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

The Hudson Escape – Pool, Hot Tub, & 13 private acres of fun!

The Hudson Escape – Pool, Hot Tub, & 13 private acres of fun!

Hudson NY
8.45 mi from city center
At this vacation home, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free vacation home also has a garden.
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
$139 nightly
The price is $155 total per night
$155 total
Aug 5 - Aug 6
Total with 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 a garden, a picnic area, and barbecue grills.
Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat

Great Barrington MA
14.73 mi from city center
$310 nightly
The price is $346 total per night
$346 total
Aug 17 - Aug 18
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has 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. Helpful staff is there to provide a safe deposit box at the front desk, as well as offer insight about the area. Additional amenities include a sauna, free WiFi in public areas, and an outdoor tennis court.
Pool
Kitchen
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++

Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++

Lenox MA
16.4 mi from city center
Guests of this vacation home enjoy features like an indoor pool, a hot tub, and an arcade/game room. Other amenities at this family-friendly vacation home include laundry facilities, local meal delivery service, and a garden.
Secluded Catskill Estate • Pool + Hot Tub + Fire Pit | Sleeps 24 | River House

Secluded Catskill Estate • Pool + Hot Tub + Fire Pit | Sleeps 24 | River House

Catskill NY
15.8 mi from city center
At this vacation home, guests have access to an arcade/game room, laundry facilities, and barbecue grills.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
17.22 mi from city center
$138 nightly
The price is $155 total per night
$155 total
Aug 30 - Aug 31
Total with taxes and fees
At Berkshire Mountain Lodge, guests have access to an indoor pool, free WiFi in public areas, and a hot tub. If you decide to drive, there's free parking. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Other amenities at this golf aparthotel include a business center, an arcade/game room, and laundry facilities.
Private Yacht on Catskill Creek

Private Yacht on Catskill Creek

Catskill NY
17.36 mi from city center
$253 nightly
The price is $283 total per night
$283 total
Aug 5 - Aug 6
Total with taxes and fees
At this houseboat, guests enjoy features like beach towels.
Brookside Mountain Retreat | 13BR | Heated Pool, Hot Tub + Game Room

Brookside Mountain Retreat | 13BR | Heated Pool, Hot Tub + Game Room

Stephentown NY
17.64 mi from city center
This vacation home features a hot tub and a garden. This smoke-free vacation home also has barbecue grills.
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
282 Cairo Junction Rd Catskill NY
19.66 mi from city center
$218 nightly
The price is $235 total per night
$235 total
Sep 2 - Sep 3
Total with taxes and fees
There's free parking if you drive.
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd Williamstown MA
19.88 mi from city center
$121 nightly
The price is $135 total per night
$135 total
Aug 23 - Aug 24
Total with taxes and fees
Guests staying at Huttopia Berkshires enjoy an outdoor pool, free WiFi in public areas, and a picnic area. You can put free parking to good use if you drive. Staff members can help with accommodation requests, and provide front-desk service during limited hours.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
20.8 mi from city center
$128 nightly
The price is $143 total per night
$143 total
Aug 31 - Sep 1
Total with 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 aparthotel include a gym, free WiFi in public areas, and a business center.
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 $135 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.