / night

30

Vacation home in Hurley

Maidenhead / Hurley

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
Enjoy a family gathering or friends reunion in this beautiful stylish home. Equipped with all you could need for a special occasion. Situated in a pretty 'no through access' village with a wonderfully active community. The property has stunning gardens inclu  …see more

from $1464 / night

$4148 - $7625 / week

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from $1464 / night

(5) Very Good 

10

Vacation apartment in Windsor

Windsor and Maidenhead / Windsor

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Ask about pets
A spacious modern ground floor apartment, conveniently situated within 15/20mn walk to Windsor town centre and with easy access to M4, M25, M3 & Heathrow. The property provides the following accommodation; entrance hall, spacious lounge, modern open plan kitchen w  …see more

from $99 / night

$692 / week

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from $99 / night

(2) Good 

25

Home rental in Maidenhead

Windsor and Maidenhead / Maidenhead

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Private garden
Sept 2016 update: We are very pleased to announce that our hot water system has now been upgraded to ensure great supply and pressure of hot water in both bathrooms and all taps at all times. Welcome to our comfortable house in Maidenhead perfect for groups up to 7 p  …see more

from $122 / night

$854 / week

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from $122 / night

(3) Very Good 

12

Vacation bungalow in Datchet

Windsor and Maidenhead / Datchet

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Ask about children
  • Private garden
Modern, spacious and tastefully furnished bungalow near Heathrow, Windsor and easy links to London. Secure gated parking with gardens. Wireless internet, TV, fully fitted kitchen with quartz worktops. Windsor and LEGOLAND is within easy reach via car. The accommodation  …see more

from $122 / night

$793 / week

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from $122 / night

15

Vacation apartment in Windsor

Windsor and Maidenhead / Windsor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
A quirky two bedroom two bathroom apartment in a former convent about one mile from Windsor town centre. This apartment is set in lovely grounds and has plenty of parking. It is located on the first floor and has a lovely spiral staircase to the top floor bedroom with v  …see more

from $147 / night

$824 - $1129 / week

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from $147 / night

(2) Excellent 

11

Vacation home with golf nearby in Ascot

Windsor and Maidenhead / Ascot

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Car not necessary
  • Private garden
Secluded Luxury Property - set within idyllic golf course. Benefiting from use of the course and club house facilities, bar,sauna,restaurant and gym.5 bedrooms 2 ground floor bedrooms with en suites, 3 further bedrooms to first floor with a family bathroom.Entra  …see more

from $187 / night

$1307 - $2294 / week

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from $187 / night

(8) Excellent 

18

Vacation cottage in Holyport

Windsor and Maidenhead / Holyport

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
Perfectly located in the village with two great pubs either end of the street who serve great food and beverages. The village is fantastically located for Windsor Castle, LEGOLAND, Bray ( The Fat Duck and The Waterside Inn)and London ( 19mins train ride). It has a sunli  …see more

from $129 / night

$897 / week

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from $129 / night