Vacation rentals in Old Chatham, NY

Best vacation rentals and Airbnb offers in Old Chatham, NY

Ghent Getaway, Minutes from Hudson

Apartment, Old Chatham

Ghent Getaway, Minutes from Hudson is a apartment in Old Chatham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Ghent Getaway, Minutes from Hudson

Ghent Getaway, Minutes from Hudson is a apartment in Old Chatham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $967.

From$138/night

Show›

Spacious 1-bedroom apartment in peaceful East Chatham with WiFi

Apartment, Old Chatham

Spacious 1-bedroom apartment in peaceful East Chatham with WiFi is a apartment in Old Chatham, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

Read more

About Spacious 1-bedroom apartment in peaceful East Chatham with WiFi

Spacious 1-bedroom apartment in peaceful East Chatham with WiFi is a apartment in Old Chatham, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,175.

From$168/night

Show›

Chatham Cozy Country Retreat

Holiday Home, Old Chatham

Chatham Cozy Country Retreat is a holiday home in Old Chatham, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Chatham Cozy Country Retreat

Chatham Cozy Country Retreat is a holiday home in Old Chatham, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,303.

From$186/night

Show›

NEW RENO - Historic Loft w/views of the Berkshires

Country House, Old Chatham

NEW RENO - Historic Loft w/views of the Berkshires is a country house in Old Chatham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About NEW RENO - Historic Loft w/views of the Berkshires

NEW RENO - Historic Loft w/views of the Berkshires is a country house in Old Chatham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,369.

From$196/night

Show›

Vacation rentals with a pool in Old Chatham, NY

Add a pool to the search when you want an easy place to cool off between outings.

Eagles Perch on the Hudson River

Apartment, Old Chatham

Eagles Perch on the Hudson River is a apartment in Old Chatham, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

Read more

About Eagles Perch on the Hudson River

Eagles Perch on the Hudson River is a apartment in Old Chatham, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,514.

From$216/night

Show›

-Private renovated farmhouse along the Hudson surrounded by State Park Land

Country House, Old Chatham

-Private renovated farmhouse along the Hudson surrounded by State Park Land is a country house in Old Chatham, with pool access and kitchen access. This stay gives travelers a comfortable…

Read more

About -Private renovated farmhouse along the Hudson surrounded by State Park Land

-Private renovated farmhouse along the Hudson surrounded by State Park Land is a country house in Old Chatham, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,744.

From$535/night

Show›

Scenic Hilltop Home, Hot Tub, Fireplace, Home Gym

Holiday Home, Old Chatham

Scenic Hilltop Home, Hot Tub, Fireplace, Home Gym is a holiday home in Old Chatham, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the…

Read more

About Scenic Hilltop Home, Hot Tub, Fireplace, Home Gym

Scenic Hilltop Home, Hot Tub, Fireplace, Home Gym is a holiday home in Old Chatham, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,512.

From$645/night

Show›

6 person HOT TUB! New 1855 Riverfront Farmhouse with Pickleball & PS5!

Holiday Home, Old Chatham

6 person HOT TUB! New 1855 Riverfront Farmhouse with Pickleball & PS5! is a holiday home in Old Chatham, with pool access and kitchen access. This stay gives travelers a comfortable base…

Read more

About 6 person HOT TUB! New 1855 Riverfront Farmhouse with Pickleball & PS5!

6 person HOT TUB! New 1855 Riverfront Farmhouse with Pickleball & PS5! is a holiday home in Old Chatham, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,771.

From$824/night

Show›

Vacation rentals with parking in Old Chatham, NY

Find vacation rentals that make arriving by car easier.

1800s Carriage house in Berkshires / Hudson Valley

Country House, Old Chatham

1800s Carriage house in Berkshires / Hudson Valley is a country house in Old Chatham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley is a country house in Old Chatham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,655.

From$236/night

Show›

Ridgeview Retreat | Valley Views • Sleeps 6

Apartment, Old Chatham

Ridgeview Retreat · Valley Views · Sleeps 6 is a apartment in Old Chatham, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

Read more

About Ridgeview Retreat | Valley Views • Sleeps 6

Ridgeview Retreat · Valley Views · Sleeps 6 is a apartment in Old Chatham, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,052.

From$293/night

Show›

Suite 2 - Quiet and private accommodations in a country setting.

Holiday Home, Old Chatham

Suite 2 - Quiet and private accommodations in a country setting. is a holiday home in Old Chatham, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

Read more

About Suite 2 - Quiet and private accommodations in a country setting.

