Chester Rentals
From $167 per night (USD)VRBO
Room in Historic Inn! 20 Minutes to Okemo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy a private room, bathroom & shower in the historic Chester Inn, circa 1780. This charming property is conveniently ...
From $167 per night (USD)VRBO
From $200 per night (USD)VRBO
King & Queen Suite in Historic Inn Circa 1780
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Enjoy a private room, bathroom, shower & Fireplace in the historic Chester Inn, circa 1780. This charming property is co ...
From $200 per night (USD)VRBO
From $344 per night (USD)VRBO
Cheerful residential home with lots of space
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Completely renovated spacious home, about 20 minutes from Okemo Mountain! 3 bedrooms, 2 1/2 bathrooms, pool table, air h ...
From $344 per night (USD)VRBO
From $553 per night (USD)Expedia
Log Cabin Retreat - Chester, VT 25 Acres + State Forest Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to your own private Vermont retreat — a beautiful hilltop log cabin set on 25 peaceful acres bordering Williams R ...
From $553 per night (USD)Expedia
From $319 per night (USD)VRBO
Vermont Charm in the 1840 Gideon Lee House
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sunshine, flowers, Farmers' Markets, hikes and starry nights are here. Scents fill the air and the birds are calling. S ...
From $319 per night (USD)VRBO
From $352 per night (USD)Expedia
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Sportsman themed, real log cabin that has comfortable wood stove & hearth, plus backup regular heat. Bathroom with show ...
From $352 per night (USD)Expedia
From $508 per night (USD)VRBO
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Gather with family and friends at our spacious home nestled in the Vermont woods. The Blue Moon Bungalow is your home a ...
From $508 per night (USD)VRBO
From $532 per night (USD)VRBO
Amazing Custom Home on 40+ Acres
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Beautiful views and lots of privacy but still only 2 miles from town. 5 bedrooms and 6 bathrooms with exercise room, gam ...
From $532 per night (USD)VRBO
From $861 per night (USD)VRBO
Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 8
Lovingly updated antique 6 bedroom home in the historic Stone Village of Chester, VT. Sleeps 8+ comfortably making it t ...
From $861 per night (USD)VRBO
From $428 per night (USD)Expedia
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to 'Smokeshire Hilltop Farmhouse!' This lovely 5-bedroom, 2-bathroom vacation rental sits on a plateau above the ...
From $428 per night (USD)Expedia
From $568 per night (USD)VRBO
Indoor Hot Tub Room/10 Miles to Okemo
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Great Central Vermont location! Private but easy to get too. Ten miles to Okemo/Jackson Gore. Skiing, golfing, hiking, s ...
From $568 per night (USD)VRBO
From $758 per night (USD)VRBO
Vacation Rental - Choose from 5 nearby mountains or relax in peace & comfort
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
This charming cabin offers 3 bedrooms, 2 full baths, a spacious living room area with wood burning stove, Finished basem ...
From $758 per night (USD)VRBO
From $1212 per night (USD)VRBO
Work, Ski, Relax - Big Restored 1860s Farmhouse
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Come up solo or bring friends and family to our unique and lovingly renovated estate! Our charming 1860’s farmhouse slee ...
From $1212 per night (USD)VRBO
From $162 per night (USD)VRBO
Whimsical Room & Private Bathroom in Historic Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy a private room & bathroom with tub in the historic Chester Inn, circa 1780. This charming property is conveniently ...
From $162 per night (USD)VRBO
From $192 per night (USD)VRBO
Honeymoon Suite with Jacuzzi Tub in Historic Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy a private room, bathroom & shower in the historic Chester Inn, circa 1780. This charming property is conveniently ...
From $192 per night (USD)VRBO
From $556 per night (USD)Expedia
Private Chester Home w/ Deck, Mins to Skiing!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Spacious, private and fully outfitted for a group getaway to Vermont, this 3-bedroom, 3-bath vacation rental is ready fo ...
From $556 per night (USD)Expedia
From $186 per night (USD)VRBO
Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Adorable Cozy Cottage - sits on a mountainside with an OMG view- ideal for Cyclist, Skiers, Fall Leaf Peakers, Summer ge ...
From $186 per night (USD)VRBO
From $161 per night (USD)Expedia
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
- Bedrooms:
- 0
- Bathrooms:
- 2
- Sleeps:
- 4
Off-Grid Hideaway in the Vermont Hills — Peace, Privacy & Pure Simplicity Please read the full description before booki ...
From $161 per night (USD)Expedia
From $558 per night (USD)VRBO
Amazing Vermont Farmhouse, perfect or fall and winter getaways!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Looking for the perfect Vermont escape? Mountain views, cool breezes, fall leaves and newly fallen snow...all of this an ...
