Vacation rentals in Milton

4.87 out of 5 average rating, 109 reviews

A serene morning on the lake is depicted, with two individuals paddling a kayak through mist-covered water. The surrounding landscape features dense trees and gentle hills, while soft light reflects off the calm surface, creating a peaceful atmosphere.

Vacation home in Natick

Private Lakefront with game room/Newly renovated

Ideal private location on crystal clear Lake Cochituate! Peaceful quiet spot w amazing view only 20 min to Boston & 1 or 2 min drive to anything u could need Fun game room &free use of tandem kayak & paddleboard and fishing Sliding barn door separates main king bedroom, bath, & open kitchen & livingroom from the back 2 queen beds, game room & bath Im always available to answer questions + provide tips, but I also respect your privacy & want u to feel comfy & independent 》25 6 person 3 car limit

4.97 out of 5 average rating, 265 reviews

The charming entrance of the cottage is framed by vibrant greenery and colorful flowers. Two wooden chairs are positioned in front of the entrance, welcoming guests. A decorative flag flutters above the door, completing the inviting scene.

Guesthouse in Annisquam

Annisquam Village Bunny Cottage

This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070

4.96 out of 5 average rating, 307 reviews

The spacious bedroom features two queen beds with light green bedding, positioned beside a large window that allows natural light to fill the room. A modern bathroom is visible in the background, with neutral tones and elegant fixtures. Wooden benches provide additional seating.

Apartment in Winthrop

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.

5 out of 5 average rating, 115 reviews

A comfortable seating area features a light-colored armchair with a decorative pillow. Natural light enters through a window, which is dressed with a light shade. A modern fireplace adds a touch of elegance against the crisp white wall.

Home in Plymouth

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.

4.82 out of 5 average rating, 325 reviews

A serene outdoor seating area is surrounded by lush greenery, featuring two dark wooden chairs and a small table. A natural landscape includes a gently flowing brook nearby, with a weathered bench positioned to enjoy the peaceful view.

Home in Plymouth

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.

4.86 out of 5 average rating, 113 reviews

An aerial view captures the scenic coastline and sandy beach lined with boats. A variety of residential buildings dot the landscape, interspersed with greenery. The neighborhood showcases the charm of coastal living, with the sea and a pier visible in the background.

Apartment in Swampscott

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.

4.97 out of 5 average rating, 701 reviews

A charming cottage exterior features a blue front door, surrounded by vibrant flower planters. A small patio set with a table and chairs is positioned beneath a blue umbrella, adjoining a white picket fence with a view of the lake in the background.

Tiny home in Greenville

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.

5 out of 5 average rating, 22 reviews

Home in Scituate

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!

4.93 out of 5 average rating, 41 reviews

Home in Plymouth

The Lake House Paradise!

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!

4.86 out of 5 average rating, 101 reviews

A set of wooden stairs leads up to a balcony area, featuring two simple chairs and a potted plant. The space is bathed in natural light, with a clear blue sky visible above and hints of the surrounding greenery.

Condo in Pawtucket

🏡🏡🤩😍 Beautiful apartment perfect location.💎💜

The house with the green roof. Truly beautiful, absolutely lovely. No hidden cleaning fees. You would be renting out the whole upstair apartment. Free Private parking for 3+ vehicles, free Wi-Fi (Verizon Fios), self check in, complimentary water, coffee and tea. Extra air mattress available by request only. A home away from home, A+ neighborhood Max people 5 please. Any questions big or small please do not hesitate to ask thank you RE.00385-STR

4.96 out of 5 average rating, 102 reviews

A well-maintained outdoor area is highlighted, featuring a grassy lawn leading up to stone steps. The house, adorned with dark siding, is framed by a large tree and offers a welcoming seating arrangement on the porch. Clear skies provide ample natural light.

Condo in Gloucester

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!

4.97 out of 5 average rating, 144 reviews

Home in Smithfield

Luxury Home | Fire Pit | Beach | Grill | 2 Decks

Welcome to Stillwater.House - a custom built Airbnb. Our premier luxury home is situated overlooking a picturesque running river and 92 acre pond. Built in 2020, this beautiful 2,600 sq ft, five bedroom, four bath home boasts breathtaking views, nestled in the picturesque Georgiaville Village. Enjoy the views on TWO decks with plenty of outdoor seating, couches and a brand new gas grill! RE.02492-STR

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Milton vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Milton's top sights

Star Market3 locals recommend

Ashmont Grill56 locals recommend

South Shore Plaza29 locals recommend

Sophia's Grotto7 locals recommend

Fornax Bread Company4 locals recommend

Steel & Rye4 locals recommend

Other great vacation rentals in Milton

4.77 out of 5 average rating, 154 reviews

A serene waterfront view showcases a calm pond surrounded by trees in autumn colors. An inviting sandy beach area features bright blue adirondack chairs and a kayak resting on the shore, reflecting a peaceful outdoor setting.

Condo in Plymouth

Clear Pond Pet Friendly Inn

4.95 out of 5 average rating, 174 reviews

The living area features a stone fireplace and a flat-screen television mounted above. The space includes a mix of comfortable seating, such as a blue sofa and patterned armchairs. Exposed wooden beams and a spiral staircase add architectural interest to the cozy environment.

Cottage in Stow

White Pine Cottage

4.93 out of 5 average rating, 91 reviews

A wooden observation deck is surrounded by tall trees, providing views of a calm waterway reflecting the soft colors of the sky. The scene conveys a sense of tranquility, enhanced by the natural surroundings and the serene water's edge.

Guest suite in Duxbury

Guest suite on cranberry bog, 1 mile from beach

5 out of 5 average rating, 8 reviews

A two-story, light blue house is shown, featuring a well-maintained landscape with shrubs and small trees. A stone wall borders the property, and a concrete walkway with steps leads to a wooden deck at the entryway.

Apartment in North End

Beautiful and spacious lovely home

4.95 out of 5 average rating, 21 reviews

A person is seen kayaking on calm waters during sunset, with a stunning sky displaying shades of pink and orange. Nearby islands are visible in the distance, complementing the serene outdoor setting.

Home in Hull

Every room a water view updated kitchen & bath

4.85 out of 5 average rating, 33 reviews

Apartment in Brighton

The Curie-Perfect for Monthly Stays

4.91 out of 5 average rating, 123 reviews

An outdoor covered porch is depicted with a round dining table surrounded by four chairs. A gas grill is positioned near a seating area that includes a couch and two lounge chairs. The home's wooden shingles provide a natural backdrop.

Home in Gloucester

Gloucester Beach House, near Good Harbor Beach!