Essex Holiday Houses | Expedia.co.nz

Essex Holiday Homes
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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.

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Our top choices for Essex holiday homes

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

A bathroom with a white vanity, a mirror with lights, a toilet, and a window.

A living room with a brown leather sofa, a flat-screen TV mounted on the wall, a dining table with chairs, and a patterned rug.

A modern kitchen with white cabinetry, a wooden dining table, and a built-in TV.

1. The Essex of Gloucester

The Essex of Gloucester

Gloucester

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 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"

Katie B.

The price is NZ$426

NZ$426

includes taxes & fees

14 Sept - 15 Sept

The Essex of Gloucester

A staircase with wooden steps leading to a room with a wooden ceiling.

A cozy attic bedroom with wooden walls, a sloped ceiling, and a skylight. There are three beds arranged in a U-shape, a small table, and a bench.

A modern living room with a blue sofa, a coffee table, and a TV displaying 'Fast & Furious 8'. A kitchen with wooden cabinets and a dining area is visible in the background.

A white door with a glass panel, a wooden staircase, and a television on a wooden stand.

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

Oceanside Village Home~Private Fenced Yard~Reserved Parking

Gloucester

9.6 out of 10, Exceptional, (14 reviews)

9.6/10

Exceptional

(14 reviews)

"The home was warm and inviting upon our arrival. We loved the home. Rachel responds immediately with any questions. Cape Ann is beautiful and convenient to Boston. We loved our visit and felt at home! "

Melenia s.

The price is NZ$686

NZ$686

includes taxes & fees

27 Aug - 28 Aug

Oceanside Village Home~Private Fenced Yard~Reserved Parking

A living room with a sectional sofa, a wooden coffee table, and a ceiling fan.

A bedroom with a bed, a ceiling fan, a window with curtains, a door, and a small shelf with a plant.

A two-story house with a front porch, a small staircase leading to the entrance, and a mailbox.

A backyard with a barbecue grill, outdoor seating, and a garden with white flowers.

3. Cozy two bedroom house in the heart of Gloucester

Cozy two bedroom house in the heart of Gloucester

Gloucester

9.4 out of 10, Exceptional, (18 reviews)

9.4/10

Exceptional

(18 reviews)

"For our one night stay it was perfect, Clean and comfortable, plenty of basic's, bedding, towels and kitchen supply's."

CHARLES

The price is NZ$684

NZ$684

includes taxes & fees

21 Sept - 22 Sept

Cozy two bedroom house in the heart of Gloucester

A marina with boats docked at the pier, reflecting the sunset sky.

A garden with a wooden gate, neatly trimmed hedges, and a house in the background.

A living room with a peach-colored armchair, a matching ottoman, a beige sofa, and a patterned throw pillow.

A residential area with a well-maintained garden, a metal arch structure, and houses with visible chimneys.

4. Cripple Cove Apartment in historic home across from harbour in Gloucester, MA

Cripple Cove Apartment in historic home across from harbour in Gloucester, MA

East Gloucester

9.6 out of 10, Exceptional, (37 reviews)

9.6/10

Exceptional

(37 reviews)

"Linda was so kind and what a fun little home she opened up to us! "

Hillary M.

The price is NZ$738

NZ$738

includes taxes & fees

2 Sept - 3 Sept

Cripple Cove Apartment in historic home across from harbour in Gloucester, MA

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

A bedroom with a wooden bed, a nightstand, a radiator, and a window with blinds.

A cozy living room with a piano, a sofa, and a coffee table.

A spacious living room with a fireplace, a sofa with patterned cushions, a bookshelf, and a large window with curtains.

5. 2BR Historic Marblehead Home+Minutes to Beach

2BR Historic Marblehead Home+Minutes to Beach

Marblehead Historic District

10.0 out of 10, Exceptional, (25 reviews)

10/10

Exceptional

(25 reviews)

"Enjoyed our stay. "

Mary D.

The price is NZ$734

NZ$734

includes taxes & fees

9 Sept - 10 Sept

2BR Historic Marblehead Home+Minutes to Beach

A spacious living room with a large window, a sofa, a coffee table, a chair, and a TV mounted on the wall.

A patio with a round glass table and four chairs, an umbrella, and a wooden deck.

A kitchen with wooden cabinets, a black countertop, and a view of a marina through large windows.

