
Vacation rentals in Shirley
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Top-rated vacation rentals in Shirley
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Private sanctuary in the city w/ patio & backyard
Enjoy much needed R&R or alone time in this elegant 500-sqft master suite. A quiet space in a nice neighborhood amidst a buzzing metropolis, accessed through a private gated entrance. Sit back in the hammock, taking in the soothing sounds of water and birds chirping under the bright sky, having a private picnic in the backyard. In the winter, a ski resort is also conveniently accessible for fun in the snow. With the sights & sounds of the city mere minutes from the property to be explored. ~
4.95 out of 5 average rating, 140 reviews
Brand New Rustic Retreat | Private Apartment
Relax in this brand-new apartment on a quiet property in Pepperell. Attached to a larger home, this apartment above the garage is separate from the rest of the home with private entrances. Constructed in 2024, it features a beautiful kitchen, living area, a huge deck with patio set, and washer/dryer. It has one bedroom upstairs with an en-suite bath and a pull out couch with a full sized mattress downstairs. Great for those visiting family in the area, working, or attending weddings or events.
5.0 out of 5 average rating, 10 reviews
Cute & Cozy Groton apartment w/private patio
Cozy apartment with your own private patio; 5-min walk to downtown, shops, cafes, library & restaurants; hop on the Nashua River Rail trail where and walk/bike to neighboring towns. Enjoy all Groton has to offer, miles of hiking trails, rent a canoe or kayak, golf, horse riding, fishing, apple, pumpkin & berry picking; walk up to Bancroft Castle on Gibbet Hill where “Little Women" was filmed & enjoy the view. Don’t miss a visit to Groton Hill Music, our world class music performance venue 🎶
4.95 out of 5 average rating, 154 reviews
The Nutty Bird Lakehouse
Charming lakefront featuring 2 cozy bedrooms comfortably accommodating up to 4 guests, w/2 bathrooms. Nestled in nature, this home offers breathtaking lake views—perfect for relaxing with a good book and a hot cup of coffee. Enjoy the propane firepit on lower deck. For those looking for adventure, each season brings unique activities: swim, hike, and fish in the summer, or enjoy ice skating, sledding, snowshoeing, & scenic drives in winter. Embrace the beauty and tranquility year-round!
5.0 out of 5 average rating, 39 reviews
Private Apartment with 2 bedrooms
Quiet retreat for a Groton stay in restored circa1800 house. Off street parking, two bedrooms and bathroom, kitchen with washer and dryer. 1st floor bedroom room with french doors, king size bed, private bathroom with shower (+shelf), toilet, Duravit sink, heated floors and towel warmer. 2nd floor bedroom with vaulted ceilings and queen size bed, single bed, sofa and clothes storage. 2nd floor has a baby gate. Private entrance so you can come and go. No smoking anything anywhere.
4.96 out of 5 average rating, 24 reviews
Fitchburg In-Law Apartment
This spacious one-bedroom apartment in a quiet neighborhood has a private walk-in entrance with all the comforts of home. A full bath and kitchen, living room with TV, Laundry, WiFi, and a single bedroom with a queen bed. Tucked away from the hustle and bustle but close enough for any New England activity. Nearby Wachusett Mountain has plenty of hiking, skiing, and more for outdoor enthusiasts. Fitchburg State, Franklin-Pierce and Keene State are a short drive for visiting Parents.
5.0 out of 5 average rating, 28 reviews
Pool•1000mbpsWiFi•DeepTub•Fireplace•Full Kitchen
Welcome to Echo Point™️ Luxury Home 15min drive to Wachusett Mountain [The Space] Amenities and services → large 40x20 Pool (memorial day-9/1)SemiPrivate → Well-equipped kitchen → King Bed | Queen Bed | 2 Full beds → AC in all main rooms (memorial day-9/1) → Netflix/Roku → 6 seat Dining → On-Site Parking → Garden patio → Prep Vanity Add my listing to your Wishlist by clicking the ❤️ in the upper-right corner. Entire space is included in this rental. Please, make yourself at home.
4.86 out of 5 average rating, 28 reviews
Newly renovated, spacious, clean, 3 bedroom home.
Whether traveling for business or pleasure, this ideally located, pet-friendly home in North Chelmsford, Massachusetts, is accessible to major highways and commuter rails. The home is close to major hospitals, universities, and concert venues. The area is rich in America’s history and is surrounded by historical sites to visit all within minutes. The beautiful, light, airy living space boasts all the comforts of home. Our goal is to give you the best travel experience possible.
5.0 out of 5 average rating, 263 reviews
Farmhouse Guest Apartment
Welcome to our quiet private guest apartment! Our property, is surrounded by fields, woods, gardens, and a pond. You will enter through a shared entrance & stairway to the second floor in our home, but have an entire 725 sq. ft. guest apartment all to yourself that includes a living room, full kitchen, bathroom, and large bedroom with a desk. It has ample light with views of fields, stone walls, Christmas trees and our barn. Out back we have a pool, table & chairs you may use.
5.0 out of 5 average rating, 110 reviews
Stunning Sterling Sanctuary: Unwind on the Water!
Feel your worries drift away along the freshwater when you stay at this spacious 3-bedroom, 1.5-bath Sterling vacation rental! Nestled on the serene shores of East Waushacum Pond, this home ensures a fun-filled stay for all. Spend your days exploring the water-by kayak or paddle board-and put your toes in the sand at Sterling Town Beach! When the sun sets, cook a delicious dinner on the gas grill and roast s'mores over the fire for dessert. Adventure is calling -book now!
5.0 out of 5 average rating, 38 reviews
Guest home in downtown Fitchburg
10% off if booking 1 bedroom only. Exclusive use of the house but please do select the correct number of guests to display the final fee. Spread out in this centrally-located (downtown/urban) home built in the 1800s - where each room has been curated in a timeless tone, with relaxation and comfort in mind. Convenient to FSU, Game On Sports Complex, Fitchburg Art Museum, the commuter rail to Boston, Applewild School, Wachusett Mountain, Great Wolf Lodge etc.
4.95 out of 5 average rating, 131 reviews
Historic Loft with bathroom & kitchenette
A beautiful 1840s barn loft steps away from miles of hiking trails. Fully separate and private entrance, bathroom, and kitchenette. Enjoy a serene, rustic cabin atmosphere with a historic brick hearth and exposed beams. Southeast facing windows overlook patio, garden and ruins. Off the beaten path but only 5 min. to Rte 2, Rte 495, and Boston commuter rail. Drive times w/o traffic: 45 min. Boston, 20 min. Lowell/ Rte 3, Burlington, Bedford, Nashua 30 min.
4.91 out of 5 average rating, 475 reviewsPopular amenities for Shirley vacation rentals
Other great vacation rentals in Shirley

Country Retreat
4.99 out of 5 average rating, 93 reviews
Secluded Rustic Lakeside Cabin - Perfect Escape
4.94 out of 5 average rating, 85 reviews
Woody's scenic Hay Farm
4.89 out of 5 average rating, 61 reviews
Historical New England retreat
4.98 out of 5 average rating, 49 reviews
Bright and Cozy 1 BR Basement Apartment.
5.0 out of 5 average rating, 6 reviews
Downtown Groton | Hot Tub, King Beds, & Rail Trail
5.0 out of 5 average rating, 10 reviews
. Cozy Apt Near & Shops 3 Min to Boston Train Line
4.73 out of 5 average rating, 11 reviews
Fitchburg hideaway Home
5.0 out of 5 average rating, 4 reviewsDestinations to explore
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