Resorts getaways Chesterfield
Chesterfield
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Chesterfield

Nov 03 - Nov 04 ·
2 guests

Chesterfield Resorts

Chesterfield
2 guests

Adults:

2

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0

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1. The Common Man Inn & Restaurant

2. D. Hotel Suites & Spa

3. Vacation Village In The Berkshires

4. Vikings Villages Resort

Budget Resorts in Chesterfield

5. Holiday Inn Express Hotel & Suites Brattleboro By Ihg

6. Club Wyndham Bentley Brook

7. Hotel Downstreet, An Ascend Collection Hotel

Resorts in Chesterfield for Couples

8. Colonial Hotel

9. Best Western Springfield Hotel

10. The Hotel Northampton

Top Rated Resorts in Chesterfield

Resorts near Chesterfield

The Common Man Inn & Restaurant The Common Man Inn & Restaurant

The Common Man Inn & Restaurant

21 Water St
54.2 km (33.7 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Garden area
9.3
365 reviews
~ US$119 / night

The Common Man Inn & Restaurant

54.2 km (33.7 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Garden area

The Common Man Inn & Restaurant

9.3
365 reviews
From US$ 119 / night
D. Hotel Suites & Spa D. Hotel Suites & Spa

D. Hotel Suites & Spa

1 Country Club Road
70.6 km (43.9 mi) from Chesterfield
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Sauna
  • Heated swimming pool

Featuring a lift and a vending machine, the 3-star D. Hotel Suites & Spa Holyoke sits in Holyoke. This Holyoke hotel provides Wi-Fi throughout the property.

Options for an active stay feature a fitness centre and a heated pool available on site.

8.8
1005 reviews
~ US$122 / night

D. Hotel Suites & Spa

70.6 km (43.9 mi) from Chesterfield
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Sauna
  • Heated swimming pool

D. Hotel Suites & Spa

Featuring a lift and a vending machine, the 3-star D. Hotel Suites & Spa Holyoke sits in Holyoke. This Holyoke hotel provides Wi-Fi throughout the property.

Options for an active stay feature a fitness centre and a heated pool available on site.

8.8
1005 reviews
From US$ 122 / night
  • Guest favorite
Vacation Village In The Berkshires Vacation Village In The Berkshires

Vacation Village In The Berkshires

276 Brodie Mountain Road
73.7 km (45.8 mi) from Chesterfield
  • BBQ facilities
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Pool with view

Located within 25 minutes' walk of Brodie Mountain, the 5-star smoke-free Vacation Village In The Berkshires Hancock hotel includes a sunbathing terrace, a patio, and a picnic area.

A swimming pool is provided onsite the Vacation Village. An array of activities is offered in the area, such as biking, downhill skiing, and billiard.

8.6
1287 reviews
~ US$135 / night

Vacation Village In The Berkshires

73.7 km (45.8 mi) from Chesterfield
  • BBQ facilities
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Pool with view

Vacation Village In The Berkshires

Located within 25 minutes' walk of Brodie Mountain, the 5-star smoke-free Vacation Village In The Berkshires Hancock hotel includes a sunbathing terrace, a patio, and a picnic area.

A swimming pool is provided onsite the Vacation Village. An array of activities is offered in the area, such as biking, downhill skiing, and billiard.

8.6
1287 reviews
From US$ 135 / night

Budget Resorts in Chesterfield

  • Best-rated
Vikings Villages Resort Vikings Villages Resort

Vikings Villages Resort

360 Vikings Village Dr
15.6 km (9.7 mi) from Chesterfield
63
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Ironing facilities
  • Terrace

There is also private parking.

This Guilford resort provides boating, hiking, and skiing for an active pastime.

9.8
449 reviews
~ US$287 / night

Vikings Villages Resort

15.6 km (9.7 mi) from Chesterfield
63
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Ironing facilities
  • Terrace

Vikings Villages Resort

There is also private parking.

This Guilford resort provides boating, hiking, and skiing for an active pastime.

9.8
449 reviews
From US$ 287 / night
  • Top location
Holiday Inn Express Hotel & Suites Brattleboro By Ihg Holiday Inn Express Hotel & Suites Brattleboro By Ihg

Holiday Inn Express Hotel & Suites Brattleboro By Ihg

100 Chickering Drive
4.8 km (3.0 mi) from Chesterfield
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Flat-screen TV
  • Fitness centre
  • Heated swimming pool

Holiday Inn Express Hotel & Suites Brattleboro By Ihg, located 6 km from Fair Winds Farm, boasts a heated pool. This hotel has 86 rooms and features a lift and a vending machine on-site.

