Pet-friendly holiday rentals in Windham

Gorgeous Lakefront Suite Apartment (Unit 3)

Get away to a lakefront retreat in beautiful southern NH! Enjoy our 1 bedroom unit that is part of a gorgeous 3 family waterfront home. This suite comes complete with a thoughtfully decorated living room, a stocked kitchen, and furnished with a queen-sized bed and an air mattress upon request. Enjoy free shared lake access! It is 8 minutes from I-93 and a short drive to Canobie Lake Park, Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White Mountains.

The Word Barn, Exeter, NH

Charming open apartment with a loft bedroom. Hardwood floors, barn beams, butcher block counter, full galley kitchen, private bath, vaulted ceilings - as part of the renovated original Raynes Farm Barn. This apartment is clean, private and isolated, with self check-in and plenty of outside space to enjoy. Located five minutes from downtown Exeter (w/plenty of take-out/delivery options) in an idyllic country setting, neighboring 100+ acre conservation land and a large network of wooded trails.

Linden Cottage - comfort, connection, convenience

Plenty of space at Linden Cottage. Built circa 1840. Restored and modernized in 2019-20. Home is a Greek Revival, New England style farmhouse with attached barn. Nestled in old Plaistow Village, in a safe, secure location near town hall and police station. Property has two connected, separate homes, and a large barn. Your accommodations are fully furnished. 4 bedrooms, 2 baths. 40 minutes to Boston. 20 minutes to Seacoast Beaches. A calming, spacious environment to unwind and be your best self.

One Level 2 bedroom suite on private cul-de-sac

Welcome to The Sama's Airbnb. Windham was recently named the #1 town in the Granite State. Here, you will enjoy a complete newly renovated private one level 2 bedroom suite complete with full kitchen, cozy living room, 40 inch LED TV with all channels, wifi, washer and dryer, new tennis court, 1/2 basketball court and pickleball, beautifully landscaped grounds on a private cul de sac yet close to Boston, beaches, mountains, shopping, great restaurants, Searles Castle, Canobie, & Tuscan Village.

Cozy en suite w/ high ceilings

 Relax in this peaceful private en-suite with breathtaking backyard views of the tall pine forest. Lots of natural light fills the space with room darkening shades to sleep in. Enjoy cozy nights by the fireplace and a well stocked granite kitchen. Great location only minutes to the Mass Pike. 25 min to Boston, 40 min. to Gillette Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Safe walkable neighborhood.

White Pine Cottage – Cozy 3BR w/ Fireplace

Welcome to White Pine Cottage - a cozy 1930s cottage in Stow, MA with modern amenities. Great landing pad if you are coming to the area to visit family, work or a weekend getaway. Located in quiet wooded neighborhood with very little traffic. Relax by the fireplace and enjoy a soak in the whirlpool tub. Convenient to local farms, orchards, golfing, wooded trails and more. Hudson, Sudbury and Maynard's restaurants and shops 15 minutes away and big city Boston / Cambridge only 40 minutes.

Newly Finished Guest Haven in Woburn

Welcome to our newly finished in-law lower level suite in Woburn! This private 1-king bed bedroom, 1-bath retreat features a cozy living room, a well-equipped kitchenette with a private entrance. Located on a quiet dead-end street, it’s just 5 minutes from Woburn Center, 15 minutes from Encore Boston Harbor, and a 20-minute drive to downtown Boston. Perfect for business travelers or couples, enjoy a peaceful stay with easy access to dining, shopping, and entertainment. Book your stay today!

The Dreamcatcher ~ Luxury New Apt, Prime North End

Wake up in a stunningly artistic, spacious studio in the heart of Manchester’s prime North End! Just minutes from downtown’s best restaurants & attractions, this safe, quiet & private apartment is in a high-end building with luxury finishes. Designer-renovated and brand new—from interior & systems to the roof. Featuring: - Full, well-equipped kitchen 🍽️ - Dedicated workspace 💻 - Convenient parking spot 🚗 - Bright, airy space filled with natural light ☀️ Full list of amenities below 👇

Winery Bungalow w/ Vineyard Views & Wine Tasting

Private two-story bungalow located on the Marble Ridge Winery property with beautiful views of our historic barns and vineyard. Perfect for couples, friends, or professionals seeking a peaceful retreat just minutes from downtown Andover. The home features a spacious living and kitchen area, large bedroom, enclosed porch for relaxing, and in-unit laundry. Your stay includes a complimentary wine tasting and 10% off wine bottle purchases. Please review all details and photos prior to booking.

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.

Big Fish, Little Lake - Fire Pit & Pvt Beach

Please read Other Details to Note @DiamondHomeCollection on Insta Come Fish & Kayak here! Our area is full of life and peace. Wake up to the loons early in the morning and go to bed listening to the owls. Watch the turkeys or fox cross the yard. Our homes are from the 1920's, we keep them alive and for the souls who love old homes. 45 minutes to the ski destinations ocean, lakes region, and hiking. Not waterfront, we own shares of waterfront.

Winnie's Place - Freshly Renovated 1800s Farmhouse

Welcome to Winnie's! Set in the picturesque New Hampshire countryside, Winnie's is a charming traditional New England 3 bedroom, 2 bath 1890s farmhouse with modern amenities. The home is newly renovated and updated with WiFi and smart TVs, but retains its historic character. It is perfect for a family getaway, romantic weekend or change of pace for those working from home. It is a “get away” without getting too far!