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Holiday Homes in Middletown

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Our top choices for Middletown holiday homes

1. Tangerine Cottage spacious home

Tangerine Cottage spacious home
Middletown
Tangerine Cottage spacious home

2. 15-Acre Gated Wine Country Estate and 7BR Mansion, Pool, Spa ,Sleeps 18

15-Acre Gated Wine Country Estate and 7BR Mansion, Pool, Spa ,Sleeps 18
Middletown
15-Acre Gated Wine Country Estate and 7BR Mansion, Pool, Spa ,Sleeps 18

3. Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.2 out of 10, Wonderful, (31 reviews)
"Lovely place, very clean, in quiet surroundings."
United States
Brigid
The price is €151
includes taxes & fees
15 Nov - 16 Nov
Cobb Mountain Chalet King Size Suite

4. Cobb Mountain Chalet Main Floor

Cobb Mountain Chalet Main Floor
Cobb
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful view from the deck! Wind was blowing the tree in the evening and it was so peaceful. House had everything you could need."
United States
tabatha p.
The price is €187
includes taxes & fees
10 Dec - 11 Dec
Cobb Mountain Chalet Main Floor

5. Bungalow on the lake

Bungalow on the lake
Clearlake
7.8 out of 10, Good, (8 reviews)
"Great little cottage for a good price. "
United States
Danielle C.
The price is €172
includes taxes & fees
21 Nov - 22 Nov
Bungalow on the lake

6. Fully Furnished 3BR Home with a Hot Tub & Views Kelseyville.

Fully Furnished 3BR Home with a Hot Tub & Views Kelseyville.
Kelseyville
9.4 out of 10, Exceptional, (6 reviews)
"Nice place, great hot tub. We enjoyed our stay."
United States
Jessica W.
Fully Furnished 3BR Home with a Hot Tub & Views Kelseyville.

7. Watefront Getaway w/ Mtn Views & Dock in Clearlake

Watefront Getaway w/ Mtn Views & Dock in Clearlake
Clearlake
8.0 out of 10, Very good, (4 reviews)
"We had a wonderful one-night stay at this waterfront home. The location is unbeatable: right on the lake with mountain views and a private dock, and it made a perfect home base for a show at Cache Creek Winery. The host was excellent, quick to respond with clear check-in instructions, and the place was spotless when we arrived. Comfortable beds, everything we needed for the weekend, and easy to find. We would happily stay here again and recommend it to anyone visiting Clear Lake."
United States
Alison
The price is €242
includes taxes & fees
22 Nov - 23 Nov
Watefront Getaway w/ Mtn Views & Dock in Clearlake

8. Queen with Kitchenette

Queen with Kitchenette
Calistoga
Queen with Kitchenette

9. Spacious Beautiful Country Home on 8 Private Acres

Spacious Beautiful Country Home on 8 Private Acres
Kelseyville
Spacious Beautiful Country Home on 8 Private Acres

10. Jago Bay - Vineyard Home with Pool and Hot Tub

Jago Bay - Vineyard Home with Pool and Hot Tub
Lower Lake
10.0 out of 10, Exceptional, (14 reviews)
"Jago Bay Vineyards feels like you'r staying at a resort but its all for you."
United States
Robert F.
Jago Bay - Vineyard Home with Pool and Hot Tub

11. Entire Lake Front home on Beautiful Clearlake with Private Dock! See Pics!

Entire Lake Front home on Beautiful Clearlake with Private Dock! See Pics!
Lower Lake
9.2 out of 10, Wonderful, (7 reviews)
"What a beautiful, peaceful place! Our goal was to unplug and recharge this week and watching the birds and bats first thing in the morning set the tone!"
United States
Lauren R.
The price is €418
includes taxes & fees
16 Nov - 17 Nov
Entire Lake Front home on Beautiful Clearlake with Private Dock! See Pics!

12. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (19 reviews)
"Great place. Quiet, very clean, close to Healdsburg, grocery stores, etc. Very helpful and nice host. We would definitely stay here again when in the area."
United States
Mark R.
Vineyard View Retreat • Fire Pit • Wine Tasting Perks

13. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (32 reviews)
"It was clean and quiet and the host was very responsive to my needs"
United States
Debbie W.
The price is €244
includes taxes & fees
16 Nov - 17 Nov
2 Hidden Wine Country Gem Upstairs Unit

14. The Parlour House at the Fainting Couch

The Parlour House at the Fainting Couch
Cobb
The price is €464
includes taxes & fees
13 Nov - 14 Nov
The Parlour House at the Fainting Couch

15. Lakefront Retreat • Private Yard + Fireplace

Lakefront Retreat • Private Yard + Fireplace
Clearlake Oaks
The price is €499
includes taxes & fees
13 Nov - 14 Nov
Lakefront Retreat • Private Yard + Fireplace

16. Wine Country Farmhouse on a Horse Ranch w/ Hot Tub

Wine Country Farmhouse on a Horse Ranch w/ Hot Tub
Santa Rosa
10.0 out of 10, Exceptional, (75 reviews)
"The property was beautiful and the beds were so comfy! The property manager was very friendly and responsive. "
United States
Abigail M.
The price is €426
includes taxes & fees
15 Nov - 16 Nov
Wine Country Farmhouse on a Horse Ranch w/ Hot Tub

17. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Northwest Santa Rosa
9.4 out of 10, Exceptional, (24 reviews)
"very nice space "
United States
kevin c.
The price is €325
includes taxes & fees
7 Dec - 8 Dec
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

18. Cozy Cottage: Panoramic Lake Views, WiFi, Deck

Cozy Cottage: Panoramic Lake Views, WiFi, Deck
Clearlake Oaks
8.2 out of 10, Very good, (15 reviews)
"Great communication from the property owner! Easy stay, well-appointed for our brief stay - beautiful lake views, sunsets, and sunrise!"
United States
Melanie B.
The price is €221
includes taxes & fees
16 Nov - 17 Nov
Cozy Cottage: Panoramic Lake Views, WiFi, Deck

19. Hilltop Hideaway: 4 acres, Hot Tub, Stunning Views

Hilltop Hideaway: 4 acres, Hot Tub, Stunning Views
Clearlake Oaks
The price is €344
includes taxes & fees
17 Nov - 18 Nov
Hilltop Hideaway: 4 acres, Hot Tub, Stunning Views

20. Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Healdsburg
9.6 out of 10, Exceptional, (68 reviews)
"Unbelievable property – we will absolutely stay here again –Just fabulous!"
United States
Jeffrey S.
The price is €1,525
includes taxes & fees
17 Nov - 18 Nov
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
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

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Middletown Holiday Homes information

Number of reviews
304
Accommodation
588 Holiday Homes
Lowest Price
€151
Highest Price
€1,525