Gray Summit Holiday Rentals

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Holiday Rentals in Gray Summit

Exterior
Authentic Log cabin with something for everyone!
9.6 out of 10, Exceptional, (315)
"In the area to explore MO wine country and the cabin was ideally situated. Very quiet, peaceful neighborhood and convenient access to wineries."
Authentic Log cabin with something for everyone!
Property grounds
Downtown Boho Bungalow
10.0 out of 10, Exceptional, (14)
"Such a beautiful place and close to coffee shop and restaurants. Loved the city of Washington. Thank you!"
Downtown Boho Bungalow
Exterior
Cozy Cottage, we're told it's heavenly!
10.0 out of 10, Exceptional, (149)
"Perfect rustic cozy cabin!!! This cabin was close enough to explore the wineries in the area and secluded enough to enjoy time together. It was exactly wait we needed. "
Cozy Cottage, we're told it's heavenly!
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Fridge, stovetop, dishwasher, coffee/tea maker
CHARMING 2 BEDROOM HOME IN AUGUSTA
9.8 out of 10, Exceptional, (23)
"House was very clean. Plenty of towels. Chain on one toilet was off but we could fix it. Great place for ladies weekend."
CHARMING 2 BEDROOM HOME IN AUGUSTA
Interior
Beautiful Sunrise, Rural, close to town, near wineries, next to Sunset Bluffs!
10.0 out of 10, Exceptional, (8)
"Refreshing retreat for our small church. Relaxing. Everything we needed was there. Open floor plan made time together better. The fireplace and views are amazing."
The price is NZ$1,699
includes taxes & fees
2 Jun - 3 Jun
Beautiful Sunrise, Rural, close to town, near wineries, next to Sunset Bluffs!
Interior
Cute spacious Ranch - very safe area - 4 BR 2B- big fenced yard -1800 sft
9.6 out of 10, Exceptional, (7)
"Nice property. Excellent host. Very accommodating"
The price is NZ$521
includes taxes & fees
5 Jun - 6 Jun
Cute spacious Ranch - very safe area - 4 BR 2B- big fenced yard -1800 sft
Property grounds
Judge’s Quarters: Exquisite Luxury Apartment
10.0 out of 10, Exceptional, (1)
"Great location. Great place. Perfect for our girls weekend. Would stay here again!"
Judge’s Quarters: Exquisite Luxury Apartment
TV, fireplace, Netflix, books
Lake Haven - Updated Mid Century Cabin Only 35 Mins from St. Louis
9.6 out of 10, Exceptional, (107)
"We had a family wedding to attend at Westwood Hills. We were 10 minutes from the venue. My boys enjoyed getting in the kayaks, fishing. We had a beautiful day hanging on the deck. Nice family oriented cabin."
Lake Haven - Updated Mid Century Cabin Only 35 Mins from St. Louis
Outdoor spa tub
Featured on USA Today - Hot tub, Fenced Yard
10.0 out of 10, Exceptional, (16)
"This was a getaway time to celebrate a 77th birthday. The goal was to go somewhere and stay someplace new for both of us.we found it, thanks to this remodeled bank we cashed in tons of fun memories. This is definitely a 5 Star Location for a couple, a family, or a group."
The price is NZ$574
includes taxes & fees
3 Jun - 4 Jun
Featured on USA Today - Hot tub, Fenced Yard
Private kitchen
Cozy Historic WashMo home
9.8 out of 10, Exceptional, (10)
"We rented this house for a girls weekend and really enjoyed it. Cozy and comfortable, and shops and restaurants were very close"
The price is NZ$416
includes taxes & fees
3 Jun - 4 Jun
Cozy Historic WashMo home
Exterior
Cozy little house blocks from the Park & Fair Grounds. EV Charger equipped.
10.0 out of 10, Exceptional, (45)
"Warm and welcoming home with extremely comfortable beds. The host communicated with us in advance that the trash can foot pedal was not working, which was not a big deal, but the advance communication was greatly appreciated. Would definitely stay again if in the area."
The price is NZ$453
includes taxes & fees
3 Jun - 4 Jun
Cozy little house blocks from the Park & Fair Grounds. EV Charger equipped.
Fridge, microwave, oven, stovetop
Overlooking private lake Cabin for perfect getaway in Missouri
10.0 out of 10, Exceptional, (4)
"This place was immaculate, has everything u need for ur stay except groceries of course but they do have coffe some snacks smores all cooking eating utensils u need, minus a icecream scoop lol! Very kids friendly on second floor with games bunk beds tv etc! My kids LOVED IT asked if we could buy it lol! ( ages 20,17,13,10,6,2) several lizards tht were so cute, the fire pit with the rocks my 2 and 6 year old loved and fireplace I could go on and on lol ,there is SOO many things to do and madeso...
Overlooking private lake Cabin for perfect getaway in Missouri
Fridge, microwave, oven, stovetop
Kid and pet friendly 2 nd floor duplex
9.4 out of 10, Exceptional, (17)
"Everything was as expected."
The price is NZ$312
includes taxes & fees
3 Jun - 4 Jun
Kid and pet friendly 2 nd floor duplex
Fridge, microwave, oven, dishwasher
The cottage at Fourth and Elm
10.0 out of 10, Exceptional, (19)
"We really enjoyed our stay. Everything was perfect and we loved the area. "
The cottage at Fourth and Elm
4 bedrooms, iron/ironing board, WiFi, bed sheets
Mandolin Ridge Farm—Log Cabin Luxe! Pet Friendly. Livestock Guard Dogs Onsite.
10.0 out of 10, Exceptional, (1)
"This is our second stay at this beautiful property. We rang in the New Year at Mandolin Ridge and it was beautiful. We were greeted with the birth of two baby goats which was quite auspicious. The home is spacious and like going to a comfortable, beautifully appointed museum. Each room has hidden delights. A feast for the eyes indeed. The host, Loribeth, is considerate and warm as well detail oriented. It is clear she wants to provide excellence! Mandolin Ridge and Loribeth really deliver."
The price is NZ$1,114
includes taxes & fees
31 May - 1 Jun
Mandolin Ridge Farm—Log Cabin Luxe! Pet Friendly. Livestock Guard Dogs Onsite.
View from property
Mid Century Modern Home w/ Private Pool & Lake on 50 Acres
9.8 out of 10, Exceptional, (87)
"Pictures do not do this place justice. We just stayed with 6 kids and 6 adults. There were tons of activities to keep everyone busy, from swimming to kayaking to ping pong, we were never bored. The property is beautifully maintained and the bonus game room was a real hit!"
The price is NZ$2,165
includes taxes & fees
3 Jun - 4 Jun
Mid Century Modern Home w/ Private Pool & Lake on 50 Acres
5 bedrooms, iron/ironing board, free WiFi, bed sheets
Large Villa Ste A, 1 Mile to Six Flags & Hidden Valley!
9.2 out of 10, Wonderful, (28)
"It was just what we needed, a clean, well stocked place with comfortable beds. It was close to Six Flags and still quite."
The price is NZ$675
includes taxes & fees
30 May - 31 May
Large Villa Ste A, 1 Mile to Six Flags & Hidden Valley!
Exterior
Central Luxe 5br Home - Hot Tub & Views - 🥂 🍷
10.0 out of 10, Exceptional, (39)
"We loved the VRBO. A great place to unwind and relax after a long day of winery-hopping. Would definitely recommend."
The price is NZ$1,004
includes taxes & fees
2 Jun - 3 Jun
Central Luxe 5br Home - Hot Tub & Views - 🥂 🍷
Property grounds
Bee's Knees - Private Heated Pool and Hot Tub, Dog Friendly, Wineries
10.0 out of 10, Exceptional, (13)
"It was a wonderful setting for our family to gather with grandparents, children and grandchildren. We had a great time and loved the kitchen. Plenty of space and the pool and game room were used alot."
The price is NZ$2,298
includes taxes & fees
3 Jun - 4 Jun
Bee's Knees - Private Heated Pool and Hot Tub, Dog Friendly, Wineries
Fridge, microwave, oven, stovetop
BACKYARD OASIS! Cozy and charming 60s Brick ranch with relaxing gazebo over pond
9.8 out of 10, Exceptional, (16)
"Exactly what I was looking for."
BACKYARD OASIS! Cozy and charming 60s Brick ranch with relaxing gazebo over pond
Don't see what you're looking for?
See all available properties in Gray Summit
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 types of properties in Gray Summit you may be interested in

