Milton Vacation Home Rentals from CA $875: Search Top Private Vacation Homes for Rent

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Our top choices for Milton vacation homes

A modern kitchen with dark cabinets, a large island, and pendant lighting.

A kitchen with a marble countertop, a bottle of Pellegrino water, a bowl of snacks, and a framed seagull painting on the wall.

A modern kitchen with a central island, a stove, and pendant lighting.

A modern kitchen with a central island, wooden cabinets, stainless steel appliances, pendant lighting, and a dining area with a sofa and chairs.

1. Spacious 5BR Executive Retreat - 10 Min to Boston

Spacious 5BR Executive Retreat - 10 Min to Boston

Milton

The price is CA $305

CA $305

CA $770 total

includes taxes & fees

Sep 14 - Sep 15

Spacious 5BR Executive Retreat - 10 Min to Boston

A modern kitchen with white cabinetry, a central island with bar stools, stainless steel appliances, and pendant lighting.

A modern living room with a blue sofa set, a glass coffee table, and a fireplace.

A modern interior with a staircase, a dining area with a table and chairs, and a kitchen in the background.

A spacious living room with a white sofa, blue cushions, and a glass coffee table.

2. Peaceful Milton Getaway- Trails & City Nearby

Peaceful Milton Getaway- Trails & City Nearby

Milton

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Very beautiful place and clean. The hosts were very nice and gave speedy responses. "

The P.

The price is CA $1,014

CA $1,014

CA $2,003 total

includes taxes & fees

Sep 14 - Sep 15

Peaceful Milton Getaway- Trails & City Nearby

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

A room with a white door, a small window, a black mat, and a white wall.

A dining area with a white table, beige placemats, and white chairs. A purple vase with flowers is on the table.

A wooden deck with white railings, a glass door, and a metal awning.

3. Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

Dorchester

9.0 out of 10, Wonderful, (6 reviews)

9.0/10

Wonderful

(6 reviews)

"The apartment was perfect for our needs & the host communicated everything we needed without us needing to ask! Wonderful stay."

Arwen D.

The price is CA $175

CA $175

CA $283 total

includes taxes & fees

Sep 7 - Sep 8

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

A wooden front door with a glass panel and the number 383.

A wooden door with a glass panel, a balcony with a railing, and hanging flower baskets.

A two-story house with a porch decorated with flowers and American flags.

A modern kitchen with dark wood cabinets, a stainless steel refrigerator, and a dining area with a wooden table and leather chairs.

4. FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383

FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383

Quincy

9.8 out of 10, Exceptional, (52 reviews)

9.8/10

Exceptional

(52 reviews)

"Very cute property that was very clean, the host was extreme nice with great knowledge of the area and a prefect parking map!"

Alicia R.

The price is CA $191

CA $191

CA $474 total

includes taxes & fees

Sep 7 - Sep 8

FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383

A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

A living room with a wooden coffee table, a black sofa, a TV on a wooden stand, a clock on the wall, and a window with blinds.

A kitchen with open cabinets containing coffee, tea, and paper products. A coffee maker and a kettle are on the counter.

A modern living room with a flat-screen TV, a wooden coffee table, and a large potted plant.

5. Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams

Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams

Quincy

9.6 out of 10, Exceptional, (4 reviews)

9.6/10

Exceptional

(4 reviews)

"Perfect stay for the night. Communication was great and property was clean and had everything we needed."

Ryan E.

The price is CA $228

CA $228

CA $397 total

includes taxes & fees

Sep 15 - Sep 16

Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams

A kitchen with white cabinets, a tiled backsplash, and a knife block on the counter.

A wooden staircase leading to a white door with the number 39, flanked by siding and a small porch area.

A modern kitchen with white cabinets, a stainless steel refrigerator, a dining table with chairs, and a microwave.

A modern living room with a grey sectional sofa, a wooden coffee table, and a staircase with wooden steps and a white railing.

6. Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39

Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39

Quincy

9.6 out of 10, Exceptional, (54 reviews)

9.6/10

Exceptional

(54 reviews)

"Very clean and stay was enjoyable. "

Sheldon S.

The price is CA $192

CA $192

CA $475 total

includes taxes & fees

Sep 7 - Sep 8

Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39

A modern living room with a wooden floor, a black leather sofa, a wooden coffee table, a TV, and a potted plant.

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

7. Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41

Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41

Quincy

9.6 out of 10, Exceptional, (32 reviews)

9.6/10

Exceptional

(32 reviews)

"We enjoyed our stay at this place. Comfortable and plenty of space for us."

Jeff L.

The price is CA $193

CA $193

CA $477 total

includes taxes & fees

Sep 7 - Sep 8

Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41

A spacious living room with a black leather sofa, wooden coffee table, and a staircase leading to an upper floor.

A front door with a number plate, a mailbox, and a small garden planter.

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

A wooden shoe rack with a sign above it, a door, and a mirror on the wall.

