Photo by Shannon Willitts

Search Middletown Cottage Rentals from CA $212

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Browse Select Middletown Cottages

Escape to Wine County in your independant Cottage in Downtown Calistoga
Point of interest

Escape to Wine County in your independant Cottage in Downtown Calistoga

9.8 out of 10, Exceptional, (12)
"We came to Calistoga to attend and wedding. I found the Cottages on VRBO and I am so happy that I did. We found the space great for the two of us. We were able to walk to the main street. The host communicated well. We enjoyed our stay! We will be back."
The price is CA $395
CA $539 total
includes taxes & fees
Dec 30 - Dec 31
Escape to Wine County in your independant Cottage in Downtown Calistoga
Chalk Hill Cottage Close to Wineries
Exterior

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (29)
"Location is excellent, property is clean and quiet, and hosts were very responsive. This is our second time at this cottage and look forward to staying here again. "
Chalk Hill Cottage Close to Wineries
Santini Farmhouse -- Beautiful Italian style Villa, Hot Tub, Vineyard Views
Exterior

Santini Farmhouse -- Beautiful Italian style Villa, Hot Tub, Vineyard Views

10.0 out of 10, Exceptional, (39)
"The Santini Farmhouse was perfect for our girls-weekend-getaway! The house was spotless and had everything we needed (including instructions how to work everything and a great info book for all local amenities). After a hard day touring wineries the hot tub was a perfect place to unwind. ;) It's a peaceful location in beautiful wine country. Highly recommend!"
Santini Farmhouse -- Beautiful Italian style Villa, Hot Tub, Vineyard Views
TREE HOUSE, WITH INDOOR/OUTDOOR SHOWER, PRIVATE DECK, POOL & INFIINITY HOT TUB
Exterior

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, (39)
"Great place to stay. Conveniently located for our needs."
The price is CA $243
CA $326 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Comfort and Style in Our Queen Cottage
Newly Refurbished! Nest Cottage at ru's Farm.
Property grounds

Newly Refurbished! Nest Cottage at ru's Farm.

9.8 out of 10, Exceptional, (157)
"And well managed...."
Newly Refurbished! Nest Cottage at ru's Farm.
Wine Country Bungalow
Fridge, microwave, oven, stovetop

Wine Country Bungalow

10.0 out of 10, Exceptional, (34)
"We were thankful to find an affordable place in Wine Country that didn't break the bank. The beds were comfortable, lots of towels, clean bathroom with working toilets (yayI). There was a nice backyard with a BBQ that we didn't use. Note this house is smaller than it looks in the photos. The kitchen was small, but is was fine, we didn't cook while there. Basic kitchen for a short stay. This house rules insists on quite hours. Late night parties are forbidden. Which were pretty...
Wine Country Bungalow
Backyard Garden Oasis
Deep-tissue massages, Swedish massages, prenatal massages, massages

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 CA $276
CA $308 total
includes taxes & fees
Dec 27 - Dec 28
Backyard Garden Oasis
1 Bedroom Cottage Walking Distance to Down Town
Fridge, microwave, oven, stovetop

1 Bedroom Cottage Walking Distance to Down Town

10.0 out of 10, Exceptional, (48)
"This cottage in Santa Rosa’s West End neighborhood had everything we needed for my birthday weekend. The wine and milk provided by the host was a really nice touch. Bed was comfy, easy check in, everything worked well, close to good restaurants."
1 Bedroom Cottage Walking Distance to Down Town
Dan's Place. Cozy Cottage in Quiet Older Santa Rosa Neighborhood
Terrace/patio

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

The price is CA $212
CA $379 total
includes taxes & fees
Dec 27 - Dec 28
Dan's Place. Cozy Cottage in Quiet Older Santa Rosa Neighborhood
Heron House--The River House in the Redwoods
Outdoor spa tub

Heron House--The River House in the Redwoods

10.0 out of 10, Exceptional, (21)
"We had a fabulous stay. Great house with a great location. It was lovely waking up and going outside to enjoy the river and woods around us. 5 min drive from Healdsburg main streets with great stores and restaurants. Enjoyed our drive to the coast, redwoods, and vineyards! Would stay again!"
Heron House--The River House in the Redwoods
Waterfront Cottage w/ Private Pool & Lake View!
Cottage (2 Bedrooms) | Private kitchen

Waterfront Cottage w/ Private Pool & Lake View!

