Photo by Shannon Willitts

Middletown Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Middletown

Backyard Garden Oasis

3.0 star property
9.6 out of 10, Exceptional, (49)
"Cute garden area, quiet, nice all inclusive spot"
The price is AU$333
includes taxes & fees
26 Aug - 27 Aug
Backyard Garden Oasis

The Ranch at Lake Sonoma

1.0 star property
10.0 out of 10, Exceptional, (1)
"The location is fantastic, with a spectacular view on the lake if you choose a lakeview. A very genuine welcome from The Ranch team, with all detailed explanations, a map to help you to navigate around. For our first time going camping, we want definitely to come back there !"
The price is AU$104
includes taxes & fees
28 Aug - 29 Aug
The Ranch at Lake Sonoma

Clear Lake Cottages & Marina

2.5 star property
9.0 out of 10, Wonderful, (318)
"The cabin was very clean and it was in a nice and quiet location."
The price is AU$321
includes taxes & fees
27 Aug - 28 Aug
Clear Lake Cottages & Marina

Rainbow Lodge

2.0 star property
4.8 out of 10, (10)
"Dead bugs on the bathroom window ledge with the courtesy shampoo. Live spiders and earwigs. Shower leaked and Charlie wanted to come in and fix it. Should have been done before I got there. Arrived at check in time, had to wait 30 min for Charlie to get there. No ice machine. True flea bag motel. Run away!!"
The price is AU$149
includes taxes & fees
26 Aug - 27 Aug
Rainbow Lodge

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

9.2 out of 10, Wonderful, (60)
"The cottage is a comfortable house. "
Mountain Cottage near Russian River, hiking & downtown, family and pet friendly

LAKEFRONT OASIS w/ BOAT DOCK FISHERMEN SPECIAL!

8.8 out of 10, Excellent, (13)
"Right on the lake nice place to stay"
LAKEFRONT OASIS w/ BOAT DOCK FISHERMEN SPECIAL!

Casa Bella Estate in Wine Country w/ New Pool!

9.6 out of 10, Exceptional, (130)
"Great place to celebrate family members birthdays and Mother’s Day. Excellent location in Sonoma County close to wineries and easy access to SFO and Santa Rosa Airports. Walking distance to a great coffee shop and two wine tasting rooms. Nice large fenced area with pool, jacuzzi, outdoor grill and gathering area. We also enjoyed the covered front porch for relaxing and enjoying the outdoors."
The price is AU$6,680
includes taxes & fees
20 Sept - 21 Sept
Casa Bella Estate in Wine Country w/ New Pool!

Beautiful Lake Front house with Spectacular view, new deck/private dock sleep 6

9.6 out of 10, Exceptional, (55)
"So relaxing and peaceful place my family loved it unfortunately was for a short time but next time definitely will stay longer no doubt about booking it again "
The price is AU$653
includes taxes & fees
2 Sept - 3 Sept
Beautiful Lake Front house with Spectacular view, new deck/private dock sleep 6

Escape to Wine County in your independant Cottage in Downtown Calistoga

9.6 out of 10, Exceptional, (22)
"We have stayed many times at the Cottage Grove Inn and it never disappoints. "
The price is AU$627
includes taxes & fees
26 Aug - 27 Aug
Escape to Wine County in your independant Cottage in Downtown Calistoga

Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.

10.0 out of 10, Exceptional, (7)
"We had a pleasant stay at the property over the Memorial Day weekend. It’s away from the crowds but yet 15 mins from Sonoma Lake for water sports and 30 mins from Healdsburg. Amazing view and great time in the pool. "
Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.

Mandala Springs Wellness Retreat Center

3.5 star property
8.6 out of 10, Excellent, (27)
"Beautiful quiet retreat "
The price is AU$388
includes taxes & fees
26 Aug - 27 Aug
Mandala Springs Wellness Retreat Center

Cobb Mountain Chalet King Size Suite

9.8 out of 10, Exceptional, (21)
"Perfect place to stay, nice and cozy!"
The price is AU$225
includes taxes & fees
26 Aug - 27 Aug
Cobb Mountain Chalet King Size Suite

Scenic and tranquil in the heart of Sonoma wine country.

10.0 out of 10, Exceptional, (97)
"This home is beautiful and comfortable. The outside decks and gardens provide a peaceful respite from busy traveling and sightseeing. The views are lovely."
Scenic and tranquil in the heart of Sonoma wine country.

Renovated Vineyard Home - 4 BR/4 BA - Solar Pool, Spa, Views

10.0 out of 10, Exceptional, (150)
"Wonderful house and yard. Manager is excellent as well. We love staying here"
Renovated Vineyard Home - 4 BR/4 BA - Solar Pool, Spa, Views

Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg

10.0 out of 10, Exceptional, (34)
"Absolutely wonderful stay. The house was beautiful and clean, with multiple spacious common areas for family time. The Limerick Lane team was also incredibly communicative and accommodating throughout. 100% recommend."
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

10.0 out of 10, Exceptional, (63)
"Great stay, recommend in every way"
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Beautiful Lake Front Home on 5 acres...multi family vacations

9.4 out of 10, Exceptional, (30)
"Excellent lakefront property ! Amazing location and well maintained "
Beautiful Lake Front Home on 5 acres...multi family vacations

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

10.0 out of 10, Exceptional, (239)
"Wonderful accommodations for a family weekend in the wine country!"
The price is AU$3,490
includes taxes & fees
30 Aug - 31 Aug
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

Escape to Paradise: A Stunning Tuscany-Style Home with Views of Vineyards

10.0 out of 10, Exceptional, (21)
"Amazing location and charming home."
Escape to Paradise: A Stunning Tuscany-Style Home with Views of Vineyards

The Calistoga Cottage — Complimentary wine tasting at Croix included!

10.0 out of 10, Exceptional, (36)
"Our stay was outstanding. The house was exactly as listed. Clean, well maintained and an easy check in/out process. Would highly recommend!!"
The Calistoga Cottage — Complimentary wine tasting at Croix included!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Middletown Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Middletown?

Yes, there are holiday rentals close to the most popular sights in Middletown, or you can select a more secluded option if you're looking for a relaxing stay. Middletown is known for its hot springs and wineries. Make sure you have time to check out the spas and casinos during your trip.

What are some of the best holiday rentals that Middletown has to offer?

Casa Bella Estate in Wine Country w/ New Pool!: This holiday home rental outside of Middletown is located in a rural location, and has a fireplace, a BBQ and air conditioning to put you at ease in your new surroundings. It has 10 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Middletown?

Expedia has 12 holiday rentals for your stay in Middletown.

What can I see and do in Middletown?

Explore the area and family-friendly sights such as Calistoga Spit N' Cycle, or get out into nature at a spot like Boggs Mountain Demonstration State Forest. Other places in town to visit include Twin Pine Casino and Beaver Creek Vineyards.

What are holiday rentals like in Middletown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middletown. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family trips.