50 Best Cheltenham Apartments on Holiday Lettings - Estates

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Cheltenham
16 properties
Montpellier suburb
12 properties
Charlton Kings
10 properties
Pittville
6 properties
Prestbury
5 properties

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122 Vacation rentals

(4) Excellent 

20

Vacation cottage with golf nearby in Charlton Kings

Cheltenham / Charlton Kings

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
You’ll find King’s Cottage on the edge of Cheltenham in Charlton Kings. You are just minutes away from the Cotswolds and its delightful villages and exquisite countryside. Of course Cheltenham itself has so much to offer too, a vibrant regency town with fabu  …see more

from $124 / night

$682 - $782 / week

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from $124 / night

(18) Very Good 

12

Vacation apartment rental

Cheltenham / Cheltenham

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 90 mi
  • Child friendly
  • Car not necessary
The Garden Apartment has its own entrance and small terrace with garden table and chairs. The accommodation consists of a double bedroom with bathroom en-suite together with a double futon in the living room for two additional people. A £10 extra linen charge is a  …see more

from $118 / night

$1488 / week

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from $118 / night

(45) Excellent 

23

Vacation home rental

Cotswolds / Cheltenham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Living room with wood-burning stove, French doors to garden and tiled floor/dining room with kitchen area. First floor: Double bedroom with 5ft 6in bed. Further double bedroom with additional single bed (for alternative sleeping only). Bathroom with over-bath shower and  …see more

from $124 / night

$620 - $1364 / week

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from $124 / night

(12) Excellent 

20

Vacation cottage with golf nearby in Pittville

Cheltenham / Pittville

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Amazing location, ideal for a relaxing break in the Cotswolds. Family house (not a holiday chalet) in the middle of Cleeve Common, with gardens and fantastic views over historic, Regency Cheltenham Spa. Sleeps 7 people easily in 3 double bedrooms and one singl  …see more

from $199 / night

$930 - $2297 / week

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from $199 / night

(5) Very Good 

18

Vacation apartment in Prestbury

Cheltenham / Prestbury

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Individual en suite rooms or the whole apartment available. Bonus: easy access to racecourse, town and the Cotswold villages. 130.00 for 1 night, 200.00 for 2 nights. This modern style Penthouse Apartment is located in a beautiful, prime location of Cheltenham.There ar  …see more

from $162 / night

$682 - $1377 / week

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from $162 / night

(3) Excellent 

9

Vacation cottage with golf nearby in Cheltenham

Cheltenham / Cheltenham

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
Hazleford Cottage stands in the grounds of Seven Springs Cottages. It is one of six self-catering cottages offering excellent facilities for couples wishing to enjoy all that the Cotswolds and Cheltenham have to offer. It has a double bedroom, newly fitted bathroom and  …see more

from $81 / night

$385 - $484 / week

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from $81 / night

16

Vacation home rental

Cheltenham / Andoversford

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ask about children
  • Private garden
Our home is a semi detached three bedroom house on three floors. Ground floor: kitchen with dishwasher, washing machine, microwave, grill, oven, five hobs, fridge and fridge freezer. with access to the downstairs WC. Living room with seating for five, free-view and Wi  …see more

from $186 / night

$1377 / week

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from $186 / night

(1) Excellent 

18

Southam Vacation barn rental

Cheltenham / Southam

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
Furlong Barn is a beautiful property in a stunning, secluded position, enjoying uninterrupted views across Warwickshire farmland from all aspects. This comes with the added advantage of being on the edge of the pretty village of Long Itchington, with its pond and villag  …see more

from $399 / night

$2788 - $4401 / week

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from $399 / night

(1) Excellent 

30

Charlton Kings Vacation studio rental

Cheltenham / Charlton Kings

Studio 2 1 night min

  • Studio
  • Sleeps 2
  • 1 night min
  • Ask about pets
This Brand New property was built as a granny flat / nannie's flat in the grounds to our house. We have young family with four children but the Annexe is entirely self contained including its own entrance. We are in walking distance to Cheltenham Town centr  …see more

