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Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Middletown vacation 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 CA $238
CA $449 total
includes taxes & fees
Oct 26 - Oct 27
Tangerine Cottage spacious home
A large, two-story house with a front porch, surrounded by a well-maintained lawn and a fence.

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 CA $2,020
CA $3,448 total
includes taxes & fees
Nov 1 - Nov 2
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)
"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 CA $99
CA $250 total
includes taxes & fees
Oct 14 - Oct 15
Cobb Mountain Chalet King Size Suite
A wooden deck with outdoor furniture, including a wicker chair and a table with chairs.

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 CA $121
CA $301 total
includes taxes & fees
Oct 12 - Oct 13
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 CA $190
CA $283 total
includes taxes & fees
Oct 11 - Oct 12
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
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 CA $185
CA $395 total
includes taxes & fees
Oct 11 - Oct 12
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.

7. 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 CA $353
CA $729 total
includes taxes & fees
Oct 15 - Oct 16
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.

8. The Parlour House at the Fainting Couch

The Parlour House at the Fainting Couch
Cobb
The price is CA $615
CA $771 total
includes taxes & fees
Oct 9 - Oct 10
The Parlour House at the Fainting Couch
A swimming pool with a slide, a barbecue area, and a wooden deck.

9. 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 CA $178
CA $403 total
includes taxes & fees
Oct 12 - Oct 13
2 Hidden Wine Country Gem Upstairs Unit
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 location!"
United States
Riley F.
The price is CA $356
CA $713 total
includes taxes & fees
Oct 29 - Oct 30
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
A waterfront property with multiple buildings, a dock, and a palm tree.

11. 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 CA $500
CA $1,024 total
includes taxes & fees
Oct 14 - Oct 15
Lakefront, 1 King Bed, dock, mist view, electronic firepit
A living room with a red sofa, a green armchair, and a red armchair with patterned cushions. There is a coffee table with books and a lamp. The room has wooden flooring and a large window with blinds.

12. Napa Valley Retreat in Calistoga!

Napa Valley Retreat in Calistoga!
Calistoga
9.8 out of 10, Exceptional, (34 reviews)
"We had a wonderful day. Thanks for the flexibility on check-in day."
United States
linda k.
The price is CA $554
CA $717 total
includes taxes & fees
Nov 1 - Nov 2
Napa Valley Retreat in Calistoga!
A wooden deck with outdoor furniture, a pool, and a view of a marina and hills.

13. 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 CA $194
CA $482 total
includes taxes & fees
Oct 27 - Oct 28
Waterfront Luxury- 3 Plus Bedrooms
A view of a lake with trees in the foreground and hills in the background.

14. 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 CA $192
CA $341 total
includes taxes & fees
Oct 11 - Oct 12
Cozy Cottage: Panoramic Lake Views, WiFi, Deck
A modern building entrance with a stone facade, a wooden pergola, and two wall-mounted lights.

15. 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, (67 reviews)
"Unbelievable property – we will absolutely stay here again –Just fabulous!"
United States
Jeffrey S.
The price is CA $1,777
CA $2,832 total
includes taxes & fees
Oct 11 - Oct 12
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
A wooden deck with a metal railing overlooking a body of water, a stone sculpture, and a small pavilion.

16. 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)
"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 CA $284
CA $711 total
includes taxes & fees
Oct 11 - Oct 12
STUNNING Lakefront, Huge DOCK,2 Kayaks, Sleep 8, Prime fishing spot
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, (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 CA $392
CA $760 total
includes taxes & fees
Oct 13 - Oct 14
Wine Country Farmhouse with Hot Tub
A kitchen with a stove, pots, pans, and a digital clock displaying 5:41.

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

Hilltop Hideaway: 4 acres, Hot Tub, Stunning Views
Clearlake Oaks
The price is CA $228
CA $545 total
includes taxes & fees
Oct 13 - Oct 14
Hilltop Hideaway: 4 acres, Hot Tub, Stunning Views
Private kitchen

19. 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 CA $154
CA $514 total
includes taxes & fees
Oct 13 - Oct 14
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
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

Golden Haven Hot Springs

Golden Haven Hot Springs

10/10 Excellent
"I love everything about this place from the mineral spas to the real mud baths!"
Rachelle 2-night trip
Posted 3 hours ago
Golden Haven Hot Springs

Find out more about Middletown

Middletown Vacation Homes information

Number of reviews
351
Accommodation
586 Vacation Homes
Lowest Price
CA $250
Highest Price
CA $3,448

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