A bright, white room with a wooden floor, a bed, a desk, two chairs, a dresser, and large windows with a view of the outside.

6. 3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

East Gloucester

9.8 out of 10, Exceptional, (49 reviews)

9.8/10

Exceptional

(49 reviews)

"Beautiful home in a beautiful location!"

Paul H.

The price is NZ$992

NZ$992

includes taxes & fees

22 Sept - 23 Sept

3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

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

A coastal house with a balcony overlooking a road and the sea.

A bedroom with a bed, a ceiling fan, a nightstand, a dresser, and a mirror.

A living room with a sofa set, armchairs, a coffee table, and a fireplace.

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

Classic Coastal Family Home | Walk to Sea;King Bed

Gloucester

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Property was excellent, beautifully decorated with good taste, location was beautiful, everyone enjoyed the weekend stay. Rooms were clean, beds were comfortable."

Maarij K.

The price is NZ$1,714

NZ$1,714

includes taxes & fees

24 Aug - 25 Aug

Classic Coastal Family Home | Walk to Sea;King Bed

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

A dining area with a wooden table and chairs, a hanging light fixture, and a view of the kitchen through a doorway.

A living room with a blue sofa, patterned armchairs, a white coffee table, and large windows with white blinds.

A bedroom with a bed, a nightstand, a window, and a door leading to a bathroom.

8. 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, (17 reviews)

10/10

Exceptional

(17 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."

Betty

The price is NZ$1,337

NZ$1,337

includes taxes & fees

3 Sept - 4 Sept

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

A cozy living room with a fireplace, wooden beams, and comfortable seating.

A hallway with wooden flooring, a blue-framed door, and a wooden chair.

A cozy living room with two sofas, a coffee table, and a TV.

A spacious living room with a wooden coffee table, two sofas, and a patterned rug.

9. Historic 1686 Home Near Downtown l 5BR Retreat

Historic 1686 Home Near Downtown l 5BR Retreat

Beverly

9.6 out of 10, Exceptional, (16 reviews)

9.6/10

Exceptional

(16 reviews)

"Everything was lovely. The home was wonderful and communication with our host was top notch. Thank you so much!"

Terry F.

The price is NZ$1,197

NZ$1,197

includes taxes & fees

24 Aug - 25 Aug

Historic 1686 Home Near Downtown l 5BR Retreat

A room with a large window overlooking a wooden deck with white railings and a lighthouse in the distance.

A room with a desk and chair, large windows with a view of the beach and ocean, and a potted plant on the desk.

A covered porch with wooden flooring, a bench, two chairs, and a small table with a plant.

A room with large windows offering a view of a harbor with boats and a beach.

10. The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

Marblehead

9.8 out of 10, Exceptional, (21 reviews)

9.8/10

Exceptional

(21 reviews)

"Perfect location on Marblehead Neck with stunning views of the harbor. The house was just right for a family of 5 adults. We would come back and would recommend this lovely house to anyone. "

Debbie B.

The price is NZ$1,033

NZ$1,033

includes taxes & fees

1 Sept - 2 Sept

The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

A spacious living area with a large TV, a kitchen, and a dining area.

A modern living room with a TV, teal cabinet, dining area, and large windows.

A two-story house with a front yard, a pathway leading to the entrance, and a small patio area with a table and chairs.

A dining area with a wooden table and chairs, a map on the wall, a lamp, and a view of greenery through a glass door.

11. Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

Rockport

9.8 out of 10, Exceptional, (19 reviews)

9.8/10

Exceptional

(19 reviews)

"Absolutely loved this home!!! We didn’t want to leave and tried for another night , but unfortunately wasn’t able to stay because it was booked with someone else already! The location was close to down town and everyone here was as absolutely welcoming! Would love to stay again!"

Angela G.

The price is NZ$856

NZ$856

includes taxes & fees

27 Aug - 28 Aug

Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

A coastal town with a marina filled with boats, surrounded by residential buildings and a large green area.

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

A modern kitchen with white cabinetry, granite countertops, and stainless steel appliances.

A bedroom with a bed, a TV on a stand, a nightstand with a lamp, and large windows with shutters.

12. Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Rockport

10.0 out of 10, Exceptional, (44 reviews)

10/10

Exceptional

(44 reviews)

"Great stay. Will stay again for sure!"

Maryanne H.

The price is NZ$874

NZ$874

includes taxes & fees

17 Sept - 18 Sept

Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

A beach with a wooden fence, sand, and the ocean.