from $75 / night

$298 / week

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from $75 / night

(31) Excellent 

40

Vacation farmhouse in Cheltenham

Cheltenham / Cheltenham

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
*** Awarded Quality in Tourism 4 Star Gold *** Detached Cotswold stone farmhouse situated in an area of outstanding natural beauty. Situated above Woodmancote near Bishops Cleeve, the farmhouse enjoys incredible panoramic views across Cheltenham, Tewkesbury and towards  …see more

from $310 / night

$1487 - $2480 / week

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from $310 / night

(6) Excellent 

28

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
This delightful farm house is approximately 4 miles above the charming ancient Saxon town of Winchcombe and is situated on a 220 acre sheep grazing farm which comprises a small community of four homes. The house was first built in 1949 and extensively rebuilt by the cur  …see more

from $87 / night

$608 / week

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from $87 / night

(3) Excellent 

18

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Car not necessary
  • Private garden
We can accommodate up to a maximum of 5 people plus a baby. Travel cot available. The 4* Courtyard Apartment at Vine Court offers 2 bedrooms (1 double and 1 single plus a double sofa bed in the sitting room) , a large country kitchen/diner with dishwasher, range cook  …see more

from $199 / night

$682 - $930 / week

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from $199 / night

(5) Very Good 

10

Vacation apartment in Montpellier suburb

Cheltenham / Montpellier suburb

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 94 mi
  • Child friendly
  • Car not necessary
Located in the heart of the popular Montpellier area of Cheltenham, with its' abundance of designer shops, restaurants and pavement cafes, Lansdown Place is a beautiful two bedroom / two bathroom apartment in a great location. The beds can be configured as two King  …see more

from $248 / night

$1216 / week

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from $248 / night

(5) Very Good 

34

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 mi
  • Car not necessary
This lovely 2 bedroomed ground floor apartment with private and secure parking for 2 vehicles is situated in the sought after Montpellier area of Cheltenham. It offers two spacious double bedrooms, one with ensuite facilities with a double shower. The second bathroom  …see more

from $118 / night

$682 - $1612 / week

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from $118 / night

(10) Very Good 

14

Vacation studio in Cheltenham

Cheltenham / Cheltenham

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Ask about children
IN THE HEART OF THE COTSWOLDS Self catering studio apartment with all mod cons., built and furbished in 2012 in the Cotswold village of Woodmancote. Immediate area has thatched cottages, old pubs serving meals, and many beautiful footpaths. Apartment is at the foot of  …see more

from $67 / night

$335 - $366 / week

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from $67 / night

2

Vacation studio in Prestbury

Cheltenham / Prestbury

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Car not necessary
A ground floor studio annexe with its own private entrance attached to our modern 3 storey house, situated in a quiet area between Cheltenham racecourse and Pittville Park within a small gated development with secure off road parking. The studio consists of a large sit  …see more

from $81 / night

$416 / week

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from $81 / night

(5) Excellent 

11

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Private garden
An immaculate, split level interesting two bedroom period apartment with a private garden this apartment offers luxury accommodation for the discerning. ,Comfortably furnished to a high standard with a well equipped kitchen and large luxury bathroom,, with a walk in  …see more

from $224 / night

$1364 - $1674 / week

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from $224 / night

(5) Very Good 

19

Vacation cottage with golf nearby in Charlton Kings

Cheltenham / Charlton Kings

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
Nethercote Cottage stands in the grounds of Seven Springs Cottages. It is one of six self-catering cottages offering excellent facilities for couples wishing to enjoy all that the Cotswolds and Cheltenham have to offer. It has a double bedroom, newly fitted bathroom a  …see more

from $81 / night

$434 - $930 / week

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from $81 / night

(15) Excellent 

30

Vacation townhouse in Pittville

Cheltenham / Pittville

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
We would like to invite you to book some quality time at our stunning, refurbished, period property, enjoying all that Cheltenham and the Costwolds have to offer! Leave your car behind and walk to the centre of the town in 10mins, or in the opposite direction to the rac  …see more

from $186 / night

$1302 / week

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from $186 / night

9

Vacation apartment in Southam

Cheltenham / Southam

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
This one bedroom apartment is in a great location to get to the town center and Cheltenham Race course. It has recently been refurbished, and benefits from high ceilings with floor-to-ceiling sash windows, and residential parking.The dinning room has original fl  …see more

