Pet-friendly vacation rentals in Milton

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Top-rated pet-friendly home rentals in Milton

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Top guest favorite

The living area features a dark blue sofa facing a mounted flat-screen TV. A wooden coffee table is positioned in front, surrounded by natural light from nearby windows. The white walls and sleek countertops contribute to a modern, open space. A minisplit unit is visible for climate control.

Home in Lakeside Marblehead

5 out of 5 average rating, 123 reviews

Seaside Cottage

Here you are down the street from some of Marblehead's hidden gems such as Redds Pond, Browns Island & Old Burial Hill Cemetery. One car parking. 5 minute walk to the beach, shops & restaurants. Fully fenced in yard with turf grass. One bedroom with a low profile queen sized bed. In unit washer/dryer. Full bath with tub. Newly renovated kitchen with major appliances: stove, oven, dishwasher, fridge, Nespresso maker & microwave. Sheets & bath linens provided. Minisplit A/C. Home is all one level.

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Condo in Plymouth

4.77 out of 5 average rating, 154 reviews

Clear Pond Pet Friendly Inn

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

A hot tub emits a soothing green glow, surrounded by softly illuminated string lights. The tranquil outdoor setting features trees in the background and hints of nearby greenery, creating a relaxing atmosphere for evening enjoyment.

Home in Plymouth

4.83 out of 5 average rating, 322 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.

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A private wrap-around porch is shown, featuring a wooden dining table with matching chairs. Sunlight filters through, illuminating the surrounding neighborhood with cozy homes and greenery visible in the background. The space is complemented by a decorative plant on the table.

Apartment in Swampscott

4.87 out of 5 average rating, 109 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.

Top guest favorite

The historic carriage house is presented in a charming turquoise color, surrounded by lush greenery and flowering plants. Tall windows provide ample natural light. A spacious yard is visible, framed by a low stone wall and iron fence.

Guesthouse in Rockport

4.99 out of 5 average rating, 102 reviews

Carriage House | Steps to Beach| Dog Friendly

Our historic carriage house in Downtown Rockport has everything you need for the perfect getaway, all year long! A two-minute walk to beaches, shops, galleries, parks, and playground. A peaceful family and pet-friendly space with all the amenities you need for a comfortable stay: laundry, full kitchen, queen sized bed with en-suite bathroom and a sun room that converts to an extra sleeping space perfect for kids. A 5 minute walk to the train for day trips to Salem, Gloucester, and Boston!

Guest favorite

A sitting area features a classic blue wall with two framed botanical prints above a marble fireplace. An orchid in a pink pot and a small potted plant add color. A comfortable armchair and a leather sofa complete the cozy layout, enhancing the inviting atmosphere.

Apartment in South End

4.96 out of 5 average rating, 374 reviews

Charming South End Duplex (Pets Ok)

Ground floor duplex with backyard. In the heart of the South End. The best restaurants and coffee shops in Boston are within 1-2 blocks. We are pet friendly with a dog park 1 block away. A Victorian brownstone with 2 floors and a big backyard. 2 separate bedrooms (queen beds) with exposed brick and heavy duty AC units in each BR. The third bed is a queen sized Serta air mattress(easily inflatable) A massive parlor level, very spacious. Easily the best neighborhood in Boston.

Guest favorite

A charming garden area surrounds the cottage, featuring vibrant flowers and greenery. A white picket fence defines the space, while two blue shutters flank the windows. A small stone feature adds interest, and a soft gravel path leads up to the entrance.

Cottage in Gloucester

4.97 out of 5 average rating, 125 reviews

Sunny & private cottage in Lanesville Village

Sunny private 2 bedroom cottage with large garden, deck,and great Lanesville location near the ocean. In the off-season, a quiet escape -perfect for focused work, writing, painting or reading, Please contact host for discounts on longer stays (30 days + from Dec - April) Living room with large flat screen smart TV with Roku, fast internet, and lounge with pull out couch and pocket door for privacy. Dogs under 55 lbs allowed (no more than 2 ) no cats. Yard is not fenced in.

Guest favorite

A private backyard area is enclosed by tall white fencing, providing a secluded green space. Several mature trees offer shade, while a neatly maintained lawn is positioned throughout. The pathway is visible, leading towards the entrance of the yard.

Townhouse in Waltham

4.96 out of 5 average rating, 121 reviews

Boston's Luxury Home: Pet-Friendly, 4BR, Sleeps 10

Luxury, modern, bright townhouse offering a gourmet kitchen is available for your next getaway. A mere 1 min walk to Waltham Commuter Rail Station, buses to downtown, famous Moody street & Main street with 50+ restaurants, grocery stores, ALL WITHIN WALKING DISTANCE. Easy commute to anywhere within Waltham, Boston, Cambridge, Watertown. Ideal place for working professionals, families, or someone visiting Boston for the weekend. ATTACHED GARAGE PARKING INCLUDED for 2 cars.

Top guest favorite

An outdoor deck area is surrounded by greenery, featuring steps leading up to a shaded seating space under a wooden structure. Lush plants and a stone wall border the space, contributing to a sense of privacy and tranquility.

Home in Wrentham

4.88 out of 5 average rating, 104 reviews

Backyard Oasis with Hot Tub

HALF OF OUR HOME WITH PRIVATE ENTRANCES we live on other side of home private entrances to home & backyard. Private bath Kureig refrig microwave toaster oven Not a full kitchen Big screen TV 3 min Wrentham Outlets 9 min Gillette Stadium 13 min Xfinity center Shopping concert game come home soak in the hot tub . Fire-pit and private hot tub open all year round! heated lap pool Open June thru Oct Grilling area May 1st large Weber gas grill Blackstone gas. Flat grill

Top guest favorite

A wooden cabin with a sloped roof is surrounded by a snow-covered landscape. The porch is visible, along with two friendly dogs playing in the snow. Tall trees, dusted with snow, create a serene, wintry atmosphere.

Cabin in Rockport

4.97 out of 5 average rating, 447 reviews

The Solar Powered Dogtown Cabin at Applecart Farm

Beautiful hand built very private cabin with master bedroom and large loft located deep in the woods of Cape Ann. Walking distance to down town Rockport and waterfront. Friendly miniature horses just 200 feet away that children love to visit. Applecart Farm is happy to have guests of diverse backgrounds and interests. Pets are allowed only with advanced request to ensure safety of guest and residents pets. NEM 1450 plug for EV charging.

Guest favorite

A spacious yard is outlined by a wooden fence, featuring a dining set under a leafy tree. The grass is green, and a barbecue grill is visible nearby. Surrounding buildings are partly obscured by the foliage, creating a sense of privacy.

Apartment in Federal Hill

4.89 out of 5 average rating, 115 reviews

West End / Federal Hill Line 2 bed, double parlour

Large full apartment with yard in a great location. Between Atwells & Broadway and walkable to Downcity in 10 minutes. Enjoy dozens of restaurants, cafes, shops, studios, and attractions all in the neighborhood. Multiple breweries, farmer’s markets, art pop-ups and murals in immediate area. We are happy to host well behaved pets - please let us know some details about your pets in advance so we can let you know if it will be a good fit

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Apartment in Ipswich

4.85 out of 5 average rating, 278 reviews

Comfortable house, close to beach and downton IPSW

This home has all you need for your business or gateway in New England . With everything a Nice hotel has to offer ,this will be your home away from home. The Kitchen is fully equipped and you will have the entire place for yourself . You will be in walking distance to the train station in dowtown Ipswich and biking distance to the beach and Crane's Castle. Also you can explore Cannoing or paddling on the nearby Ipswich River.