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 rental 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

A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

1. BLUSH: Boutique TINY homeprivate spawalk to town

Chatham

scott B.

$270 nightly

Sep 23 - Sep 24

Total with taxes and fees

A camping setup with a metal chair and a table by a river in a forest.

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

Chatham

Jess S.

$293 nightly

Sep 23 - Sep 24

Total with taxes and fees

A wooden interior with a dining table, chairs, and a window with a view of greenery outside.

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

Chatham

Sue G.

$270 nightly

Sep 23 - Sep 24

Total with taxes and fees

A modern building with a wooden deck and a door.

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

Old Chatham

Terri E.

$479 nightly

Sep 23 - Sep 24

Total with taxes and fees

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

5. Micosta Leisure Inn

Hudson

Kim

$118 nightly

Oct 1 - Oct 2

Total with taxes and fees

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

6. Berkshire Mountain Lodge

Pittsfield

Robert

$108 nightly

Oct 22 - Oct 23

Total with taxes and fees

A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

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

Catskill

Justin

$209 nightly

Sep 23 - Sep 24

Total with taxes and fees

A wooden deck with a staircase leading to a covered porch area.

8. All comforts of home

Hudson

Georgine

$118 nightly

Sep 27 - Sep 28

Total with taxes and fees

9. All the comforts of home

Hudson

Julie B.

$126 nightly

Oct 1 - Oct 2

Total with taxes and fees

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

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

New Lebanon

Varun M.

$203 nightly

Sep 23 - Sep 24

Total with taxes and fees

A backyard with a fire pit, wooden deck, and string lights.

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

Stottville

Ross O.

$324 nightly

Sep 23 - Sep 24

Total with taxes and fees

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

12. Vacation Village in the Berkshires

Williamstown

Jacob

$122 nightly

Sep 23 - Sep 24

Total with taxes and fees

A poolside dining area with a table set for a meal, surrounded by a pool and greenery.

13. Hudson NY’S Country Serenity Guest Suite.

Hudson

David P.

$337 nightly

Sep 23 - Sep 24

Total with taxes and fees

A wooden cabin with a porch, a door, and a window.

14. Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake

Linda R.

$165 nightly

Sep 23 - Sep 24

Total with taxes and fees

A dining area with a table set for two, a vase with flowers, and a bottle of wine.

15. 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 23 - Sep 24

Total with taxes and fees

A snow-covered outdoor area with a fire pit, tables, and chairs.

16. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Hancock

Maura D.

$190 nightly

Sep 23 - Sep 24

Total with taxes and fees

A modern interior with a staircase, wooden flooring, a dining area, and a brick wall.

17. Catskill Cottage Walk to Downtown & River Views

Catskill

Bryan S.

$156 nightly

Sep 28 - Sep 29

Total with taxes and fees

A spacious living room with a dining area, a kitchen, and a large window.

18. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

$235 nightly

Sep 29 - Sep 30

Total with taxes and fees

A kitchen with white cabinetry, granite countertops, and a window with blinds.

19. Charming loft cottage in tranquil Germantown with WiFi, AC

Germantown

Kanna S.

$226 nightly

Sep 29 - Sep 30

Total with taxes and fees

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

20. Cozy 1-bedroom studio in serene Great Barrington with AC

Great Barrington

Shelly B.

$148 nightly

Sep 29 - Sep 30

Total with taxes and fees

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Top Chatham Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"Great place to stay in the Berkshires in the summer! Best price in the area for a busy weekend at Tanglewood. All other options were ridiculously expensive, Resort had great amenities. The indoor pool and outdoor hot tub where much appreciated after our trip out from the Boston area. Highly recommend this resort any time of year for ski season or summer/Fall sightseeing."

The Red Lion Inn

10/10 Excellent

"This is a wonderful, historic inn. Check out the Red Lion Den for music. We heard a terrific local group. We ate in the Tavern and the food was tasty. This is not a luxurious place. It dates back to the 1700s. But it is really charming. My friends and I stayed in a suite in an out building. We had a low-ceiled living room downstairs, which was a. great place to talk and catch up. The bedroom situation was a little funky because the bathroom was right next to the bed in one of two sleeping areas upstairs and the door really squeaked when it opened and closed. But that was about our only complaint. I'd be delighted to return."

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 rental 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 11 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. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

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

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

5. Micosta Leisure Inn

6. Berkshire Mountain Lodge

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

8. All comforts of home

9. All the comforts of home

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

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

12. Vacation Village in the Berkshires

13. Hudson NY’S Country Serenity Guest Suite.

14. Taborton Harvest Boulder Pines Cabin in the woods

15. Charming Yacht on Catskill Creek

16. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

17. Catskill Cottage Walk to Downtown & River Views

18. 1800s Carriage house in Berkshires / Hudson Valley

19. Charming loft cottage in tranquil Germantown with WiFi, AC

20. Cozy 1-bedroom studio in serene Great Barrington with AC

Find vacation rentals that suit your style

Top Chatham Hotel Reviews

Vacation Village in the Berkshires

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