An aerial view of a town with a prominent red brick building, a church with a steeple, and a large white building with a dome.

Essex Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Essex vacation rentals

A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a stainless steel sink.

1. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (14 reviews)
"Very clean and perfect place to stay while we were in a wedding at the Beauport! The host checked in often and made us feel very welcomed and at home"
United States
Katie B.
The price is CA $372
CA $464 total
includes taxes & fees
Oct 27 - Oct 28
The Essex of Gloucester
A covered outdoor deck with a grill, a table with chairs, and an umbrella.

2. 2b apt loft Downtown Ipswich

2b apt loft Downtown Ipswich
Ipswich
9.0 out of 10, Wonderful, (52 reviews)
"Everything was fabulous, but the access via the spiral staircase was a not for someone physically compromised."
United States
Helen M.
The price is CA $219
CA $391 total
includes taxes & fees
Oct 19 - Oct 20
2b apt loft Downtown Ipswich
A modern kitchen with stainless steel appliances, light grey cabinets, and a tiled backsplash.

3. Riverview charming apt near beach

Riverview charming apt near beach
Ipswich
9.6 out of 10, Exceptional, (43 reviews)
"Lovely place- close to town and had amazing views of the river."
United States
Stacia S.
The price is CA $205
CA $417 total
includes taxes & fees
Sep 30 - Oct 1
Riverview charming apt near beach
A staircase with wooden steps leading to a room with a wooden ceiling.

4. Oceanside Village Home~Private Fenced Yard~Reserved Parking

Oceanside Village Home~Private Fenced Yard~Reserved Parking
Gloucester
9.6 out of 10, Exceptional, (15 reviews)
"Sparking clean property. Plenty of main floor gathering space (kitchen/dining/livingroom) with good separation of sleeping quarters, giving the opportunity for privacy and rest. Pretty back yard with Adirondack chairs to enjoy while reading or just resting. Easy drive to the main attractions of Gloucester and/or Rockport. All this and responsive owners too! "
United States
Karen T.
The price is CA $305
CA $749 total
includes taxes & fees
Oct 22 - Oct 23
Oceanside Village Home~Private Fenced Yard~Reserved Parking
A modern kitchen with stainless steel appliances, white cabinets, and a large window.

5. NEWLY RENOVATED STUDIO CLOSE TO DOWNTOWN IPSWICH

NEWLY RENOVATED STUDIO CLOSE TO DOWNTOWN IPSWICH
Ipswich
9.8 out of 10, Exceptional, (31 reviews)
"Nice and clean. Close enough to walk to things in town."
United States
Pastor Chris
The price is CA $205
CA $369 total
includes taxes & fees
Oct 20 - Oct 21
NEWLY RENOVATED STUDIO CLOSE TO DOWNTOWN IPSWICH
A kitchen with wooden cabinets, a central island with bar stools, a built-in bookshelf, and a view through glass doors.

6. Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (57 reviews)
"Nice home with great kitchen and all the amenities."
United States
rick b.
The price is CA $194
CA $518 total
includes taxes & fees
Oct 20 - Oct 21
Beach Life Bliss - steps to the beach
A dining table set with white plates, bowls, and glasses, accompanied by a vase of yellow tulips.

7. Charming apt -2 Bedroom -Close to Beach/Sleeps 6

Charming apt -2 Bedroom -Close to Beach/Sleeps 6
Ipswich
9.4 out of 10, Exceptional, (31 reviews)
"Perfect location!"
United States
Jill H.
The price is CA $205
CA $399 total
includes taxes & fees
Oct 19 - Oct 20
Charming apt -2 Bedroom -Close to Beach/Sleeps 6
A marina with boats docked, a clear sky, and a street with parked cars.

