Villa vacation rentals in Boston

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Top-rated villa rentals in Boston

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Villa in Gloucester

Over By Good Harbor: Phenomenal views and just

Just up the street from Good Harbor Beach, this well-appointed and perfectly located vacation rental is the ideal home base for your Gloucester beach vacation with family or friends. Over By Good Harbor sits prominently on a grassy knoll with abundant views of Good Harbor Beach and the sea beyond. The main floor wraparound porch is rivaled only by its large second-floor deck--the views only get better as you go up! The home is also just a short stroll down the street (0.2 miles) to Good Harbor's soft sand and sparkling waves. Enjoy the ocean breezes from your front porch or the verdant lawn planted with tiger lilies on the backyard deck. Inside, the open concept living room invites to you to gather or relax with family or friends and enjoy the flat screen tv and gas fireplace. Just beyond is an adjacent den with queen pullout sofa, widescreen TV, air conditioning, and door to back yard. The large eat-in kitchen is fully equipped with center island, large table and has a door to a back deck, the perfect place to grill. The second floor has three bedrooms, including a large King master with mini-split air conditioner, ensuite bath, walk in closet and sliders to the upper deck with superb views, another King bedroom with mini-split air conditioner, walk in closet and a smaller bedroom with double futon and window a/c. The washer and dryer are conveniently located at this level adjacent to another full bath with oval tub and shower. The garden level features a complete suite perfect for in-laws or an au pair. With Over by Good Harbor as your home base, you'll enjoy all that Gloucester and greater Cape Ann has to offer. When you are not at the beach, you'll find whale watching, fine cuisine, art galleries and shops all within a short drive. No smoking. GROUND FLOOR Living Room: Gas fireplace, multiple seating areas, and a wide screen TV with Roku. Kitchen: Electric range, microwave, dishwasher, disposal, granite countertops, breakfast bar, and a large dining table with chairs. Den: Flat screen TV, a mini split a/c, and access to the back deck and yard. Bathroom 1: Half bath. SECOND FLOOR Bedroom 1: Prime bedroom with King bed and a sliding door to the upper deck. Also includes a mini-split a/c, a ceiling fan, an extra-large walk-in closet, and an en-suite bath. Full Bathroom 1: Ensuite to the Master, with jetted tub, separate shower and dressing table. Bedroom 2: This room contains a King bed and a sliding door to the deck. Also includes a large walk-in closet, mini-split a/c, ceiling fan and flat screen TV. Bedroom 3: This room contains a double day bed, bureau, an a/c unit, and a deep closet. Full Bathroom 2: Oval tub and shower. Laundry: The washer and dryer is conveniently located at this level. GARDEN LEVEL A complete in-law or au pair suite with fully-applianced kitchen, a full bath, washer/dryer, living area and separate bedroom. EXTERIOR The two decks offer magnificent ocean views. There are two spacious yards. The back yard features a gas grill, outdoor seating, and an outdoor shower to rinse off the sand after the beach. PARKING There is parking for 5 cars.

Jun 14 – 21

G$185,279 GYD per night

Guest favorite

Villa in Newton

4.91 out of 5 average rating, 45 reviews

Explore Boston in style! Dream home, pool, sauna.

Relax in this calm, elegant lovely home with fully equipped high-end kitchen, 4 modern bathrooms, private fenced garden with hot tub and cold pool. Conveniently located in South Newton - one of the most desirable and safe suburbs of Boston. 3 minutes walk to a temple, 15-20 minutes drive to downtown Boston, 8 minutes drive to BC, 20 minutes drive to Babson, Bentley, Harvard & MIT. 25 minutes walk to a T (Green line "Newton Highlands"). Great restaurants and shopping areas within minutes drive.

Nov 13 – 20

G$143,921 GYD per night

Guest favorite

Room in Boston

4.86 out of 5 average rating, 7 reviews

Charming & Cozy Bedroom for Single or Couple

Welcome to our century-old home. Just a 5-minute walk away is Reservation Park for morning exercises or relaxation. Our serene neighborhood boasts tall evergreen trees. Our historic house was featured in the movie Spotlight, earning recognition with the 2016 Academy Award. Convenience is key with nearby bus routes (35, 36, 37, 38, 34, 34E, 40) to the Orange Line subway. Major amenities are a 15-minute walk away. Parking is available. Boston College is a 15-minute drive away. Warmly welcome!

