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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Middletown holiday homes

A covered porch with two grey upholstered chairs and a small table, wooden railings, and a window with a curtain.

1. Tangerine Cottage spacious home

Tangerine Cottage spacious home
Middletown
The price is £220
includes taxes & fees
22 Oct - 23 Oct
Tangerine Cottage spacious home
A covered outdoor deck with a table and chairs, a grill, and a bottle of wine.

2. 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 £139
includes taxes & fees
27 Oct - 28 Oct
Cobb Mountain Chalet King Size Suite
A lakeside view with a wooden dock extending into the water, a grassy area, and a building with large windows.

3. 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 £153
includes taxes & fees
22 Oct - 23 Oct
Bungalow on the lake
A hallway with wooden walls and a blue door, leading to a room with a bed and a table.

4. Cobb Mountain Chalet Main Floor

Cobb Mountain Chalet Main Floor
Cobb
9.4 out of 10, Exceptional, (21 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 £162
includes taxes & fees
25 Oct - 26 Oct
Cobb Mountain Chalet Main Floor
A wooden pathway leading to a house with a view of a lake and mountains.

5. 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 £210
includes taxes & fees
22 Oct - 23 Oct
Watefront Getaway w/ Mtn Views & Dock in Clearlake
A bedroom with a large bed, a dining table with chairs, a small table with a lamp, and a view of the sea through large windows.

6. 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 £370
includes taxes & fees
22 Oct - 23 Oct
Entire Lake Front home on Beautiful Clearlake with Private Dock! See Pics!
A modern kitchen with stainless steel appliances, grey cabinets, and a marble backsplash.

7. The Parlour House at the Fainting Couch

The Parlour House at the Fainting Couch
Cobb
The price is £404
includes taxes & fees
22 Oct - 23 Oct
The Parlour House at the Fainting Couch
A swimming pool with a slide, a barbecue area, and a wooden deck.

8. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (31 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
The price is £214
includes taxes & fees
25 Oct - 26 Oct
2 Hidden Wine Country Gem Upstairs Unit
A view of a lake with trees in the foreground and hills in the background.

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

Cozy Cottage: Panoramic Lake Views, WiFi, Deck
Clearlake Oaks
8.4 out of 10, Very good, (14 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 £196
includes taxes & fees
1 Nov - 2 Nov
Cozy Cottage: Panoramic Lake Views, WiFi, Deck
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

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

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (17 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.
The price is £312
includes taxes & fees
29 Oct - 30 Oct
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
A spacious living area with a large window, wooden ceiling beams, and a cozy seating arrangement.

11. ❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤

❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤
Healdsburg
10.0 out of 10, Exceptional, (15 reviews)
"Awesome stay. Highly recommended"
United States
sharon p.
❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤
A waterfront property with multiple buildings, a dock, and a palm tree.

12. Lakefront, 1 King Bed, dock, mist view, electronic firepit

Lakefront, 1 King Bed, dock, mist view, electronic firepit
Lower Lake
7.4 out of 10, Good, (3 reviews)
"Host was very welcoming and we had many amenities, including the dock, movies, and foosball. Overall, enjoyed the stay very much. Minor issues existed but were resolved fairly quickly"
United States
Vishnu N.
The price is £532
includes taxes & fees
22 Oct - 23 Oct
Lakefront, 1 King Bed, dock, mist view, electronic firepit
An outdoor patio with a wooden deck, a table with chairs, and a door with a hanging light fixture.

13. 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 £375
includes taxes & fees
26 Oct - 27 Oct
Wine Country Farmhouse on a Horse Ranch w/ Hot Tub
A wooden deck with two chairs facing a body of water and mountains in the background.

14. STUNNING Lakefront, Huge DOCK,2 Kayaks, Sleep 8, Prime fishing spot

STUNNING Lakefront, Huge DOCK,2 Kayaks, Sleep 8, Prime fishing spot
Clearlake Oaks
9.6 out of 10, Exceptional, (62 reviews)
"This was the second time my family has stayed on this property and we enjoyed it very much. You’re right on the lake, so it’s very enjoyable for children to be able to fish and enjoy the water."
United States
Lauren R.
The price is £357
includes taxes & fees
25 Oct - 26 Oct
STUNNING Lakefront, Huge DOCK,2 Kayaks, Sleep 8, Prime fishing spot
A kitchen with a stove, pots, pans, and a digital clock displaying 5:41.

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

Hilltop Hideaway: 4 acres, Hot Tub, Stunning Views
Clearlake Oaks
The price is £286
includes taxes & fees
4 Nov - 5 Nov
Hilltop Hideaway: 4 acres, Hot Tub, Stunning Views
Private kitchen

16. 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, (23 reviews)
"very nice space "
United States
kevin c.
The price is £279
includes taxes & fees
3 Nov - 4 Nov
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A large house with a swimming pool, outdoor seating, and a covered patio area.

17. Sanctuary Estate - Wine Tastings Included

Sanctuary Estate - Wine Tastings Included
Geyserville
10.0 out of 10, Exceptional, (44 reviews)
"Really great experience and the house and all of the different sleeping areas was a hit with everyone and all of the kids."
United States
Chad N.
The price is £3,816
includes taxes & fees
27 Oct - 28 Oct
Sanctuary Estate - Wine Tastings Included
A deck with outdoor seating, hot tubs, and a glass door leading to a forested area.

18. River View Lodge - Hot Tub and Tastings Included

River View Lodge - Hot Tub and Tastings Included
Healdsburg
9.6 out of 10, Exceptional, (75 reviews)
"Wonderful vacation and location. "
United States
Leslie M.
The price is £867
includes taxes & fees
3 Nov - 4 Nov
River View Lodge - Hot Tub and Tastings Included
A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

19. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! The area is beautiful, peaceful and quiet. The house is clean, well maintained and equipped. Really enjoyed it and look forward to our next visit."
United States
Tina A.
The price is £275
includes taxes & fees
26 Oct - 27 Oct
Wine Country Cottage Escape
A spacious dining area with wooden chairs and a central table, a kitchen with modern appliances, and a view of the outdoors.

20. Vineyard Vue - Wine Tastings Included

Vineyard Vue - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (39 reviews)
"Stayed here on a couples trip to Napa and Sonoma. It was a perfect home base for the trip, had everything we needed and the two masters suites were almost identical which was a nice bonus so both couples felt equally comfortable."
United States
Chris N.
The price is £1,246
includes taxes & fees
3 Nov - 4 Nov
Vineyard Vue - Wine Tastings Included
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

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta

8/10 Good
"Basic stay. Room was clean, location is convenient and great price for the area. But, rooms need renovation- we had an issue with turning the water on in the shower. Maintenance was there quickly and told us you had to hold it a certain way to make it work..not great. Other than that stay was fine."
Tony 2-night trip
Posted 2 hours ago
Dry Creek Inn MOD Collection by Sonesta

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
467
Accommodation
594 Holiday Homes
Lowest Price
£139
Highest Price
£3,816