8. Harborside Oasis ★ Harbor View ★ Heart of Downtown

Harborside Oasis ★ Harbor View ★ Heart of Downtown
Rockport
9.8 out of 10, Exceptional, (39 reviews)
"I couldn’t have asked for a better experience or location!! We loved every second we were there"
United States
Nicholas L.
The price is CA $178
CA $414 total
includes taxes & fees
Oct 6 - Oct 7
Harborside Oasis ★ Harbor View ★ Heart of Downtown
A living room with a fireplace, a television mounted on the wall, and a variety of decorative items including plants and a large vase.

9. Charming Retreat

Charming Retreat
East Gloucester
10.0 out of 10, Exceptional, (22 reviews)
"Parking was great...easy access to visiting all of Cape Ann"
United States
Margaret
The price is CA $241
CA $495 total
includes taxes & fees
Oct 6 - Oct 7
Charming Retreat
A harbor with boats docked, a pier, and houses along the shore.

10. Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
Rockport
9.8 out of 10, Exceptional, (43 reviews)
"This is our second year staying at Gigi's place. It's such a great location and value. It offers everything we like during the off season without the crowds and is such a clean and comfortable place to stay."
United States
Victoria P.
The price is CA $163
CA $399 total
includes taxes & fees
Oct 5 - Oct 6
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
A wooden staircase with a railing leading to a covered deck area.

11. 3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
Gloucester
10.0 out of 10, Exceptional, (19 reviews)
"Rachel was very responsive and attentive, excellent host. The house was in a great location, clean, and very comfortable. Would stay there again should the need arise."
United States
Betty
The price is CA $482
CA $1,039 total
includes taxes & fees
Oct 7 - Oct 8
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
A coastal town with houses along the shoreline, a beach, and a rocky outcrop.

12. Downtown Rockport · King Bed w/Parking · Walk to Train

Downtown Rockport · King Bed w/Parking · Walk to Train
Rockport
9.8 out of 10, Exceptional, (42 reviews)
"Easy online hub with videos and guides for any questions, directions etc about the place. Located in a great area to walk to most main locations in Rockport. Host was very responsive."
United States
Ben J.
The price is CA $176
CA $454 total
includes taxes & fees
Oct 28 - Oct 29
Downtown Rockport · King Bed w/Parking · Walk to Train
A beach with houses in the background and people engaging in various activities.

13. Oceanview Kingsize South End Studio NO FINAL CLEANING FEE

Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
Rockport
9.8 out of 10, Exceptional, (222 reviews)
"Excellent above garage large studio in a superb Rockport location central to everything. Hosts were gracious and warm and made the overnight stay a good one. Highly recommend."
United States
Eugene
The price is CA $276
CA $349 total
includes taxes & fees
Oct 15 - Oct 16
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
A beach with a wooden fence, sand, and the ocean.

14. Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows

Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows
Salisbury Beach
9.8 out of 10, Exceptional, (7 reviews)
"I booked a last minute stay for some time at the ocean. The booking/check in process was so easy with very detailed instructions sent the day of my arrival. The place was exactly as pictured, a well-appointed, clean cottage, with everything I needed. The host also left a welcome gift that was thoughtful and useful. I walked the few blocks to the ocean everyday, multiple times a day to walk for hours on the beaches. I got food from a nice little Italian restaurant (Capri) just a block away. The...
United States
Maura
The price is CA $113
CA $537 total
includes taxes & fees
Oct 1 - Oct 2
Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows
A bedroom with a wooden bed, bedside tables, a nightstand, and a door to a hallway.

15. 3B apt Downtown Ipswich

3B apt Downtown Ipswich
Ipswich
10.0 out of 10, Exceptional, (24 reviews)
"Great spot perfect for our family! "
United States
Tabatha D.
The price is CA $229
CA $439 total
includes taxes & fees
Oct 13 - Oct 14
3B apt Downtown Ipswich
A crowded beach with people swimming and sunbathing, tents, and beach chairs.

16. Ocean Breeze / 8-Minute Walk to Beach

Ocean Breeze / 8-Minute Walk to Beach
East Gloucester
10.0 out of 10, Exceptional, (20 reviews)
"Very clean and quaint. There is definitely noise you can hear from upstairs but not in a way that was bothersome. We enjoyed our stay!"
United States
Jessica M.
The price is CA $211
CA $482 total
includes taxes & fees
Oct 15 - Oct 16
Ocean Breeze / 8-Minute Walk to Beach
A kitchen with white cabinets, a dining table with chairs, and a hanging light fixture.

