Compare Chatham Vacation Rentals

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Chatham Rentals

Micosta Leisure Inn

Micosta Leisure Inn

3 out of 5
3007 County Rd 20, Hudson, NY
Free Cancellation
Reserve now, pay when you stay
8.84 mi from city center
$144 nightly
The price is $156 total per night
$156 total
Jul 13 - Jul 14
Total includes taxes and fees
Guests of Micosta Leisure Inn enjoy free WiFi in public areas, a terrace, and laundry facilities. If you drive, put free parking to good use. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include barbecue grills, a picnic area, and a garden.
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

12.22 mi from city center
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

10.48 mi from city center
At this vacation home, guests enjoy karaoke, an outdoor pool, and a hot tub. Other amenities at this beach vacation home include an arcade/game room, laundry facilities, and a garden.
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA
16.11 mi from city center
The Ponds at Foxhollow features an indoor pool, an outdoor pool, and a gym. Free parking is available if you drive. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include a sauna, free WiFi in public areas, and an outdoor tennis court.
Pool
Kitchen
The Kemble- Built by a US Secretary of State in Lenox

The Kemble- Built by a US Secretary of State in Lenox

15.94 mi from city center
Guests of this villa enjoy features like a gym, a sauna, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities, barbecue grills, and a garden.
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

18.48 mi from city center
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Deluxe Queen Room with 2 Queen Beds

Deluxe Queen Room with 2 Queen Beds

2 out of 5
18.51 mi from city center
$129 nightly
The price is $144 total per night
$144 total
Aug 3 - Aug 4
Total includes taxes and fees
This vacation home features an outdoor pool and laundry facilities.
Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods

19.86 mi from city center
$148 nightly
The price is $164 total per night
$164 total
Jul 7 - Jul 8
Total includes taxes and fees
At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has barbecue grills.
Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience

19.86 mi from city center
$160 nightly
The price is $178 total per night
$178 total
Jul 7 - Jul 8
Total includes taxes and fees
Guests staying at this cabin have access to laundry facilities, a garden, and barbecue grills.
Postcard Cabins Eastern Catskills

Postcard Cabins Eastern Catskills

2 out of 5
282 Cairo Junction Rd, Catskill, NY
19.66 mi from city center
$214 nightly
The price is $231 total per night
$231 total
Aug 3 - Aug 4
Total includes taxes and fees
There's free parking if you drive.
Kitchen
Pet friendly
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd, Hancock, MA
20.4 mi from city center
$179 nightly
The price is $200 total per night
$200 total
Jul 7 - Jul 8
Total includes taxes and fees
At Jiminy Peak Mountain Resort, guests enjoy ski-in/ski-out access, an outdoor pool, and a gym. You can put free parking to good use if you drive. Front-desk staff can answer questions 24/7, and assist with luggage storage, securing valuables, and concierge services. Other amenities at this ski condominium resort include outdoor tennis courts, free WiFi in public areas, and meeting rooms.
Pool
Parking included
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
20.8 mi from city center
$117 nightly
The price is $131 total per night
$131 total
Jul 7 - Jul 8
Total includes taxes and fees
Vacation Village in the Berkshires features an indoor pool, an outdoor pool, and a children's pool. If you decide to drive, there's free parking. The front desk is staffed 24 hours a day to help with access to locker space and concierge services. Other amenities at this family-friendly condo building include a gym, free WiFi in public areas, and a business center.
Pool
Parking included
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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 Large Group Rentals

How to Book Vacation Rentals in Chatham



🏠 What is the best price for Chatham vacation rentals?

Chatham vacation rentals range in price, starting at $131 per night.


🏠 What types of vacation rentals in Chatham can I rent?

Orbitz offers a wide range of Chatham rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Chatham condo rentals.


🏠 Is it free to cancel my Chatham vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Chatham vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Chatham. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Chatham?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Chatham apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Chatham?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Chatham package deals will get you even more savings.

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