A 24-hour fitness center, along with fitness classes, is included at the Holiday Inn Express to help guests maintain their physical well-being.

8.7
161 reviews
~ US$100 / night

Holiday Inn Express Hotel & Suites Brattleboro By Ihg

4.8 km (3.0 mi) from Chesterfield
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Flat-screen TV
  • Fitness centre
  • Heated swimming pool

Holiday Inn Express Hotel & Suites Brattleboro By Ihg

Holiday Inn Express Hotel & Suites Brattleboro By Ihg, located 6 km from Fair Winds Farm, boasts a heated pool. This hotel has 86 rooms and features a lift and a vending machine on-site.

A 24-hour fitness center, along with fitness classes, is included at the Holiday Inn Express to help guests maintain their physical well-being.

8.7
161 reviews
From US$ 100 / night
Club Wyndham Bentley Brook Club Wyndham Bentley Brook

Club Wyndham Bentley Brook

1 Corey Road
74.3 km (46.2 mi) from Chesterfield
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Laundry
  • Sauna
  • Outdoor swimming pool

Club Wyndham Bentley Brook Hotel Hancock offers 152 rooms and an adult pool with a hot tub. Situated right by ski slopes and a ski mountain, this hotel provides guests with ski equipment hire.

The Bentley Brook spoils guests with a Jacuzzi and a sauna along with such activities as snow skiing, hiking, and billiard. Guests can work out in a hotel fitness centre during their stay.

9.1
287 reviews
~ US$167 / night

Club Wyndham Bentley Brook

74.3 km (46.2 mi) from Chesterfield
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Laundry
  • Sauna
  • Outdoor swimming pool

Club Wyndham Bentley Brook

Club Wyndham Bentley Brook Hotel Hancock offers 152 rooms and an adult pool with a hot tub. Situated right by ski slopes and a ski mountain, this hotel provides guests with ski equipment hire.

The Bentley Brook spoils guests with a Jacuzzi and a sauna along with such activities as snow skiing, hiking, and billiard. Guests can work out in a hotel fitness centre during their stay.

9.1
287 reviews
From US$ 167 / night

Resorts in Chesterfield for Couples

Hotel Downstreet, An Ascend Collection Hotel Hotel Downstreet, An Ascend Collection Hotel

Hotel Downstreet, An Ascend Collection Hotel

40 Main Street
53.8 km (33.5 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Indoor swimming pool

Located merely 14 minutes' stroll from All Saints Episcopal Church, the 4-star smoke-free Hotel Downstreet, An Ascend Collection Hotel North Adams boasts a Jacuzzi and a sauna.

Such leisure options as a swimming pool, a fitness centre will ensure a more relaxing stay. The accommodation offers skiing and ping pong for guests to practise sports.

8.5
204 reviews
~ US$108 / night

Hotel Downstreet, An Ascend Collection Hotel

53.8 km (33.5 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Indoor swimming pool

Hotel Downstreet, An Ascend Collection Hotel

Located merely 14 minutes' stroll from All Saints Episcopal Church, the 4-star smoke-free Hotel Downstreet, An Ascend Collection Hotel North Adams boasts a Jacuzzi and a sauna.

Such leisure options as a swimming pool, a fitness centre will ensure a more relaxing stay. The accommodation offers skiing and ping pong for guests to practise sports.

8.5
204 reviews
From US$ 108 / night
Colonial Hotel Colonial Hotel

Colonial Hotel

625 Betty Spring Road
59.7 km (37.1 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Sauna
  • Indoor swimming pool

Located 25 minutes' walk from the American Dunn State Public Park, which offers the thrill of discovering something beautiful, Colonial Hotel Gardner offers a restaurant.

An indoor pool comes with a hot tub.

8.1
402 reviews
~ US$130 / night

Colonial Hotel

59.7 km (37.1 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Sauna
  • Indoor swimming pool

Colonial Hotel

Located 25 minutes' walk from the American Dunn State Public Park, which offers the thrill of discovering something beautiful, Colonial Hotel Gardner offers a restaurant.

An indoor pool comes with a hot tub.

8.1
402 reviews
From US$ 130 / night
Best Western Springfield Hotel Best Western Springfield Hotel

Best Western Springfield Hotel

818 Charlestown Road
40.7 km (25.3 mi) from Chesterfield
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Leisure/ TV room
  • Fitness centre
  • Indoor swimming pool

Nestled in a business area of Springfield, the comfortable 3-star Best Western Springfield Hotel offers air-conditioned rooms.

