Chicago\92s Best Vacation Rentals - Vacation Rentals in Essex County

NORTHEAST KINGDOM AT NEALPOND VT From US $301
         

10.0 (46 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Secluded 2BR Cabin w Hot Tub, Pond, Trails, WiFi From US $514
         

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10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Explore the Northeast Kingdom! Home w/Deck From US $516
         

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New
Cottage
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Cozy Mountain View Retreat From US $274
         

10.0 (21 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Vermont cabin on a brook close to White Mountains VAST From US $254
         

Luxury Places to Stay in Essex County

Over 117+ Luxury Places to Stay in or Near Essex County
WOW! Must Read "Reviews" on this 4-5 BR. 2 BA. w/Game Rm Lake Front Home From US $564
         

Island Pond Apartment on VAST Trail – 3BR, 2BA From US $480
         

9.2 (5 Reviews)
Apartment
  • Air Conditioner
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  • TV
Kingdom Trails Retreat | Hot Tub, Sauna & Mt Views From US $444
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Essex County

Over 1+ Top-Rated Vacation Rentals with a Pool in or Near Essex County

Pet-Friendly Vacation Rentals in Essex County

Over 47+ Pet-Friendly Vacation Rentals in or Near Essex County
Lakeview Farmhouse with Beach Access From US $350
         

New
House
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  • View
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Charming motel with AC and WiFi in enjoyable Canaan From US $130
         

New
House
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  • Pet Friendly
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Cabin at Hidden Falls Farm From US $307
         

9.4 (38 Reviews)
Cabin
  • Parking
  • Pet Friendly
  • TV
Charming 2-bedroom cabin in fabulous Norton From US $272
         

2.0 (1 Review)
Cabin
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Peaceful 2-bedroom apartment with AC in charming Canaan From US $184
         

Large Vacation Homes & Villas in Essex County

Over 13+ Large Vacation Homes & Villas in or Near Essex County
Lakefront Cabin in Vermont on Great Averill Lake in Averill, VT. From US $390
         

9.8 (12 Reviews)
Cabin
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Under Canvas White Mountains From US $316
         

Vermont getaway-your home away from home! From US $343
         

10.0 (34 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Pet-Friendly Canaan Home: Deck, Grill & Yard! From US $300
         

10.0 (4 Reviews)
House
  • Parking
  • Pet Friendly
  • TV
Rustic & Historic Guildhall Farmhouse w/Fire Pit! From US $280
         

Private waterfront, Island Pond 5 bedroom From US $437
         

New
Cabin
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  • Wellness Facilities

Essex County Vacation Rentals and Airbnb Places to Stay Under $200

Over 41+ Essex County Vacation Rentals and Airbnb Places to Stay Under $200
Cozy cottage From US $194
         

9.8 (7 Reviews)
House
  • Parking
  • TV
  • View
South of the Border Room 6 From US $121
         

10.0 (1 Review)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
South of the Border VT Room 8 From US $160
         

8.8 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
South of the Border VT Room 4 From US $160
         

New
Apartment
  • Air Conditioner
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  • Pet Friendly
South of the Border VT Room 9 From US $160
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
South of the Border VT Room 6 From US $160
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Essex County

Over 44+ Instantly Bookable Vacation Homes in or Near Essex County
Peaceful Cottage - Relax, Kayak, Swim From US $381
         

10.0 (2 Reviews)
Cottage
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Mountain View Log Cabin in the White Mountains From US $364
         

10.0 (2 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Northeast Kingdom Post and Beam home on Miles Pond VT From US $334
         

Island Pond Apartment on VAST Trail – 2BR, 1BA From US $315
         

9.8 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Waterfront mid-century modern From US $342
         

9.0 (2 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Security/Safety
Island Pond Apartment on VAST Trail – 1BR, 1BA From US $254
         

6.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV

About Essex County Vacation Rentals

With more than 126 Essex County vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Chicagosbestvacationrentals and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Essex County.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Chicagosbestvacationrentals Essex County, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Essex County. Places to stay near Essex County are 476.63 ft² on average, with prices averaging US $307 a night.

Chicagosbestvacationrentals makes it easy and safe to find and compare vacation rentals in Essex County with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Essex County

Type Count
Vacation Homes 54
Cabin Rentals 26
Holiday Apartments 20
Hotels 12
Cottages 8
Ski Chalet Rentals 2
Others 1

Use these Quick Filters to Find a Vacation Rental in Essex County

Pro Tip: Chicagosbestvacationrentals makes it easy to compare the best listings on Chicagosbestvacationrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Chicagosbestvacationrentals homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Essex County.

Weather in Essex County

View the weather forecast for Essex County before booking your Essex County Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Complexes around Essex County, VT


Essex County Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Essex County?
How many vacation rentals are available in Essex County?

Currently, the total number of properties listed in 2026 is over 126 in the Essex County area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Essex County.