Suite 2 - Quiet and private accommodations in a country setting. is a holiday home in Old Chatham, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,910.

From$416/night

Show›

Farm Stay at Kinderhook Farm in Valatie, New York

Holiday Home, Old Chatham

Farm Stay at Kinderhook Farm in Valatie, New York is a holiday home in Old Chatham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Farm Stay at Kinderhook Farm in Valatie, New York

Farm Stay at Kinderhook Farm in Valatie, New York is a holiday home in Old Chatham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,989.

From$427/night

Show›

Pet-friendly vacation rentals in Old Chatham, NY

Bring your pet along with stays that welcome four-legged travelers.

Lovely 1-bedroom apartment in newly renovated historic house

Apartment, Old Chatham

Lovely 1-bedroom apartment in newly renovated historic house is a apartment in Old Chatham, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for…

Read more

About Lovely 1-bedroom apartment in newly renovated historic house

Lovely 1-bedroom apartment in newly renovated historic house is a apartment in Old Chatham, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, fireplace, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,273.

From$182/night

Show›

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Holiday Home, Old Chatham

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck is a holiday home in Old Chatham, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

Read more

About 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck is a holiday home in Old Chatham, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,716.

From$245/night

Show›

Deluxe cottage retreat!

Holiday Home, Old Chatham

Deluxe cottage retreat! is a holiday home in Old Chatham, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Deluxe cottage retreat!

Deluxe cottage retreat! is a holiday home in Old Chatham, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,335.

From$334/night

Show›

Newly Renovated Cabin in the Country

Cabin, Old Chatham

Newly Renovated Cabin in the Country is a cabin in Old Chatham, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Newly Renovated Cabin in the Country

Newly Renovated Cabin in the Country is a cabin in Old Chatham, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,495.

From$356/night

Show›

Vacation rentals with a kitchen in Old Chatham, NY

Compare stays with kitchen access for longer trips and easier meals.

Charming 3-bedroom Ski house in Hancock 2.5 Miles from Jimmy Peak

Holiday Home, Old Chatham

Charming 3-bedroom Ski house in Hancock 2.5 Miles from Jimmy Peak is a holiday home in Old Chatham, with parking, kitchen access, and room for a group. This stay gives travelers a…

Read more

About Charming 3-bedroom Ski house in Hancock 2.5 Miles from Jimmy Peak

Charming 3-bedroom Ski house in Hancock 2.5 Miles from Jimmy Peak is a holiday home in Old Chatham, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,289.

From$184/night

Show›

Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)

Condo, Old Chatham

Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox) is a condo in Old Chatham, with pet-friendly space and kitchen access. This stay gives travelers a…

Read more

About Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)

Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox) is a condo in Old Chatham, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,579.

From$226/night

Show›

Dharma Grove - Bask in the Light

Holiday Home, Old Chatham

Dharma Grove - Bask in the Light is a holiday home in Old Chatham, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Dharma Grove - Bask in the Light

Dharma Grove - Bask in the Light is a holiday home in Old Chatham, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,814.

From$402/night

Show›

Charming 5-bedroom Vacation House in Chatham

Country House, Old Chatham

Charming 5-bedroom Vacation House in Chatham is a country house in Old Chatham, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

Read more

About Charming 5-bedroom Vacation House in Chatham

Charming 5-bedroom Vacation House in Chatham is a country house in Old Chatham, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,123.

From$446/night

Show›

Family-friendly vacation rentals in Old Chatham, NY

Plan a trip with stays that give families more room to spread out.

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Apartment, Old Chatham

2 Bed Berkshire Apt minutes to Jiminy Peak Ski is a apartment in Old Chatham, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski is a apartment in Old Chatham, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,300.

From$186/night

Show›

2 Bed Berkshire Getaway @ Stephentown Hotel

Apartment, Old Chatham

2 Bed Berkshire Getaway @ Stephentown Hotel is a apartment in Old Chatham, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About 2 Bed Berkshire Getaway @ Stephentown Hotel

2 Bed Berkshire Getaway @ Stephentown Hotel is a apartment in Old Chatham, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,405.

From$201/night

Show›

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Cottage, Old Chatham

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck is a cottage in Old Chatham, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck is a cottage in Old Chatham, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,046.

From$224/night

Show›

Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2 bath

Holiday Home, Old Chatham

Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2 bath is a holiday home in Old Chatham, with kitchen access and a quieter setting. This stay gives travelers a…

Read more

About Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2 bath

Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2 bath is a holiday home in Old Chatham, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,045.

From$292/night

Show›