Search Vacation Homes in Old Chatham

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
24 Jan - 26 Jan
In two weeks
31 Jan - 2 Feb
In one month
14 Feb - 16 Feb
In two months
14 Mar - 16 Mar

Compare 392 Vacation Homes in Old Chatham with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (234)
"Very lovely place to stay. Everything was clean and the owner made everything simple."
The price is AED 551
AED 837 total
includes taxes & fees
21 Jan - 22 Jan
Berkshire Village Carriage House - Super Private!!
Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing
view of the back decks and steps down to our private dock

Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing

10.0 out of 10, Exceptional, (128)
"Stayed at the house over Christmas with family. The house is well-appointed with excellent heat. Hosts were excellent at communicating with us when we had questions."
Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing
Spectacular views and close to Great Barrington.
Private kitchen

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Vacation home just 11 minutes from MVP Arena
Kitchen

Vacation home just 11 minutes from MVP Arena

2.0 star property
9.6 out of 10, Exceptional, (11)
"Nii's place was very clean and served its purpose for our visit to Delmar. The property was exactly as the pictures showed it."
Vacation home just 11 minutes from MVP Arena
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Pool

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

10.0 out of 10, Exceptional, (22)
"Great house that has everything for the family vacation "
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Beautiful Berkshire Farm House on 160+ Acres
Exterior

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (36)
"This was our second group visit to the Berkshire Farm House, and we plan to go back again! That fact says it all. "
Beautiful Berkshire Farm House on 160+ Acres
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Living area

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.4 out of 10, Exceptional, (20)
"Well located and comfortable "
The price is AED 621
AED 1,264 total
includes taxes & fees
31 Jan - 1 Feb
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
4 Bdrm Modern Victorian with Tree House and playground
Gorgeous chef with 6 burner professional gas range

4 Bdrm Modern Victorian with Tree House and playground

9.8 out of 10, Exceptional, (105)
"The house was lovely; every bedroom was nicely furnished with plenty of linens. The kitchen was amazing and was a great place for everyone to gather around and cook; the way the table opened up to the outdoor space was wonderful, but since it was snowing, we didn't get to really use it. The bathrooms were stunning with really nice showers, and there were plenty of nice touches. Galina was kind host who was easy to reach. I would definitely stay again and recommend the place to anyone in the...
4 Bdrm Modern Victorian with Tree House and playground
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Exterior

Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

10.0 out of 10, Exceptional, (116)
"Bright, spacious and clean house on a hill. Prompt and helpful host. "
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Hudson Valley and The Berkshires getaway
Kitchen and dining room

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (5)
"We loved our stay on Stone Ledge Rd in Hillsdale. We have stayed at Vrbo properties in Hillsdale two prior holiday weeks leading up to the New Year and this was by far the best set-up for us—gorgeous views through the wrap-around windows, easy and comfortable sleeping arrangements for the 6 of us, plenty of sofa space for reading, watching movies, just hanging out. Ben was very responsive when a mixture of drizzle and freezing temperatures made the driveway slippery and we were able to park in...
Hudson Valley and The Berkshires getaway
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Comfortable New Decor in Living Room Equipped w Smart TV and Deck

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

10.0 out of 10, Exceptional, (63)
"It was an amazing stay. The host was very proactive and helpful. "
The price is AED 962
AED 1,969 total
includes taxes & fees
20 Jan - 21 Jan
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!
Start Your Day Right - Enjoy Complimentary Fresh Bagels From Around the Corner!

BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!

2.0 star property
8.8 out of 10, Excellent, (3)
"Property is lovely and very well maintained. We stayed for over 10 days and it was a perfect home away from home. Owners are very kind and accommodating — when I couldn’t find a hair dryer one was delivered to the house within a couple of hours. They also offered to relocate us if we were bothered by the nearby forest fire, which was not necessary. I hope we’ll have the opportunity to stay again."
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!
Spacious Luxury Berkshire's Estate on 21 acres
Exterior

Spacious Luxury Berkshire's Estate on 21 acres

Spacious Luxury Berkshire's Estate on 21 acres
Comfortable Berkshires retreat on mtn resort, SISO
Exterior

Comfortable Berkshires retreat on mtn resort, SISO

The price is AED 1,183
AED 2,443 total
includes taxes & fees
20 Jan - 21 Jan
Comfortable Berkshires retreat on mtn resort, SISO
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Breakfast Nook - wake up to the best sunshine ever!

