Cuttyhunk Holiday Homes from €285: Search Top House Rentals

Cuttyhunk Holiday Homes
Massachusetts
United States of America
Holiday Homes
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A coastal landscape with a sandy beach, grassy areas, and a small island with a lighthouse.

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Our top choices for Cuttyhunk holiday homes

A wooden dining table with a lace tablecloth, surrounded by wooden chairs. A potted plant is on the table.

A single-story house with a front porch, a garage, and a well-maintained lawn.

A living room with a sofa, armchairs, a coffee table with a plant, a side table with a lamp, and a window with curtains.

A wooden-paneled room with a wicker chair, a small table with a lamp, and a door leading outside.

1. Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

Dartmouth

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Great location. Near ButtonWood Park. Quiet neighborhood. Enjoyed my stay."

richard m.

The price is €285

€285

includes taxes & fees

22 Oct - 23 Oct

Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

A room with a white dresser, a lamp, a window with blinds, and a view of a deck and houses outside.

A living room with a brown leather sofa, a dining table with chairs, a TV on a stand, and a lamp.

A bedroom with a bed, a nightstand, a TV, and a window with curtains.

A residential street with houses, a speed limit sign, a utility pole, and a clear sky.

2. Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St

Fairhaven

Backyard Retreat / 5 Min > Beach & Main St

A water park with a large central pool, multiple slides, and a variety of play structures.

A room with a wooden interior, a chair, a table, and large windows offering a view of a grassy field and a bridge.

A living room with a brown sofa, a blue armchair, and a wooden coffee table.

A living room with a fireplace, a recliner, and a television on a mantel.

3. Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Fairhaven

9.6 out of 10, Exceptional, (40 reviews)

9.6/10

Exceptional

(40 reviews)

"The most perfect spot! Our host and the neighbors were so nice and gave us great tips! Would definitely stay again"

Jainessa

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

A room with a white bedside table, a lamp, a wicker basket, and a blue chair.

A modern living room with a fireplace, a television, and a kitchen area with white cabinets and a countertop.

A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with stools.

A kitchen with white cabinets, a granite countertop, a window with blinds, and a wicker basket on the ceiling.

4. Ellery Bungalow #51- Island Calm Near Newport

Ellery Bungalow #51- Island Calm Near Newport

Middletown

9.6 out of 10, Exceptional, (97 reviews)

9.6/10

Exceptional

(97 reviews)

"We had a wonderful stay!"

Stacey

Ellery Bungalow #51- Island Calm Near Newport

A single-story house with a grey siding exterior, a front door with a blue doorbell, and a small front yard with a gravel pathway and various plants.

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and an oven.

A modern kitchen with white cabinets, a stainless steel refrigerator, and a built-in island with stools. There is a fireplace with a white mantel and a flat-screen TV mounted above it.

A modern living room with a brown sofa, a wooden coffee table, and three potted plants. There is a kitchen area with white cabinets, a microwave, and an oven.

5. Ellery Beach Bungalow #45- A Refined Island Escape

Ellery Beach Bungalow #45- A Refined Island Escape

Middletown

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Beautiful area, walking distance to the beach and restaurants, nice clean house"

Dana N.

Ellery Beach Bungalow #45- A Refined Island Escape

A backyard with a seating area, a white fence, and a variety of plants.

A bedroom with a bed, a desk, a chair, a ceiling fan, and a window with blinds.

A modern kitchen with stainless steel appliances, white cabinetry, and a bar stool.

A staircase with wooden steps and a white wall.

6. Delightful 3-bedroom house with AC in Oak Bluffs

Delightful 3-bedroom house with AC in Oak Bluffs

Oak Bluffs

The price is €1,031

€1,031

includes taxes & fees

30 Oct - 31 Oct

Delightful 3-bedroom house with AC in Oak Bluffs

A modern kitchen with dark cabinets, a central island, and a dining area with a wooden table and white chairs.

A residential house with a driveway, a mailbox, and a well-maintained lawn.

A modern kitchen with dark cabinetry, a central island, and a large window providing natural light.

A spacious kitchen with a central island, a dining area with a large table and chairs, and a chandelier.

7. Beach house walking distance to Second Beach

Beach house walking distance to Second Beach

Easton's Point

10.0 out of 10, Exceptional, (35 reviews)

10/10

Exceptional

(35 reviews)

"This is a hidden gem, off the beaten path, yet accessible to all the splendors of this beautiful area. The home is spacious and welcoming. The kitchen offers the opportunity to cook all meals comfortably if wanted. The fire pit is a definite bonus."

