Litchfield Area Rentals
From $1510 per night (USD)VRBO
Longpond House
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to Longpond House—a luxury mountain retreat set on a breathtaking 40-acre estate. The crown jewel of L ...
From $1510 per night (USD)VRBO
From $3445 per night (USD)VRBO
Farm stay at Longpond Cellars & Farms
- Bedrooms:
- 6
- Bathrooms:
- 9
- Sleeps:
- 18
Summary: Private 40-acre farm-stay! Experience the serenity of Longpond Cellars & Farms. Offering four beautifully reno ...
From $3445 per night (USD)VRBO
From $574 per night (USD)VRBO
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Relax and recharge with family and friends at this welcoming four-bedroom, two-bath home in the heart of Goshen. Close ...
From $574 per night (USD)VRBO
From $1011 per night (USD)VRBO
Lakeville Lodge - Family Friendly Home with Pool & Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Lakeville Lodge is a 3 bed, 2.5 bath retreat just 2.5 hrs from NYC and 3 hours from Boston, located in a quiet ...
From $1011 per night (USD)VRBO
From $468 per night (USD)VRBO
Golden Shore Cottage A Boutique Waterfront Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Wake to the quiet beauty of Candlewood Lake as morning mist drifts across the water and the first rays of sunlight shimm ...
From $468 per night (USD)VRBO
From $644 per night (USD)VRBO
Avi River House
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a luxury private river home with two bed, two bath, and full kitchen, living room, dining room, and waterfront bal ...
From $644 per night (USD)VRBO
From $510 per night (USD)VRBO
Bluestone Cottage | Historic Goshen Retreat with Saltwater Pool, Cozy Charm & Year Round Adventures
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Bluestone Cottage | Historic Goshen Retreat with Pool & Litchfield County Charm Bluestone Cottage isn't ...
From $510 per night (USD)VRBO
From $1108 per night (USD)Expedia
Litchfield Hills Modern Design Escape w/a Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
20 minutes from Salisbury School & Hotchkiss School, ideal accommodations for graduations, reunions, family weekends, an ...
From $1108 per night (USD)Expedia
From $1154 per night (USD)VRBO
Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Wake up to lake views, spend the day swimming from your private dock, and end the evening watching sunset over Highland ...
From $1154 per night (USD)VRBO
From $309 per night (USD)Expedia
Coming Soon! #32- Sleeps 10!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to Litchfield County. This stylish and fully renovated 3-bedroom, 2.5-bath apartment offers the perfect blend of ...
From $309 per night (USD)Expedia
From $857 per night (USD)VRBO
Historic 1802 Farmhouse Near Litchfield & Skiing
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Stay at the historic Erastus Lyman Home, an 1802 farmhouse overlooking a working farm in Goshen, Connecticut. This spaci ...
From $857 per night (USD)VRBO
From $622 per night (USD)VRBO
NYC-Area Escape • Game Room • Firepit • Chef's Kitchen • Near Boarding Schools
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
New Milford is waiting for you at this beautiful 3-bedroom house. Inside, guests find a king bed and two queen beds, per ...
From $622 per night (USD)VRBO
From $1048 per night (USD)VRBO
Waterfront House & Guest House Available in Winchester, CT!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Located in Winchester, Connecticut, this spacious waterfront property is perfect for families and groups looking to rela ...
From $1048 per night (USD)VRBO
From $233 per night (USD)Expedia
#33- Newly Constructed - Luxury Collection
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
While our primary mode of communication is through messaging, we want you to feel secure and supported at all times. Fo ...
From $233 per night (USD)Expedia
From $178 per night (USD)VRBO
Tiny Home Away From Home - Complete Privacy, Peace
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
A tastefully decorated detached house; 1 br, 1 bath. Clean, comfortable, and charming house with ultimate privacy. Nob ...
From $178 per night (USD)VRBO
From $873 per night (USD)VRBO
Beautiful new home with lake access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful new modern farmhouse. New to VRBO but many reviews on the other popular vacation rental site. Close to all pr ...
From $873 per night (USD)VRBO
From $144 per night (USD)VRBO
Cozy private room in a shared home with a Full-size bed and private bathroom.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your New Milford adventure begins at this 1-bedroom shared home. Inside, guests find a nice full bed perfect for a restf ...
From $144 per night (USD)VRBO
From $589 per night (USD)VRBO
Sun filled cottage in the woods
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A wonderful nature treat awaits. Our home is located on 10 acres bordered by land preserves in a densely wooded area wit ...
From $589 per night (USD)VRBO
From $793 per night (USD)VRBO
Bespoke Litchfield - Family Friendly, Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Experience this beautifully curated Litchfield Hills retreat sleeping 14 guests. This high-design sanctuary features a c ...
From $793 per night (USD)VRBO
From $392 per night (USD)Expedia
Ann Inn - Downtown Milford Apartment
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
<p>Located in New Milford, this welcoming apartment brings it all within your reach. Thanks to the convenient onsite par ...
From $392 per night (USD)Expedia
From $2207 per night (USD)VRBO
The 1775 Colonel Benjamin Tallmadge House on the Litchfield Green
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
A young nation. A young couple. Colonel Benjamin Tallmadge, legendary commander of the Culper Spy Ring—General George W ...
From $2207 per night (USD)VRBO