Chatham Rentals
From $274 per night (USD)VRBO
Sugar Shack - 300 square feet of pure sweetness.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A very Romantic-Private-Peaceful OASIS yet steps from quintessential Main Street lined with restaurants, brewery, shops, ...
From $274 per night (USD)VRBO
From $458 per night (USD)VRBO
2,000 sq ft loft located \"downtown\" with access to dining..shops...movie theater
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located on Main Street in “downtown” Chatham, chathamLoft75 is a 2,000 sq ft fully furnished second floor space that has ...
From $458 per night (USD)VRBO
From $286 per night (USD)VRBO
HunnyHAUS: Deluxe TINY*private spa*walk to town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Reserve this thoughtfully curated space just 2.5 hours from NYC or Boston. You'll fall in love with this Romantic-Privat ...
From $286 per night (USD)VRBO
From $333 per night (USD)Expedia
Harmony House in Hudson Valley- Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to the Harmony House, located within walking distance of the charming and historic Chatham town square. This coz ...
From $333 per night (USD)Expedia
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Renovated Chatham Home ~ Half Mi to Downtown!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Discover a quiet retreat in this stunning 4-bedroom, 2.5-bath vacation rental in Chatham, NY. Unwind and enjoy the charm ...
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From $296 per night (USD)Expedia
BLUSH: Boutique TINY home*private spa*walk to town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cozy in at this Romantic-Private-Peaceful OASIS & just steps from quintessential Main St. Indulgences abound in this one ...
From $296 per night (USD)Expedia
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9 acres of elegant gardens, rolling lawns, wooded paths and a private pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Explore 9 private acres of elegant gardens, rolling lawns, meadows, and wooded paths, complete with an (unheated) privat ...
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From $366 per night (USD)VRBO
Nordic Cabin: Light-Filled + Spacious w/Firepit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Nordic Cabin is a mid-century, Scandinavian-inspired home on 6 acres of woods—just 2 hrs from NYC! Bright, li ...
From $366 per night (USD)VRBO
From $220 per night (USD)VRBO
La Petite Maison, Chatham, NY
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Quiet, country setting one mile from downtown Chatham Village with private parking. Enjoy a very comfortable stay with m ...
From $220 per night (USD)VRBO
From $151 per night (USD)VRBO
Chatham Cozy Country Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Bright, two bedroom, one bathroom, open concept duplex (I live on the other side) with vaulted ceilings. Fully furnished ...
From $151 per night (USD)VRBO
From $230 per night (USD)VRBO
Cozy Chatham Retreat
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This charming house gives you a quiet sense of calm, while still being close enough to great places to dine, gain inspir ...
From $230 per night (USD)VRBO