A shared lounge and a golf course are provided for a truly enjoyable stay. Guests can join canyoning, hiking, and billiard.

8.8
214 reviews
~ US$164 / night

Best Western Springfield Hotel

40.7 km (25.3 mi) from Chesterfield
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Leisure/ TV room
  • Fitness centre
  • Indoor swimming pool

Best Western Springfield Hotel

Nestled in a business area of Springfield, the comfortable 3-star Best Western Springfield Hotel offers air-conditioned rooms.

A shared lounge and a golf course are provided for a truly enjoyable stay. Guests can join canyoning, hiking, and billiard.

8.8
214 reviews
From US$ 164 / night

Party Resorts in Chesterfield

The Hotel Northampton The Hotel Northampton

The Hotel Northampton

36 King Street
65.6 km (40.8 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Terrace

The comfortable The Hotel Northampton enjoys a central location and provides easy access to Smith College Museum of Art only 9 minutes' walk away. The highlights of this 3-star hotel include a vending machine and a lift, it also offers Wi-Fi in public areas.

8.7
398 reviews
~ US$186 / night

The Hotel Northampton

65.6 km (40.8 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Terrace

The Hotel Northampton

The comfortable The Hotel Northampton enjoys a central location and provides easy access to Smith College Museum of Art only 9 minutes' walk away. The highlights of this 3-star hotel include a vending machine and a lift, it also offers Wi-Fi in public areas.

8.7
398 reviews
From US$ 186 / night
The Williams Inn The Williams Inn

The Williams Inn

101 Spring Street
60.2 km (37.4 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Flat-screen TV
  • Live entertainment

The 4-star designer The Williams Inn Williamstown offers quick access to The Soldiers' Monument, located a mere 6 minutes' walk away.

A shared lounge and a golf course are also featured at this Williamstown hotel.

9.4
152 reviews
~ US$246 / night

The Williams Inn

60.2 km (37.4 mi) from Chesterfield
  • Restaurant
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Flat-screen TV
  • Live entertainment

The Williams Inn

The 4-star designer The Williams Inn Williamstown offers quick access to The Soldiers' Monument, located a mere 6 minutes' walk away.

A shared lounge and a golf course are also featured at this Williamstown hotel.

9.4
152 reviews
From US$ 246 / night
The Upper Pass Lodge The Upper Pass Lodge

The Upper Pass Lodge

420 Magic Mountain Access Road
39.3 km (24.4 mi) from Chesterfield
  • Restaurant
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Skiing
  • Outdoor swimming pool

A car park is provided on site.

Guests will take advantage of hiking, skiing, and cycling available for an active pastime.

8.1
148 reviews
~ US$103 / night

The Upper Pass Lodge

39.3 km (24.4 mi) from Chesterfield
  • Restaurant
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Skiing
  • Outdoor swimming pool

The Upper Pass Lodge

A car park is provided on site.

Guests will take advantage of hiking, skiing, and cycling available for an active pastime.

8.1
148 reviews
From US$ 103 / night

Golf Resorts in Chesterfield

Chalet 239-Boutique Hotel Chalet 239-Boutique Hotel

Chalet 239-Boutique Hotel

239 Vermont Route 100
29.3 km (18.2 mi) from Chesterfield
  • Picnic area/ Tables
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Patio

Situated a stone's throw from Sports Oddyssey Ski Shop, the comfortable Chalet 239-Boutique Hotel West Dover offers proximity to various city highlights.

9
188 reviews
~ US$234 / night

Chalet 239-Boutique Hotel

29.3 km (18.2 mi) from Chesterfield
  • Picnic area/ Tables
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Patio

Chalet 239-Boutique Hotel

Situated a stone's throw from Sports Oddyssey Ski Shop, the comfortable Chalet 239-Boutique Hotel West Dover offers proximity to various city highlights.

9
188 reviews
From US$ 234 / night
Holiday Inn Club Vacations Mount Ascutney Resort Holiday Inn Club Vacations Mount Ascutney Resort

Holiday Inn Club Vacations Mount Ascutney Resort

485 Hotel Road
62.6 km (38.9 mi) from Chesterfield
  • BBQ facilities
  • Free parking
  • Express check-in/ -out
  • Air conditioning
  • Live entertainment
  • Outdoor swimming pool

The 4-star Holiday Inn Club Vacations Mount Ascutney Resort Brownsville provides proximity to American Precision Museum, which is located around 7 km away.

