Vacation rentals in Ashland

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Top-rated vacation rentals in Ashland

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Guest favorite
The exterior view showcases a spacious two-story building with a gray siding finish. A large patio area is visible, furnished with a table and chairs, surrounded by lush green grass and trees. The large windows invite natural light, enhancing the serene outdoor setting.
Apartment in Framingham
4.9 out of 5 average rating, 293 reviews

Spacious 2 Br with All The Comforts Of Home

This a quaint apartment . Not your typical hotel room. In a country setting but 5-10 minutes from great shopping, restaurants, parks, colleges and major highways. Boston is 22.5 miles away. Fenway Park is 20 miles. Worcester is 17 miles. Private location overlooking conservation land. Walk to great hiking and biking trails but car needed for other activities. Full kitchen, laundry room and living room in addition to 2 br and bath. It has the comfort of a home away from home. Please NO PETS.

Top guest favorite
The exterior of a two-level home is depicted, surrounded by lush green lawns and mature trees. A pathway leads to the welcoming entrance, flanked by garden beds featuring various plants. The house features a traditional design with large windows allowing for ample natural light.
Home in Holliston
4.97 out of 5 average rating, 110 reviews

All New Private Country Setting (2 Level-No Share)

We built this 2 level home 6 years ago and it is located on Washington St in the towns Historic district. The home is set back from street with a long country style driveway. We designed it with large windows in all rooms, welcoming the sunlight and peaceful setting. Access to clean and empty garage for storage (No parking). We have no personal items in the guest level - all closets and dressers are empty and yours for full use! Co Host reside in lower separate entrance suite. Nothing Shared.

Top guest favorite
A charming farmhouse stands amidst a lush garden, surrounded by vibrant purple irises. The white exterior of the house contrasts beautifully with the greenery, providing a serene atmosphere. Tall trees and a manicured lawn enhance the inviting landscape of the property.
Guest suite in Weston
4.99 out of 5 average rating, 183 reviews

Flower Farm Getaway 2BR, 20 Min To Boston

Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 20 minutes from Boston. Only a mile from the Mass Pike & Rt. 128 (I-95). Centrally located to all Rt. 128 businesses, colleges & hospitals. A 7-min drive to Riverside Green line “D” subway stop into Boston (parking available), or commuter rail stops (Auburndale, Wellesley & Kendal Green Stations). It's a 20-minute drive to Amtrak's "Route 128" station to NYC and points south.

Top guest favorite
The kitchen features a modern layout with white cabinets and granite countertops. Stainless steel appliances, including a French door refrigerator, are complemented by a tiled backsplash. Natural light enters through multiple windows, illuminating the spacious area. Two area rugs add warmth to the tiled floor.
Home in Framingham
4.98 out of 5 average rating, 253 reviews

2BR Lovely 1900s Home | 25 Min to Boston | 1200ft²

Welcome to our Charming 1900s House! 1200sqft 2nd/Top Floor Private Apartment @ our 3-Rental Property **Children 10+ Welcome** Granite Kitchen w/ Dishwasher - Fully Equipped w/ Essentials & Cookware Tiled Bathroom w/ Bathtub & Shower 2 Queen Bedrooms 2 Desks & Chairs Reclining Sofa & Glider Loveseat Laundry Room (Basement) Patio & Grill Driveway Parking—2 Spaces Private Entrance 25 Min Drive to Boston 15 Min Walk to Train 5 Min Walk to Jack's Abby 3 Min Walk to Park Deep Cleaned & Sanitized

Top guest favorite
A serene bedroom suite features a spacious bed with a light blue quilt, flanked by two windows allowing natural light. A cozy sitting area includes a comfortable couch with patterned pillows, and decorative rugs are placed on the hardwood floor, enhancing the inviting ambiance.
Guest suite in Dover
4.97 out of 5 average rating, 302 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

Graceful country oasis in a renovated 125 year old historic home, 35 minutes driving time from downtown Boston. (Important-stair climbing required to reach bedroom suite.) I welcome quiet, mature guests as this is a very peaceful (non-party)environment. We are located on a scenic road in sophisticated Dover, Ma, a commuter/country setting, with miles of hiking trails and roads ideal for cycling. I have owned and loved this home for 35 years and take great joy in its charm and outdoor spaces.

Top guest favorite
A spacious living area features a vaulted ceiling, large windows allowing natural light, and a comfortable sofa. A wooden coffee table sits at the center, complemented by patterned armchairs. Adjacent, a farmhouse dining table accommodates six, enhancing the open layout.
Place to stay in Sherborn
4.98 out of 5 average rating, 322 reviews

Entire Historic Carriage House with Fireplace & AC

Escape to our charming Carriage House in the Historic District of Sherborn which offers the feel of a country retreat without being far from civilization. Great for travelers looking for a peaceful getaway, checking out nearby colleges or attending a celebration like a wedding or graduation. You will love the feel of the Carriage House, its spacious living and dining room, well-equipped kitchen, and the beautiful grounds. Check us out on IG @carriagehousema. NEW in 2022: Mini-split AC!

