
Chesterfield long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Relax—Stayz takes the hassle out of booking monthly rentals in Chesterfield. The wide selection available and useful search filters make finding your home away from home a breeze. Whether you’re looking for fast Wi-Fi for remote working, a fully equipped kitchen for home cooking or a pool where you can relax with a good book, you’re sure to find it on Stayz. Many long-term rentals in Chesterfield are great for kids and welcome four-legged friends, too. What's more, some offer monthly discounts on extended-stay homes and weekly discounts on shorter-term rentals.
Featured long stay living spaces - Chesterfield
Showing deals for:15 Feb - 15 Mar
Image gallery for Private St Peters Home Patio Pool Table

Private St Peters Home Patio Pool Table
St. Peters
Image gallery for The Fox Den Suite — Cozy, playful, and memorable.

The Fox Den Suite — Cozy, playful, and memorable.
St. Charles
Image gallery for Adorable Two-Person Bungalow nestled in the cozy town of Augusta, MO!

Adorable Two-Person Bungalow nestled in the cozy town of Augusta, MO!
Augusta
Image gallery for Romantic Augusta Cottage w/ hot tub

Romantic Augusta Cottage w/ hot tub
Augusta
Image gallery for Spacious 4BR Family Home Near Historic St. Charles & STL

Spacious 4BR Family Home Near Historic St. Charles & STL
St. Charles
Image gallery for Cozy and Comfortable Home in West County

Cozy and Comfortable Home in West County
Ballwin
Image gallery for Peaceful and cozy equestrian saturated retreat

Peaceful and cozy equestrian saturated retreat
Pacific
Image gallery for Coca Cola Cottage-Stay & Play Near Purina Farms w/private Pet Friendly back yard

Coca Cola Cottage-Stay & Play Near Purina Farms w/private Pet Friendly back yard
Pacific
Image gallery for 3-bedroom vacation home just 20 minutes from Six Flags St. Louis

3-bedroom vacation home just 20 minutes from Six Flags St. Louis
Ballwin
Image gallery for Modern Boutique Stay w/ Plush King Bed- Hare Suite

Modern Boutique Stay w/ Plush King Bed- Hare Suite
St. Charles
Image gallery for Beautifull *4BDR/ 2Bath *Home Close to Parks and Downtown!

Beautifull *4BDR/ 2Bath *Home Close to Parks and Downtown!
St. Louis
Image gallery for The Holly House. Comfort and Stylish charm.

The Holly House. Comfort and Stylish charm.
Belleville
Image gallery for Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi

Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi
St. Louis
Image gallery for The Loft on Main | Steps to Dining & Nightlife

The Loft on Main | Steps to Dining & Nightlife
St. Charles
Image gallery for Private 3-Acre Retreat • Koi Pond & Waterfall

Private 3-Acre Retreat • Koi Pond & Waterfall
Chesterfield
Image gallery for Madison House 2 - Spacious 2BR Home Steps from Historic Downtown St. Charles

Madison House 2 - Spacious 2BR Home Steps from Historic Downtown St. Charles
St. Charles
Image gallery for Honky Tonk Hideaway | 2BR Near Historic Main St

Honky Tonk Hideaway | 2BR Near Historic Main St
St. Charles
Image gallery for Affordable Peaceful Cozy House in STL

Affordable Peaceful Cozy House in STL
St. Louis
Image gallery for Cozy 2 bedroom + sleeping are close to Grant's Farm trail & 15 min. to downtown

Cozy 2 bedroom + sleeping are close to Grant's Farm trail & 15 min. to downtown
St. Louis
Image gallery for Hidden Gem in the ❤ of STL

Hidden Gem in the ❤ of STL
St. Louis
Image gallery for Backstage Loft Above Honky Tonk

Backstage Loft Above Honky Tonk
St. Charles
Image gallery for Enjoy the best view in Washington, Missouri!

Enjoy the best view in Washington, Missouri!
Washington
Image gallery for Abby's Oasis. 1 BR, 1B tiny house with extra sleeping loft

Abby's Oasis. 1 BR, 1B tiny house with extra sleeping loft
Union
Image gallery for Stunning 1890's Home - Sleeps 8!

Stunning 1890's Home - Sleeps 8!
St. Charles
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Great discounts on monthly rentals in Chesterfield
You’ll often find discounted rates for long stays of over 28 days on Stayz, making stays of a month or more excellent value.
Entire homes, maximum privacy
Looking for your own place to retreat to? On Stayz, you'll enjoy secluded stays with entire monthly rental homes just for you.
Pet-friendly monthly rentals
Many homes welcome guests with animal companions, so you don’t have to leave your pet at home.
Chesterfield Furnished monthly rentals for remote workers
Find your perfect home office set up. There are plenty of stays on Stayz with dedicated workspaces and fast Wi-Fi so that you can take your work with you.
Monthly stays with practical kitchens
Most furnished extended-stay rentals in Chesterfield come with well-equipped kitchens ideal for home cooking, so you can enjoy healthy meals in or even host your own dinner parties.
Long-term rentals with parking in Chesterfield
Take advantage of the ‘amenities’ filter to find monthly stays with their very own parking spot for the ultimate in convenience.
Wheelchair-accessible holiday rentals
Stayz offers a range of monthly rental homes designed to accommodate everyone for a comfortable and inclusive extended stay.
Holiday rentals in Chesterfield with pool
Stayz's handy search filters will help you find monthly holiday homes with swimming pools so that you can relax in your very own pool.
Rentals with free cancellation in Chesterfield
Plans change. We get that. With Stayz, you can search, select 'free cancellation,' and see all rentals in Chesterfield with flexible cancellation policies.