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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 100 Cottages in Middletown with updated reviews, rates, and availability.

Wine Country Bungalow

Wine Country Bungalow

10.0 out of 10, Exceptional, (37)
"Pleasant neighborhood for a family stay."
Wine Country Bungalow
TREE HOUSE, WITH INDOOR/OUTDOOR SHOWER, PRIVATE DECK, POOL & INFIINITY HOT TUB
Chic Cabin deck

TREE HOUSE, WITH INDOOR/OUTDOOR SHOWER, PRIVATE DECK, POOL & INFIINITY HOT TUB

TREE HOUSE, WITH INDOOR/OUTDOOR SHOWER, PRIVATE DECK, POOL & INFIINITY HOT TUB
Comfort and Style in Our Queen Cottage
Dining

Comfort and Style in Our Queen Cottage

9.8 out of 10, Exceptional, (41)
"Delightful cottage and environs. Very relaxing and quiet. Responsive and friendly management."
The price is SAR 634
SAR 853 total
includes taxes & fees
25 Feb - 26 Feb
Comfort and Style in Our Queen Cottage
Backyard Garden Oasis
Property grounds

Backyard Garden Oasis

3.0 star property
9.6 out of 10, Exceptional, (42)
"The Backyard Garden Oasis was quiet and secluded. We enjoyed walking along the quiet street in the morning. The owner is a helpful host. "
The price is SAR 728
SAR 811 total
includes taxes & fees
25 Feb - 26 Feb
Backyard Garden Oasis
Healdsburg Cottage Walk to the Plaza, Workspace
Healdsburg Cottage entrance

Healdsburg Cottage Walk to the Plaza, Workspace

10.0 out of 10, Exceptional, (224)
"We thoroughly enjoyed our stay at Kelly and David's Healdsburg Cottage. It was spotlessly clean with a very comfortable bed and an excellent shower. We appreciated the fine coffees available when we arrived and Kelly's responsiveness and care in handling a question we had about adjusting the thermostat during a radical change in the weather while we were there. Truly a charming and comfortable base for exploring Healdsburg and its surrounding area. We will definitely want to stay here when we...
Healdsburg Cottage Walk to the Plaza, Workspace
Sunny View Cottage in the Beautiful Wine Country
Kitchen/Dining

Sunny View Cottage in the Beautiful Wine Country

10.0 out of 10, Exceptional, (264)
"We thoroughly enjoyed our stay at the cottage for a girls' getaway! It was comfortable and quiet, and perfect for our needs. The only hiccup was a power/water outage for a few hours our first night, which was completely beyond anyone's control. When I texted the owners to report it, they responded immediately and followed up with PG&E.We can't wait to go back!"
Sunny View Cottage in the Beautiful Wine Country
1 Bedroom Cottage Walking Distance to Down Town
Exterior

1 Bedroom Cottage Walking Distance to Down Town

10.0 out of 10, Exceptional, (50)
"The West End cottage presented as advertised, conveniently located in the historic area of Santa Rosa within walking distance of old town. The cottage had all the comforts of home, was quiet and peaceful. "
1 Bedroom Cottage Walking Distance to Down Town
Dan's Place. Cozy Cottage in Quiet Older Santa Rosa Neighborhood
Exterior detail

Dan's Place. Cozy Cottage in Quiet Older Santa Rosa Neighborhood

The price is SAR 555
SAR 978 total
includes taxes & fees
25 Feb - 26 Feb
Dan's Place. Cozy Cottage in Quiet Older Santa Rosa Neighborhood
Escape to Wine County in your independant Cottage in Downtown Calistoga
Exterior

Escape to Wine County in your independant Cottage in Downtown Calistoga

9.8 out of 10, Exceptional, (13)
"We have stayed many times at the Cottage Grove Inn and it never disappoints. "
The price is SAR 1,031
SAR 1,394 total
includes taxes & fees
25 Feb - 26 Feb
Escape to Wine County in your independant Cottage in Downtown Calistoga
Waterfront Cottage w/ Private Pool & Lake View!
Living area

Waterfront Cottage w/ Private Pool & Lake View!

3.0 star property
Waterfront Cottage w/ Private Pool & Lake View!
Kelseyville Cottage: Private Deck & On-Site Winery
Kelseyville Vacation Rental | 1BR | 1BA | 500 Sq Ft | 3 Steps Required

Kelseyville Cottage: Private Deck & On-Site Winery

2.0 star property
10.0 out of 10, Exceptional, (75)
"Really enjoyed the Derby Day at the winery. Thank you for a wonderful stay."
Kelseyville Cottage: Private Deck & On-Site Winery
Waterfront Cottage w/ Private Pool & Lake View!
Lakeport Vacation Rental | 2BR | 1BA | 952 Sq Ft | Step-Free Access

Waterfront Cottage w/ Private Pool & Lake View!

9.2 out of 10, Wonderful, (39)
"This was in a really great location. Close to stores & the lake. The place was perfect inside but needed blinds in the living & dining areas. Pool was beautiful but so cold we couldn’t swim. Plus, pool was for tall people! We were never able to touch the bottom. A little scary at times.over all beautiful place! A dock access would have been great too!"
Waterfront Cottage w/ Private Pool & Lake View!
Chalk Hill Cottage Close to Wineries

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (31)
"We spent 3 nights at Beaux Maison Sonoma Cottage and my wife and I loved it. Very comfy, well equipped and loved the fire pit it the evenings. And the location was great too - on Chalk Hill Road, so in the country but only 15 minutes from Healdsburg and close to many wineries. And only 35 minutes to Calistoga. For future trips for just the two of us, would definitely try to stay again!"
Chalk Hill Cottage Close to Wineries
Newly Refurbished! Nest Cottage at ru's Farm.
Exterior

Newly Refurbished! Nest Cottage at ru's Farm.

