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Vacation Homes in Middletown

Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.
Enjoy expansive views of the surrounding landscape from the large windows in this stylish living area.

Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.

10.0 out of 10, Exceptional, (6)
"We had a pleasant stay at the property over the Memorial Day weekend. It’s away from the crowds but yet 15 mins from Sonoma Lake for water sports and 30 mins from Healdsburg. Amazing view and great time in the pool. "
Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.
LAKEFRONT OASIS w/ BOAT DOCK FISHERMEN SPECIAL!
Enjoy casual dining on the water with a round table set amidst a serene outdoor seating area.

LAKEFRONT OASIS w/ BOAT DOCK FISHERMEN SPECIAL!

9.4 out of 10, Exceptional, (12)
"Right on the lake nice place to stay"
LAKEFRONT OASIS w/ BOAT DOCK FISHERMEN SPECIAL!
Sonoma Wine Country Retreat: Scenic, tranquil, bucolic, Hot Tub
Relax on the deck with a serene mountain view, surrounded by lush plants and a comfortable seating area.

Sonoma Wine Country Retreat: Scenic, tranquil, bucolic, Hot Tub

10.0 out of 10, Exceptional, (95)
"The home was very clean, was lovely as advertised with a beautiful yard and views. The host was helpful and we had a wonderful time."
Sonoma Wine Country Retreat: Scenic, tranquil, bucolic, Hot Tub
Wine Country Harvest Vacation Home
Enjoy casual outdoor meals at this patio with a grill station and dining area.

Wine Country Harvest Vacation Home

9.8 out of 10, Exceptional, (82)
"The house is beautiful, the location allows easy access to key locations. We loved our stay. "
Wine Country Harvest Vacation Home
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
Relax in the hot tub on the deck, surrounded by a fence.

Charming Country Home Nestled In Kenwood Village the heart of the wine country.

10.0 out of 10, Exceptional, (200)
"Cozy accommodations for a local wedding were great. "
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
Cobb Mountain Chalet King Size Suite
Cozy living space with a dining area, sofa, and TV, perfect for relaxing and enjoying meals together.

Cobb Mountain Chalet King Size Suite

9.8 out of 10, Exceptional, (20)
"Perfect place to stay, nice and cozy!"
$133 nightly
The price is $146
Aug 7 - Aug 8
Total includes taxes and fees
Cobb Mountain Chalet King Size Suite
Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8
Surrounded by lush greenery and mountains, this pool area offers a serene escape.

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

10.0 out of 10, Exceptional, (22)
"We come to the valley every year for my wife’s bday. This property did not disappoint. Only issue was coffee grounds were not cleaned out of coffee maker leaving a moldy mess. Would rent again. "
Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Classic hallway with ornate door, framed artwork, and comfortable seating area.

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

10.0 out of 10, Exceptional, (237)
"Wonderful accommodations for a family weekend in the wine country!"
$1,885 nightly
The price is $2,133
Aug 12 - Aug 13
Total includes taxes and fees
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
The Lake Cottage on Soda Bay-Pet Friendly, Private Deck, Dock & Kayaks
Relax by the water's edge in this serene outdoor seating area, complete with a picnic table and kayaks for a leisurely paddle.

The Lake Cottage on Soda Bay-Pet Friendly, Private Deck, Dock & Kayaks

10.0 out of 10, Exceptional, (66)
"Nice weekend by the lake Great fishing experience "
The Lake Cottage on Soda Bay-Pet Friendly, Private Deck, Dock & Kayaks
Beautiful Lake Front house with Spectacular view, new deck/private dock sleep 6
Enjoy a serene lakeside retreat with a deck, table, and chairs.

Beautiful Lake Front house with Spectacular view, new deck/private dock sleep 6

9.6 out of 10, Exceptional, (55)
"So relaxing and peaceful place my family loved it unfortunately was for a short time but next time definitely will stay longer no doubt about booking it again "
$409 nightly
The price is $430
Sep 2 - Sep 3
Total includes taxes and fees
Beautiful Lake Front house with Spectacular view, new deck/private dock sleep 6
1 Block To St. Helena Main Street Shops-Restaurants! Avail August 4-9, 23-29
Relax by the serene pool surrounded by lush greenery and comfortable seating.

