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Holiday Homes in Middletown

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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Middletown and around

3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006
Fridge, microwave, oven, stovetop

3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006

10.0 out of 10, Exceptional, (128)
"The house was very nice and central to all Napa has to offer. The hosts were incredibly quick to respond and provided everything we needed and more.The location is quite but you can walk to Main Street. We'd stay here again!"
3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006
Scenic and tranquil in the heart of Sonoma wine country.
Terrace/patio

Scenic and tranquil in the heart of Sonoma wine country.

10.0 out of 10, Exceptional, (96)
"This home is beautiful and comfortable. The outside decks and gardens provide a peaceful respite from busy traveling and sightseeing. The views are lovely."
Scenic and tranquil in the heart of Sonoma wine country.
Casa Pavone, by Vinifera Homes
Outdoor pool, a heated pool

Casa Pavone, by Vinifera Homes

10.0 out of 10, Exceptional, (7)
"Casa Pavone was beautiful inside and out. It is very spacious for you to spread out with your friends and family. We enjoyed sitting outside listening to the water in the stream next to the property. We had everything we needed and enjoyed the quiet setting. Thanks Harman for being there if we needed."
Casa Pavone, by Vinifera Homes
Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.
Interior

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

10.0 out of 10, Exceptional, (7)
"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.
Charming Lake View house with WiFi, AC in tranquil Clearlake Oaks
Terrace/patio

Charming Lake View house with WiFi, AC in tranquil Clearlake Oaks

Charming Lake View house with WiFi, AC in tranquil Clearlake Oaks
LAKEFRONT OASIS w/ BOAT DOCK FISHERMEN SPECIAL!
Outdoor dining

LAKEFRONT OASIS w/ BOAT DOCK FISHERMEN SPECIAL!

8.8 out of 10, Excellent, (13)
"Right on the lake nice place to stay"
LAKEFRONT OASIS w/ BOAT DOCK FISHERMEN SPECIAL!
The Lake Cottage on Soda Bay-Pet Friendly, Private Deck, Dock & Kayaks
Interior

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

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

10.0 out of 10, Exceptional, (201)
"Cozy accommodations for a local wedding were great. "
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
The Calistoga Cottage — Complimentary wine tasting at Croix included!
Outdoor spa tub

The Calistoga Cottage — Complimentary wine tasting at Croix included!

10.0 out of 10, Exceptional, (36)
"Our stay was outstanding. The house was exactly as listed. Clean, well maintained and an easy check in/out process. Would highly recommend!!"
The Calistoga Cottage — Complimentary wine tasting at Croix included!
The Perch - Luxury House on the Lake
Interior

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
Property grounds

Charming Wine Country Home w/Hot Tub near Downtown

9.6 out of 10, Exceptional, (11)
"The home was very clean, stocked for guests, and the owner was great to communicate with. Zero complaints "
The price is €444
includes taxes & fees
19 Aug - 20 Aug
Charming Wine Country Home w/Hot Tub near Downtown
Home near Sonoma & Calistoga in heart of Wine Country
Fridge, microwave, oven, stovetop

Home near Sonoma & Calistoga in heart of Wine Country

9.4 out of 10, Exceptional, (45)
"Great stay. Everything in great shape and clean. "
Home near Sonoma & Calistoga in heart of Wine Country
Cobb Mountain Chalet King Size Suite
Smart TV

Cobb Mountain Chalet King Size Suite

9.8 out of 10, Exceptional, (20)
"Perfect place to stay, nice and cozy!"
The price is €128
includes taxes & fees
19 Aug - 20 Aug
Cobb Mountain Chalet King Size Suite
heiter house- a kenwood gem, private, hot tub with views, and centrally located
Exterior

heiter house- a kenwood gem, private, hot tub with views, and centrally located

8.0 out of 10, Very good, (1)
"We had two couples head to Napa for a short trip. Such a cute cottage and perfect for Sonoma excursions. Napa requires going over or around the mountains but it’s not bad. Hot tub was great. Cottage was well appointed. Coffee pot is on the small side for 3 coffee drinkers. No complaints. Helpful binder of info. Bedrooms were spacious. Primary bath could be updated but certainly enough room. "
The price is €586
includes taxes & fees
19 Aug - 20 Aug
heiter house- a kenwood gem, private, hot tub with views, and centrally located
Twin A Frame Homes. Large main house. OPTIONAL 2nd house for an additional fee.
Interior

Twin A Frame Homes. Large main house. OPTIONAL 2nd house for an additional fee.

9.6 out of 10, Exceptional, (106)
"Kids loved the house and had fun easter hunting. As for us adults, very successful and lobe the house and area.the best house we ever rented. "
Twin A Frame Homes. Large main house. OPTIONAL 2nd house for an additional fee.
Magnolia Ranch Vineyards | Historic house in Healdsburg with lovely private yard
Exterior

Magnolia Ranch Vineyards | Historic house in Healdsburg with lovely private yard

10.0 out of 10, Exceptional, (13)
"Comfy beds, great location & views. 1 mile from town - very peaceful and nice sized 2 bedroom home. Perfect for a coupes wine tasting. "
Magnolia Ranch Vineyards | Historic house in Healdsburg with lovely private yard
Sonoma Valley Vacation Home
Spices, dining tables

Sonoma Valley Vacation Home

9.6 out of 10, Exceptional, (43)
"Very nice place. Only ate simple meals at the house but the kitchen was well equipped. Great hot tub. Quiet neighborhood. "
Sonoma Valley Vacation Home
Napa Valley Retreat in Calistoga!
Fridge, microwave, oven, stovetop

Napa Valley Retreat in Calistoga!

9.8 out of 10, Exceptional, (30)
"Quaint two bedroom had everything we needed to enjoy our 3 night stay in Calistoga. Close to great food, wineries, soaking in hot springs, and hiking. Would definitely stay here again."
The price is €622
includes taxes & fees
18 Sept - 19 Sept
Napa Valley Retreat in Calistoga!
Majestic Rock House
Outdoor dining

Majestic Rock House

9.6 out of 10, Exceptional, (34)
"Everything was great except the treated fand filtered well water had an offensive smell. We heated it and made our coffee with no issues. "
Majestic Rock House
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Fridge, microwave, oven, stovetop

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

10.0 out of 10, Exceptional, (63)
"Great stay, recommend in every way"
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
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

The Sandman Santa Rosa Sonoma, Ascend Hotel Collection

The Sandman Santa Rosa Sonoma, Ascend Hotel Collection

10/10 Excellent
"Great place to stay. Pool area and bar very good. Used the bbq area also very good. Room spacious clean and good amenities. All staff were fantastic. Plenty of places to eat in the area and lots are within walking distance. "
Jason 2-night trip
Posted 18 hours ago
The Sandman Santa Rosa Sonoma, Ascend Hotel Collection