8. Pet-Friendly 3BR Retreat • Easy Boston, Logan Airport & I-93 Access w/Parking 37

Pet-Friendly 3BR Retreat • Easy Boston, Logan Airport & I-93 Access w/Parking 37

Quincy

9.2 out of 10, Wonderful, (40 reviews)

9.2/10

Wonderful

(40 reviews)

"Everything was absolutely excellent."

Rafael M.

The price is CA $191

CA $191

CA $474 total

includes taxes & fees

Sep 7 - Sep 8

Pet-Friendly 3BR Retreat • Easy Boston, Logan Airport & I-93 Access w/Parking 37

A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a glass table and leather sofas.

A brown door with a number '2' and a keypad lock.

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

A staircase with wooden steps and balusters, a brown leather sofa with cushions, a round coffee table, and a potted plant.

9. Exclusive Summer Offer · Spacious 4BR Boston Stay w/ Parking & Pet-Friendly 37/2

Exclusive Summer Offer · Spacious 4BR Boston Stay w/ Parking & Pet-Friendly 37/2

Dorchester

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Was clean and easy to get into. Good amount of parking and easy to contact host with questions!"

Julie C.

The price is CA $191

CA $191

CA $518 total

includes taxes & fees

Sep 7 - Sep 8

Exclusive Summer Offer · Spacious 4BR Boston Stay w/ Parking & Pet-Friendly 37/2

A staircase with white balusters and blue handrails leading to a room with a bed and a painting on the wall.

A modern kitchen with white cabinetry, a gas stove, and a dining area with wooden chairs and a vase of flowers.

A modern living room with a brown leather sofa, a round wooden coffee table, and a potted plant.

A wooden door with a glass panel, a mailbox, and a house number.

10. Pet friendly 5-Bedroom 3-full bath Boston Home, Subway access & Scenic View 76

Pet friendly 5-Bedroom 3-full bath Boston Home, Subway access & Scenic View 76

Dorchester

9.8 out of 10, Exceptional, (18 reviews)

9.8/10

Exceptional

(18 reviews)

"Our stay was excellent, the property was clean and spacious with everything we needed. The host was responsive and very helpful before and throughout the trip."

Clark A.

The price is CA $570

CA $570

CA $1,107 total

includes taxes & fees

Sep 14 - Sep 15

Pet friendly 5-Bedroom 3-full bath Boston Home, Subway access & Scenic View 76

A spacious living area with a wooden floor, a sofa, a dining table with chairs, a small round table, and a black refrigerator.

A modern living room with a sectional sofa, a round marble table, a wall-mounted fan, and a mural of a rope bridge.

A compact kitchen with dark cabinets, a microwave, a toaster, and a sink.

A compact living space with a dining area, a kitchen, and a black refrigerator.

11. Charming garden level 1 bedroom 1 bath apartment in Brockton

Charming garden level 1 bedroom 1 bath apartment in Brockton

Brockton

8.0 out of 10, Very good, (15 reviews)

8.0/10

Very good

(15 reviews)

"Pet friendly"

John

The price is CA $124

CA $124

CA $231 total

includes taxes & fees

Oct 1 - Oct 2

Charming garden level 1 bedroom 1 bath apartment in Brockton

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

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

A staircase with white railings leading to a porch with a white balustrade.

A bedroom with a bed, nightstands, a chair, and a rug.

12. Centrally located in the heart of Boston near T

Centrally located in the heart of Boston near T

Dorchester

9.4 out of 10, Exceptional, (30 reviews)

9.4/10

Exceptional

(30 reviews)

"Excellent stay! "

Melissa R.

The price is CA $253

CA $253

CA $626 total

includes taxes & fees

Sep 8 - Sep 9

Centrally located in the heart of Boston near T

A modern living room with a flat-screen TV, a white sofa, a coffee table, and decorative items.

A dining area with a glass table, grey upholstered chairs, and a red vase with flowers.

A two-story house with a front porch, a small garden with gravel and plants, and a clear sky.

A modern kitchen with wooden cabinets, a marble countertop, and a bar area with stools.

13. Lorenzo Inn

Lorenzo Inn

Dorchester

9.8 out of 10, Exceptional, (9 reviews)

9.8/10

Exceptional

(9 reviews)

"Beautiful house. Very well furnished and equipped. Friendly host. Comfortable beds. Easy to quickly get town centre in an Uber. Highly recommend."

patrick

The price is CA $360

CA $360

CA $531 total

includes taxes & fees

Sep 20 - Sep 21

Lorenzo Inn

A neatly arranged bedroom with a bed, bedside tables, a dresser, and a window providing natural light.

A dining area with a table and chairs, a window with blinds, and a view of a house outside.

A kitchen with a dining table, chairs, and a countertop with a vase of flowers.

A two-story house with a front porch, a brick foundation, and a white door.

14. Cozy three-bedroom home close to Boston w/ plenty of parking

Cozy three-bedroom home close to Boston w/ plenty of parking

North Braintree

10.0 out of 10, Exceptional, (54 reviews)

10/10

Exceptional

(54 reviews)

"Great overall stay!"

Chris R.