1 Block To St. Helena Main Street Shops-Restaurants! Avail August 4-9, 23-29

10.0 out of 10, Exceptional, (259)
"This house is great and exactly as shown. Jill was incredibly thoughtful in her communication and we so appreciated that the checkout process was easy. Quick walk to town but the house was so perfect that we preferred staying in most nights for dinner! Would highly recommend. "
1 Block To St. Helena Main Street Shops-Restaurants! Avail August 4-9, 23-29
Gorgeous Views, Pool and Hot Tub, 12 mins to HB Plaza
Relax in a serene, setting surrounded by lush greenery and enjoy the inviting pool and patio area.

Gorgeous Views, Pool and Hot Tub, 12 mins to HB Plaza

10.0 out of 10, Exceptional, (169)
"Lovely setting. Cant wait to return!"
Gorgeous Views, Pool and Hot Tub, 12 mins to HB Plaza
Calistoga Vineyard House
Relax in this serene living room with a patio offering a vineyard view and seating area.

Calistoga Vineyard House

10.0 out of 10, Exceptional, (49)
"Had an amazing stay, very comfortable and close to Calistoga! Don’t hesitate to book! Very private and quiet. "
Calistoga Vineyard House
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg
Enjoy a backyard with a swimming pool surrounded by lush landscaping and a shaded pergola.

Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg

10.0 out of 10, Exceptional, (34)
"Absolutely wonderful stay. The house was beautiful and clean, with multiple spacious common areas for family time. The Limerick Lane team was also incredibly communicative and accommodating throughout. 100% recommend."
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg
The Perch - Luxury House on the Lake
Enjoy a serene view of the lake from the deck, complete with a table and bench for dining or relaxation.

The Perch - Luxury House on the Lake

9.8 out of 10, Exceptional, (57)
"We spent all our time out back.....Very nice."
The Perch - Luxury House on the Lake
Charming Wine Country Home w/Hot Tub near Downtown
Stroll through a serene garden oasis, surrounded by a variety of plants and flowers, and a decorative lattice fence.

Charming Wine Country Home w/Hot Tub near Downtown

9.6 out of 10, Exceptional, (10)
"The home was very clean, stocked for guests, and the owner was great to communicate with. Zero complaints "
$453 nightly
The price is $509
Aug 11 - Aug 12
Total includes taxes and fees
Charming Wine Country Home w/Hot Tub near Downtown
Tropical Lakefront Retreat with Private Dock & Kayaks
Relax on the patio overlooking the water, surrounded by trees and a building in the background, with a comfortable seating area under a shaded canopy.

Tropical Lakefront Retreat with Private Dock & Kayaks

10.0 out of 10, Exceptional, (82)
"Waterfront house very clean lots of space outdoors . Lovely home would definitely come back."
Tropical Lakefront Retreat with Private Dock & Kayaks
Home near Sonoma & Calistoga in heart of Wine Country
Enjoy cooking with a double sink and dishwasher in this well-equipped kitchen.

Home near Sonoma & Calistoga in heart of Wine Country

9.4 out of 10, Exceptional, (44)
"Wonderful to stay here. Beautiful place."
Home near Sonoma & Calistoga in heart of Wine Country
Direct Lake Front Paradise Cove #1 In Reviews - Beach - Launch - Traeger Smoker
Enjoy a serene lakeside retreat with a patio featuring a round table, comfortable chairs, and a grill.

Direct Lake Front Paradise Cove #1 In Reviews - Beach - Launch - Traeger Smoker

9.8 out of 10, Exceptional, (199)
"Great trip. We plan to do it again next year. "
Direct Lake Front Paradise Cove #1 In Reviews - Beach - Launch - Traeger Smoker
Heart of Wine Country, Cute Cottage w/Hot Tub
Fully equipped kitchen with refrigerator, microwave, oven, and stove.

Heart of Wine Country, Cute Cottage w/Hot Tub

9.4 out of 10, Exceptional, (27)
"We enjoyed our stay in this home although it was very brief. A great location in Windsor. "
Heart of Wine Country, Cute Cottage w/Hot Tub
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.
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Top Middletown Hotel Reviews

La Quinta Inn & Suites Santa Rosa Sonoma

La Quinta Inn & Suites Santa Rosa Sonoma

10/10 Excellent
"Restfull and excellent"
Isabel 1-night trip
Posted 13 hours ago
La Quinta Inn & Suites Santa Rosa Sonoma