from $124 / night

$720 / week

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from $124 / night

8

Vacation home in Guiting Power

Cheltenham / Guiting Power

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
The Coach House is a detached property in the grounds of the Grade II listed 16th century Old Rectory. Hawling is an unspoilt village eight miles from Cheltenham, situated at the highest point of the Cotswolds.The nearest shop and pub at Guiting Power is  …see more

from $207 / night

$1448 - $2123 / week

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from $207 / night

13

Vacation home accommodation

Cheltenham / Cheltenham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
Self-catering house in a quiet residental area on the Western side of Cheltenham affording easy access to the M5 North to Tewkesbury, Worcester and Birmingham. Staverton and Gloucester are easily accessible by quiet back roads or main carriageway. "Riverside"  …see more

from $186 / night

$744 / week

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from $186 / night

(10) Excellent 

12

Vacation chalet rental

Cheltenham / Charlton Kings

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Wellinghill Lodge is a newly constructed chalet situated down a quiet lane overlooking fields leading to the Cotswold Way, yet just minutes in a car from the centre of Cheltenham. Look out the window and see the hens strutting freely in the field. Enjoy fresh eggs for b  …see more

from $100 / night

$490 - $496 / week

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from $100 / night

(1) Excellent 

9

Apartment rental in Montpellier suburb with golf nearby

Cheltenham / Montpellier suburb

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Suitable for children age 5+
  • Car not necessary
We are offering a 2 bedroom apartment adjoining our Longworth villa. The apartment includes a lounge/dining area. A contemporary kitchen including electric hob/cooker washing machine. Bathroom with basin, w.c. and P shape bath/shower. Double bedroom with double bed ward  …see more

from $185 / night

$726 - $1860 / week

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from $185 / night

9

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
This property is located in the heart of Cheltenham Town Centre with all amenities on your doorstep. The 2nd floor houses a Large Kitchen area, Newly fitted with Electric Oven and Hob, Washer dryer, Fridge and Freezer, Large Living/dining room with a feature firep  …see more

from $224 / night

$1563 / week

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from $224 / night

(3) Very Good 

16

Home rental in Cheltenham

Cotswolds / Cheltenham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Car not necessary
Originally built in the 1850's The Coach House was once a two story stone workshop with views overlooking Leckhampton Hill. It was extended, modernised and refurbished in 2011, becoming a 1 bedroomed detached house. With it's own private entrance and patio,  …see more

from $93 / night

$558 / week

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from $93 / night

(35) Excellent 

24

Vacation apartment in Cheltenham

Cheltenham / Cheltenham

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 35 mi
  • Suitable for children age 5+
  • Car not necessary
Voted no.1 holiday rental in Cheltenham on Tripadvisor. Affordable Luxury is our ethos..That is why we have Quality furnishing, give Great service. and have a true desire for our guests to feel relaxed and at home. We are one of the very few to be Awarded a Trip Advis  …see more

from $137 / night

$557 - $2474 / week

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from $137 / night

(4) Very Good 

9

Vacation b&b in Cheltenham

Cotswolds / Cheltenham

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
  • Ask about pets
  • Private garden
This beautifully presented family run Bed and Breakfast is located in picturesque country side area of Cheltenham with views looking across the lower Cotswolds to the Famous Cheltenham Race Course. Situated at the bottom of Cleeve hill is this 6 bedroom modern house whi  …see more

from $124 / night

$806 - $3541 / week

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from $124 / night

18

Vacation home with golf nearby in Pittville

Cheltenham / Pittville

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Private garden
A lovely chalet style bungalow with 2 downstairs bedrooms and a family bathroom with shower and bath, 3 upstairs bedrooms and 3 bathrooms upstairs, making this a fantastic house for family reunions, those re-locating, sedate hen parties and anyone looking for a home fr  …see more