Oct 25 – Nov 1

G$19,669 GYD per night

Guest favorite

Room in Boston

5.0 out of 5 average rating, 5 reviews

Cozy Room with 2 Beds and Den: Sofa & TV@3rd Floor

Mar 22 – 29

G$19,026 GYD per night

Guest favorite

Room in Boston

5.0 out of 5 average rating, 6 reviews

Charming & Cozy Large Room with 2 Single Beds & TV

Nov 12 – 19

G$23,833 GYD per night

Guest favorite

Villa in Cambridge

4.99 out of 5 average rating, 187 reviews

Phil's Harvard & MIT Home

* An entire apartment with a Harvard bedroom and an MIT bedroom Right at the heart of Harvard University, we are seconds away from university facilities and key attractions, making it a perfect place to stay if you are interested in exploring Harvard. The house is in traditional Victorian style with a lot of history while the interior was renovated in 2016. There are two bedrooms of unique styles: The Harvard and MIT rooms. * Please view my other listings for renting one of the bedrooms only

Aug 18 – 25

G$69,253 GYD per night

Guest favorite

Villa in Manchester-by-the-Sea

4.97 out of 5 average rating, 37 reviews

Secluded 20 Acre 10BR ultra contemporary Retreat

Family gatherings and family reunions. Make those family memories at this ultra contemporary take on a tree house. Original design based off the iconic Farnsworth house, updated with 10 Bed rooms of individual climate control atop of 20 acres of wildlife. Designer kitchen for the professional chef. Privacy that most movie stars long for. 5 min to beaches 10 min to Gloucester 20 min to historic Salem 45 min to Boston. Pesticide free landscaping Great location for family gatherings and reunions

Feb 25 – Mar 4

G$211,970 GYD per night

Villa in Gloucester

4.6 out of 5 average rating, 5 reviews

Sunset Cove: Waterfront home in the Goose Cove

Waterfront on the Annisquam River in Gloucester, this exceptional vacation rental boasts wonderful views of the river and of Ipswich Bay. You will never forget the sunsets seen from the deck or from the delightful gazebo. This home has a custom kitchen, spacious open concept living/dining room and lots of windows. There are two master bedroom suites with full baths on two separate floors as well as a sleeper sofa in the living room. There are water views from just about every window. Multiple

Oct 5 – 12

G$123,234 GYD per night

Villa in Gloucester

4.67 out of 5 average rating, 3 reviews

Helena House: European flair, close to Plum Cove

Situated on a knoll in Gloucester's Bay View neighborhood, Helena House offers peekaboo views of Ipswich Bay from the second floor bedroom with deck. Decorated with a European sensibility, the home is sunny, comfortable and cheerful, with hardwood floors throughout. A Queen Anne-style house, you can access the second floor via a front staircase that leads from the living room or from the back staircase via the kitchen. The bedrooms upstairs have AC units for comfort and the separated WC and

Nov 26 – Dec 3

G$83,230 GYD per night

Villa in Gloucester

Perrywinkle: Waterfront on Gloucester’s Rocky Neck

Waterfront on Gloucester’s Rocky Neck. Swim from your private beach or from your tidal dock and enjoy the waters of scenic Gloucester Harbor. Nestled close to the shore, vistas abound from its ample deck and most interior rooms. The view of sailboats, Gloucester’s fabled boulevard and the “Greasy Pole” are sure to amaze. Rocky Neck offers a choice of fine restaurants, boutiques and galleries. View work by local artists, or learn about some of the famous artists that resided in the nation’s

G$88,679 GYD per night

Villa in Rockport

4.67 out of 5 average rating, 3 reviews

Pleasant House in Rockport: Old-world charm and

This gorgeous in-town Victorian vacation rental home offers the best of all worlds; it has been beautifully renovated, but it retains the old-world charm of 14 foot ceilings, huge windows and large rooms. Modern updates include all new baths, windows, refinished hardwood floors, walls and woodwork. The house is perfectly situated just a short walk to Rockport Harbor, two beaches, restaurants, galleries, shops and the world-renowned Shalin Liu Performing Arts Center. The house has two

Sep 5 – 12

G$196,199 GYD per night

Villa in Gloucester

Salt Island Views: Walking distance to both Good

Good Harbor Beach, one of Gloucester's finest stretches of sand, is just a five minute walk from this comfortable ocean-view vacation rental home. Spend the day at the beach where you can swim, soak in the sun, or walk at low tide out to picturesque Salt Island. Prefer to stay at the house? Relax and read a book on its expansive deck taking in the views of the sparkling Atlantic with sailboats parading by. Inhale the fresh salt air, and listen to the muffled sound of the waves lapping the

May 27 – Jun 3

G$167,285 GYD per night