A covered porch with a round table and chairs, a window, and a view of a building outside.

A living room with a sofa, a coffee table, a TV, and a kitchen in the background.

A room with a dark blue sofa, a white coffee table, a patterned rug, a bed with white bedding, and a small table with a lamp.

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

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

Salisbury Beach

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Clean, quiet & quaint! Perfect for a couple’s get away!"

Shannon S.

The price is NZ$709

NZ$709

includes taxes & fees

31 Aug - 1 Sept

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

A dark-colored, two-story house with a symmetrical design, featuring a central door flanked by two windows, and a small porch area with decorative elements.

A living room with a sofa, armchair, coffee table, and a rug. There is a desk with a lamp and a chair.

A compact kitchen with wooden cabinets, a microwave, and a small dining area with two black chairs.

A small, compact room with a white desk and two black chairs. There are three framed pictures on the wall, and a white door is visible.

14. Cozy Salem Getaway. Historic Home Near All the Sights

Cozy Salem Getaway. Historic Home Near All the Sights

Salem

9.6 out of 10, Exceptional, (61 reviews)

9.6/10

Exceptional

(61 reviews)

"Beautiful 2 bedroom, close to everything , host was wonderful, we will be back. "

Charlene

The price is NZ$786

NZ$786

includes taxes & fees

24 Aug - 25 Aug

Cozy Salem Getaway. Historic Home Near All the Sights

A wooden deck with a table and chairs, overlooking a body of water and a distant building.

A house with a balcony overlooking a body of water, a lawn, and a small deck with chairs.

A spacious living area with a dining table, chairs, a sofa, and a staircase with a railing.

A spacious living area with a staircase, a bookshelf, and a view of the outdoors.

15. Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!

Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!

Gloucester

10.0 out of 10, Exceptional, (15 reviews)

10/10

Exceptional

(15 reviews)

"Wonderful views, great location, easy access to all of Cape Ann."

Stacey W.

The price is NZ$1,413

NZ$1,413

includes taxes & fees

24 Aug - 25 Aug

Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!

A modern kitchen with white cabinetry, a central island with bar stools, and a window with a view of the outside.

A modern living room with a fireplace, a large TV, and a framed picture of a beach.

A modern loft apartment with a high ceiling, a large window, a beige sofa, a white coffee table, and a flat-screen TV mounted on the wall.

A white outdoor seating area with a white fence, covered with a blue and white patterned fabric.

16. Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!

Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!

Marblehead

10.0 out of 10, Exceptional, (31 reviews)

10/10

Exceptional

(31 reviews)

"great place and location"

Kacey C.

The price is NZ$775

NZ$775

includes taxes & fees

21 Sept - 22 Sept

Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!

A modern kitchen with white cabinets, stainless steel appliances, and a teal backsplash.

A modern living space with a dining area, kitchen, and seating area.

A beige sofa with decorative pillows, a woven round table, and a bottle of wine.

A wooden deck with a metal fence, a showerhead, and a water spigot attached to a white house siding.

17. Ospreys Landing: a Charming Plum Island Cottage close to Historic Newburyport

Ospreys Landing: a Charming Plum Island Cottage close to Historic Newburyport

Newburyport

The price is NZ$1,202

NZ$1,202

includes taxes & fees

1 Sept - 2 Sept

Ospreys Landing: a Charming Plum Island Cottage close to Historic Newburyport

A hammock in a room with large windows, a wooden ceiling, and a view of the city.

A spacious living room with a high ceiling, wooden beams, a large window, a hammock, and a television.

A spacious living area with a wooden staircase, a flat-screen TV, a leather sofa, and a glass coffee table.

A deck with a fire pit, wooden chairs, and string lights.

18. The widow’s walk your very own spa experience

The widow’s walk your very own spa experience

Marblehead

9.4 out of 10, Exceptional, (21 reviews)

9.4/10

Exceptional

(21 reviews)

"Great! Lots of activities on property. House is beautiful! You can access the wrap around deck around the widows walk"

Lucy Danielle R.

The price is NZ$1,202

NZ$1,202

includes taxes & fees

1 Sept - 2 Sept

The widow’s walk your very own spa experience

A wooden deck with wicker furniture and a white chair, overlooking a beach with a rocky shoreline and a clear blue sky.

A modern living room with a white console table holding decorative bowls and a grey armchair.

