Compare Chatham Vacation Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Chatham Rentals

5 STAR ESTATE w/ POOL, POND, ARCADE, GYM, TRAILS! ASK ABOUT FANTASTIC DISCOUNT!

5 STAR ESTATE w/ POOL, POND, ARCADE, GYM, TRAILS! ASK ABOUT FANTASTIC DISCOUNT!

3.65 mi from city center
Guests of this vacation home enjoy a water park, an outdoor pool, and a gym. Other amenities at this family-friendly vacation home include an arcade/game room, a library, and laundry facilities.
Pool
Kitchen
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
The price is $156 per night
$156
includes taxes & fees
$144 per night
May 10 - May 11
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 a garden, barbecue grills, and a picnic area.
Kitchen
Pet friendly
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

13.04 mi from city center
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Kitchen
Washer
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
Private Access To Laurel Lake, Enjoy Lake Life

Private Access To Laurel Lake, Enjoy Lake Life

16.53 mi from city center
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat

13.98 mi from city center
At this vacation home, guests have access to barbecue grills.
Kitchen
Pet friendly
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

15.8 mi from city center
At this vacation home, guests have access to an arcade/game room, laundry facilities, and barbecue grills.
Pool
Kitchen
Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

18.69 mi from city center
The price is $1,037 per night
$1,037
includes taxes & fees
$959 per night
May 7 - May 8
This vacation home features a hot tub, an arcade/game room, and a library. Other amenities at this family-friendly vacation home include laundry facilities and barbecue grills.
Hot Tub
Kitchen
Postcard Cabins Eastern Catskills

Postcard Cabins Eastern Catskills

2 out of 5
282 Cairo Junction Rd, Catskill, NY
19.66 mi from city center
The price is $200 per night
$200
includes taxes & fees
$185 per night
May 11 - May 12
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
The price is $150 per night
$150
includes taxes & fees
$134 per night
May 7 - May 8
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 tours or tickets, luggage storage, and securing valuables. Other amenities at this ski condominium resort include outdoor tennis courts, free WiFi in public areas, and meeting rooms.
Pool
Parking included
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

20.5 mi from city center
The price is $474 per night
$474
includes taxes & fees
$468 per night
May 7 - May 8
This vacation home offers a gym, a sauna, and a hot tub. Additional amenities include an arcade/game room, laundry facilities, and a garden.
Pool
Hot Tub
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
The price is $127 per night
$127
includes taxes & fees
$114 per night
May 19 - May 20
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
Don't see what you're looking for?
See all available properties in Chatham
View all properties
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 $127 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.

More Places To Stay in Chatham

Recommended Vacation Rental Locations