50 Best Cheltenham Apartments on Holiday Lettings - Estates

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Cheltenham
18 properties
Montpellier suburb
14 properties
Charlton Kings
10 properties
Pittville
8 properties
Prestbury
5 properties

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118 Vacation rentals

(11) 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 $189 / night

$882 - $2334 / week

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from $189 / night

(4) 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 $120 / night

$693 / week

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from $120 / 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 $70 / night

$351 - $945 / week

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from $70 / night

(3) 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 fabulous sho  …see more

from $126 / night

$693 - $794 / week

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from $126 / night

(30) 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 $315 / night

$2079 - $2520 / week

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from $315 / 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 $76 / night

$416 / week

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from $76 / 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 are the  …see more

from $177 / night

$1235 / week

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from $177 / night

(18) Very Good 

12

Vacation apartment rental

Cheltenham / Cheltenham

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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 added  …see more

from $114 / night

$643 - $1733 / week

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from $114 / night

(10) Very Good 

14

Vacation studio in Cheltenham

Cheltenham / Cheltenham

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • 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 $69 / night

$341 - $372 / week

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from $69 / night

(2) Excellent 

10

Vacation apartment in Cheltenham

Cheltenham / Cheltenham

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly
Location, location, location! Contemporary apartment set in the heart of Montpellier in Cheltenham Spa. Open plan living space with no convenience spared. Complimentary wifi, Sky TV and parking permit. Located within a stones throw of Cheltenham Ladies College and the  …see more

from $226 / night

$1197 - $3150 / week

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from $226 / 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 $164 / night

$567 - $1273 / week

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from $164 / 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 communa  …see more

from $174 / night

$1008 / week

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from $174 / night

6

Apartment rental in Montpellier suburb

Cheltenham / Montpellier suburb

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
Recently new to our portfolio, Luxury Apartments are proud to offer this 1 bedroom apartment situated a few minutes from Montpellier. This third floor apartment has been refurbished throughout, giving it a modern but homely feel. Beautiful views can be seen from sash wi  …see more

from $177 / night

$1059 / week

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from $177 / night

(5) Excellent 

11

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • 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 $221 / night

$1323 - $1386 / week

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from $221 / night

6

Vacation apartment in Cheltenham

Cheltenham / Cheltenham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
This spacious one bedroom apartment located in the Suffolks close to Montpellier and Cheltenham town. This apartment benefits from a large bedroom, separate bathroom with free standing bath, cloakroom, shower room, utility area and living room.The apartment has been new  …see more

from $114 / night

$693 / week

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from $114 / 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 $152 / night

$819 - $1853 / week

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from $152 / 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 $89 / night

$618 / week

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from $89 / night

(14) Excellent 

21

Cheltenham Vacation apartment rental

Cheltenham / Cheltenham

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Car not necessary
  • Air conditioning
Apartment 3 is a one bedroom, Five Star, Gold Award apartment in the very heart of Cheltenham. Private parking space provided immediately outside.Ideal for any of the Cheltenham Festivals or for seeing the Cotswolds. Please use "Contact the Owner" form to send an ema  …see more

from $179 / night

$990 / week

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from $179 / night

(3) Very Good 

19

Cottage rental in Charlton Kings

Cheltenham / Charlton Kings

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Windrush Cottage stands in the grounds of Seven Springs Cottages. It is one of six self-catering cottages offering excellent facilities for families and groups wishing to enjoy all that the Cotswolds and Cheltenham have to offer. It has a double bedroom and two twin bed  …see more

from $133 / night

$693 - $1071 / week

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from $133 / 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 the re  …see more

from $265 / night

$1638 / week

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from $265 / night

(1) Very Good 

5

Apartment rental in Montpellier suburb

Cheltenham / Montpellier suburb

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
The living room has tall ceilings with pretty cornering, and two large Georgian sash windows flood light into this luxury service apartment. Adding character to this lovely, light room. The comfortable sofa bed and arm chair face an exquisite large marble fireplace.The  …see more

from $189 / night

$1097 - $3176 / week

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from $189 / 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 $189 / night

$1399 / week

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from $189 / night

(6) Very Good 

16

Vacation cottage in Charlton Kings

Cheltenham / Charlton Kings

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Sherbourne Cottage stands in the grounds of Seven Springs Cottages. It is one of six self-catering cottages offering excellent facilities for families and groups wishing to enjoy all that the Cotswolds and Cheltenham have to offer. It has one double and one twin bedroom  …see more

from $101 / night

$492 - $819 / week

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from $101 / 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 for r  …see more

from $63 / night

$429 - $1103 / week

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from $63 / 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, this uniqu  …see more

from $95 / night

$567 / week

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from $95 / night

9

Vacation apartment in Southam

Cheltenham / Southam

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 $158 / night

$945 / week

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from $158 / 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 $409 / night

$1988 - $3157 / week

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from $409 / night

(3) Excellent 

9

Vacation cottage with golf nearby in Cheltenham

Cheltenham / Cheltenham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 $85 / night

$378 - $630 / week

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from $85 / 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.<br><br><br><br>The nearest shop and  …see more

from $208 / night

$1112 - $1523 / week

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from $208 / 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 Size  …see more

from $252 / night

$1235 / week

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from $252 / night

13

Vacation cottage rental

Cheltenham / Charlton Kings

1 2 Min stay varies

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

from $70 / night

$353 - $630 / week

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from $70 / 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 $189 / night

$1323 / week

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from $189 / 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 $158 / night

$630 - $1386 / week

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from $158 / night

(2) Excellent 

18

Home accommodation in Cheltenham

Cotswolds / Cheltenham

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets
A beautiful two bedroom, three storey home with a garden in a quiet area within a five minute walk to the town centre or the spectacular Pittville Park. If you have a car, you're in the middle of the Cotswolds where you can explore beautiful ltiny towns with thatched c  …see more

from $164 / night

$1008 / week

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from $164 / 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 $177 / night

$1008 / week

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from $177 / night

(11) Very Good 

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 $188 / night

$738 - $1890 / week

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from $188 / night

(2) Good 

15

Vacation apartment in Cheltenham

Cheltenham / Cheltenham

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Car not necessary
This contemporary second floor apartment with two double bedrooms 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 Street,  …see more

from $171 / night

$914 - $1071 / week

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from $171 / night

(8) Very Good 

16

Vacation cottage in Charlton Kings

Cheltenham / Charlton Kings

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Ask about pets
  • Private garden
The elegant Regency Spa Town of Cheltenham is located on the western boundaries of the Cotswolds seven miles east of Gloucester and within easy reach of the M5. It is a bustling popular shopping destination with wonderful regency buildings and beautiful flower beds and  …see more

from $121 / night

$504 - $605 / week

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from $121 / night

(1) Excellent 

13

Cheltenham Vacation apartment rental

Cotswolds / Cheltenham

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
This recently refurbished garden flat is the former servants' quarters in a Grade 2 listed Regency villa with its own entrance and courtyard garden. It is 10 minutes walk from the centre of Cheltenham town with its historic buildings, restaurants and festival locations  …see more

from $101 / night

$492 - $624 / week

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from $101 / night

(2) Excellent 

4

Vacation barn in Cheltenham

Cheltenham / Cheltenham

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
The Coach House is situated on the A38 halfway between Gloucester and Tewkesbury, and about 5 miles west of Cheltenham. It provides an ideal base for exploring the Cotswolds, The Forest of Dean, or even the Wye Valley and beyond to the Welsh hills.The barn has  …see more

from $101 / night

$441 / week

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from $101 / night