Holiday rentals in Ashland

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Top-rated holiday rentals in Ashland

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

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Guest favourite

Home in Rockport

5 out of 5 average rating, 43 reviews

New South End Home Quiet Lane To Old Garden Beach

Newer furnished home, 1/2 mile walk to quaint Bearskin Neck with Rockport shops & galleries. Old Garden Beach 1/4 mile walk down a quiet unpaved lane. 3 BR/3 Bath home available for summer weekly vacations. Family friendly, 3 prkg spaces, 2 decks, new appliances (laundry, microwave & dishwasher), hardwood floors, new rugs & beds, full basement w/ pool table, fenced yard. Several beaches, hiking trails nearby or take a train to Salem, Newburyport, or Boston. Longer term winter rental available

Guest favourite

Flat 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

Home in Rockport

5 out of 5 average rating, 3 reviews

Rockport Vacation Home, ocean views, 2 bed/1 bath

Beautiful, spacious, 2-bed/1-bath with ocean views. Lovely South End location with large yard and ample off-street parking. Beautiful hardwood floors, cable TV, Wifi, washer/dryer. Walk to cove on public path and close to several great beaches (Cape Hedge, Long Beach, Old Garden and Pebble Beach) and public ocean paths. High-season (June-Sept.) stays less than one week can only be booked based on last minute availability. Last minute inquiries are welcome as are winter or extended stay rates.

Guest favourite

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 favourite

Home in Coventry

4.87 out of 5 average rating, 127 reviews

Awesome 3 bed vacation lake house. Great location!

Three bedroom house right on Johnson’s Pond with private water access right in the back yard. House features queen master with deck overlooking the pond. 2nd bedroom features a full bed with twin bunk bed above along with a stand alone twin bed. 3rd bedroom has a queen bed. Perfect for one or two couples to share. Full kitchen and laundry along with WiFi and streaming services. Use of 2 kayaks and pedal boat. Just two miles from I-95, so everything in southern New England is just minutes away!!

Superhost

Cottage in Fairhaven

4.85 out of 5 average rating, 53 reviews

family friendly bayside get away

Secluded getaway. Right on the beach! Perfect for an all-in-one, off-the-grid vacation. This cottage is a hidden gem featuring an oversized patio with outdoor dining table and grill. The beach is so close you could cast a fishing line right off the patio. The calm bay waters are fed by the "gulf stream" so the water is always comfortable in season. Perfect for kayaking or a safe place to let the kids frolic for hours. EMAIL ME FOR A LINK TO A VIRTUAL TOUR CHECKOUTS ARE RESTRICTED ON SATURDAY

Guest favourite

Home in Scituate

4.94 out of 5 average rating, 18 reviews

Button Beach Cottage

Capture the breeze of the coast at Button Beach Cottage! •5 min walk to beach. •Brand new remodel. •Family friendly. •Oceanview balcony. •Luxury bunk room. •Dedicated workspace. •Outdoor dining area on spacious deck directly off kitchen. •Access to lifeguard beach Primary BR: king bed, TV, reading nook, ocean view & balcony. BR #2: queen bed, dedicated work space, ocean view & balcony. Bunk room: 5 twin beds with play space. Full bath on each floor. Tub, standing shower, washer & dryer.

Guest favourite

Cottage in Oakland Beach

4.98 out of 5 average rating, 137 reviews

Renovated cottage w water views and walk to beach

This beautiful cottage has waterviews from most rooms. 1st floor has 4 season porch, Living room opens to white kitchen w quartz countertops, dining area , bedroom and 1/2 bath. 2nd floor has 2 bedrooms & full bath with laundry. Outdoor sitting at Small table in the front garden & Adirondack chairs in the backyard. 1/2 block to the beach, kayak, fishing, boat launch, cafe & 2 restaurants. Home has been renovated w love and caring. No parties. Please be considerate of cleaning person.

Superhost

Flat 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 favourite

Home in Rockport

5 out of 5 average rating, 14 reviews

Adorable renovated house, steps from Front Beach

This charming home was recently fully renovated. The brand new kitchen features stunning granite countertops and stainless steel appliances. The large living/dining room features a 55" flat-screen TV comfy seatingnd a dining table for 4. There is a king bed in the Master Bedroom, along with a TV, ceiling fan, and air conditioning. The second bedroom has a twin daybed, with a second twin trundle bed underneath. The backyard features a patio with a seating for 4 and a gas grill.

Guest favourite

Home in North Falmouth

5 out of 5 average rating, 14 reviews

Luxury-Waterfront-Pets OK-Large Family-Bike Path

***WATERFRONT LUXURY HOME*** Ideal Monthly Stay for Large Family Pet Friendly Picturesque Wing Pond Kayaks (kids and adult), SUP'S, Row Boat, fishing Bike Path out front door Waterfront Outdoor Dining for 12 Soaring 9-18 ft. ceilings Waterfront Indoor Dining for 10 Chef Kitchen 18 Foot Kitchen Island Wolf/Viking/Miele Appliances Walk in Pantry Waterfront floor to ceiling windows 4,000+ SQ FT Lux Beds/Bedding Business Class Wifi Oversized Stone Fireplace Waterfront Master Suite

Guest favourite

Home in Scituate

5 out of 5 average rating, 19 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!