Kelley

The price is €705

€705

includes taxes & fees

4 Nov - 5 Nov

Beach house walking distance to Second Beach

A wooden deck with a built-in bench and a small enclosed area with a door.

A modern interior with a staircase, wooden flooring, and a bar area with stools.

A modern kitchen with stainless steel appliances, white cabinets, and a dining area set for four.

A modern living room with a gray sectional sofa, a round coffee table, and a patterned rug.

8. 4br & 2ba Ranch style house w/ huge backyard!

4br & 2ba Ranch style house w/ huge backyard!

PORTSMOUTH

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"Fantastic spot - house was great for visiting with family. Basemen is a great spot for kids to escape. "

Emo C.

The price is €572

€572

includes taxes & fees

4 Nov - 5 Nov

4br & 2ba Ranch style house w/ huge backyard!

A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

A two-story house with a front porch, a door with a window, and a chimney.

A spacious living area with a fireplace, a dining table, and a sofa.

A serene garden with a pond, wooden bridge, and various plants.

9. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"This place was just what we needed! Would definitely stay again. Cozy and feels very homey! Thanks!"

Chris S.

The price is €737

€737

includes taxes & fees

8 Oct - 9 Oct

Oak Bluffs 4BR • 5 Min Drive to Downtown

A spacious living area with a high ceiling, a dining table, and a kitchen area.

A spacious living room with a brick fireplace, a large window, and a wooden coffee table.

A bedroom with a bed, a desk, and a TV. There are three windows providing natural light.

A spacious room with a large wooden dining table, comfortable seating, and large windows offering a view of the outdoors.

10. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Oak Bluffs

9.6 out of 10, Exceptional, (10 reviews)

9.6/10

Exceptional

(10 reviews)

"The host was very responsive.We definitely recommend this house as family friendly."

Karen M.

The price is €951

€951

includes taxes & fees

6 Oct - 7 Oct

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A two-story house with a garage, a well-maintained lawn, and mature trees.

A bedroom with two single beds, a bedside table with a lamp, and a door leading to another room.

A residential backyard with a bird feeder, a wooden fence, and a house with a red exterior and white trim.

A dining area with a table set for six, a chandelier, and large windows offering a view of the outdoors.

11. Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow

Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow

Falmouth

Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow

A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

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

A two-story house with a covered patio area featuring a grill, outdoor furniture, and a large umbrella.

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

12. Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Falmouth

10.0 out of 10, Exceptional, (224 reviews)

10/10

Exceptional

(224 reviews)

"Great location "

Stephanie B.

The price is €467

€467

includes taxes & fees

1 Nov - 2 Nov

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a patterned tablecloth and a vase of flowers.

A single-story house with a porch, surrounded by a well-maintained lawn and trees.

A living room with a brown sofa, a glass cabinet, a black coffee table, and patterned rugs.

13. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Oak Bluffs

9.8 out of 10, Exceptional, (10 reviews)

9.8/10

Exceptional

(10 reviews)

"The property was clean, private, and peaceful."

Sherri R.

The price is €1,216

€1,216

includes taxes & fees

6 Oct - 7 Oct

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

A circular stone patio with Adirondack chairs and a small table in a forested area.

A residential house with a wooden staircase leading to a front door, a garage door, and a window with a white frame.

A modern kitchen with stainless steel appliances, a dining area with a wooden table, and white cabinetry.

A hallway with a wooden floor, a beige sofa, a white door, and nautical-themed decorations.

14. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

Oak Bluffs

7.0 out of 10, Good, (12 reviews)

7.0/10

Good

(12 reviews)

"Loved this spot. Perfect central island location. Fantastic owner with an incredible response time. Would recommend this property to all5 stars"

Eli R.

The price is €631

€631

includes taxes & fees

6 Oct - 7 Oct

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

A two-story house with a stone facade, a covered patio, and a well-maintained garden.

A house with a well-maintained lawn and a stone pathway leading to the entrance.

An outdoor patio area with a fire pit, seating, and a pool.

A swimming pool with a pergola and outdoor seating area.

15. Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks

Oak Bluffs

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Brenda and Derek were amazing hosts. They have a beautifully landscaped property with all the amenities needed for a relaxing family vacation. They are super responsive and take a lot of pride in giving their guests a top-notch experience. We will definitely consider staying at their properties again."

Lamar A.

The price is €3,345

€3,345

includes taxes & fees

12 Oct - 13 Oct

Beautiful Estate with salt water pool & pond with kayaks

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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