A calm river with clear water, surrounded by dense greenery and trees.

Holiday Homes in Middletown

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

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 AU$410
includes taxes & fees
13 Sept - 14 Sept
Tangerine Cottage spacious home
A room with three beds, a ceiling fan, and a window with curtains.

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
The price is AU$2,505
includes taxes & fees
14 Sept - 15 Sept
15-Acre Gated Wine Country Estate and 7BR Mansion, Pool, Spa ,Sleeps 18
A covered outdoor deck with a table and chairs, a grill, and a bottle of wine.

3. Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.2 out of 10, Wonderful, (30 reviews)
"The property is very clean and quiet. A lovely place to stay! "
United States
MIKE
The price is AU$252
includes taxes & fees
13 Sept - 14 Sept
Cobb Mountain Chalet King Size Suite
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 AU$303
includes taxes & fees
21 Sept - 22 Sept
Cobb Mountain Chalet Main Floor
A wooden deck leading to a building with a large window overlooking a lake and hills.

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 AU$288
includes taxes & fees
14 Sept - 15 Sept
Bungalow on the lake
A wooden pathway leading to a house with a view of a lake and mountains.

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

Watefront Getaway w/ Mtn Views & Dock in Clearlake
Clearlake
7.4 out of 10, Good, (3 reviews)
"Nice little house on the lake. Is a cabin style house for sure. Host is awesome great communication and makes sure u have what u need.Will return for sure."
United States
Arlen H.
The price is AU$388
includes taxes & fees
13 Sept - 14 Sept
Watefront Getaway w/ Mtn Views & Dock in Clearlake
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

7. 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)
"The house was just like advertised. Great location to visit the surrounding area."
United States
David S.
The price is AU$543
includes taxes & fees
21 Sept - 22 Sept
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
A modern kitchen with stainless steel appliances, grey cabinets, and a marble backsplash.

8. The Parlour House at the Fainting Couch

The Parlour House at the Fainting Couch
Cobb
The price is AU$1,030
includes taxes & fees
14 Sept - 15 Sept
The Parlour House at the Fainting Couch
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, (13 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 AU$358
includes taxes & fees
13 Sept - 14 Sept
Cozy Cottage: Panoramic Lake Views, WiFi, Deck
A swimming pool with a slide, a barbecue area, and a wooden deck.

10. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (30 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 AU$348
includes taxes & fees
13 Sept - 14 Sept
2 Hidden Wine Country Gem Upstairs Unit
A wooden deck with outdoor furniture, a pool, and a view of a marina and hills.

11. Waterfront Luxury- 3 Plus Bedrooms

Waterfront Luxury- 3 Plus Bedrooms
Clearlake Oaks
9.4 out of 10, Exceptional, (28 reviews)
"The comfort and privacy"
United States
Beverly D.
The price is AU$465
includes taxes & fees
15 Sept - 16 Sept
Waterfront Luxury- 3 Plus Bedrooms
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.

12. 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
9.4 out of 10, Exceptional, (6 reviews)
"Spent a quiet long weekend here with my family. Made use of the dock and fished nearly the whole time. This place was perfect for us. "
United States
Chris C.
The price is AU$742
includes taxes & fees
1 Oct - 2 Oct
Entire Lake Front home on Beautiful Clearlake with Private Dock! See Pics!
A waterfront property with multiple buildings, a dock, and a palm tree.

13. 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 AU$898
includes taxes & fees
22 Sept - 23 Sept
Lakefront, 1 King Bed, dock, mist view, electronic firepit
A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

14. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is AU$515
includes taxes & fees
14 Sept - 15 Sept
Wine Country Cottage Escape

15. 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 AU$561
includes taxes & fees
23 Sept - 24 Sept
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A bedroom with a bed, a window, an air conditioning unit, a nightstand, and a door.

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

Hilltop Hideaway: 4 acres, Hot Tub, Stunning Views
Clearlake Oaks
The price is AU$525
includes taxes & fees
29 Sept - 30 Sept
Hilltop Hideaway: 4 acres, Hot Tub, Stunning Views
An outdoor dining area with a stone barbecue, a pool, and a view of the mountains.

17. Calistoga Vista-Pool, Hot Tub - Tastings Included

Calistoga Vista-Pool, Hot Tub - Tastings Included
Calistoga
10.0 out of 10, Exceptional, (4 reviews)
"This home is wonderful! So comfortable and clean, the grounds and landscape are serene and stunning, the town is charming and welcoming. And the complimentary tasting at Croix was fabulous; we loved everything about it! "
United States
Bethany T.
The price is AU$2,613
includes taxes & fees
29 Sept - 30 Sept
Calistoga Vista-Pool, Hot Tub - Tastings Included
A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

18. Wildflower

Wildflower
Windsor
10.0 out of 10, Exceptional, (1 review)
"Very accommodating home with all the essentials. Awesome backyard for the dogs, great location and communication. "
United States
Keri S.
The price is AU$1,301
includes taxes & fees
16 Sept - 17 Sept
Wildflower
A house with a swimming pool surrounded by lush greenery and a small waterfall feature.

19. Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (32 reviews)
"Would return again, The space was larger than it looked in photos."
United States
Keriann
The price is AU$494
includes taxes & fees
17 Sept - 18 Sept
Cozy Wine Country Guesthouse with Private Pool & Yard
A living room with a wooden dining table set for four, a black sofa, and a small coffee table.

20. Charming Wine Country Home w/Hot Tub near Downtown

Charming Wine Country Home w/Hot Tub near Downtown
Santa Rosa
9.6 out of 10, Exceptional, (20 reviews)
"Loved this place. Everything was labeled making the house easy to find things."
United States
Joel B.
The price is AU$688
includes taxes & fees
17 Sept - 18 Sept
Charming Wine Country Home w/Hot Tub near Downtown
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

Harvest Inn

Harvest Inn

10/10 Excellent
"A peaceful oasis with beautiful grounds"
Andrew 1-night trip
Posted 1 hour ago
Harvest Inn

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
188
Accommodation
591 Holiday Homes
Lowest Price
AU$252
Highest Price
AU$2,613