The price is CA $305

CA $305

CA $673 total

includes taxes & fees

Sep 7 - Sep 8

Cozy three-bedroom home close to Boston w/ plenty of parking

A spacious living area with a dining table set for six, a sofa, and a kitchen in the background.

A staircase with white walls and wooden steps leading to a landing.

A hallway with a wooden floor, a painting of the Mona Lisa on the wall, a sign reading "Best this home," and a small plant on a console table.

A modern kitchen with wooden cabinets, a white refrigerator, and a dishwasher.

15. Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17

Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17

Randolph

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Great stay! Host was very responsive to any questions. Family friendly house with lots of beds and a wide open living room. Easy check in and check out process. Nice central location to all that the Boston area has to offer."

Anonymous traveller

The price is CA $234

CA $234

CA $652 total

includes taxes & fees

Sep 7 - Sep 8

Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17

A living room with a brown leather sofa, a black coffee table, and a television on a wooden stand.

A wooden console table with a vase of flowers, a stack of books, and a bowl. Two upholstered chairs are in front.

A hotel room with a bed, two patterned chairs, a small table with a plant, a TV, and a window with a view of a snowy street.

16. Stylish 4 Bedroom Townhouse in Boston, Walkable to Train, Quiet & Safe Area 76

Stylish 4 Bedroom Townhouse in Boston, Walkable to Train, Quiet & Safe Area 76

Dorchester

9.8 out of 10, Exceptional, (21 reviews)

9.8/10

Exceptional

(21 reviews)

"Close walk to redline train. Walkable restaurants in area. Good location for using public transportation to get to downtown. Property very clean. Host responsive to inquiry’s."

shelly H.

The price is CA $469

CA $469

CA $881 total

includes taxes & fees

Sep 7 - Sep 8

Stylish 4 Bedroom Townhouse in Boston, Walkable to Train, Quiet & Safe Area 76

A spacious living room with a grey sofa, wooden flooring, a flat-screen TV, and a staircase.

A dining area with a wooden table and chairs, a small potted plant, and a red bow on the door.

A bedroom with a bed, two bedside tables, a wall-mounted light fixture, and a window with curtains.

A modern kitchen with white cabinetry, a stainless steel refrigerator, a built-in oven, and a microwave.

17. Large 5BR Peaceful House near Perry Beach • Pet-Friendly w/Parking 284

Large 5BR Peaceful House near Perry Beach • Pet-Friendly w/Parking 284

Quincy

9.8 out of 10, Exceptional, (80 reviews)

9.8/10

Exceptional

(80 reviews)

"Nice quiet street perfect for families and close to Boston."

Alisa O.

The price is CA $235

CA $235

CA $706 total

includes taxes & fees

Sep 7 - Sep 8

Large 5BR Peaceful House near Perry Beach • Pet-Friendly w/Parking 284

A patio with outdoor furniture, a wooden fence, and a brick wall.

A compact kitchen with white cabinets, a dining area with a small table and bar stools, a fireplace, and a cityscape painting on the wall.

A hotel room with a bed, a desk, a chair, a fireplace, and a cityscape painting on the wall.

A bathroom with a toilet, sink, and shower.

18. Gorgeous Beacon Hills Studio next to State house

Gorgeous Beacon Hills Studio next to State house

Beacon Hill

9.6 out of 10, Exceptional, (37 reviews)

9.6/10

Exceptional

(37 reviews)

"Loved the private outdoor patio"

Robin P.

The price is CA $260

CA $260

CA $501 total

includes taxes & fees

Sep 20 - Sep 21

Gorgeous Beacon Hills Studio next to State house

A spacious living area with a large sectional sofa, a glass coffee table, and a view of the outdoors through large windows.

A modern kitchen with wooden cabinetry, stainless steel appliances, and a hardwood floor.

A spacious living area with a fireplace, a large window, and a kitchen area with modern appliances.

A dining area with a table set for four, white chairs, a green wall with a 'Let's Party' sign, and a window with curtains.

19. Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

Westwood

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Easy-to-find location and charming accommodations. Everything was organized well and very clean. Would highly recommend this listing."

Eva O.

The price is CA $197

CA $197

CA $302 total

includes taxes & fees

Oct 1 - Oct 2

Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

A modern kitchen with white cabinets, a built-in dishwasher, a coffee maker, and a clock on the wall.

A modern living room with a dark sofa, a small side table, a round dining table with four chairs, and a large window with blinds.

A modern living room with a sofa, a couch, a dining table with a vase of flowers, and a large window with blinds.

20. New 3 beds in Southie! W/D in unit.

New 3 beds in Southie! W/D in unit.

South Boston

8.0 out of 10, Very good, (1 review)

8.0/10

Very good

(1 review)

"This location close to many attractions and has a long flight of stairs up to the apartment. Please note that No parking is provided with your stay. The bedding is comfy and the apartment is well stocked. The managers were helpful and accommodating to us offering suggestions. "

Kimberly B.

The price is CA $224

CA $224

CA $431 total

includes taxes & fees

Sep 7 - Sep 8

New 3 beds in Southie! W/D in unit.

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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