3.0 star property
Waterfront Cottage w/ Private Pool & Lake View!
Escape to Wine Country in your independant Cottage in Downtown Calistoga
Point of interest

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 CA $395
CA $539 total
includes taxes & fees
Dec 30 - Dec 31
Escape to Wine Country in your independant Cottage in Downtown Calistoga
Mill Creek by Avantstay Modern Design, Patio, Hot Tub
Living area

Mill Creek by Avantstay Modern Design, Patio, Hot Tub

3.0 star property
Mill Creek by Avantstay Modern Design, Patio, Hot Tub
Kelseyville Cottage: Private Deck & On-Site Winery
Outdoor dining

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!
Fridge, microwave, stovetop, dishwasher

Waterfront Cottage w/ Private Pool & Lake View!

9.2 out of 10, Wonderful, (38)
"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!
Enjoy a Slice Of Country--Two miles to Downtown Healdsburg
Property grounds

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
Cool, LUX Family Cottage in Calistoga's Western Hills
TV, fireplace

Cool, LUX Family Cottage in Calistoga's Western Hills

8.6 out of 10, Excellent, (7)
"This property has a WOW factor. The design and decorative details are impeccable and the place is super cozy. The beds are wonderful, and the separate cottage is the perfect place for guests who need more privacy. It was enjoyable to be immersed within nature. We saw wild turkeys, jack rabbits and deer on the property. The steps to the upstair bedroom in the main cabin are pretty steep, so if there's someone with mobility issues, it could be a problem. Overall, a stunning property. We would go...
Cool, LUX Family Cottage in Calistoga's Western Hills
Sunny View Cottage in the Beautiful Wine Country
Fridge, microwave, oven, stovetop

Sunny View Cottage in the Beautiful Wine Country

10.0 out of 10, Exceptional, (261)
"We have been coming to the area for several years when we come to visit our son. This was the best rental we have stayed in. Very comfortable accommodations and great location. The kitchen was well stocked with everything we needed, as was the bathroom. Beautiful, quiet location, yet near shopping, and all the area has to offer. We will be back!"
Sunny View Cottage in the Beautiful Wine Country
Healdsburg Cottage Walk to the Plaza, Workspace
Terrace/patio

Healdsburg Cottage Walk to the Plaza, Workspace

10.0 out of 10, Exceptional, (222)
"Great location just as advertised. The cottage had everything we needed and was very clean. We both thought the bed was really comfortable. "
Healdsburg Cottage Walk to the Plaza, Workspace
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

Clear Lake Cottages & Marina
View from property

Clear Lake Cottages & Marina

2.5 star property
9.0 out of 10, Wonderful, (290)
"The property itself is beautiful, peaceful and a safe place to walk around. The area surrounding and driving through to get to the property is another story. We stayed Lakefront , so beautiful! We will stay again! "
The price is CA $185
CA $206 total
includes taxes & fees
Jan 2 - Jan 3, 2025
Clear Lake Cottages & Marina
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Interior

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

10.0 out of 10, Exceptional, (220)
"Great place and good location to host 4 couples to celebrate our 50th birthdays. Thank you!"
The price is CA $2,368
CA $3,026 total
includes taxes & fees
Dec 29 - Dec 30
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
Exterior

The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018

10.0 out of 10, Exceptional, (223)
"Our family stayed at the St. Helena House while attending a memorial. The house exceeded our expectations. It was beautifully decorated, comfortable, and homey with many wonderful nooks to read, views of the vineyards out of every window, and a beautiful well stocked kitchen. The beds were very comfortable. The bathrooms were fine with fluffy towels and plenty of hot water with good water pressure in the showers. The owner was very welcoming and available for any questions. It rained all...
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
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 CA $212 and CA $395 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.
What is there to do in Middletown near my cottage?
If you’d like to explore the sights of Middletown, find your way to Langtry Estate and Vineyards. It’s popular among locals and visitors alike.