Holiday rentals in New Ipswich

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Top-rated holiday rentals in New Ipswich

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

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Top guest favourite

A charming Cape-style house is positioned amidst vibrant autumn foliage. The white exterior is complemented by a wooden addition with a gabled roof, while landscaped grass and low shrubs surround the entrance. Sunlight filters through the trees, enhancing the inviting atmosphere.

Cottage in Temple

Quiet Cape-style cottage with garden in the woods.

Enjoy a tranquil get-away in a rural New England town. Just over an hour from Boston, and a perfect gateway to the Monadnock Region. Wonderful area to hike, bike, ski. Near other little towns with plenty of venues in the arts, music, and dining, or dine in with a fully-equipped kitchen, large dining area with a flower garden view. Huddle around the fireplace or outdoor fire pit to view stars & fireflies and hear owls and crickets! Awake in a quiet paradise. Internet is 110/112 MB WELCOME ALL!

4.96 out of 5 average rating, 72 reviews

Top guest favourite

A quaint cabin sits amidst lush greenery, framed by tall trees. The blue exterior features a welcoming porch, flanked by blooming white hydrangeas. A well-kept lawn complements the serene landscape, providing a peaceful retreat in a natural setting.

Guest house in New Ipswich

"The Porch" Your cozy home away from home!

Welcome to The Porch! Ready for a mini vacation, or just a place to hang out, or work from? You are most welcome here! . This cozy cabin is very flexible and user friendly! It is private to only your group! The downstairs with all it offers, is for one or two person stays. The upstairs becomes available if you enter 3 or more people. This building is in the backyard of our home, as in photos on our Airbnb site, Other info is listed there also! Info book is in room! Welcome! (no pets)

4.95 out of 5 average rating, 428 reviews

Top guest favourite

The exterior of The Ginger Bed is showcased, featuring a light green facade with white trim around the windows and door. A welcoming orange door is prominently displayed, surrounded by a landscaped area with colorful mums and autumn foliage.

Guest suite in Ashburnham

The Ginger Bed King Suite

Come for the lovely country setting, the winter beauty, amenities, neighborhood, convenience, privacy, spaciousness, and the comfortable bed. Close to many wonderful hiking/biking paths, rail trails, Wachusett ski area, Jewel Hill, Lake Wampanoag, Kirby area. WI-FI, TV ( Hulu and Netflix), refrigerator, microwave, coffee/tea maker, reading lights, table area, continental breakfast, parking... Good for couples, solo and business travelers. (Key pad for Covid safe entry) Everyone is welcome!

4.98 out of 5 average rating, 541 reviews

Top guest favourite

Chalet in Rindge

Cabin & Sauna on Lake Monomonac

Beautiful Finnish House and a Sauna on Lake Monomonac. 2 Queen bedrooms, full kitchen and bathroom. Maximum occupancy 4. Perfect for a family reunion, get together or event. Authentic Finnish wood burning sauna, boat dock, kayaks, canoes, nature, wildlife, birding, walking, running, hiking, biking, snow skiing ATV, UTV, snowmobiling. Close to Mt Monadnock, Mt. Wachusett, Pats Peak, Granite Gorge Mountain Peak, and Crotched Mountain for hiking and skiing. 1 hr. from Boston 4 hrs. from NYC

5.0 out of 5 average rating, 52 reviews

Top guest favourite

A cascading waterfall flows over natural rocks, surrounded by lush greenery. Delicate pink flowers in the foreground enhance the serene setting, where the sound of rushing water and natural beauty create a peaceful atmosphere.

Guest house in Wilton

Cottage beside a waterfall

Our 1840’s renovated grist mill is located in the beautiful Monadnock Region. The house and cottage are situated on twelve acres and includes gardens, an orchard, berry bushes, grape vines, beehives, a dog, and a tremendous waterfall. We are close to many of nature’s gems including Mount Monadnock, Pack Monadnock, the Heald Tract hiking trails, skiing, snowshoeing and swimming. Also the acclaimed MacDowell Arts Center, Andy’s Summer Playhouse, Andres Institute of Art and the Waldorf Schools.

4.94 out of 5 average rating, 689 reviews

Guest favourite

A bright kitchen is featured, showcasing wooden beams and vintage wallpaper. A dining table with blue chairs is set for two, while a modern sink, a stove, and a refrigerator are integrated into stylish cabinetry. Natural light filters through a large window, illuminating the warm wooden floor.

Tiny home in New Ipswich

Quaint, Historic Tiny Home

The history of this “little red shed” is as storied as New Ipswich herself. Built in 1804, she was a law office, a post office, then a tiny cigar store. This home strikes the perfect balance of historic charm and modern hospitality. It includes newly remodeled half bath with shower, a fully stocked kitchen, AC/heat, wifi, and both a loft bed and pullout sofa. Sat in the heart of charming downtown New Ipswich, on the Barr Estate, this remodeled space offers a truly one of a kind experience.