A wooden table with a grey planter containing green succulents.

A coastal residential area with houses near the beach, a rocky outcrop, and a lighthouse in the distance.

19. Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

Rockport

10.0 out of 10, Exceptional, (38 reviews)

10/10

Exceptional

(38 reviews)

"Great location and the host is very responsive. "

Heather P.

The price is NZ$1,252

NZ$1,252

includes taxes & fees

9 Sept - 10 Sept

Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

A spacious living room with a high ceiling, wooden beams, a sofa, a blue armchair, a coffee table, and a dining area with a table and chairs.

A covered patio with a wooden table and chairs, surrounded by a white railing.

A white house with a green door, black shutters, and two potted plants on the front steps.

A harbor with boats docked, a red building, and a stone wall.

20. Historic Renovation, Walk to Front Beach and Shopping

Historic Renovation, Walk to Front Beach and Shopping

Rockport

9.8 out of 10, Exceptional, (9 reviews)

9.8/10

Exceptional

(9 reviews)

"This house worked well for our family with seven people of all ages and really enjoyed our first trip to the Rockport/Gloucester area. Hopefully we'll get a chance to return and would highly recommend the area and property."

Dan K.

The price is NZ$1,125

NZ$1,125

includes taxes & fees

21 Sept - 22 Sept

Historic Renovation, Walk to Front Beach and Shopping

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

Hampton Inn Boston - Logan Airport

8/10 Good

"Had to call twice late at night for airport shuttle, but room was clean, well stocked, and quiet. Eggs at breakfast buffet seemed to be made from plastic, but very convenient to have breakfast included"

Letitia 1-night trip

Posted 4 hours ago

Hampton Inn Boston - Logan Airport

Hawthorne Hotel

8/10 Good

"Nice historic hotel. Close to the fun."

teresa 1-night trip

Posted 7 hours ago

Hawthorne Hotel

SpringHill Suites by Marriott Boston Peabody

8/10 Good

"SpringHill Suites is a convenient, reliable place to stay in Peabody. Not a lot of frills, but reasonably priced and in a central location."

Lauren M 1-night trip

Posted 8 hours ago

SpringHill Suites by Marriott Boston Peabody

Sonesta Select Boston Danvers

10/10 Excellent

"Our stay was very comfortable. The staff were very helpful and friendly making our stay even better! An added bonus was how close we were to restaurants, shopping, Salem, and The Cabot in Beverly."

Marcella 2-night trip

Posted 10 hours ago

Sonesta Select Boston Danvers

Holiday Inn Express Boston - Saugus by IHG

8/10 Good

"Great room. A little road noise but great room!"

Andre 1-night trip

Posted 10 hours ago

Holiday Inn Express Boston - Saugus by IHG

Comfort Inn & Suites Logan International Airport

10/10 Excellent

"Everything was great during my stay"

Peter 1-night trip

Posted 12 hours ago

Comfort Inn & Suites Logan International Airport

TownePlace Suites Boston Logan Airport/Chelsea

10/10 Excellent

"Perfect location free shuttle to airport"

Juaquin 1-night trip

Posted 13 hours ago

TownePlace Suites Boston Logan Airport/Chelsea

Find out more about Essex

Essex Holiday Homes information

Number of reviews	352
Accommodation	598 Holiday Homes
Lowest Price	NZ$426
Highest Price	NZ$1,714

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Book Holiday Homes in Essex on Expedia.com

Holiday Homes in Essex

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Essex holiday homes

1. The Essex of Gloucester

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

3. Cozy two bedroom house in the heart of Gloucester

4. Cripple Cove Apartment in historic home across from harbour in Gloucester, MA

5. 2BR Historic Marblehead Home+Minutes to Beach

6. 3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

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

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

9. Historic 1686 Home Near Downtown l 5BR Retreat

10. The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

11. Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

12. Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

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

14. Cozy Salem Getaway. Historic Home Near All the Sights

15. Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!

16. Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!

17. Ospreys Landing: a Charming Plum Island Cottage close to Historic Newburyport

18. The widow’s walk your very own spa experience

19. Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

20. Historic Renovation, Walk to Front Beach and Shopping

Find holiday rentals that suit your style

Top Essex Hotel Reviews

Hampton Inn Boston - Logan Airport

Find out more about Essex

Essex Holiday Homes information

Explore a world of travel with Expedia