Middletown Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Check dates for Middletown hotels

Vacation Rentals in Middletown

Wooded Restful Retreat, with broad scenic views, outdoor dining

Healdsburg CA

With a stay at this vacation home, you'll be centrally located in Healdsburg, a 1-minute drive from Russian River and 6 minutes from Healdsburg Plaza.

Kitchen

Washer

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

St Helena CA

$2,036 nightly

$2,306 total

Sep 7 - Sep 8

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in St. Helena, within a 15-minute drive of Castello di Amorosa and Calistoga Hot Springs.

Kitchen

Washer

Majestic Rock House

Clearlake CA

Located in Clearlake, this vacation home is on the waterfront, a 1-minute drive from Clear Lake and 6 minutes from Borax Lake.

Kitchen

Washer

Cozy Woodland Escape, Hot Tub, Redwood + Water Views, mins from spas in Napa

Santa Rosa CA

When you stay at this vacation home in Santa Rosa, you'll be on the waterfront, within a 15-minute drive of Safari West and Calistoga Hot Springs.

Hot Tub

Kitchen

Tropical Lakefront Retreat with Private Dock & Kayaks

Clearlake Oaks CA

Located in Clearlake Oaks, this vacation home is on a lake, within a 5-minute drive of Clear Lake and Shannon Ridge Winery.

Kitchen

Washer

Escape to Paradise: A Stunning Tuscany-Style Home with Views of Vineyards

Napa CA

With a stay at this vacation home in Napa, you'll be within a 10-minute drive of Mumm Napa and Quintessa.

Pool

Hot Tub

Picturesque sunset views perfect for couples, families and fishermen

Lakeport CA

Located in Lakeport, this vacation home is on the waterfront, a 2-minute drive from Clear Lake and 9 minutes from Lakeport Speedway.

Kitchen

Washer

2 Hidden Wine Country Gem Upstairs Unit

Santa Rosa CA

With a stay at this vacation home in Santa Rosa (Scenic Brush Creek), you'll be within a 15-minute drive of Graton Resort and Casino and Santa Rosa Memorial Hospital.

Pool

Kitchen

Cozy Wine Country Guesthouse with Private Pool & Yard

Santa Rosa CA

With a stay at this vacation home in Santa Rosa, you'll be within a 15-minute drive of Graton Resort and Casino and Rincon Valley Community Park Dog Park.

Pool

Hot Tub

Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8

Calistoga CA

With a stay at this vacation home, you'll be centrally located in Santa Rosa, within a 15-minute drive of Calistoga Hot Springs and Safari West.

Pool

Kitchen

Napa Valley: St Helena Designer Home & Guest House + Spool + Peloton Bike/Tread

St Helena CA

With a stay at this vacation home in St. Helena (Downtown St. Helena), you'll be within a 15-minute drive of Castello di Amorosa and Calistoga Hot Springs.

Pool

Hot Tub

5 Bedroom wine Country Home, Grill, Hot Tub, Granny unit in Santa Rosa

Santa Rosa CA

Located in Santa Rosa, this vacation home is in a rural location, within a 5-minute drive of Santa Rosa Memorial Hospital and Sonoma County Fairgrounds.

Hot Tub

Kitchen

Don't see what you're looking for?

See all available properties in Middletown

View all properties

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.