9.8 out of 10, Exceptional, (160)
"We had a wonderful experience in the cozy cottage. Kristen went out of her way to make it a lovely stay. Our Bella Winery tour with Mike was a great addition. "
Newly Refurbished! Nest Cottage at ru's Farm.
Enjoy a Slice Of Country--Two miles to Downtown Healdsburg
Deck seating area

Enjoy a Slice Of Country--Two miles to Downtown Healdsburg

10.0 out of 10, Exceptional, (60)
"What a lovely little property! The location was great and a very short drive into town and close to many wineries. We spent every morning sitting out on the cute patio drinking coffee and listening to the birds under the beautiful trees. And it was the best stocked house we have ever stayed in! Great selection of spices for cooking and all the other essentials. Fantastic!"
Enjoy a Slice Of Country--Two miles to Downtown Healdsburg
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown

Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown

9.8 out of 10, Exceptional, (37)
"My husband and I had a wonderful week at the Carma Cottage. The location just off Healdsburg Square makes it so easy to dine, shop, and visit wineries — no car needed! The house itself is very comfortable and there is an ample kitchen and dining area for nights you would rather stay in and cook. Would recommend with enthusiasm!"
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown
Heron House--The River House in the Redwoods

Heron House--The River House in the Redwoods

10.0 out of 10, Exceptional, (22)
"Home is situated in a very quiet and scenic location on the river, with a nice deck with outside dining and hot tub. Property had kayaks and other river equipment available, too. Home was clean, with a lovely kitchen and rooms. We would stay here again. "
Heron House--The River House in the Redwoods
Vineyard View Home with a Complimentary Wine Tasting
Dining

Vineyard View Home with a Complimentary Wine Tasting

9.0 out of 10, Wonderful, (6)
"The house itself was very nice and the owner was very communicative for the most part. Outside of that, we unfortunately had a very negative experience as the location of the house was over 2.5 miles from town (Where the listing had shown it to be) which resulted in us being stranded in town on the final night of our stay. This difference was material, and the location was the sole reason we booked it as we anticipated transportation being difficult and had a busy weekend of wedding events...
Vineyard View Home with a Complimentary Wine Tasting
Escape to wine country in your independent cottage in downtown Calistoga
Terrace/patio

Escape to wine country in your independent cottage in downtown Calistoga

10.0 out of 10, Exceptional, (3)
"We made the Calistoga CA area our base for our recent trip and the Cottage Grove Inn served as a great place to stay."
The price is SAR 1,031
SAR 1,394 total
includes taxes & fees
25 Feb - 26 Feb
Escape to wine country in your independent cottage in downtown Calistoga
Escape to Wine Country in your independant Cottage in Downtown Calistoga
Exterior

Escape to Wine Country in your independant Cottage in Downtown Calistoga

10.0 out of 10, Exceptional, (1)
"Loved everything Ellen was very accommodating ,pleasant and polite As well as professional The furnishings were very up scale and same style as my home One suggestion The tv should be more accessible so it does not block AC when pulled out from the wall I’m not being critical because I love this place. I will stay there every time I would ever be close to Calistoga. AND I adore Ellen personally and professionally!!👍❤️"
The price is SAR 1,031
SAR 1,394 total
includes taxes & fees
25 Feb - 26 Feb
Escape to Wine Country in your independant Cottage in Downtown Calistoga
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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Other property types in Middletown

Backyard Garden Oasis
Property grounds

Backyard Garden Oasis

3.0 star property
9.6 out of 10, Exceptional, (42)
"The Backyard Garden Oasis was quiet and secluded. We enjoyed walking along the quiet street in the morning. The owner is a helpful host. "
The price is SAR 728
SAR 811 total
includes taxes & fees
25 Feb - 26 Feb
Backyard Garden Oasis
Clear Lake Cottages & Marina
Outdoor pool

Clear Lake Cottages & Marina

2.5 star property
9.0 out of 10, Wonderful, (295)
"It was clean, quiet and all requirements met. "
The price is SAR 484
SAR 539 total
includes taxes & fees
25 Feb - 26 Feb
Clear Lake Cottages & Marina
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Family / Kitchen

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

10.0 out of 10, Exceptional, (222)
"This is a beautiful home in a quaint location to build special memories. We will definitely return!!"
The price is SAR 6,000
SAR 7,665 total
includes taxes & fees
3 Mar - 4 Mar
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
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.

Frequently asked questions

How much do cottages in Middletown cost?
Expect to pay between SAR 555 and SAR 1,031 per night for cottages in Middletown. No matter your budget, an epic stay is only clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Middletown with Expedia?
Expedia has some wonderful cottages in Middletown, so start planning for a memorable stay close to nature. If you have a budget, click on how much you want to spend and the star rating of your property. Or take advantage of our filters to search for cottages with free WiFi or a pool. We’ll help you find the right digs whatever your escape looks like.
How can I find cheap cottages in Middletown?
Expedia is here to help you look for cheap cottages in Middletown. To discover your dream stay in a matter of clicks, use our convenient filter tool to refine your search results by amenities, star rating and budget.