from $310 / night

$1488 - $6200 / week

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from $310 / night

(3) Excellent 

10

Montpellier suburb Vacation apartment rental

Cheltenham / Montpellier suburb

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
This beautiful one-bedroom serviced apartment in Cheltenham is located in the fashionable district of Lansdown. Drift upstairs via the fabulous spiral staircase to the spacious bedroom, and enjoy the light and airy living room's balcony which boasts views of the co  …see more

from $172 / night

$992 / week

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from $172 / night

(2) Good 

7

Montpellier suburb Vacation apartment rental

Cheltenham / Montpellier suburb

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
An ideal location to stay to sample unique Montpellier living... boutique shopping and many bespoke restaurants bars and cafes. These brand new Apartments are furnished to a very high standard, Tastefully Decorated Whilst Still Retaining The Elegant Period Features Of T  …see more

from $174 / night

$992 / week

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from $174 / night

14

Vacation home rental

Cheltenham / Pittville

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
This end of terrace house is situated in a quiet backwater of the town centre and is ideally situated for events at the Racecourse, University and Literature Festival. Street parking is available witha permit supplied by the owner or pay and display car park at the rear  …see more

from $186 / night

$868 / week

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from $186 / night

8

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
St James Walk apartment is a spacious 1 bedroom property in the heart of Cheltenham town centre, with easy access to Fitness First and the The Brewery leisure complex, which includes some of Cheltenham's finest bars and restaurants, also just a stones throw away ar  …see more

from $174 / night

$1216 / week

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from $174 / night

(6) Excellent 

34

Cheltenham Vacation apartment rental

Cheltenham / Cheltenham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Private garden
Our apartment is comfortable with all you need to make your stay enjoyable, plus a few extras. The two bedroomed garden apartment is part of a period property, well equipped and stylish. Close to the action of Montpellier and the Suffolks, you can enjoy your stay, whet  …see more

from $149 / night

$992 - $1414 / week

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from $149 / night

(5) Excellent 

19

Vacation apartment in Montpellier suburb

Cheltenham / Montpellier suburb

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
A beautiful Regency two bedroom apartment in the heart of the Montpellier, Cheltenham. Tastefully furnished and decorated, the limestone quarry tiled living room leads onto a peaceful paved garden. If it's chilly then cosy up on the large comfortable sofas with t  …see more

from $261 / night

$1612 / week

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from $261 / night

12

Vacation home in Cheltenham

Cheltenham / Cheltenham

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Car not necessary
  • Private garden
Perfect budget "home from home" accommodation for town centre events, company staff and parents visiting University.This dormer bungalow is ideally suited to people who cannot manage stairs easily as the main bedroom and bathroom are on the ground floo  …see more

from $124 / night

$620 - $682 / week

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from $124 / night

10

Apartment rental in Montpellier suburb

Cheltenham / Montpellier suburb

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Car not necessary
Croft House is a beautiful, one-bedroom luxury serviced apartment situated in one of the most spectacular Grade II Regency villas in Cheltenham. Spread across the first floor of this striking building, the apartment offers access to two balconies from the open plan loun  …see more

from $199 / night

$1172 - $1346 / week

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from $199 / night

(5)  

15

Vacation apartment rental

Cheltenham / Cheltenham

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Car not necessary
This luxurious ground floor studio apartment with a king-sized double bed, is situated in a side street just off the main Promenade in the centre of town, and includes a parking space in a gated, secure private car park. It is within easy walking distance of the High S  …see more

from $93 / night

$496 - $589 / week

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from $93 / night

(1) Excellent 

5

Vacation home accommodation

Cheltenham / Leckhampton

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
Down a quiet back water, you'll find a recently refurbished Coach House. With a modern sleek white kitchen, boasting wooden underfloor heating throughout into the living room. Going upstairs to a tastefully designed double bedroom, where you can relax leaving your  …see more

from $149 / night

$806 - $1823 / week

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from $149 / night

12

Cheltenham Vacation apartment rental

Cotswolds / Cheltenham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Ideally located in Cheltenham town centre, our 2 bedroom modern top floor (third floor) flat is near to Cheltenham's popular shops, restaurants and bars. Montpellier is a 5 minute walk. Overlooking Leckhampton in the distance, the balcony provides a pleasant space  …see more

from $62 / night

$422 - $1085 / week

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from $62 / night