Chatham Vacation Rentals from $139: Search Short-Term Rentals

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Our top choices for Chatham vacation rentals

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

Chatham

Sue G.

$303 nightly

Aug 24 - Aug 25

Total with taxes and fees

2. BLUSH: Boutique TINY homeprivate spawalk to town

Chatham

scott B.

$286 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Chatham

Jessica V.

$366 nightly

Aug 23 - Aug 24

Total with taxes and fees

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

Old Chatham

Terri E.

$556 nightly

Sep 9 - Sep 10

Total with taxes and fees

5. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Lenox

$372 nightly

Aug 17 - Aug 18

Total with taxes and fees

Classic Tent, Garden View | Outdoor dining

6. Gatherwild Ranch

Germantown

$194 nightly

Aug 26 - Aug 27

Total with taxes and fees

7. Micosta Leisure Inn

Hudson

philippe

$133 nightly

Aug 16 - Aug 17

Total with taxes and fees

8. Berkshire Mountain Lodge

Pittsfield

Karilyn

$125 nightly

Aug 31 - Sep 1

Total with taxes and fees

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Top Chatham Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"A nice place to stay in the Berkshires."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Loved our two-day stay at the Black Swan Inn. We were in the area because we were taking a few programs at the Kripalu Center for one of the days. The room itself was clean, the hall areas could do with better maintenance (which is why I gave that 4 stars) The staff was helpful with any questions. Continental breakfast was decent (though they could do with better coffee). We wished we could have enjoyed the Indian restaurant "Mint" next door, which I hear is really good, but they were closed on Tuesdays, so it was a matter of timing..., but we hope to have a chance next time we are in the area. One of my favorite parts of the property is that it sits by a clean lovely lake, and there are seating areas to enjoy the view anytime of day just to unwind. They also have kayak rentals for those who enjoy the activity. Another wonderful treat- it is near High Lawn Farm, only a 3-min drive from the Inn. It is beautiful there, and cute Jersey cows roam freely, when they are ready they go on their own time into a building where they lay on heated water beds while being milked (I kid you not!). Their dairy products and ice-cream are excellent, worth taking the short drive there. The town center of Lee has some nice restaurants and boutiques within a 5-8 min drive. It was a memorable stay and hope to be back there again soon."

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"My husband and I just wanted to get away to quiet. Did we get that! The check in was flawless. They communicated via text daily if we needed and resupplies. The unit was nestled in a secluded spot. We did not see anyone else. The unit was clean and well appointed. The bathroom was generous considering the situation. The touches from a 'phone lock box' and books on how to relax or play cards were wonderful. The bed took a little to get used to but slept so well! It was a wonderful time in nature. We loved the dry wood and smores kits!!!"

Berkshires Untold

8/10 Good

"Lovely man at check in for our overnight ( to see Hugh Jackman at 7 pm at Tanglewood lucky us!👍 Checked that food would be available in their bar upon our trying as has driven 2+ hrs assured yes until just before 10 pm closing. Called once on way back at 9:10 for 10 min drive to dbl check as hungry. Woman said no, they stopping serving at 9... luckily she rec one place nearby which was still open for food til midnight! Wow in Lenox! Very packed loud and fun w locals & Jackman fans..got wines, friendly bartenders, ordered yummy plates of tacos , sandwich and ended eve on a great note . Go to OMBRA if hungry after 9! Small complaint this am also.. we ordered a bagel & a berry salad from the hotel's brkfst menu to go as needed to drive back home mid am.. Opened it and about 1/2 cup of mixed berries ..for $11.00... Think the bagel was 8. Oh well -worth the splurge to see Hugh 💕and only 10 min drive to Tanglewood & downtown Lenox! Hotel not walkable to anything but ez parking & very cute interior & bar & seating areas!"

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 $139 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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental near Chatham is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

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 Kinderhook Lake. The Mac-Haydn Theatre and Queechy Lake 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. Sugar Shack - 300 square feet of pure sweetness.

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

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

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

5. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

6. Gatherwild Ranch

7. Micosta Leisure Inn

8. Berkshire Mountain Lodge

9. Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

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

11. Vacation Village in the Berkshires

12. Sleepy Hollow Lake Home w/ Deck, Pool Access!

13. All comforts of home

14. All the comforts of home

15. Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

16. Sleepy Hollow Lake Home w/ Deck, Pool Access!

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

18. Cozy Riverside Berkshires Retreat

19. Mtn-View Retreat in Huson Valley: Great for Groups

20. 2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

Find vacation rentals that suit your style

Top Chatham Hotel Reviews

Berkshire Mountain Lodge

Find out more about Chatham

Explore a world of travel with Expedia

Frequently asked questions

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2. BLUSH: Boutique TINY homeprivate spawalk to town