Studio Suite, 1 King Bed
Sonesta ES Suites St. Louis - Chesterfield
3.0 star property
8.2 out of 10, Very good, (1011)
"I ended up booking the property because of the kitchen it turns out that the property itself was really nice everything was very clean it was extremely comfortable the area was quiet and the staff was very friendly and accommodating we will definitely come back to this property again in the near future"
The price is NZ$167
includes taxes & fees
18 Jun - 19 Jun
Sonesta ES Suites St. Louis - Chesterfield
Lobby sitting area
The Wildwood Hotel
3.5 star property
8.8 out of 10, Excellent, (1290)
"I love soft beds but this one was almost too soft, I thought I was falling all night. Also the pool is extremely cold and I couldn’t take my grandson swimming which was disappointing."
The price is NZ$210
includes taxes & fees
3 Jun - 4 Jun
The Wildwood Hotel
Exterior
Drury Plaza Hotel St. Louis Chesterfield
3.0 star property
9.6 out of 10, Exceptional, (1000)
"Staff was professional and kind."
The price is NZ$263
includes taxes & fees
10 Jun - 11 Jun
Drury Plaza Hotel St. Louis Chesterfield
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Gray Summit holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Gray Summit. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Gray Summit. Seeing all the best attractions is bound to make you fall in love with Gray Summit. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Gray Summit short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Gray Summit?

Yes, we give you a choice of holiday rentals where you'll be just 8.9 mi (14.4 km) from Six Flags St. Louis, providing a secluded option if you'd like a quiet spot to stay. Gray Summit is known for its sporting events.

What can I see and do in Gray Summit?

While exploring the area, visit family-friendly sights like Six Flags St. Louis, or get outside and enjoy nature at Route 66 State Park. Augusta Winery and Montelle Winery are a couple of places you'll find in the wider area.

What are holiday rentals like in Gray Summit?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Gray Summit. Holiday rentals feature extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for small groups.

Recent reviews of Gray Summit properties
Expedia verified reviews