Photo by Shannon Willitts

Search Middletown Cottage Rentals from CA $212

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Mar 28 - Mar 30
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Apr 4 - Apr 6
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Apr 18 - Apr 20
In two months
May 16 - May 18

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, (13)
"We have stayed many times at the Cottage Grove Inn and it never disappoints. "
The price is CA $393
CA $528 total
includes taxes & fees
Mar 19 - Mar 20
Escape to Wine County in your independant Cottage in Downtown Calistoga
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 $277
CA $309 total
includes taxes & fees
Mar 19 - Mar 20
Backyard Garden Oasis
Mountain Cottage near Russian River, hiking & downtown, family and pet friendly
Terrace/patio

Mountain Cottage near Russian River, hiking & downtown, family and pet friendly

9.2 out of 10, Wonderful, (55)
"Cute property! It’s a little rustic, but has everything you need. The location is beautiful and convenient to Healdsburg. "
Mountain Cottage near Russian River, hiking & downtown, family and pet friendly
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
Waterfront Cottage w/ Private Pool & Lake View!
Fridge, microwave, stovetop, dishwasher

Waterfront Cottage w/ Private Pool & Lake View!

9.2 out of 10, Wonderful, (40)
"Nice little house, good for a couple or small family. Great view of the lake in the back yard."
Waterfront Cottage w/ Private Pool & Lake View!
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, (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
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 $393
CA $528 total
includes taxes & fees
Mar 19 - Mar 20
Escape to Wine Country in your independant Cottage in Downtown Calistoga
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown
Smart TV, books

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

9.8 out of 10, Exceptional, (38)
"We had a perfect experience. The house is very clean and functional and the location simply cannot be beat. The local management company was very responsive and helpful. We stayed for 2 weeks and really got a feel for living in town given the proximity to restaurants, coffee shops, highways, wineries etc. I would highly recommend this house and we will absolutely be back if they will have us."
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown
Waterfront Cottage w/ Private Pool & Lake View!
Cottage (2 Bedrooms) | Interior

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
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
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 CA $242
CA $325 total
includes taxes & fees
Mar 19 - Mar 20
Comfort and Style in Our Queen Cottage
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 $377 total
includes taxes & fees
Mar 19 - Mar 20
Dan's Place. Cozy Cottage in Quiet Older Santa Rosa Neighborhood
Healdsburg Cottage Walk to the Plaza, Workspace
Terrace/patio

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
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
Wine Country Bungalow
Fridge, microwave, oven, stovetop

Wine Country Bungalow

10.0 out of 10, Exceptional, (37)
"Pleasant neighborhood for a family stay."
Wine Country Bungalow
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
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, (51)
"I had a great stay at this cozy VRBO cottage while attending a K9 training program. The home was clean, comfortable, and just a short 1.5-block walk to a lovely neighborhood park—perfect for unwinding after training sessions. The backyard was a great bonus, with a picnic table to relax and enjoy the fresh air. Highly recommend for anyone looking for a quiet, convenient stay!"
1 Bedroom Cottage Walking Distance to Down Town
Chalk Hill Cottage Close to Wineries
Exterior

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (32)
"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
Charming King Cottage
1 bedroom, WiFi

Charming King Cottage

9.6 out of 10, Exceptional, (10)
"We loved this cozy spot! Warm, easy to find.It is notably across the highway road from downtown Calistoga, so walking at night is less ideal."
The price is CA $270
CA $363 total
includes taxes & fees
Mar 19 - Mar 20
Charming King Cottage
Newly Refurbished! Nest Cottage at ru's Farm.
Property grounds

Newly Refurbished! Nest Cottage at ru's Farm.

10.0 out of 10, Exceptional, (162)
"This was a long weekend for my husband and me. We loved Ru's farm and Healdsburg, we will be back!"
Newly Refurbished! Nest Cottage at ru's Farm.
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
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 $277
CA $309 total
includes taxes & fees
Mar 19 - Mar 20
Backyard Garden Oasis
Clear Lake Cottages & Marina
View from property

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 CA $191
CA $214 total
includes taxes & fees
Mar 25 - Mar 26
Clear Lake Cottages & Marina
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Outdoor dining

Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

10.0 out of 10, Exceptional, (220)
"This is our second time renting Willian's home in Kenwood. This home is absolutely stunning and fully equipped with everything you need for a family or group of friends gathering. Fold-out bunk beds, 3 pack and plays, a high chair, tennis and pickle ball rackets, sidewalk chalk and great kitchen and bathroom products. Linens are great quality as well. Chateau St Jean and many other wineries are minutes away. We will absolutely rent this home again and will recommend it to others.Only issue is...
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
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?
Prepare to pay between CA $212 and CA $393 per night for cottages in Middletown. No matter your budget, a wonderful stay is just a click or two 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?
We think a getaway should be a walk in the park, so if you’re looking for cottages in Middletown at an affordable rate, Expedia has your back. Save those pennies and choose an economical option far from the hustle and bustle, or splurge on a 5-star cottage to treat your loved ones.
How can I find cheap cottages in Middletown?
With Expedia’s user-friendly filter tool, sourcing cheap cottages in Middletown is a breeze. To discover properties that are friendly on the wallet, narrow your search results by amenities, star rating and budget.
What is there to do in Middletown near my cottage?
Once you’ve checked in to your hotel, set out and discover the awesome things Middletown has on offer. Beaver Creek Vineyards is a top attraction to add to your must-see list.