Staying at the Holiday Inn Brownsville, guests can dive in an indoor pool. The area is known for hiking, basketball, and ping pong.

8.8
216 reviews
~ US$231 / night

Holiday Inn Club Vacations Mount Ascutney Resort

62.6 km (38.9 mi) from Chesterfield
  • BBQ facilities
  • Free parking
  • Express check-in/ -out
  • Air conditioning
  • Live entertainment
  • Outdoor swimming pool

Holiday Inn Club Vacations Mount Ascutney Resort

The 4-star Holiday Inn Club Vacations Mount Ascutney Resort Brownsville provides proximity to American Precision Museum, which is located around 7 km away.

Staying at the Holiday Inn Brownsville, guests can dive in an indoor pool. The area is known for hiking, basketball, and ping pong.

8.8
216 reviews
From US$ 231 / night
  • Great deal
Red Roof Inn Plus+ South Deerfield - Amherst Red Roof Inn Plus+ South Deerfield - Amherst

Red Roof Inn Plus+ South Deerfield - Amherst

9 Greenfield Road
48.7 km (30.3 mi) from Chesterfield
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Flat-screen TV
  • Laundry
  • Sun loungers

Offering an indoor pool and a game area, the 3-star Red Roof Inn Plus+ South Deerfield - Amherst is 2.7 km from the butte-like Sugarloaf Mountain. The hotel offers Wi-Fi in public areas as well as cash machine/banking services and a 24-hour front desk.

6.5
421 reviews
~ US$67 / night

Red Roof Inn Plus+ South Deerfield - Amherst

48.7 km (30.3 mi) from Chesterfield
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Flat-screen TV
  • Laundry
  • Sun loungers

Red Roof Inn Plus+ South Deerfield - Amherst

Offering an indoor pool and a game area, the 3-star Red Roof Inn Plus+ South Deerfield - Amherst is 2.7 km from the butte-like Sugarloaf Mountain. The hotel offers Wi-Fi in public areas as well as cash machine/banking services and a 24-hour front desk.

6.5
421 reviews
From US$ 67 / night

Honeymoon Resorts in Chesterfield

210 Cedarbrook Queen Studio 210 Cedarbrook Queen Studio

210 Cedarbrook Queen Studio

8463 Us Route 4
79.8 km (49.6 mi) from Chesterfield
  • Cookware/ Kitchen utensils
  • Tours/Ticket assistance
  • Flat-screen TV
  • Heating
  • Fitness centre
  • Heated swimming pool

The comfortable 210 Cedarbrook Queen Studio Killington hotel includes air-conditioned rooms and is located approximately 10 minutes by car from Snowdon Quad.

Other facilities include an outdoor swimming pool.

9.3
31 reviews
~ US$179 / night

210 Cedarbrook Queen Studio

79.8 km (49.6 mi) from Chesterfield
  • Cookware/ Kitchen utensils
  • Tours/Ticket assistance
  • Flat-screen TV
  • Heating
  • Fitness centre
  • Heated swimming pool

210 Cedarbrook Queen Studio

The comfortable 210 Cedarbrook Queen Studio Killington hotel includes air-conditioned rooms and is located approximately 10 minutes by car from Snowdon Quad.

Other facilities include an outdoor swimming pool.

9.3
31 reviews
From US$ 179 / night
Jiminy Peak Mountain Resort Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

37 Corey Road
74.5 km (46.3 mi) from Chesterfield
  • BBQ facilities
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Heated swimming pool

Positioned 1.4 km from Ioka Valley Farm and about 10 minutes' drive from Ramblewild Adventure Park Recreation Center, the 3-star Jiminy Peak Mountain Resort Hancock presents 2 outdoor tennis courts. Featuring a restaurant, the resort is located a few steps from Jiminy Peak Mountain Resort.

You can spend time by a heated pool, which comes with a hot tub. Guests staying at this accommodation are welcome to join fitness classes at a fitness centre.

8.5
112 reviews
~ US$179 / night

Jiminy Peak Mountain Resort

74.5 km (46.3 mi) from Chesterfield
  • BBQ facilities
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Heated swimming pool

Jiminy Peak Mountain Resort

Positioned 1.4 km from Ioka Valley Farm and about 10 minutes' drive from Ramblewild Adventure Park Recreation Center, the 3-star Jiminy Peak Mountain Resort Hancock presents 2 outdoor tennis courts. Featuring a restaurant, the resort is located a few steps from Jiminy Peak Mountain Resort.

