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Featured Cottages in Middletown

Fridge, microwave, stovetop, dishwasher
Waterfront Cottage w/ Private Pool & Lake View!
9.0 out of 10, Wonderful, (31)
"This is an older but nicely remodeled home. Beautiful views even with a rainy weekend. The lake laps right up to the edge of the property. Very close to town for entertainment but far enough away that you can get alone time. We would make 2 very strong recos. Put up curtains or blinds in the living room; it's disconcerting that the neighbors can see right in. Also, leave an instruction sheet for the TV; it was very challenging trying to figure out how the remote worked and what options were...
Waterfront Cottage w/ Private Pool & Lake View!
Property grounds
Newly Refurbished! Nest Cottage at ru's Farm.
10.0 out of 10, Exceptional, (148)
"We thoroughly loved staying here!!!"
Newly Refurbished! Nest Cottage at ru's Farm.
Property grounds
Charming Town Cottage in the Heart of Wine Country
9.2 out of 10, Wonderful, (62)
"A short trip for me and my adult daughter, so the two rooms and shared bath were perfect! Comfy beds! Kitchen had all our basic needs met- we ate our meals out since everything was in walking distance in the town! Really appreciated the location! Owner was very attentive and the process to check in was easy. They even gave a birthday cake for my daughter’s 26th birthday! Very thoughtful!! Definitely a great place to stay!"
Charming Town Cottage in the Heart of Wine Country
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Exterior
Chalk Hill Cottage Close to Wineries
10.0 out of 10, Exceptional, (12)
"We recently stayed at Chalk Hill Cottage with our two little Yorkies. The property was the perfect size and had first class amenities. The location is awesome, too! The Hosts are quick to respond to questions and are very kind and considerate. We recommend highly!"
Chalk Hill Cottage Close to Wineries
Property grounds
Wine Country Garden Cottage
9.8 out of 10, Exceptional, (57)
"The cottage was our base for a few days of touring wine country. The cottage is a lovely hide-away in a quiet neighborhood. Due to the weather, we didn't take advantage of the outside amenities. The kitchen is well equipped. There were a few minor maintenance issues that have been reported to the property manager. Note: The upper parking spot is quite steep and your car may bottom out when entering or leaving."
Wine Country Garden Cottage
Pool
Dry Creek Cottage - Healdsburg
9.8 out of 10, Exceptional, (131)
"Second time at this property- it’s quiet and relaxing. The pool and hot tub felt amazing after a long day of exploring."
Dry Creek Cottage - Healdsburg
Fridge, microwave, oven, stovetop
Wine Country Bungalow
10.0 out of 10, Exceptional, (27)
"The property had a fully stocked kitchen and close to downtown Santa Rosa but not a walkable distance. My family was very comfortable there and even enjoyed the game room/garage."
Wine Country Bungalow
Interior
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown
9.8 out of 10, Exceptional, (30)
"Super charming, very comfortable home - just a short stroll away from the main square. Made a great base for our family visit."
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown
Beach/ocean view
MEM WKEND SPEC -20% OFF HOLIDAY RATE, 2nt min+100 credit 4 nonmotor watersports
8.8 out of 10, Excellent, (8)
"cute place ACROSS the street from the water. It was still very pretty. Unfortunately our wifi was out the whole weekend and the house was ice cold when we arrived. Once the place warmed up we were able to enjoy ourselves"
MEM WKEND SPEC -20% OFF HOLIDAY RATE, 2nt min+100 credit 4 nonmotor watersports
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
Fridge, microwave, oven, stovetop
Sunny View Cottage in the Beautiful Wine Country
10.0 out of 10, Exceptional, (246)
"Sunny View Cottage is comfortable, well-equipped, and charming. The location is quiet and rural but very close to great wineries, restaurants (we loved Walter Hansel’s Bistro, just around the corner), and hiking/biking trails. We would definitely stay here again next time we are in the area."
Sunny View Cottage in the Beautiful Wine Country
Fridge, microwave, oven, stovetop
1 Bedroom Cottage Walking Distance to Down Town
10.0 out of 10, Exceptional, (41)
"This is a sweet cottage in a great location-easy access to downtown and other area destinations."
1 Bedroom Cottage Walking Distance to Down Town
Property grounds
Heron House--The River House in the Redwoods
9.8 out of 10, Exceptional, (17)
"Loved this house for a weekend getaway. We loved taking advantage of the deck, grill, and river access. Short drive to the town square and wineries."
Heron House--The River House in the Redwoods
Fridge, microwave, oven, stovetop
Windmill Cottage - Peaceful & Quiet on 5 acres
10.0 out of 10, Exceptional, (9)
"We liked the house. Everything is very convenient. The views are nice. The birds songs are impressing."
The price is AU$722
includes taxes & fees
9 June - 10 June
Windmill Cottage - Peaceful & Quiet on 5 acres
Exterior
Escape to Wine County in your independant Cottage in Downtown Calistoga
10.0 out of 10, Exceptional, (2)
"Charming clean and super well located."
The price is AU$655
includes taxes & fees
30 May - 31 May
Escape to Wine County in your independant Cottage in Downtown Calistoga
Fridge, microwave, stovetop, dishwasher
Newly renovated Wine Country Historic Cottage
10.0 out of 10, Exceptional, (11)
"It’s a small and humble home in a historic neighborhood. A lot of love has been poured into it, and it was such a charming place to stay while we explored the Santa Rosa area! The appliances are modern and pro grade, the bathroom and shower are perfect size, and the hot tub is even placed to provide good privacy during the evening. Definitely a place we will refer our friends and family to!"
Newly renovated Wine Country Historic Cottage
Pool
Great Price! Sunset Beach Cottage with Lovely garden, beach, and boat dock!
9.8 out of 10, Exceptional, (21)
"Fished a tournament this week on clear lake it was a perfect spot for a group of guys to stay and be close to the lake"
Great Price! Sunset Beach Cottage with Lovely garden, beach, and boat dock!
Property grounds
Healdsburg Cottage Walk to the Plaza, Workspace
10.0 out of 10, Exceptional, (205)
"This cottage was by far one of best we have stayed in. Immaculate, charming, everything we needed. Lovely!"
Healdsburg Cottage Walk to the Plaza, Workspace
Exterior
Free wifi & free parking. Charming In-Town Cottage In California Wine Country
9.2 out of 10, Wonderful, (77)
"Cute place full of antique furniture."
Free wifi & free parking. Charming In-Town Cottage In California Wine Country
Deep-tissue massages, Swedish massages, prenatal massages, massages
Backyard Garden Oasis
3.0 star property
9.6 out of 10, Exceptional, (41)
"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 AU$325
includes taxes & fees
6 June - 7 June
Backyard Garden Oasis
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See all available properties in Middletown
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.

Other property types in Middletown

Middletown Cottages information

Number of reviews
1,027
Accommodation
95 Cottages
Lowest Price
AU$325
Highest Price
AU$722

Frequently asked questions

How much do cottages in Middletown cost?
Cottages in Middletown range between AU$325 and AU$722 per night. These properties offer a chance to reconnect with nature — at a price you can afford. This price was 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.
What is there to do in Middletown near my cottage?
The most useful travel accessory is a well-thought-out travel plan. Langtry Estate and Vineyards is a wonderful spot to start your exploration of Middletown.

Recent Reviews in Middletown
Expedia verified reviews