Top guest favorite
A historic stone farmhouse is set on a spacious green lawn, complemented by a vibrant red barn in the background. Tall trees provide shade, and a carefully arranged stone border outlines the lush garden area, creating a tranquil outdoor setting.
Farm stay in Hopkinton
4.96 out of 5 average rating, 147 reviews

1790 Stone Manor Farm

This historic New England farm and home is on almost 7 acres of land with mature gardens and places to hike, it is a warm and inviting place to spend lovely summer days by the pool and enjoy warm nights by the fire in the fall and winter. Kitchen and bathrooms all renovated. Located centrally in Ma- 90/495 interchange. Located 45 minutes from Boston, beach, history, mountains, lakes, & NE sports. This home is in historic Hopkinton, where the Boston Marathon starts, center of MA.

Top guest favorite
A spacious living area showcases large windows that invite natural light and views of the surrounding landscape. Comfortable seating includes a couch and armchair, complemented by a decorative fish tank. A dining table is visible in the background, enhancing the open and airy atmosphere.
Guest suite in Uxbridge
5 out of 5 average rating, 287 reviews

Zen Inspired Retreat with Private Forest Trails

Zig-Zag Trails blends modern comfort with the charm of rural living. Set on 65+ acres of private meadows and forests, our master guest suite is the perfect retreat to relax and recharge. Explore scenic zig-zagging trails, perfect for hiking, mountain and E-biking, and unwinding in nature—a haven for outdoor enthusiasts and homebodies alike. 📍 1 hour from Boston 📍 35 minutes from Providence 📍 25 minutes from Worcester Escape to Zig-Zag Trails—where tranquility meets adventure.

Guest favorite
A stylish wooden bed frame with a floral-patterned comforter and two pillows is featured in the sleeping area. A bedside table with a lamp stands next to the bed, and a wooden dresser is positioned nearby against the wall.
Apartment in Framingham
4.96 out of 5 average rating, 303 reviews

Comfortable apartment in Framingham

Newly renovated basement apartment. Private entrance and living space which includes a kitchen, bedroom, hallway and bathroom. The kitchen has a microwave and refrigerator, but no stove. Very clean and well maintained. Comfortable queen size bed. Driveway space for 1 car and plenty of street parking. Great location. Walking distance to Dunkin' Donuts, Domino's Pizza, and local shops. Less than 2 miles from the Mass Pike. No Pets / No Smoking inside

Guest favorite
A well-lit sleeping area features a spacious bed covered with a light-colored blanket. A desk and chair are positioned near a window with blinds. A decorative plant sits in a pot beside a wooden dresser, adding a touch of greenery to the neutral palette.
Guest suite in Marlborough
4.86 out of 5 average rating, 300 reviews

Professional Accommodations!

Across from Lake Williams near 20 and 495, completely separate entrance and parking, all newly renovated, central air, high speed fios internet, 43 inch smart tv, desk, mini fridge, microwave in separate eating area, walk to Dunkin Donuts, Your completely private space! Walk to restaurant with indoor and outdoor seating. For your safety during Covid I keep 72 hours Between guests and have unit professionally cleaned!

Top guest favorite
A comfortable seating area is highlighted by two stylish armchairs and a soft sofa. Natural light filters through large windows that overlook the greenery outside. A modern rug is placed on the wooden floor, complementing the decor, while a lamp and coat rack add functional touches.
Home in Framingham
4.97 out of 5 average rating, 100 reviews

Cozy en suite w/ high ceilings

Enjoy this peaceful oasis with backyard views of the tall pine forest and soothing sounds of a patio waterfall. Private entrance en suite features off street parking, air conditioning, easy access to major amenities. 10 minutes to Mass Pike. 5 minutes to Framingham State University.  Very safe and easily walkable neighborhood. Use of propane fire pit upon request. 

Top guest favorite
A leather recliner sofa is positioned in a light-filled living area, complemented by a large painting of a serene landscape. A full-size refrigerator and a TV stand are visible, providing essential amenities. An entryway is seen in the background, leading to additional rooms.
Guesthouse in Framingham
4.97 out of 5 average rating, 312 reviews

Private guest house on beautiful country road

Welcome to Grove Street Studio - our detached guest house which sits right behind our home on one of the most beautiful streets in the area. This two-room studio has everything you need for a comfortable stay including your own deck looking out to the woods behind. Perfect for for a hotel alternative for someone working temporarily at nearby businesses.

Popular amenities for Ashland vacation rentals