17. The Duval House

The Duval House
Downtown Gloucester
9.4 out of 10, Exceptional, (20 reviews)
"We had a wonderful stay. The house was very nice and the room was very clean. Can’t wait to come back!"
United States
Jennifer H.
The price is CA $299
CA $693 total
includes taxes & fees
Oct 28 - Oct 29
The Duval House
An aerial view of a coastal town with a marina filled with boats, surrounded by residential buildings and a clear blue sky.

18. The Bookstore · Private Parking · King Beds · Downtown Rockport

The Bookstore · Private Parking · King Beds · Downtown Rockport
Rockport
10.0 out of 10, Exceptional, (43 reviews)
"It’s the cutest; has everything you’ll need and only a five minute walk to downtown and on-site parking is a plus! The host is attentive and check-in was a breeze."
United States
Nicki B.
The price is CA $240
CA $594 total
includes taxes & fees
Sep 29 - Sep 30
The Bookstore · Private Parking · King Beds · Downtown Rockport
A modern living room with a sofa, a coffee table, and a TV on a stand. There is a kitchen in the background with a fridge and a microwave.

19. Witchy Hideaway Cottage; Close to Beaches, Salem & Train to Boston

Witchy Hideaway Cottage; Close to Beaches, Salem & Train to Boston
Beverly
10.0 out of 10, Exceptional, (6 reviews)
"Great little spot if you need to stay close to downtown Salem. Would recommend!"
United States
Corey W.
The price is CA $382
CA $662 total
includes taxes & fees
Oct 26 - Oct 27
Witchy Hideaway Cottage; Close to Beaches, Salem & Train to Boston
A spacious room with a high ceiling, a large bed, a green dining area, and a view of the outdoors.

20. 1 Mi to Downtown Salem: Studio w/ Fire Pit Access

1 Mi to Downtown Salem: Studio w/ Fire Pit Access
Salem
9.8 out of 10, Exceptional, (28 reviews)
"This property is a nice place to stay, especially for two people. There is enough space for two people, and the amenities meet the needs of the guests. "
United States
Heather E.
The price is CA $194
CA $588 total
includes taxes & fees
Sep 30 - Oct 1
1 Mi to Downtown Salem: Studio w/ Fire Pit Access
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.
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Top Essex Hotel Reviews

Comfort Inn & Suites Logan International Airport

Comfort Inn & Suites Logan International Airport

10/10 Excellent
"Very comfortable large room. Mexican Restaurant next door was great too!"
Jennifer 1-night trip
Posted 1 hour ago
Comfort Inn & Suites Logan International Airport

Find out more about Essex

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . Seeing all the best attractions is bound to make you fall in love with Essex. Who knows, you may even be tempted to extend your vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Essex?

Yes, we give you a choice of vacation rentals in Essex near Essex Shipbuilding Museum, or you can choose a more remote option if you're looking for a relaxing stay. Visitors to Essex speak positively about the riverfront and restaurants in this destination. Make sure you have time to check out the shopping while you're in the area.

What are some of the best vacation home rentals that Essex has to offer?

Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots: This vacation home rental near Essex offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a hot tub and a selection of books.

How many vacation rentals will I find in Essex?

With 7 Expedia vacation rentals, you're sure to find just the right place for your Essex stay.

What can I see and do in Essex?

Cultural attractions include Essex Shipbuilding Museum and Cogswell's Grant, whereas Essex River and Stavros Reservation are a couple of picturesque spots to enjoy the outdoors. In the larger area, you’ll find Castle Hill on the Crane Estate and Crane Beach.

What are vacation rentals like in Essex?

Vacation rentals are private properties you can book for a few days or a quick weekend in Essex. Vacation rentals provide amenities such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family trip.