Chatham Vacation Rentals from $120: Search Short-Term Rentals

Q: What are some of the best vacation home rentals that Chatham has to offer?

Catskill Cottage Walk to Downtown & River Views : This vacation home near Chatham offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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Our top choices for Chatham vacation rentals

1. BLUSH: Boutique TINY homeprivate spawalk to town

Chatham

scott B.

$281 nightly

Sep 22 - Sep 23

Total with taxes and fees

2. Sugar Shack - 300 square feet of pure sweetness.

Chatham

Sue G.

$281 nightly

Sep 22 - Sep 23

Total with taxes and fees

3. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham

Jess S.

$305 nightly

Sep 20 - Sep 21

Total with taxes and fees

4. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Old Chatham

Terri E.

$513 nightly

Sep 22 - Sep 23

Total with taxes and fees

5. Micosta Leisure Inn

Hudson

Kim

$136 nightly

Sep 20 - Sep 21

Total with taxes and fees

6. All comforts of home

Hudson

Georgine

$118 nightly

Sep 27 - Sep 28

Total with taxes and fees

7. All the comforts of home

Hudson

Julie B.

$115 nightly

Sep 20 - Sep 21

Total with taxes and fees

8. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Catskill

Rosemary

$209 nightly

Sep 21 - Sep 22

Total with taxes and fees

9. Berkshire Mountain Lodge

Pittsfield

Robert

$108 nightly

Oct 18 - Oct 19

Total with taxes and fees

10. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Stottville

Kathy A.

$311 nightly

Sep 20 - Sep 21

Total with taxes and fees

11. Hudson NY’S Country Serenity Guest Suite.

Hudson

David P.

$340 nightly

Sep 22 - Sep 23

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

12. NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Varun M.

$203 nightly

Sep 20 - Sep 21

Total with taxes and fees

Classic Tent, Garden View | Outdoor dining

13. Gatherwild Ranch

Germantown

$243 nightly

Sep 23 - Sep 24

Total with taxes and fees

14. Vacation Village in the Berkshires

Williamstown

Sarah

$122 nightly

Sep 20 - Sep 21

Total with taxes and fees

15. Pet Friendly Glamping • Hot Tub • Fire Pit • Patio

Ravena

Richard H.

$206 nightly

Sep 29 - Sep 30

Total with taxes and fees

16. Ideal location for summer and winter activities with plenty of outdoor space.

Hillsdale

Kenny

$339 nightly

Sep 20 - Sep 21

Total with taxes and fees

17. Charming Yacht on Catskill Creek

Catskill

"We had never stayed overnight on a boat before and were a little nervous. Now we can't wait to stay on one again! Melissa and AJ were so accommodating and extremely nice....perfect place to stay if seeing a concert at Catskill Point. They dropped us off at concert and picked us up on pontoon - how fun is that? To wake up to a sunny and serene morning while having coffee on the creek was priceless. I never do reviews but felt compelled to do this one only because if you are having...

Frances K.

$233 nightly

Sep 19 - Sep 20

Total with taxes and fees

18. Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake

Linda R.

$165 nightly

Sep 18 - Sep 19

Total with taxes and fees

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

Catskill

Jessica R.

$321 nightly

Sep 29 - Sep 30

Total with taxes and fees

20. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

$243 nightly

Sep 20 - Sep 21

Total with taxes and fees

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Top Chatham Hotel Reviews

Country Inn & Suites by Radisson, Downtown Albany New York

10/10 Excellent

"Very comfortable beds, clean, climate controlled via wall thermostat and vent so no noisy, air-blasting under-window unit. Window opens a few inches too. Plenty of space. Toilet is adult height and non-slippery tub. Parking adequate. Location in area of bus depot and parking lots near expressway, a five+minute less than pleasant walk to anything but also not far from the main commercial street. My credit card was charged twice and it took several days of pleading with staff to get it fixed."

The Red Lion Inn

8/10 Good

"Bedding and bed were lovely. excellent to have good lighting at sink as well as a magnified mirror! Often lacking in places we have stayed. AC had trouble cooling the room down until we turned it on full blast. too much ambient light from floodlight on property next door and from hall (I finally turned off hallway light which helped. ) Common areas and halls need some brightening up with fresh, lighter paint--seemed dingy. Was terribly frustrating trying to make the Nespresso machine work. We do not own one and there were NO INSTRUCTIONS. You should assume people do not know how to operate any appliances like that and should have a card with directions. We gave up and went to the Tavern where we had lovely coffee and breakfast. Also had a great dinner in Tavern after our arrival. The patch burrata salad was superb. As was our waitress."

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"I really love staying here. It’s no nonsense clean and i feel safe traveling as a woman alone… However they really need to step up their morning breakfast. I eat gluten free and they never have any. I’ve asked for ivermectin a month now and they just tell me they will mention it…."

Find out more about Chatham

Everything you need to know about Chatham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chatham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chatham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chatham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chatham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chatham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $120 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chatham rentals

At Expedia, we put the best Chatham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chatham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chatham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chatham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Things to do in Albany

Frequently asked questions

Are there vacation rentals in Chatham?

Yes, we have vacation rentals close to top points of interest in Chatham, or you can go with a secluded option if you want a relaxing place to stay. Chatham is known for its theaters and restaurants.

What are some of the best vacation home rentals that Chatham has to offer?

Catskill Cottage Walk to Downtown & River Views: This vacation home near Chatham offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Chatham?

With 12 Expedia vacation rentals, you're sure to find just the right place for your Chatham stay.

What can I see and do in Chatham?

While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Art Omi International Arts Center - Fields Sculpture Park. The Mac-Haydn Theatre and Martin Van Buren National Historic Site are a couple of places you'll find in the larger area.

What are vacation rentals like in Chatham?

Vacation rentals are privately owned properties you can stay in for several days or more in Chatham. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family getaway.

Chatham Vacation Rentals

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Check prices for these dates

Our top choices for Chatham vacation rentals

1. BLUSH: Boutique TINY home*private spa*walk to town

2. Sugar Shack - 300 square feet of pure sweetness.

3. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

4. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

5. Micosta Leisure Inn

6. All comforts of home

7. All the comforts of home

8. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

9. Berkshire Mountain Lodge

10. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

11. Hudson NY’S Country Serenity Guest Suite.

12. NEW RENO - Chalet-style farm loft near Tanglewood

13. Gatherwild Ranch

14. Vacation Village in the Berkshires

15. Pet Friendly Glamping • Hot Tub • Fire Pit • Patio

16. Ideal location for summer and winter activities with plenty of outdoor space.

17. Charming Yacht on Catskill Creek

18. Taborton Harvest Boulder Pines Cabin in the woods

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

20. 1800s Carriage house in Berkshires / Hudson Valley

Find vacation rentals that suit your style

Top Chatham Hotel Reviews

Country Inn & Suites by Radisson, Downtown Albany New York

Find out more about Chatham

Explore a world of travel with Expedia

Frequently asked questions

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1. BLUSH: Boutique TINY homeprivate spawalk to town