A rustic wooden barn, a calm river, and autumn-colored trees.

Essex Vacation Rentals

Dates

November 2026

December 2026

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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

Gloucester

Katie B.

SAR 935 total

includes taxes & fees

1 Dec - 2 Dec

A covered outdoor deck with a grill, a table with chairs, and an umbrella.

2. 2b apt loft Downtown Ipswich

Ipswich

Helen M.

SAR 824 total

includes taxes & fees

11 Nov - 12 Nov

A modern kitchen with stainless steel appliances, light grey cabinets, and a tiled backsplash.

3. Riverview charming apt near beach

Ipswich

DAVID A.

SAR 918 total

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with stainless steel appliances, white cabinets, and a large window.

4. NEWLY RENOVATED STUDIO CLOSE TO DOWNTOWN IPSWICH

Ipswich

Dawne

SAR 852 total

includes taxes & fees

16 Nov - 17 Nov

A lakeside patio with Adirondack chairs and a small table, surrounded by lush greenery and a view of the lake.

5. Spacious Lakefront Escape w/ 3 Baths + Bonus Bed

Essex

Veronica B.

SAR 1,655 total

includes taxes & fees

16 Nov - 17 Nov

A neatly made bed with a grey headboard, a bedside lamp, and a blue and white patterned rug.

6. Re-listed: Adorable Condo Beverly - Salem - Halloween

Beverly

Christine L.

SAR 968 total

includes taxes & fees

30 Nov - 1 Dec

A harbor with boats docked, a pier, and houses along the shore.

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

Rockport

Heidi K.

SAR 927 total

includes taxes & fees

16 Nov - 17 Nov

A wooden staircase with a railing leading to a covered deck area.

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

Gloucester

Betty

SAR 2,364 total

includes taxes & fees

12 Nov - 13 Nov

A modern living room with a brown sofa, a dining table set with plates and glasses, and a blue accent wall with a geometric pattern.

9. Fresh Design-Walk to Salem-Food-Train Station

Beverly

Christine L.

SAR 961 total

includes taxes & fees

16 Nov - 17 Nov

A harbor with numerous boats and a prominent building with a clock tower in the background.

10. ♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

Marblehead Historic District

Arianna

SAR 1,059 total

includes taxes & fees

30 Nov - 1 Dec

A living room with a flat-screen TV, wooden flooring, a black sofa, a glass coffee table, and a window with blinds.

11. Central Salem Retreat 2bd W/ parking

Salem

Valerie

A coastal town with houses along the shoreline, a beach, and a rocky outcrop.

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

Rockport

Leanna S.

SAR 1,142 total

includes taxes & fees

11 Nov - 12 Nov

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.

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

Beverly

Corey W.

SAR 1,005 total

includes taxes & fees

11 Nov - 12 Nov

A two-story house with a wrap-around porch, a curved driveway, and a view of a large body of water.

14. Classic Coastal Family Home | Walk to Sea;King Bed

Gloucester

Maarij K.

SAR 3,287 total

includes taxes & fees

11 Nov - 12 Nov

A marina with boats docked, a clear sky, and a street with parked cars.

15. Harborside Oasis ★ Harbor View ★ Heart of Downtown

Rockport

Wesley G.

SAR 955 total

includes taxes & fees

11 Nov - 12 Nov

12 foot long couch for two people to stretch out on.

16. Apartment with private rooftop deck with ocean views

Rockport

Eli T.

SAR 1,027 total

includes taxes & fees

1 Dec - 2 Dec

A cozy living room with wooden walls, a large flat-screen TV, a grey sofa, and a coffee table with a vase of flowers.

17. Salem Haunted Happenings Retreat

Salem

Miranda

A modern kitchen with a large island, white cabinets, and a view of a garden through a sliding glass door.

18. Historic Marblehead Nautical Home • Minutes to Salem

Marblehead Historic District

Kevin H.

SAR 1,755 total

includes taxes & fees

7 Dec - 8 Dec

An aerial view of a coastal town with a marina filled with boats, surrounded by residential buildings and a clear blue sky.

19. The Bookstore · King Beds · Walk to Beach · Private Parking

Rockport

Dave

SAR 1,516 total

includes taxes & fees

1 Dec - 2 Dec

A coastal-themed storefront with a wooden sign, a chalkboard sign, and a white picket fence.

20. Fall Asleep to Waves — Steps to Shops & Dining

Rockport

Dominique

SAR 1,430 total

includes taxes & fees

11 Nov - 12 Nov

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Find vacation rentals that suit your style

Top Essex Hotel Reviews

Two individuals in white robes by a window overlooking a body of water with a distant shoreline.

Beauport Hotel Gloucester

Downtown Gloucester

10/10 Excellent

Kim

A coastal scene with a sandy beach, rocky outcrops, and a lighthouse in the distance.

The Wylie Inn and Conference Center at Endicott College

Beverly

10/10 Excellent

The room was clean and comfortable. The staff friendly and helpful. There were two things I really liked. The first was that there is a quiet time between 11:00 pm and 7:00 am. We've all stayed in hotels where there is a loud party going on in the room next door. The second was the ability to cast from your personal device to the TV, so you have access to every streaming service you pay for.. a very nice feature. I would definitely stay again.

