Resort Chatham

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We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Resorts in Chatham

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 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
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
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 1 Bedroom - Vacation Village in the Berkshires Resort - Hancock

1 Bedroom - Vacation Village in the Berkshires Resort - Hancock

2 out of 5
Hancock
Stay at this resort in Williamstown. Enjoy a fitness center and air conditioning. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located ...
1 Bedroom - Vacation Village in the Berkshires Resort - Hancock
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!
Hot SKI-in SKI-out Rentals Bentley Brook Resort!

Hot SKI-in SKI-out Rentals Bentley Brook Resort!

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 ...
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury

Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury

hancock
Stay at this resort in Hancock. Enjoy free WiFi, a fitness center, and tennis courts. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are ...
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort

Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort

Hancock
Stay at this resort in Hancock. Enjoy free WiFi, a fitness center, and tennis courts. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are ...
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
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
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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
29 Resorts
Lowest Price
NZ$176
Highest Price
NZ$332
Popular accommodation
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants, Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base, Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out, 1 Bedroom - Vacation Village in the Berkshires Resort - Hancock, SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!, Hot SKI-in SKI-out Rentals Bentley Brook Resort!, Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury , Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort , Bentley Brook: Ultimate Ski-In Ski-Out -Crazy

Top trending hotels in Chatham

Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

2.5 out of 5
37 Route 9W, Glenmont, NY
Fully refundable
The price is NZ$194 per night from 2 Jan to 3 Jan
NZ$194
includes taxes & fees
2 Jan - 3 Jan 2025
Book a stay at this business-friendly hotel in Glenmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Comfort Inn Glenmont - Albany South
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$192 per night from 2 Jan to 3 Jan
NZ$192
includes taxes & fees
2 Jan - 3 Jan 2025
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
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$332 per night from 7 Jan to 8 Jan
NZ$332
includes taxes & fees
7 Jan - 8 Jan 2025
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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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$176 per night from 1 Jan to 2 Jan
NZ$176
includes taxes & fees
1 Jan - 2 Jan 2025
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
Don't see what you're looking for?
See all available properties in Chatham
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.