Holiday rentals near Old Courthouse Square

We found 579 holiday rentals — enter your dates for availability

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November 2025

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Choose the right private holiday rental within easy reach of Old Courthouse Square. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as a garden and pool. No matter what you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Old Courthouse Square

Showing deals for:30 Jan - 6 Feb

Welcome to our Wine Country Estate! 5,500 SF, sleeping for 12 & pool with views!

Exceptional

(57 reviews)

Sonoma County Wine Country Vineyard Estate with Pool!

Santa Rosa, CA

7% off

for 7 nights, 1 home

NZ$2,941 per night

includes taxes & fees

Exceptional

(12 reviews)

SONOMA CREEK VILLA NEW PICKLEBALL COURT, heated pool, hot tub, gated, EV Charger

Kenwood, CA

8% off

for 7 nights, 1 villa

NZ$2,413 per night

includes taxes & fees

Exceptional

(133 reviews)

Casa Bella Estate in Wine Country w/ New Pool!

Kenwood, CA

8% off

for 7 nights, 1 home

NZ$3,574 per night

includes taxes & fees

Exceptional

(278 reviews)

Sunny View Cottage in the Beautiful Wine Country

Santa Rosa, CA

8% off

for 7 nights, 1 cottage

NZ$419 per night

includes taxes & fees

Enjoy a beautiful sunset by the firepit.

Exceptional

(135 reviews)

Wine Country Escape: Luxury Estate, Pool, Sauna, Steam, Spa, Views, 5+ Bedrooms

Santa Rosa, CA

8% off

for 7 nights, 1 home

NZ$3,813 per night

includes taxes & fees

Cozy bedroom featuring a comfortable queen bed, abundant natural sunlight.

Exceptional

(11 reviews)

True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard

Healdsburg, CA

8% off

for 7 nights, 1 cottage

NZ$696 per night

includes taxes & fees

Indoor - Outdoor Living Overlooking acres of Pinot Noir

Exceptional

(82 reviews)

Modernist Compound With Expansive Views Overlooking Bellflower Vineyards

Santa Rosa, CA

8% off

for 7 nights, 1 home

NZ$1,119 per night

includes taxes & fees

Peaceful, canyon and creek side setting. Comfortable front garden and entry.

Exceptional

(131 reviews)

Kenwood Cottage-Canyon & Creek Setting, No cleaning fee, Tesla Charger.

Kenwood, CA

8% off

for 7 nights, 1 home

NZ$842 per night

includes taxes & fees

Exceptional

(49 reviews)

Relax in the most beautiful, secluded setting Sonoma County has to offer

Santa Rosa, CA

8% off

for 7 nights, 1 home

NZ$1,519 per night

includes taxes & fees

Beautiful pool, hot tub, bar, seating area with room for all.

Exceptional

(134 reviews)

Sonoma Valley-Beautiful Glen Ellen Wine Country Retreat - Amenities Galore!

Glen Ellen, CA

8% off

for 7 nights, 1 home

NZ$2,596 per night

includes taxes & fees

Exceptional

(241 reviews)

Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

Kenwood, CA

12% off

for 7 nights, 1 home

NZ$2,971 per night

includes taxes & fees

The spacious grounds feature comfortable seating around the pool and on the oversized deck overlooking vineyards.

Exceptional

(42 reviews)

Year-Round Heated Pool | Hot Tub | Fire Pit | Huge Lawn | Vineyard Views

Kenwood, CA

8% off

for 7 nights, 1 villa

NZ$2,426 per night

includes taxes & fees

Exceptional

(68 reviews)

Studio cottage retreat in a vineyard setting

Santa Rosa, CA

16% off

for 7 nights, 1 cottage

NZ$410 per night

includes taxes & fees

Excellent

(13 reviews)

Gable by AvantStay | Beautiful 3.5 Acre Oasis w/ Gorgeous Views, Pool & Hot Tub

Santa Rosa, CA

9% off

for 7 nights, 1 home

NZ$1,457 per night

includes taxes & fees

Prettiest tennis court in sonoma county ! The eagles often circle above to watch

Exceptional

(11 reviews)

Tennis paradise in sonoma wine country

Forestville, CA

8% off

for 7 nights, 1 home

NZ$2,541 per night

includes taxes & fees

View southwest across rear of estate. Pool, spa, and bocce court just past spa.

Exceptional

(138 reviews)

Wine Country Estate: Year-round Pool, Spa, Bocce, Exceptional Private Location

Kenwood, CA

14% off

for 7 nights, 1 home

NZ$1,841 per night

includes taxes & fees

Exceptional

(10 reviews)

Adorable 1 BD 1 BA in one of SR's best neighborhoods!

Santa Rosa, CA

9% off

for 7 nights, 1 cottage

NZ$463 per night

includes taxes & fees

Excellent

(12 reviews)

Malvasia by AvantStay | Luxe Wine Country Retreat

Santa Rosa, CA

9% off

for 7 nights, 1 home

NZ$2,197 per night

includes taxes & fees

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Find properties near top attractions in Old Courthouse Square

Old Courthouse Square

Find the best place to stay - Old Courthouse Square

Aerial View of the Estate with A Private Vineyard

Premier Host

Luxurious 7-Acre Estate & Guest House on Private Vineyard, With Pool & Game Room

Sleeps 14 · 6 bedrooms · 4+ bathrooms

Premier Host

As featured on CBS's Staycation! Luxury Retreat Overlooking Sonoma Valley

Sleeps 8 · 4 bedrooms · 4+ bathrooms

Premier Host

Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

Sleeps 12 · 7 bedrooms · 9+ bathrooms

Escape to Wine County in your independant Cottage in Downtown Calistoga

Sleeps 3 · 1 bedroom · 1 bathroom

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Enjoy full kitchens, laundry, pools, gardens and more
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