Nicole

A bar area with wooden ceiling beams, hanging pendant lights, and a bar stocked with various bottles. There are six wooden bar stools with cushioned seats.

Briar Barn Inn

Rowley

10/10 Excellent

Great staff, beautiful aesthetic and charming. We happened upon the Briar Barn looking for a quaint place to sleep for the night. This place was beyond our expectations and we are already planning another visit, with friends, to stay and see the sights of the area. We are New Yorkers and were so impressed by they service, the cleanliness, the vibe, the amenities and the space. We will come back and recommend to others.

Anonymous traveler

A coastal beach scene with a large house on a rocky outcrop, a sandy beach with people, and a clear blue sky.

The Vista

East Gloucester

10/10 Excellent

I wasn't expecting much when I booked with Vista, but as soon as I got there I was impressed. The staff was friendly and made you feel welcome and took the time to explain everything you needed to know while staying there. Our room was a little dated, but it was spacious, and very clean! I love to travel and I have to say it was one of the cleanest places I've stayed at. When I booked I was concerned about the view I would be getting based off of others reviews...but I was pleasantly surprised...

morgan

A poolside area with outdoor seating, a fire pit, and a building with multiple balconies and outdoor lighting.

Ocean House Hotel at Bass Rocks

East Gloucester

10/10 Excellent

Norwich

A residential house with a stone pathway leading to the front door, surrounded by lush greenery and flowering plants.

Addison Choate Inn

Rockport

10/10 Excellent

Craig

The Cabot Lodge

Beverly

10/10 Excellent

Bruce

An outdoor seating area with wicker furniture and blue cushions, featuring a fire table and umbrellas.

Salem Waterfront Hotel & Suites

Salem

10/10 Excellent

Myra

A hotel with outdoor seating, fire pits, and a well-lit facade.

The Cove At Salem

Salem

10/10 Excellent

Emily

A wooden deck with outdoor seating, overlooking a body of water and a rocky shoreline.

Bearskin Neck Motor Lodge

Rockport

10/10 Excellent

Mary Beth

A covered porch with stone walls, wicker furniture, and a view of a house in the background.

Castle Manor Inn

Gloucester

10/10 Excellent

My husband and I recently stayed here and had a fantastic time. The property is beautiful and the Inn is so inviting! We have never stayed in this type of Inn before and we were pleasantly surprised how comfortable and relaxed we felt in a home-like setting such as this. The room was great and we had a gorgeous view of trees, a pond, and the incredible skyline of Massachusetts. We are used to pretty sunsets and sunrises in Southern California, but we do not have the fall trees that make these...

Shelby

A restaurant with large windows overlooking a marina.

The Hotel at Cape Ann Marina

Gloucester

10/10 Excellent

Shelley

A coastal building with a garden and a rocky shoreline.

The Yankee Clipper Inn

Rockport

10/10 Excellent

We booked this adorable B&B because of its great reviews. We had never visited the coast of mass before and were not disappointed. The staff went above and beyond to take care of us. Mike moved us to a beautiful room after having some issues with a toilet in our room. They made reservations for us when looking for a nice ocean front restaurant. The Inn is equipped with all you need and the cooked to serve breakfast was outstanding. We walked around the property and enjoyed views from every...

kerry

A brick building with a central entrance, a brick pathway leading to the entrance, and a lawn with scattered leaves.

The Merchant

Downtown Salem

10/10 Excellent

Amy

A yellow building with a black door, white columns, and a brick pathway leading to the entrance.

The Salem Inn

Salem

10/10 Excellent

This was our second stay here and we always enjoy ourselves! Breakfast made to order in the morning and easy ordering online the night before. Plenty of options for dinner around the area as well as shopping and attractions. The beds are super soft and cozy and the windows bring in lots of natural light. If you are going to come here, stay in a jacuzzi suite! The jetted tub is beyond relaxing and some of those rooms have fireplaces as well. I would definitely come back and stay again!

Lauren

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.

Essex Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Essex vacation rentals

1. The Essex of Gloucester

2. 2b apt loft Downtown Ipswich

3. Riverview charming apt near beach

4. NEWLY RENOVATED STUDIO CLOSE TO DOWNTOWN IPSWICH

5. Spacious Lakefront Escape w/ 3 Baths + Bonus Bed

6. Re-listed: Adorable Condo Beverly - Salem - Halloween

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

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

9. Fresh Design-Walk to Salem-Food-Train Station

10. ♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

11. Central Salem Retreat 2bd W/ parking

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

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

14. Classic Coastal Family Home | Walk to Sea;King Bed

15. Harborside Oasis ★ Harbor View ★ Heart of Downtown

16. Apartment with private rooftop deck with ocean views

17. Salem Haunted Happenings Retreat

18. Historic Marblehead Nautical Home • Minutes to Salem

19. The Bookstore · King Beds · Walk to Beach · Private Parking

20. Fall Asleep to Waves — Steps to Shops & Dining

Find vacation rentals that suit your style

Top Essex Hotel Reviews

Beauport Hotel Gloucester

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Essex?

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

How many vacation rentals will I find in Essex?

What can I see and do in Essex?

What are vacation rentals like in Essex?