4.98 out of 5 average rating, 59 reviews

Guest favourite

Home in Ashburnham

Cozy, year-round Lakefront Retreat.

Nestled in nature at the end of a quiet, wooded road, this cozy waterfront home overlooks peaceful Winnekeag Lake and is surrounded by cedars and maple trees. Wake to glowing sunrises over the water and the call of loons. Spend summer days swimming, kayaking, and fishing, or explore scenic hiking trails nearby. In winter, enjoy and unwind by the fireplace after skiing, and , relax in the radiant sunroom with heated floors and windows on 3 sides—perfect for taking in the beauty of the lake.

5.0 out of 5 average rating, 14 reviews

Top guest favourite

A grassy backyard extends towards a calm lake, with a wooden deck featuring a barbecue grill. In the background, a row of chairs lines the shore, complementing the natural setting of trees and water.

Home in Ashburnham

Lake House with island and boats to cruise on!

This is a wonderful place to put aside your busy life. No matter the season, our lake home is the feel of relaxation, cozy and comfort. Whatever yours is, you will have the best of all seasons here. Spring flowers popping up, summer water fun, beautiful fall foliage and winter ice-skating, just to name a few. Start the day with a warm cup of coffee watching the sun rise over the trees. Fill the rest with fun and adventures. Finish it with a campfire, s'mores and a nice glass of wine.

4.96 out of 5 average rating, 70 reviews

Top guest favourite

A modern home features a combination of dark siding and natural wood accents, positioned among tall trees. A welcoming porch extends from the entrance, complemented by an American flag. The surrounding area includes a gravel path and vibrant greenery, providing a serene atmosphere.

Home in Jaffrey

Willow Falls Home ~Hot tub & Waterfront

Constructed waterfall views are just feet away from you! Not far from Boston, RI or CT, this newly designed home is located at a privately viewed pond, in New England, near Mt. Monadnock! Kick back, relax & listen to the water falling in a screened-in gazebo, or in the outdoor hot tub! Or view it all at the picture windows and enjoy the solitude at this picturesque retreat! Inside you'll find multiple lounging areas, luxurious beds, a fully stocked kitchen and a fun game room.

4.98 out of 5 average rating, 106 reviews

Top guest favourite

A warm kitchen area features wooden paneling and a round dining table set for two. A small, cozy electric stove is situated near the table. The space is complemented by a full-size refrigerator and a microwave, with decorative touches on the walls.

Flat in New Ipswich

Quiet country apartment in farmland setting.

Cozy studio located on 90 acres of private property that includes conservation woodland and fields, perfect for a challenging hike and wildlife viewing. Apartment has 1 queen bed with roll out cot and a full bathroom with shower and selection of towels. The fully equipped kitchen comes with a refrigerator, microwave, and the washer and dryer downstairs mean less packing. When not out and about exploring the countryside there is WiFi and a smart TV to keep you entertained.

4.96 out of 5 average rating, 143 reviews

Guest favourite

A comfortable sofa is positioned near a window with sheer curtains, allowing natural light to illuminate the space. A decorative pillow with text is placed on the sofa, while a glass of wine rests on a wooden table outside, visible through the window.

Cabin in Winchendon

The little house on Mirror Pond

Escape to our fully renovated tiny pond house on the serene Mirror Pond. Perfect for up to 4 guests, enjoy swimming, kayaking, or floating on tubes. Unwind by the fire pit, barbecue on the deck, or cozy up by the fireplace with board games on cooler days. With great WiFi, it’s also ideal for a peaceful work retreat. Whether you're here to relax, or get some work done, this tranquil hideaway offers the perfect blend of adventure and relaxation.

4.96 out of 5 average rating, 134 reviews

Guest favourite

A bright living space features a comfortable sofa, a modern electric fireplace, and a television mounted on the wall. Natural light filters through the room, complemented by houseplants and a decorative bowl on a wooden coffee table. The open layout connects to an adjoining area.

Flat in Peterborough

Cute, Quiet, Art-Filled Apt.

This above-garage apartment is cozy and comfortable. Perfect getaway! Just 1.5 miles from Peterborough in the beautiful Monadnock region this gem has easy access to trails (backyard) and lakes. Quality linens, tasteful decor, great coffee and a spot to stash all your gear in the breezeway. Guests share main entrance with owners (but separate dwelling) who respect your privacy. Apartment access thru narrow stairs off breezeway.

4.92 out of 5 average rating, 131 reviews