Photo by Matthew Walls

Middletown Chalets

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3
No exact matches found, but these alternatives could be just right

Recommended hotels in Middletown

A single-story house with a covered porch, a small garden, and a wooden fence in the background.

1. The Well House with outdoor seating and loft!

The Well House with outdoor seating and loft!
Middletown
9.4 out of 10, Exceptional, (3 reviews)
"this was a very neat cozy apartment, perfect location. One block from Main Street in Middletown. Very clean, great host, five star."
United States
louis s.
$176 nightly
The price is $176
Nov 9 - Nov 10
Total with taxes and fees
The Well House with outdoor seating and loft!
A stone structure in a grassy field with trees and hills in the background.

2. Love Shack private retreat

Love Shack private retreat
Middletown
9.4 out of 10, Exceptional, (3 reviews)
"Natural light, high ceilings, ac, good WiFi and tv, great location, thoughtful host. "
United States
Gretchen F.
$180 nightly
The price is $180
Nov 9 - Nov 10
Total with taxes and fees
Love Shack private retreat
A wooden deck with wicker furniture and a metal table, overlooking a vineyard and hills.

3. Garden house with gas fireplace

Garden house with gas fireplace
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"It was a quaint country house. The host was attentive, but also left us to ourselves. The house was clean. A/C worked well. It was very comfortable."
United States
Amy
$192 nightly
The price is $192
Nov 8 - Nov 9
Total with taxes and fees
Garden house with gas fireplace
A single-story house with a front porch, a red door, and a small front yard.

4. Tangerine Cottage spacious home

Tangerine Cottage spacious home
Middletown
$280 nightly
The price is $280
Nov 7 - Nov 8
Total with taxes and fees
Tangerine Cottage spacious home
A two-story house with a central entrance, a covered porch, and a symmetrical facade.

5. 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
$2,009 nightly
The price is $2,170
Nov 12 - Nov 13
Total with taxes and fees
15-Acre Gated Wine Country Estate and 7BR Mansion, Pool, Spa ,Sleeps 18
An outdoor patio with tables and chairs, a central fire pit, and a view of the street and houses in the background.

6. The Inn on Pine

The Inn on Pine
3.0 star property
Calistoga
9.6 out of 10, Exceptional, (1,000 reviews)
"Great location and wonderful staff. Good breakfast and clean rooms!"
United States
Kara
$147 nightly
The price is $169
Nov 22 - Nov 23
Total with taxes and fees
The Inn on Pine
A rooftop patio with outdoor seating, a fire pit, and a view of the surrounding landscape.

7. Calistoga Motor Lodge and Spa

Calistoga Motor Lodge and Spa
4.0 star property
Calistoga
8.8 out of 10, Excellent, (554 reviews)
"It was a great place to stay!"
United States
TRACI
$222 nightly
The price is $256
Nov 29 - Nov 30
Total with taxes and fees
Calistoga Motor Lodge and Spa
A single-story motel with a beige exterior, a covered porch, and a driveway leading to the entrance.

8. The Fainting Couch Boutique Hotel

The Fainting Couch Boutique Hotel
2.0 star property
Cobb
9.6 out of 10, Exceptional, (50 reviews)
"We loved staying here. It was so clean and beautiful.🤗 Thank you"
United States
Jenny
$160 nightly
The price is $178
Nov 10 - Nov 11
Total with taxes and fees
The Fainting Couch Boutique Hotel
A building with a stone facade, large windows, and a covered entrance.

9. Best Western Plus Stevenson Manor

Best Western Plus Stevenson Manor
2.5 star property
Calistoga
9.4 out of 10, Exceptional, (1,000 reviews)
"Great stay"
United States
Ignacio
$149 nightly
The price is $171
Dec 6 - Dec 7
Total with taxes and fees
Best Western Plus Stevenson Manor
A hotel room with a fireplace, two beds, a large TV, and a balcony with a view.

10. Geyserville Inn

Geyserville Inn
3.5 star property
Geyserville
9.2 out of 10, Wonderful, (1,001 reviews)
"Beautiful property and the staff was wonderful. Would definitely stay here again"
United States
Lori
$139 nightly
The price is $158
Dec 1 - Dec 2
Total with taxes and fees
Geyserville Inn
A vintage car parked in front of a house with a covered patio and a small garden.

11. Dr. Wilkinson's Backyard Resort and Mineral Springs, a Member of Design Hotels

Dr. Wilkinson's Backyard Resort and Mineral Springs, a Member of Design Hotels
4.0 star property
Calistoga
9.4 out of 10, Exceptional, (388 reviews)
"The most amazing and relaxing place on earth. Low key, easy vibe!! Staff was excellent! Seven was a 10/10!!"
United States
Cloie
$240 nightly
The price is $277
Nov 30 - Dec 1
Total with taxes and fees
Dr. Wilkinson's Backyard Resort and Mineral Springs, a Member of Design Hotels
A hotel entrance with a signboard, a covered outdoor seating area, and a staircase leading to the building.