You can spend time by a heated pool, which comes with a hot tub. Guests staying at this accommodation are welcome to join fitness classes at a fitness centre.

8.5
112 reviews
From US$ 179 / night
Holiday Inn & Suites Pittsfield-Berkshires By Ihg Holiday Inn & Suites Pittsfield-Berkshires By Ihg

Holiday Inn & Suites Pittsfield-Berkshires By Ihg

One West Street
78.9 km (49.0 mi) from Chesterfield
  • Restaurant
  • 24-hour reception
  • Air conditioning
  • Flat-screen TV
  • Live entertainment
  • Heated swimming pool

Featuring a sun deck, spa therapy, and a golf course, the 4-star Holiday Inn & Suites Pittsfield-Berkshires By Ihg enjoys a convenient location 17 minutes' walk from Pittsfield Mall. Boasting a swimming pool along with an American restaurant, the hotel is located a few steps from the Your Berkshire Community Museum.

7.2
232 reviews
~ US$99 / night

Holiday Inn & Suites Pittsfield-Berkshires By Ihg

78.9 km (49.0 mi) from Chesterfield
  • Restaurant
  • 24-hour reception
  • Air conditioning
  • Flat-screen TV
  • Live entertainment
  • Heated swimming pool

Holiday Inn & Suites Pittsfield-Berkshires By Ihg

Featuring a sun deck, spa therapy, and a golf course, the 4-star Holiday Inn & Suites Pittsfield-Berkshires By Ihg enjoys a convenient location 17 minutes' walk from Pittsfield Mall. Boasting a swimming pool along with an American restaurant, the hotel is located a few steps from the Your Berkshire Community Museum.

7.2
232 reviews
From US$ 99 / night

4 Star Resorts in Chesterfield

The Pointe At Castle Hill Resort & Spa The Pointe At Castle Hill Resort & Spa

The Pointe At Castle Hill Resort & Spa

2940 Route 103
54.4 km (33.8 mi) from Chesterfield
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Flat-screen TV
  • Fitness centre
  • Indoor swimming pool

Offering a shared lounge and a golf course, the smoke-free The Pointe At Castle Hill Resort & Spa Proctorsville lies in a rural area of Proctorsville, approximately 6 km from Jackson Gore Ski Area and within a 10-minute drive of Congregational Church of Ludlow. This 3-star resort features a swimming pool, a fitness centre and high-speed Internet access in public areas.

After a busy day you can recover in a solarium, a Jacuzzi, and a sauna or indulge in a hot stone massage, a sports massage, and a prenatal massage. Activities such as hiking, skiing, and billiard can be arranged by this Proctorsville hotel. The Pointe also features conference facilities and complimentary wireless internet access for those arriving on business.

8.2
225 reviews
~ US$206 / night

The Pointe At Castle Hill Resort & Spa

54.4 km (33.8 mi) from Chesterfield
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Flat-screen TV
  • Fitness centre
  • Indoor swimming pool

The Pointe At Castle Hill Resort & Spa

Offering a shared lounge and a golf course, the smoke-free The Pointe At Castle Hill Resort & Spa Proctorsville lies in a rural area of Proctorsville, approximately 6 km from Jackson Gore Ski Area and within a 10-minute drive of Congregational Church of Ludlow. This 3-star resort features a swimming pool, a fitness centre and high-speed Internet access in public areas.

After a busy day you can recover in a solarium, a Jacuzzi, and a sauna or indulge in a hot stone massage, a sports massage, and a prenatal massage. Activities such as hiking, skiing, and billiard can be arranged by this Proctorsville hotel. The Pointe also features conference facilities and complimentary wireless internet access for those arriving on business.

8.2
225 reviews
From US$ 206 / night

Are you in a hurry?

Here is a quick list of Resorts in Chesterfield, selected based on their rating

Name of hotel Accommodation Rating Price, $
The Common Man Inn & Restaurant

9.3 / 10

(365 Reviews)

From 119$
D. Hotel Suites & Spa

8.8 / 10

(1005 Reviews)

From 122$
Vacation Village In The Berkshires

8.6 / 10

(1287 Reviews)

From 135$
Vikings Villages Resort

9.8 / 10

(449 Reviews)

From 287$
Holiday Inn Express Hotel & Suites Brattleboro By Ihg

8.7 / 10

(161 Reviews)

From 100$

Location