Are there vacation rentals with a dedicated workspace in Milton?

Yes! Work meets play with ease at over 70 vacation rentals in Milton featuring dedicated workspaces. Stay connected and productive in your home away from home.

Do apartment rentals in Milton have free parking?

Absolutely! We offer over 30 apartment rentals with free parking in Milton. Enjoy a tailored experience with all the comforts you desire.

Where should I stay in Milton?

Make yourself at home in Milton by choosing from our most frequently booked neighborhoods. We have over 280 vacation rentals in Hyde Park, over 280 vacation rentals in West Street - River Street, and over 2,580 vacation rentals in Montclair.

Are there family-friendly vacation rentals in Milton?

Milton has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Do apartment rentals in Milton have wifi?

Absolutely! We offer over 50 apartment rentals with wifi in Milton. Enjoy a tailored experience with all the comforts you desire.

Are there pet-friendly vacation rentals in Milton?

Four-legged friends are welcome in Milton. Choose from more than 30 vacation rentals for guests traveling with pets.

What are the most popular amenities for House Rentals in Milton?

Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with free parking, over 40 homes with a kitchen, over 50 homes with wifi, over 50 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

How much does it cost to stay in house rentals in Milton?

Experience the best of Milton with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Do apartment rentals in Milton have a kitchen?

Absolutely! We offer over 40 apartment rentals with a kitchen in Milton. Enjoy a tailored experience with all the comforts you desire.

Do apartment rentals in Milton have air conditioning?

Absolutely! We offer over 50 apartment rentals with air conditioning in Milton. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Milton

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Milton

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Winthrop

4.96 out of 5 average rating, 301 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Superhost

Condo in Plymouth

4.77 out of 5 average rating, 154 reviews

Clear Pond Pet Friendly Inn, Winter months 50% off

This pond front property offers a relaxing atmosphere with beautiful views of your private beach for swimming, kayaking and canoeing. You're a stone's throw from the Plymouth Rock, Plantation, and Plymouth Beach, along with all the restaurants and shops along the waterfront. Boston, Cape Cod, Nantucket, and Martha's Vineyard are only minutes from your doorstep. There is a walking trail for pets around an adjacent cranberry bog. Fire pits, private patio, and beach for your outdoor pleasure!

Guest favorite

Home in Plymouth

5 out of 5 average rating, 104 reviews

Updated Antique in Historic Downtown Plymouth

Updated antique colonial within walking distance to everything historic Downtown Plymouth has to offer- waterfront, boating, shops, restaurants, historic sites, and more. Fenced in backyard with patio overlooking gorgeous, well-maintained garden. Patio has large farm table with umbrella and Weber grill, great for entertaining! This charming in-town location offers you the best of both worlds - walking distance to everything while also being cozy and comfortable to enjoy a day at home to relax.

Guest favorite

Home in Plymouth

4.82 out of 5 average rating, 300 reviews

Historic 1 Bed/In Town/Best Location/Hot tub/deck

PLEASE DO NOT BOOK WEEKENDS/HOLIDAYS/SUMMERS in advanced. I only use this 1 bed to fill gaps when the larger listing for this home isn't rented (mostly midweek) Beautifully restored historic home, directly in town, steps away from the Pilgrims 1st settlement, ocean, award winning restaurants, historic attractions, shops, nightlife, entertainment, tours,ferries, etc. Directly on the town brook/gristmill. Deck with view, firepit, hot tub, grill. Comfortable/clean/cozy bed, working wood stove.

Guest favorite

Vacation home in Natick

4.89 out of 5 average rating, 100 reviews

Private Lakefront with game room/Newly renovated

Entire house is brand new with automated blinds w the front of the house facing 180 degee view of lake. Large game room House screams airbnb set down secluded quiet rd on the lake but a min or 2 to any type of store or restaurant you are looking for w tons to do in area. Sliding barn door separates main living area/main bedroom and kitchen from game room & other 2 bedrooms & extra full bath - returns all texts instantly -Free use of paddle board/kayak -No events -3 car 6 person limit 》25 yr

Guest favorite

Apartment in Salem

4.98 out of 5 average rating, 372 reviews

Winter Island Retreat

Effective 4/1/23, NON Owner occupied listings have a 3% impact fee that is charged on the total expenses associated with the rental. Winter Island Retreat is a OWNER OCCUPIED listing that is the place; For total relaxation. Watch the sunrise and experience the Atlantic Ocean. Enjoy your favorite beverage while rocking in an Adirondack chair on the patio. Inhale the smell of the ocean breeze and fragrant sea roses. Winter Island Retreat is an experience like no other in the Witch City.

Superhost

Apartment in Swampscott

4.89 out of 5 average rating, 101 reviews

Ocean views, Large Deck, Grill, Kid/Dog Friendly

The product of a complete gut renovation in 2020. The unit is 300 yards to Fisherman's Beach at the bottom of the street. The apartment is the 1st floor of a two family home (our family lives upstairs). It consists of 2 bedrooms, 2 full baths, pro kitchen, open living/dining area. The driveway can fit 2 cars (tight). There is additional parking at the bottom of the street. Please see house rules settings for holiday minimum bookings. We are pet friendly, but require case by case approval.

Guest favorite

Tiny home in Greenville

4.97 out of 5 average rating, 663 reviews

Tiny Home Eco-Cottage w/ Lake View + Pet Friendly

Good things definitely come in pet friendly, environmentally conscious, small packages. Solar upgrade makes this lake front cottage 100% energy efficient. Built with an open, thoughtful design offering private bath, washer/dryer, full kitchen, Hotel Suite Luxury bedding and Tempur-Pedic mattress, blazing fast wifi, 46"HDTV (w/ Netflix, Sling, Prime and Plex), private deck with nice lake view. Cozy, charming and stocked with everything you could want for a perfect vacation or staycation.

