We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Chatham

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0+ rooms, 2+ guests
Distance from
1 km
Price per night
S$0
S$1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
50 rentals in Chatham.
Sort by:
Tripadvisor Sort
CLOSE TO SKIING /HOT TUB /FIBER OPTIC WIFI/ 1NIGHT CANYON RANCH CHEF AVAILABLE, holiday rental in Chatham

CLOSE TO SKIING /HOT TUB /FIBER OPTIC WIFI/ 1NIGHT CANYON RANCH CHEF AVAILABLE

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Relax in the Country - Peace, quiet and family friendly, holiday rental in Chatham

Relax in the Country - Peace, quiet and family friendly

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Country estate on 100 acres perfect for families, holiday rental in Chatham

Country estate on 100 acres perfect for families

4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Beauty in the Berkshires, holiday rental in Chatham

Beauty in the Berkshires

6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
Secluded and Private Location in the Mountains yet close to Skiing & attractions, holiday rental in Chatham

Secluded and Private Location in the Mountains yet close to Skiing & attractions

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town., holiday rental in Chatham

4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town.

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Newly Renovated 1910 Farmhouse - Walk To Town - Perfect Berkshire Retreat, holiday rental in Chatham

Newly Renovated 1910 Farmhouse - Walk To Town - Perfect Berkshire Retreat

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Heaven Cant Wait, On Beautiful Kinderhook, holiday rental in Chatham

Heaven Cant Wait, On Beautiful Kinderhook

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Charming, Quiet, Modern, Wooded, River Front, holiday rental in Chatham

Charming, Quiet, Modern, Wooded, River Front

3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
More info
Check-in
Check-out
Designer Home with Panoramic Views near Hudson, holiday rental in Chatham

Designer Home with Panoramic Views near Hudson

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Save time - get the best Chatham rentals sent straight to your email!
Charming Farmhouse Steps from Downtown West Stockbridge, holiday rental in Chatham

Charming Farmhouse Steps from Downtown West Stockbridge

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Cabin on forest road, holiday rental in Chatham

Cabin on forest road

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!, holiday rental in Chatham

Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Quiet Guest House In The Green River Valley, holiday rental in Chatham

Quiet Guest House In The Green River Valley

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Two Rooms with En-Suite in Quiet Woodland, holiday rental in Chatham

Two Rooms with En-Suite in Quiet Woodland

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Carriage House Charmer, holiday rental in Chatham

Carriage House Charmer

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Historical Dutch Gem In The Hudson Valley, holiday rental in Chatham

Historical Dutch Gem In The Hudson Valley

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Private Hillsdale Home With Views Of Catamount., holiday rental in Chatham

Private Hillsdale Home With Views Of Catamount.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
The Home in Malden Bridge, Columbia County, New York, holiday rental in Chatham

The Home in Malden Bridge, Columbia County, New York

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Morning Face - Berkshire estate with heated pool, views and privacy., holiday rental in Chatham

Morning Face - Berkshire estate with heated pool, views and privacy.

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Long term availability Berkshire chalet with hot tub and fast WIFI, holiday rental in Chatham

Long term availability Berkshire chalet with hot tub and fast WIFI

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Hudson River Beach House, holiday rental in Chatham

Hudson River Beach House

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Stunning New Construction All SeasonLakefront Home, holiday rental in Chatham

Stunning New Construction All SeasonLakefront Home

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Cozy apartment overlooking our small farm.  Family Friendly., holiday rental in Chatham

Cozy apartment overlooking our small farm. Family Friendly.

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Secluded Family-Friendly Home, holiday rental in Chatham

Secluded Family-Friendly Home

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Hillhouse Log Cabin, holiday rental in Chatham

Hillhouse Log Cabin

3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Bellavista Country Estate - The Library Suite, holiday rental in Chatham

Bellavista Country Estate - The Library Suite

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Pineview - Ideal Escape, holiday rental in Chatham

Pineview - Ideal Escape

6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Roaring Rapids Cottage, holiday rental in Chatham

Roaring Rapids Cottage

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Total Privacy! Tanglewood Retreat With Berkshire Views!, holiday rental in Chatham

Total Privacy! Tanglewood Retreat With Berkshire Views!

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Cedar Chest, holiday rental in Chatham

Cedar Chest

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Modern Cozy Wooded Retreat, holiday rental in Chatham

Modern Cozy Wooded Retreat

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Leisure home with beach front property, holiday rental in Chatham

Leisure home with beach front property

6 bedrooms
3 bathrooms
Sleeps 25
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Bassinova-on-Hudson, holiday rental in Chatham

Bassinova-on-Hudson

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Bellavista Country Estate - Rose Suite, holiday rental in Chatham

Bellavista Country Estate - Rose Suite

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Beautiful Bellavista Country Estate, holiday rental in Chatham

Beautiful Bellavista Country Estate

8 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Historic Gem Near Hudson, NY, holiday rental in Chatham

Historic Gem Near Hudson, NY

1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Brook Hill Farm House, holiday rental in Chatham

Brook Hill Farm House

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Tentrr Signature Site - Berkshire Mountain Hideaway, holiday rental in Chatham

Tentrr Signature Site - Berkshire Mountain Hideaway

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Hudson Valley Berkshires Cottage, holiday rental in Chatham

Hudson Valley Berkshires Cottage

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
A Beautiful Retreat In a Stunning Home and Landscaped Lawns, holiday rental in Chatham

A Beautiful Retreat In a Stunning Home and Landscaped Lawns

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Chalet near 4 ski resorts with hot tub, holiday rental in Chatham

Chalet near 4 ski resorts with hot tub

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Spacious secluded  yet close to everything, holiday rental in Chatham

Spacious secluded yet close to everything

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Winter Wonderland, minutes to Hudson and Berkshires, holiday rental in Chatham

Winter Wonderland, minutes to Hudson and Berkshires

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Tentrr Signature Site - WATER + WOODS, holiday rental in Chatham

Tentrr Signature Site - WATER + WOODS

1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Tentrr Signature Site - The Lodge's Campsite, holiday rental in Chatham

Tentrr Signature Site - The Lodge's Campsite

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
NEW! Nature Lover’s Haven - Ski, Golf, Fish, Hike!, holiday rental in Chatham

NEW! Nature Lover’s Haven - Ski, Golf, Fish, Hike!

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Secluded House with Picturesque Views in Historic Old Chatham, NY, holiday rental in Chatham

Secluded House with Picturesque Views in Historic Old Chatham, NY

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
1850s Barn Conversion with fenced in yard near Hudson River, holiday rental in Chatham

1850s Barn Conversion with fenced in yard near Hudson River

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
NEW! Cozy Retreat w/ Hot Tub on Sleepy Hollow Lake, holiday rental in Chatham

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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
PreviousNext
1
Frequently Asked Questions about Chatham