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (118)
"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Stockbridge Home, Come Experience The Berkshires!

Stockbridge Home, Come Experience The Berkshires!

10.0 out of 10, Exceptional, (24)
"We enjoyed everything about this lovely house in the Berkshires--the latest appliances, thoughtful details (throws on all the beds and sofas), a great backyard. Would highly recommend! "
Stockbridge Home, Come Experience The Berkshires!
Amore Estate - beautiful room with many places to explore and relax in.
October MNT FARM!!

Amore Estate - beautiful room with many places to explore and relax in.

9.4 out of 10, Exceptional, (21)
"Fantastic, large house with tons of places to explore in the house and on the property. We came for a long weekend with 3 families and both the adults and kids felt quickly at home and really enjoyed our stay. We cannot wait to some back!"
Amore Estate - beautiful room with many places to explore and relax in.
PRISTINE CAPE COD ON THE CREEK! 4 Large Bedrooms - 8 Guests!
Room

PRISTINE CAPE COD ON THE CREEK! 4 Large Bedrooms - 8 Guests!

9.2 out of 10, Wonderful, (93)
"Nice house, good location. Much bigger inside than it looks! The house worked well for us with handicap needs, other than the small step into the house. "
PRISTINE CAPE COD ON THE CREEK! 4 Large Bedrooms - 8 Guests!
2 bedroom town house with game room
Game room

2 bedroom town house with game room

6.4 out of 10, (13)
"Comfortable and presentable. Location is great for going downtown or shopping in general. Restaurants are very close by. Property manager was easy to communicate with."
The price is AED 331
AED 551 total
includes taxes & fees
20 Jan - 21 Jan
2 bedroom town house with game room
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
Athens Vacation Rental | 3BR | 2BA | 2 Stories | Stairs Required | 1,400 Sq Ft

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

9.0 out of 10, Wonderful, (20)
" The house has a beautiful location and the view of the lake is beautiful. There are several things to do in the surrounding areas such as hiking, horseback riding, shopping and nice restaurants. The house was overall nice. It has a combination of very nice updates and a few needed updates. The couches are extremely uncomfortable. Our host was responsive for the most part."
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
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.
Don't see what you're looking for?
See all available properties in Old Chatham
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Old Chatham

Beautiful Estate w/pool, gym, pond, trails, arcade! Perfect for family/friends!
Beautiful Bellavista Country Estate! Create Timeless Memories w/ Family/ Friends

Beautiful Estate w/pool, gym, pond, trails, arcade! Perfect for family/friends!

9.6 out of 10, Exceptional, (85)
"We had fun! Game room great! Spacious and comfortable. Never got to enjoy outdoors, so maybe another trip in the future!"
Beautiful Estate w/pool, gym, pond, trails, arcade! Perfect for family/friends!
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1756)
"Room was right across from the pool. Beautiful view of the mountain five min drive to the base. Beautiful pool and outdoor jacuzzi. Had an amazing stay! Cant wait to go back!"
The price is AED 689
AED 792 total
includes taxes & fees
20 Jan - 21 Jan
Vacation Village in the Berkshires
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Welcome to The Freeman Berkshires

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (32)
"We had such a lovely time at this property! The space is gorgeous and the outside is perfect for walking around and exploring with the dogs. We had 18 people staying overnight and we all fit well (with the addition of some curtains for privacy) and had our own space to hide away in when needed. It was stocked with pretty much everything we needed, including firewood, glass vases for wedding decorations, tons of dishware, throw blankets, etc. Our group made wonderful memories here - thank you!"
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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.