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Holiday Homes in Middletown

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 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
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, (30 reviews)
"My husband and I cannot stop talking about this beautiful, serene gem. Each room was immaculate. The sofas were so cozy and plenty of soft blankets! The market is equipped with everything & just a few minutes away. We are house hunting & can’t wait to return to the chalet!"
United States
Roberta F.
The price is €170
includes taxes & fees
28 Sept - 29 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.

3. 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 €192
includes taxes & fees
28 Sept - 29 Sept
Cobb Mountain Chalet Main Floor
A wooden deck leading to a building with a large window overlooking a lake and hills.

4. 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 €177
includes taxes & fees
27 Sept - 28 Sept
Bungalow on the lake
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 €246
includes taxes & fees
27 Sept - 28 Sept
Watefront Getaway w/ Mtn Views & Dock in Clearlake
A wooden deck with outdoor furniture, a pool, and a view of a marina and hills.

6. Waterfront Luxury- 3 Plus Bedrooms

Waterfront Luxury- 3 Plus Bedrooms
Clearlake Oaks
9.4 out of 10, Exceptional, (29 reviews)
"The comfort and privacy"
United States
Beverly D.
The price is €305
includes taxes & fees
27 Sept - 28 Sept
Waterfront Luxury- 3 Plus Bedrooms
A view of a lake with trees in the foreground and hills in the background.

7. 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 €213
includes taxes & fees
27 Sept - 28 Sept
Cozy Cottage: Panoramic Lake Views, WiFi, Deck
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

8. 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 location!"
United States
Riley F.
The price is €355
includes taxes & fees
29 Sept - 30 Sept
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
A modern kitchen with stainless steel appliances, grey cabinets, and a marble backsplash.

9. The Parlour House at the Fainting Couch

The Parlour House at the Fainting Couch
Cobb
The price is €663
includes taxes & fees
8 Oct - 9 Oct
The Parlour House at the Fainting Couch
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.

10. 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 €453
includes taxes & fees
1 Oct - 2 Oct
Entire Lake Front home on Beautiful Clearlake with Private Dock! See Pics!
A house with a deck, a dining table with chairs, a blue umbrella, and a welcome mat.

11. Calistoga Vineyard Getaway - Hot Tub and Tastings Included

Calistoga Vineyard Getaway - Hot Tub and Tastings Included
Calistoga
8.8 out of 10, Excellent, (58 reviews)
"Our stay here was fun and convenient! It was cozy and comfortable. "
United States
Bryan M.
Calistoga Vineyard Getaway - Hot Tub and Tastings Included
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 €678
includes taxes & fees
26 Oct - 27 Oct
Lakefront, 1 King Bed, dock, mist view, electronic firepit
A swimming pool with a slide, a barbecue area, and a wooden deck.

13. 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 €237
includes taxes & fees
4 Oct - 5 Oct
2 Hidden Wine Country Gem Upstairs Unit

14. 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 €335
includes taxes & fees
29 Sept - 30 Sept
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
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 €321
includes taxes & fees
29 Sept - 30 Sept
Hilltop Hideaway: 4 acres, Hot Tub, Stunning Views
A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

16. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is €319
includes taxes & fees
27 Oct - 28 Oct
Wine Country Cottage Escape
An outdoor patio with a wooden deck, a table with chairs, and a door with a hanging light fixture.

17. Wine Country Farmhouse with Hot Tub

Wine Country Farmhouse with Hot Tub
Santa Rosa
10.0 out of 10, Exceptional, (74 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 €506
includes taxes & fees
27 Sept - 28 Sept
Wine Country Farmhouse with Hot Tub
An outdoor dining area with a stone barbecue, a pool, and a view of the mountains.

18. 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.
Calistoga Vista-Pool, Hot Tub - Tastings Included
A wooden deck with a metal railing overlooking a body of water, a stone sculpture, and a small pavilion.

19. 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, (60 reviews)
"We enjoyed our 5night stay at this lake house. The property is everything and more than advertised."
United States
Estelle F.
The price is €448
includes taxes & fees
28 Sept - 29 Sept
STUNNING Lakefront, Huge DOCK,2 Kayaks, Sleep 8, Prime fishing spot
A house with a swimming pool surrounded by lush greenery and a small waterfall feature.

20. Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (33 reviews)
"Wonderful stay!"
United States
Adam C.
The price is €324
includes taxes & fees
28 Sept - 29 Sept
Cozy Wine Country Guesthouse with Private Pool & Yard
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, an Ascend Collection Hotel

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

8/10 Good
"Basic room, but clean and comfortable"
Tiffany 1-night trip
Posted 3 hours ago
The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
336
Accommodation
588 Holiday Homes
Lowest Price
€170
Highest Price
€678