12. UpValley Inn & Hot Springs Napa Valley, an Ascend Collection Hotel

UpValley Inn & Hot Springs Napa Valley, an Ascend Collection Hotel
3.0 star property
Calistoga
9.0 out of 10, Wonderful, (1,001 reviews)
"Rooms were decent for the price an accommodating staff:"
United States
Catherine
$167 nightly
The price is $193
Nov 30 - Dec 1
Total with taxes and fees
UpValley Inn & Hot Springs Napa Valley, an Ascend Collection Hotel
A two-story house with a wrap-around porch, surrounded by lush greenery and trees.

13. The Bergson, BW Signature Collection

The Bergson, BW Signature Collection
3.0 star property
Calistoga
9.2 out of 10, Wonderful, (1,000 reviews)
"Nice hotel in a great location. Would stay there again."
United States
Carrie
$131 nightly
The price is $151
Dec 6 - Dec 7
Total with taxes and fees
The Bergson, BW Signature Collection
A white building with a covered porch, potted plants, and a bicycle.

14. Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center
3.5 star property
Cobb
8.8 out of 10, Excellent, (39 reviews)
"Waterfront cabins were amazing. The location and wildlife were serene, fantastic place to stay."
United States
Carmino
$152 nightly
The price is $170
Nov 8 - Nov 9
Total with taxes and fees
Mandala Springs Wellness Retreat Center
A two-story building with a covered outdoor seating area, a fire pit, and a sign indicating a no-entry zone.

15. Golden Haven Hot Springs

Golden Haven Hot Springs
2.5 star property
Calistoga
9.6 out of 10, Exceptional, (1,008 reviews)
"Loved this place!!!"
United States
Brittany
$209 nightly
The price is $240
Nov 9 - Nov 10
Total with taxes and fees
Golden Haven Hot Springs
A Best Western hotel with a large sign, multiple balconies, and a covered walkway.

16. Best Western El Grande Inn

Best Western El Grande Inn
3.0 star property
Clearlake
7.8 out of 10, Good, (541 reviews)
"Clean room! Staff was great too! Definitely recommend"
United States
Sean
$170 nightly
The price is $190
Nov 7 - Nov 8
Total with taxes and fees
Best Western El Grande Inn
Front of property

17. Calistoga Wine Way Inn

Calistoga Wine Way Inn
3.0 star property
Calistoga
9.0 out of 10, Wonderful, (650 reviews)
"A very good place to stay. The house is so clean, and the host is so friendly and helpful."
United States
Zhaoqi
$160 nightly
The price is $184
Nov 11 - Nov 12
Total with taxes and fees
Calistoga Wine Way Inn
A hotel with a prominent entrance, a well-lit facade, and a landscaped front garden.

18. Hampton Inn & Suites Windsor - Sonoma Wine Country

Hampton Inn & Suites Windsor - Sonoma Wine Country
2.5 star property
Windsor
9.2 out of 10, Wonderful, (1,001 reviews)
"Great location and great staff."
United States
Gunjan
$122 nightly
The price is $140
Nov 13 - Nov 14
Total with taxes and fees
Hampton Inn & Suites Windsor - Sonoma Wine Country
A covered outdoor deck with a table and chairs, a grill, and a bottle of wine.

19. 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
$153 nightly
The price is $169
Nov 8 - Nov 9
Total with taxes and fees
Cobb Mountain Chalet King Size Suite
A multi-story hotel with a central archway, balconies, and a parking area.

20. Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta
3.0 star property
Healdsburg
8.2 out of 10, Very good, (1,000 reviews)
"Nice to stay in for a weekend in wine country"
United States
Antoine
$119 nightly
The price is $138
Nov 15 - Nov 16
Total with taxes and fees
Dry Creek Inn MOD Collection by Sonesta
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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Learn more about Middletown

Soak in mineral-rich waters at Harbin Hot Springs, where hiking trails lead to peaceful meditation areas. Wine lovers can sample local vintages at family-owned tasting rooms along Middletown's charming main street.

See all hotels in Middletown
A calm river with clear water, surrounded by dense greenery and trees.
Photo by Matthew Walls
Open Photo by Matthew Walls

Top reviews in Middletown

A single-story motel with a beige exterior, a covered porch, and a driveway leading to the entrance.
The Fainting Couch Boutique Hotel

The Fainting Couch Boutique Hotel

The Fainting Couch Boutique Hotel
Cobb

10/10 Excellent

Unique clean hotel in a quiet area
United States
Marshall
Reviewed March 24, 2025
The Fainting Couch Boutique Hotel

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