Chatham Vacation Rentals from $133: 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.

$302 nightly

Aug 24 - Aug 25

Total with taxes and fees

2. BLUSH: Boutique TINY homeprivate spawalk to town

Chatham

scott B.

$299 nightly

Aug 19 - Aug 20

Total with taxes and fees

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

Chatham

Jessica V.

$361 nightly

Aug 9 - Aug 10

Total with taxes and fees

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

Old Chatham

Terri E.

$579 nightly

Aug 31 - Sep 1

Total with taxes and fees

5. Micosta Leisure Inn

Hudson

philippe

$133 nightly

Aug 9 - Aug 10

Total with taxes and fees

6. All the comforts of home

Hudson

Julie B.

$126 nightly

Aug 9 - Aug 10

Total with taxes and fees

7. All comforts of home

Hudson

Mike

$118 nightly

Aug 9 - Aug 10

Total with taxes and fees

8. Berkshire Mountain Lodge

Pittsfield

Joseph

$138 nightly

Aug 30 - Aug 31

Total with taxes and fees

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Top Chatham Hotel Reviews

Vacation Village in the Berkshires

8/10 Good

"Place is generally good but there were few significant problems. The main problem is absence of any food place, stores or restaurants on the proximity of the property. Another problem is a mediocre soundproof. The rest was good. Convenient bed, full kitchen, balcony."

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"Large rooms … I reserved the suit which was only a little more expensive then a regular room … very clean and well maintained facility … breakfast is good.. staff was helpful. Plenty of parking … Thank tou for a very nice stay. Would certainly like to come back …."

The Yankee Inn

10/10 Excellent

"This was our fourth year in a row staying at the Inn. They have a new sitting area outside with a gas fire pit, very nice. The pool is always very well maintained. We like to stay in the older section room away from the main building, the beds are comfortable and the room is basic but clean and nice. The breakfast is as good as any other hotel brand that offers breakfast. The shopping center is right next door within walking distance, with a few places to eat. It’s a great location also to get to anywhere in the area."

The Red Lion Inn

10/10 Excellent

"Escaped into another world on each floor's hallway-the memorabilia and artwork spoke of an honest, New England history. The atmosphere was perfect for a genuine, original immersion into New England's past and LOVED going up and down the 150yr old elevator! Meals delicious w/excellent service. Only one issue we had: the AC in the room was difficult to adjust and were quite chilled even w/turning the thermostat up to 80 deg!!!!!!!!! as suggested by the front desk. Shall make this a yearly visit!"

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

10/10 Excellent

"Very nice clean new property. Simple, clean, comfortable, quiet climate control. Decor is very bland. Desk chair is klunky fake mid-century modern. Pool is about 12 yards long, looked clean. But prices for any hotel near Lenox are just crazy in peak (Tanglewood) season."

Quality Inn Great Barrington

10/10 Excellent

"Very nice front desk staff-courteous, upbeat, helpful. Room was clean but leftover trash in bin and no ice tray in refrigerator. VERY comfortable bed. Train in middle of the night was a throwback experience to a different age-i liked it but some would be frightened of the noise. Excellent location."

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 $133 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 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. 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. Micosta Leisure Inn

6. All the comforts of home

7. All comforts of home

8. Berkshire Mountain Lodge

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

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

11. Hudson NY’S Country Serenity Guest Suite.

12. Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

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

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

15. Pet Friendly • Fenced Yard • Hot Tub • Romantic

16. Vacation Village in the Berkshires

17. 1800s Carriage house in Berkshires / Hudson Valley

18. Gorgeous Mountain Views Retreat: Family & Nature

19. Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

20. Charming Cottage in the Heart of Catskill & Pet Friendly

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

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2. BLUSH: Boutique TINY homeprivate spawalk to town