Resort Chatham

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Featured Resorts in Chatham

All Season Adventures, Ski In/Ski Out,  Wyndham Bentley Brook 2 Bedroom Dlx.

All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.

2 out of 5
Lanesborough
Stay at this resort in Hancock. Enjoy a sauna, balconies, and in-room jetted tubs. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located ...
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base

Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base

Hancock
Stay at this resort in Hancock. Enjoy a fitness center, an in-room coffeemaker, and air conditioning. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
Pres Week- Bentley Brook Resort - Your Peak Winter Escape

Pres Week- Bentley Brook Resort - Your Peak Winter Escape

Hancock
Book a stay at this family-friendly resort in Hancock. Enjoy free WiFi, a fitness center, and a pool table. Popular attractions Jiminy Peak Mountain Resort and ...
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
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Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires

Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires

2 out of 5
Hancock
Stay at this resort in Williamstown. Enjoy a fitness center, in-room jetted tubs, and air conditioning. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out

Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out

Hancock
Book a stay at this ski resort in Hancock. Enjoy a fitness center, concierge services, and tennis courts. Popular attractions Jiminy Peak Mountain Resort and ...
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!

SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!

Hancock
Book a stay at this ski resort in Hancock. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster ...
SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants

In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants

Hancock
Book a stay at this ski resort in Hancock. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster ...
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy

Bentley Brook: Ultimate Ski-In Ski-Out -Crazy

Hancock
Book a stay at this family-friendly resort in Hancock. Enjoy free WiFi, a fitness center, and tennis courts. Popular attractions Jiminy Peak Mountain Resort ...
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

Hancock
Book a stay at this ski resort in Hancock. Enjoy free WiFi, a fitness center, and tennis courts. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chatham Hotel Resorts

You’ve got it made. From your amazing bae to a job you love, you know you’re truly #blessed. But your fake work rivalry with Jenny in accounting is getting pretty heated, and she just took an amazing trip. No worries. Chatham resort accommodation has that little extra something that will give you the edge in the tea room.

Travelling with the clan? You can stay at family resorts on a budget no matter how many ankle biters you’ve got. Let the kids splash in the pool while you stretch out on a chaise lounge like you own the place. You could also just leave the kids at home (and if you don’t have any, well, even better) and just do your own thing with adults-only resorts in Chatham. Just do you. Sip on tropical drinks with tiny umbrellas, take delicate bites of hors d’oeuvres (after you #foodstagram them, obvs), and add so much to your social media story, you’ll feel like a celebrity. No one at home has to know you had such a great time in Chatham without them.

Humble brag: You’ll find such great deals on lastminute.co.nz, you’ll have trouble picking just one—but at these prices, you don’t have to. Cheap holiday resorts in Chatham are just the beginning. You’re gonna love this trip so much, you’ll want five more just like it, so you might as well book them all now. Then bust out those new bathers and sunnies that got you looking like Beyoncé. You deserve it.

Chatham Resorts essential information

Accommodation
41 Resorts
Lowest Price
NZ$181
Highest Price
NZ$323
Popular accommodation
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx., Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base, Pres Week- Bentley Brook Resort - Your Peak Winter Escape, Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires, Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out, SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!, In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants, Bentley Brook: Ultimate Ski-In Ski-Out -Crazy, Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

Top trending hotels in Chatham

Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$241 per night from 20 Apr to 21 Apr
NZ$241
includes taxes & fees
20 Apr - 21 Apr
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
Life House Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
The price is NZ$224 per night from 28 Apr to 29 Apr
NZ$224
includes taxes & fees
28 Apr - 29 Apr
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$181 per night from 28 Apr to 29 Apr
NZ$181
includes taxes & fees
28 Apr - 29 Apr
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
The Yankee, Trademark Collection by Wyndham
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The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is NZ$323 per night from 12 May to 13 May
NZ$323
includes taxes & fees
12 May - 13 May
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
The Red Lion Inn
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.