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
$139 nightly
The price is $155 total per night
$155 total
Sep 21 - Sep 22
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, barbecue grills, and a picnic area.
Kitchen
Pet friendly
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

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

Coxsackie NY
10.48 mi from city center
This vacation home features karaoke, an outdoor pool, and a gym. Other amenities at this beach vacation home include a hot tub, an arcade/game room, and laundry facilities.
Pool
Hot Tub
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 barbecue grills.
Pool
Hot Tub
Pet Friendly Glamping • Hot Tub • Fire Pit • Patio

Pet Friendly Glamping • Hot Tub • Fire Pit • Patio

Ravena NY
13.11 mi from city center
$206 nightly
The price is $223 total per night
$223 total
Sep 29 - Sep 30
Total with taxes and fees
Pet Friendly Glamping • Hot Tub • Fire Pit • Patio features a hot tub and a garden.
Hot Tub
Kitchen
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.
Pool
Kitchen
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
17.22 mi from city center
$108 nightly
The price is $120 total per night
$120 total
Oct 18 - Oct 19
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.
Pool
Hot Tub
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Catskill NY
17.41 mi from city center
$321 nightly
The price is $360 total per night
$360 total
Sep 29 - Sep 30
Total with taxes and fees
Guests staying at this cabin have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
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.
Pool
Hot Tub
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
$209 nightly
The price is $226 total per night
$226 total
Sep 21 - Sep 22
Total with taxes and fees
There's free parking if you drive.
Kitchen
Pet friendly
Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook

Catskill NY
20.13 mi from city center
$327 nightly
The price is $353 total per night
$353 total
Sep 24 - Sep 25
Total with taxes and fees
This vacation home is a smoke-free vacation home.
Kitchen
Free WiFi
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
$122 nightly
The price is $136 total per night
$136 total
Sep 20 - Sep 21
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 concierge services and access to locker space. Other amenities at this family-friendly aparthotel 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 $120 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.