From $558 per night (USD)VRBO
From $335 per night (USD)Expedia
Riverfront, family fun, amazing rec room, close to Magic & Okemo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Relax on the patio on the bank of the Williams River to watch the leaves turn, explore hiking trails, enjoy the outdoor ...
From $335 per night (USD)Expedia
From $419 per night (USD)VRBO
Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Ideal to host up to 6 guests, this home on 2 acres of land is a perfect retreat for anyone looking to be in the heart of ...
From $419 per night (USD)VRBO
From $422 per night (USD)Expedia
Historic 150-year-old farmhouse, Jacuzzi included
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Step into Vermont charm this fall. Our 1869 farmhouse is your cozy home base for leaf-peeping, scenic hikes, antiquing, ...
From $422 per night (USD)Expedia
From $422 per night (USD)VRBO
Charming Chester Farmhouse near Near VT Slopes
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our 4-bedroom Chester farmhouse—blending Vermont charm with mid-century style only 15 mins from Okemo, Magic ...
From $422 per night (USD)VRBO
From $168 per night (USD)VRBO
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy a private room, bathroom & shower in the historic Chester Inn, circa 1780. This charming property is conveniently ...
From $168 per night (USD)VRBO
From $1076 per night (USD)VRBO
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Escape to a cozy Vermont cabin on 12 private acres with stunning mountain views. Just minutes from Okemo and other nearb ...
From $1076 per night (USD)VRBO
From $628 per night (USD)VRBO
Spacious 5-bedroom Historic Stone House near Okemo
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
This home is located in the heart of the Stone Village in Chester and was built in 1844 by the Clark brothers. This is o ...
From $628 per night (USD)VRBO
From $258 per night (USD)VRBO
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Pet Friendly w/ Fee (Max 1) | Close to Hiking & Skiing | On-Site Goats | Foliage Views From crisp autumn mornings to sn ...
From $258 per night (USD)VRBO
From $478 per night (USD)Expedia
Spacious 5-bedroom chalet with AC and WiFi in charming Chester
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Discover this 5-bedroom gem in Chester. This charming chalet offers a serene and lovely retreat for guests. With a mix o ...
From $478 per night (USD)Expedia
From $499 per night (USD)VRBO
FOUR SEASON HOME NEAR OKEMO
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy our lovely 3 BR home in the idyllic town of Chester. A great getaway for any of the Four Seasons. 15 minutes to Ok ...
From $499 per night (USD)VRBO
From $343 per night (USD)Expedia
Thistle House Glamping Retreat w/ Hot Tub + Sauna
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Welcome to Thistle House, a custom-built cedar tiny house surrounded by seven acres of natural landscape in be ...
From $343 per night (USD)Expedia
From $343 per night (USD)VRBO
Sage House Glamping Retreat with Hot Tub + Sauna
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Welcome to Sage House, a custom-built cedar tiny house surrounded by seven acres of natural landscape in beaut ...
From $343 per night (USD)VRBO
From $204 per night (USD)VRBO
Quaint Queen room at the Chester Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a private room & bathroom with tub in the historic Chester Inn, circa 1780. This charming property is conveniently ...
From $204 per night (USD)VRBO
From $317 per night (USD)VRBO
Hike, Ski, Unwind: Rustic Cabin w/ Deck - Chester!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
3BR/1BA Rustic Vermont Cabin | Mountain Views & Ski Access | Chester, VT | Sleeps 6 Step back from the everyday in this ...
From $317 per night (USD)VRBO
From $507 per night (USD)Expedia
Modern Cabin | Near Okemo & Chester
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Escape to this beautifully renovated three-bedroom cabin set on three private acres in Vermont's Okemo Valley. ...
From $507 per night (USD)Expedia
From $412 per night (USD)VRBO
Historic Vermont farmhouse in 100+ acres, balcony, sunroom, office, window a/c
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your charming retreat in Chester, Vermont! This 200-year old historic 2-story farmhouse in its own 170-acre v ...
From $412 per night (USD)VRBO
From $478 per night (USD)VRBO
Mountain Views Huge Deck, 20 min to Okemo Base
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Relax with the whole family at this peaceful place to stay. Recently finished renovation of this beautiful vacation hou ...
From $478 per night (USD)VRBO
From $258 per night (USD)VRBO
Cozy 1-bedroom studio in Historic Stone Village of Chester
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the beauty of Chester from this pleasant 1-bedroom studio. Guests will find a cozy queen bed and a clean bathro ...
From $258 per night (USD)VRBO
From $380 per night (USD)Expedia
Gorgeous Cedar Tiny House for a Unique Pet-Friendly Getaway in Chester, Vermont
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our custom-built cedar tiny home surrounded by seven acres of natural landscape in beautiful southern Vermont ...
From $380 per night (USD)Expedia