Middletown Cottages

Name: Escape to Wine Country in your independant Cottage in Downtown Calistoga
Price range: $367 total

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Cottages in Middletown

Backyard Garden Oasis

Middletown CA

$194 nightly

$216 total

Dec 6 - Dec 7

Total with taxes and fees

With a stay at Backyard Garden Oasis in Middletown, you'll be 2.7 mi (4.3 km) from Twin Pine Casino and 11.4 mi (18.4 km) from Chateau Montelena Winery.

Pet friendly

Parking included

Chalk Hill Cottage Close to Wineries

Healdsburg CA

With a stay at this cottage in Healdsburg, you'll be within a 15-minute drive of Chalk Hill Estate Vineyard and Kendall-Jackson Wine Estate and Gardens.

Kitchen

Pet friendly

Santini Farmhouse | A Wine Country Escape

Healdsburg CA

Located in Healdsburg, this cottage is in the mountains, within a 5-minute drive of Pedroncelli Winery and Truett Hurst.

Hot Tub

Kitchen

Mountain Cottage near Russian River, hiking & downtown, family and pet friendly

Healdsburg CA

Located in Healdsburg, this cottage is on a river, a 1-minute drive from Russian River and 5 minutes from Healdsburg Museum.

Kitchen

Washer

Wine Country Cottage in downtown Santa Rosa, CA

Santa Rosa CA

$365 nightly

$386 total

Dec 8 - Dec 9

Total with taxes and fees

With a stay at this cottage, you'll be centrally located in Santa Rosa, within a 10-minute drive of Graton Resort and Casino and Santa Rosa Creek.

Kitchen

Washer

Escape to Wine County in your independant Cottage in Downtown Calistoga

Calistoga CA

$299 nightly

$362 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

With a stay at this cottage in Calistoga, you'll be a 1-minute drive from Calistoga Hot Springs and 6 minutes from Castello di Amorosa.

Pet friendly

Air conditioning

Comfort and Style in Our Queen Cottage

Calistoga CA

$371 nightly

$445 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

Free Cancellation

With a stay at this cottage in Calistoga, you'll be a 2-minute drive from Calistoga Hot Springs and 6 minutes from Castello di Amorosa.

Air conditioning

Outdoor Space

Modern Sonoma Stay w/ Spacious Deck, Views & Prime Location Bennett

4460 Earlena Lane Santa Rosa CA

With a stay at this cottage in Santa Rosa, you'll be within a 15-minute drive of Graton Resort and Casino and Bennett Valley Golf Course.

Kitchen

Parking included

Escape to wine country in your independent cottage in downtown Calistoga

Calistoga CA

$304 nightly

$367 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

With a stay at this cottage in Calistoga, you'll be a 1-minute drive from Calistoga Hot Springs and 6 minutes from Castello di Amorosa.

Pet friendly

Air conditioning

Spacious Kelseyville Home w/ Large Lakefront Deck!

Kelseyville CA

Located in Kelseyville, this cottage is within a 5-minute drive of Mount Konocti and Clear Lake.

Kitchen

Parking included

Idyllic Kelseyville Home w/ 2 Decks + Views!

Kelseyville CA

Located in Kelseyville, this cottage is within a 5-minute drive of Mount Konocti and Clear Lake.

Pool

Kitchen

Escape to Wine Country in your independant Cottage in Downtown Calistoga

Calistoga CA

$304 nightly

$367 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

With a stay at this cottage in Calistoga, you'll be a 1-minute drive from Calistoga Hot Springs and 6 minutes from Castello di Amorosa.

Pet friendly

Air conditioning

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.