Guest favorite

Home in Scituate

5 out of 5 average rating, 18 reviews

Coastal Retreat

Welcome to our coastal rental, a charming retreat nestled in the heart of a vibrant beach town. With modern amenities and coastal decor, unwind in the light-filled spaces and savor beautiful marsh views from the well manicured backyard. Located about a mile from Main Street, you can walk or bike on the flat sidewalk to restaurants, shops and the harbor. Close by you'll also find a dog park, the beautiful public golf course, Widow's Walk and of course the beach!

Guest favorite

Home in Plymouth

4.93 out of 5 average rating, 40 reviews

Serene Lakefront Retreat: Your Perfect Getaway!

Escape to our serene lake house with breathtaking views & endless opportunities for outdoor adventure. With a dedicated workspace, stay connected while enjoying tranquility. Take a paddle on the lake with kayaks & pedal boat, or relax on the patio with outdoor fire pit. Fully furnished & decorated, feel at home cooking in the fully equipped kitchen or curling up in the cozy living room. Book your stay today and experience the magic of nature firsthand!

Superhost

Home in Scituate

4.82 out of 5 average rating, 57 reviews

Sand Hills Beach - lighthouse area -

Walking distance to sand hills beach - One mile from center of town with restaurants and shops. Nearby basketball court. Very Close to Barker Tavern. Grassy backyard . New furnishings new full bath and new mattresses. bedrooms are upstairs. There is only one full bath upstairs Totally redone 2024. Bungalow beach style home. some guests find stairs to be “ steep” … my 82 year old mom does fine with the stairs and rail!

Guest favorite

Condo in Gloucester

4.96 out of 5 average rating, 100 reviews

Luxurious beach house w/ harbor views & near beach

There isn't a better location on Cape Ann! Rocky Neck is the oldest art colony in the US. This luxurious 1br boasts ocean views & was updated w/ designer & custom features. Not only can you walk to the beach, there are amazing restaurants across the street and a wine & cheese bar featuring local art you can peruse while having a cocktail. Come and enjoy sunsets from the deck and everything else Gloucester has to offer!

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Milton vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Milton's top sights

Star Market81 locals recommend

Ashmont Grill56 locals recommend

South Shore Plaza55 locals recommend

Sophia's Grotto52 locals recommend

CVS49 locals recommend

Fornax Bread Company38 locals recommend

Other great vacation rentals in Milton

Superhost

Cabin in Plymouth

4.82 out of 5 average rating, 1,005 reviews

Traditional Log House Near Cape Cod/Boston

Guest favorite

Apartment in Brighton

4.88 out of 5 average rating, 17 reviews

The Curie

Guest favorite

Cottage in Lincoln

5 out of 5 average rating, 32 reviews

Enjoy this fully equipped cottage w fenced yard

Guest favorite

Apartment in Brighton

4.99 out of 5 average rating, 72 reviews

New 3 bedroom, 2 bath unit, meadow view!

Superhost

Guest suite in Arlington

4.85 out of 5 average rating, 80 reviews

★Modern Studio-Private Entrance,Washer+Dryer★

Guest favorite

Home in Gloucester

4.91 out of 5 average rating, 121 reviews

Gloucester Beach House, near Good Harbor Beach!

Guest favorite

Apartment in Swampscott

4.98 out of 5 average rating, 40 reviews

Ocean View Apartment 2nd Floor

Superhost

Home in East Boston

4.86 out of 5 average rating, 92 reviews

Cozy Oasis: Luxury & Modern Apt By Revere Beach

Show all

Quick stats about vacation rentals in Milton

Total rentals
130 properties
Nightly prices starting at
G$6,270 GYD before taxes and fees
Total number of reviews
4.5K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Milton?
Yes! Work meets play with ease at over 70 vacation rentals in Milton featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do apartment rentals in Milton have free parking?
Absolutely! We offer over 30 apartment rentals with free parking in Milton. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Milton?
Make yourself at home in Milton by choosing from our most frequently booked neighborhoods. We have over 280 vacation rentals in Hyde Park, over 280 vacation rentals in West Street - River Street, and over 2,580 vacation rentals in Montclair.
Are there family-friendly vacation rentals in Milton?
Milton has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do apartment rentals in Milton have wifi?
Absolutely! We offer over 50 apartment rentals with wifi in Milton. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Milton?
Four-legged friends are welcome in Milton. Choose from more than 30 vacation rentals for guests traveling with pets.
What are the most popular amenities for House Rentals in Milton?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with free parking, over 40 homes with a kitchen, over 50 homes with wifi, over 50 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in house rentals in Milton?
Experience the best of Milton with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Milton have a kitchen?
Absolutely! We offer over 40 apartment rentals with a kitchen in Milton. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Milton have air conditioning?
Absolutely! We offer over 50 apartment rentals with air conditioning in Milton. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Milton

Top-rated vacation rentals in Milton

Apartment in Winthrop

Condo in Plymouth

Home in Plymouth

Home in Plymouth

Vacation home in Natick

Apartment in Salem

Apartment in Swampscott

Tiny home in Greenville

Home in Scituate

Home in Plymouth

Home in Scituate

Condo in Gloucester

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Milton vacation rentals

Stay near Milton's top sights

Other great vacation rentals in Milton

Cabin in Plymouth

Apartment in Brighton

Cottage in Lincoln

Apartment in Brighton

Guest suite in Arlington

Home in Gloucester

Apartment in Swampscott

Home in East Boston

Quick stats about vacation rentals in Milton

Total rentals

Nightly prices starting at

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with dedicated workspaces

Frequently Asked Questions

Destinations to explore