Vacation Rentals in Essex, MA: Compare 10+ Sites & Save

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168 Best Vacation Rentals in Essex (Starting from $222)

Great Marsh House
Great Marsh House
House
Essex, MA, USA
0.9k from Essex center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
9.2

Superb

5 reviews

$586
Average price / night
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Relaxing Rivers Edge Main Street Retreat
Relaxing Rivers Edge Main Street Retreat
Apartment
Essex, MA, 01929, United States
0.1k from Essex center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
10.0

Exceptional

29 reviews

$352
Average price / night
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Robbins Island Retreat
Robbins Island Retreat
House
Essex, MA, USA
3.1k from Essex center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

2 Bedrooms4 Guests
New to Booking
$339
Average price / night
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Winter deal!  Charming 3-bedroom house on one floor in Essex
Winter deal! Charming 3-bedroom house on one floor in Essex
House
Essex, MA, 01929, United States
0.3k from Essex center

AC, Dryer, Free Parking, Heater, Internet, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$560
Average price / night
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Airstream and Ocean View Unique Gloucester Getaway
Airstream and Ocean View Unique Gloucester Getaway
House
Gloucester, MA, USA
4.6k from Essex center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Glamping

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$287
Average price / night
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Winter deal! Delightful 3-4 bed one floor, 3 baths, fireplace
Winter deal! Delightful 3-4 bed one floor, 3 baths, fireplace
House
Essex, MA, 01929, United States
0.4k from Essex center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

4 Bedrooms10 Guests
9.8

Exceptional

6 reviews

$560
Average price / night
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Ipswich Cottage Beautiful Views, 5 Mins to Beach
Ipswich Cottage Beautiful Views, 5 Mins to Beach
House
Ipswich, MA, USA
5.0k from Essex center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings, Vacation rentals

4 Bedrooms5 Guests
6.0

Review score

1 reviews

$329
Average price / night
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❤️ of Cape Ann, -  Historic Antique Colonial yet new & modern Close 2 Everything
❤️ of Cape Ann, - Historic Antique Colonial yet new & modern Close 2 Everything
House
Essex, MA, 01929, United States
0.7k from Essex center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

4 Bedrooms8 Guests
9.6

Exceptional

27 reviews

$424
Average price / night
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2 Mi to Crane Beach Waterfront Ipswich Escape!
2 Mi to Crane Beach Waterfront Ipswich Escape!
House
Ipswich, MA, USA
5.2k from Essex center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
9.5

Superb

2 reviews

$282
Average price / night
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NEW - 2 bed / 2 bath+large Deck in the center of beautiful Essex, MA
NEW - 2 bed / 2 bath+large Deck in the center of beautiful Essex, MA
House
Essex, MA, 01929, United States
0.9k from Essex center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

2 Bedrooms5 Guests
10.0

Exceptional

3 reviews

$404
Average price / night
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1 Mi to Beach Manchester-by-the-Sea Retreat!
1 Mi to Beach Manchester-by-the-Sea Retreat!
House
Manchester, MA, USA
6.0k from Essex center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$697
Average price / night
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Renovated Home with Private Pool
Renovated Home with Private Pool
House
Essex, MA, 01929, United States
1.6k from Essex center

AC, Arcade, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

5 Bedrooms10 Guests
10.0

Exceptional

6 reviews

$1720
Average price / night
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Little River Retreat
Little River Retreat
House
Gloucester, MA, USA
6.4k from Essex center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms4 Guests
6.0

Review score

1 reviews

$342
Average price / night
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Modern Cottage, Private Island, Unparalleled beauty
Modern Cottage, Private Island, Unparalleled beauty
Cottage
Essex, MA, 01929, United States
2.4k from Essex center

AC, Heater, Internet, No Smoking

1 Bedroom4 Guests
9.6

Exceptional

4 reviews

$530
Average price / night
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Elegant Gloucester Beach Getaway with Ocean Views!
Elegant Gloucester Beach Getaway with Ocean Views!
House
Gloucester, MA, USA
7.3k from Essex center

Cheap, Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$589
Average price / night
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Coastal Cottage on Private Island, overlooking the Essex Great Marsh
Coastal Cottage on Private Island, overlooking the Essex Great Marsh
Cottage
Essex, MA, 01929, United States
2.6k from Essex center

AC, Barbecue, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Microwave

2 Bedrooms5 Guests
10.0

Exceptional

10 reviews

$530
Average price / night
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Black Cove Cottage
Black Cove Cottage
House
Manchester, MA, USA
7.4k from Essex center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay, Beach rentals

2 Bedrooms5 Guests
5.0

Review score

1 reviews

$495
Average price / night
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The Essex of Gloucester
The Essex of Gloucester
House
Gloucester, MA, 01930, United States
2.8k from Essex center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

2 Bedrooms4 Guests
10.0

Exceptional

5 reviews

$222
Average price / night
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Garden Cottage By The Sea
Garden Cottage By The Sea
House
Manchester, MA, USA
7.4k from Essex center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay

2 Bedrooms5 Guests
7.0

Good

2 reviews

$517
Average price / night
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WINTER 2025 PROMO -Lakefront 2 Bed / 3 bath + Extra Bed off of living room
WINTER 2025 PROMO -Lakefront 2 Bed / 3 bath + Extra Bed off of living room
Cottage
Essex, MA, 01929, United States
3.1k from Essex center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

25 reviews

$549
Average price / night
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Gloucester Home with Large Yard 1 Mi to Beach!
Gloucester Home with Large Yard 1 Mi to Beach!
House
Gloucester, MA, USA
7.6k from Essex center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$474
Average price / night
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First Period Colonial Lodging in Gloucester MA
First Period Colonial Lodging in Gloucester MA
House
Gloucester, MA, 01930, United States
3.3k from Essex center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
10.0

Exceptional

17 reviews

$595
Average price / night
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The Barn at Asa Stone Farm
The Barn at Asa Stone Farm
House
Ipswich, MA, 01938, United States
4.2k from Essex center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

13 reviews

$1115
Average price / night
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Airstream & Ocean View: Unique Gloucester Getaway
Airstream & Ocean View: Unique Gloucester Getaway
House
Gloucester, MA, 01930, United States
4.6k from Essex center

AC, Barbecue, Crib, Fireplace, Free Parking, Heater, Kitchen, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

10 reviews

$382
Average price / night
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Elegant farmhouse in Ipswich near Crane Beach and Estate
Elegant farmhouse in Ipswich near Crane Beach and Estate
House
Ipswich, MA, 01938, United States
4.6k from Essex center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

5 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$2325
Average price / night
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Charming 5-bedroom Home by the Sea
Charming 5-bedroom Home by the Sea
House
Manchester-by-the-Sea, MA, 01944, United States
4.7k from Essex center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

5 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1005
Average price / night
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1 Mile from Cranes Beach
1 Mile from Cranes Beach
Apartment
Ipswich, MA, 01938, United States
4.8k from Essex center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
10.0

Exceptional

41 reviews

$334
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Essex.

Essex Vacation Rentals on the Map

Frequently Asked Questions

You can explore 168 verified vacation rentals in Essex. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Essex vary depending on the season, property size, and location. Rates typically start from around $222 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Essex include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Essex welcome pets. Currently, 26 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Essex often include amenities such as Fireplace/Heating, Child Friendly, and View. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.