Vacation rentals in Hillsborough County

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Top-rated vacation rentals in Hillsborough County

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Guest favorite

Guest suite in Windham

4.99 out of 5 average rating, 243 reviews

Sunny, private and peaceful apartment!

Our home sit in a private and peaceful setting. It is perfect for the business travelers looking for a place to relax at the end of the day or anyone looking for a quiet place. Close to Castleton Banquet and Conference Center, Searles Castle, Canobie Lake Park, walking & biking trails, shopping and restaurant. Centrally located between Boston, beaches and mountain and lake region. Only 16 miles from Manchester Boston Regional Airport, 36 miles from downtown Boston, 3.5 miles from Interstate 93.

Oct 19 – 26

G$28,086 GYD per night

Guest favorite

Guest suite in Deering

5.0 out of 5 average rating, 225 reviews

Elegant Lodging in the Woods ~Privacy & Comfort!

Come relax and unwind in this nicely appointed secluded, guest suite. Privacy guaranteed in this smoke free “home away from home”. Country setting surrounded by mountains, lakes, hiking, golfing, Pat's Peak, Crotched Mtn. and Mt. Sunapee. Convenient location for day trips to the seacoast, Concord or Peterborough. Cozy cathedral ceiling bedroom/living room studio, private bathroom, kitchenette/workroom. Super clean! Private locked entrance. FREE onsite parking. Only 75 minutes from Boston.

Dec 13 – 20

G$18,983 GYD per night

Guest favorite

Apartment in Concord

4.98 out of 5 average rating, 281 reviews

Sunny Side Up

Sunny 2nd floor apartment set up in the trees in downtown Concord. A half mile walk or drive to historic main street shops and food. Private off street parking Centrally located right off of interstate 93 & 89. Plenty of seasonal activities nearby: Mountain biking, Skiing/Snowboarding/Snow Shoeing, Loudon Raceway, Apple Picking, Leaf Peeping, Lakes, Rivers, Ponds, Hiking The Space: Private open concept apartment with full kitchen, 1 bedroom with attached full bathroom. Cozy gas fireplace.

Oct 16 – 23

G$25,067 GYD per night

Guest favorite

Guesthouse in Wilton

4.95 out of 5 average rating, 573 reviews

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.

Sep 20 – 27

G$31,552 GYD per night

Guest favorite

Guest suite in Merrimack

4.99 out of 5 average rating, 150 reviews

Guest suite with king bed and private entrance

Come and relax in our spacious one-bedroom basement guest suite that is comfortable and bright. It has a private entrance with off street parking. The suite has a large living area, bedroom with king bed and private bath . The location is an ideal 20 minutes from the Manchester/Boston Regional airport and 10 minutes from the Merrimack Premium Outlets as well as a wide variety of restaurants. Boston, skiing, the beach and the #1 most hiked mountain in the world are all about an hour away.

Jun 9 – 16

G$19,152 GYD per night

Guest favorite

Loft in Derry

4.99 out of 5 average rating, 543 reviews

Comfort and Convenience in a Private Studio

*Please note that we are located on a main road * Welcome! No matter what brings you to Derry, we guarantee your comfort and convenience. Our 400 square foot studio boasts privacy, style, and value. The apartment is simple, modern, and warm. Coffee, tea, and treats are provided; we want you to feel like you are home away from home. Curl up for your favorite show with Hulu Live and enjoy your morning coffee out on the balcony. The space accommodates 2 comfortably (with room for up to 4).

Jan 8 – 15

G$20,387 GYD per night

Guest favorite

Guesthouse in New Ipswich

4.94 out of 5 average rating, 300 reviews

"The Porch" Your cozy home away from home!

Welcome to The Porch! Ready for a mini vacation, or just a place to hang out at, 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 rentals. 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!

Nov 21 – 28

G$17,667 GYD per night

Guest favorite

Home in Mont Vernon

4.96 out of 5 average rating, 136 reviews

Serenity on the Pond ~ Private Waterfront, Hot Tub

Experience 32 acres of stunning pond views! Immerse yourself in tasteful decor and luxurious amenities: fully equipped kitchen, outdoor spa hot tub, king bed, exercise room, yoga room, and boats to explore Horton Pond. Tucked away in the woods, Horton's Heron is a haven for wildlife - with frequent visits from beavers, geese, deer, bald eagles, turkeys, and more. Explore nearby hiking trails, ski slopes, enchanting waterfalls, and more great attractions all within easy reach!

Aug 23 – 30

G$193,954 GYD per night

Guest favorite

Guest suite in Hollis

4.98 out of 5 average rating, 115 reviews

Pine Estate - Private suite

Welcome to our spacious guesthouse located - 2 miles from Nashua - 5 minutes drive to the highway - 40 minutes to Boston and minutes from Hollis. Hollis is an active farming community offering beautiful orchards, nature paths, art studios and a winery. Beautiful private yard with a large patio where you can relax and enjoy nature at its best. Our place is ideal for a weekend get-away or business travelers. Please note there will be no exception to the no pets policy.

Nov 1 – 8

G$23,897 GYD per night

Guest favorite

Apartment in Derry

4.95 out of 5 average rating, 194 reviews

Victorian Charm.

Welcome travelers to your home away from home, in this stylish 1000sqft Victorian getaway! We offer charm, character & convenience. Enjoy your morning coffee in the turret, all the wonder of being outside (5 window view), yet all comforts of the warmth within. We are 40 minutes from Boston & 1.5 hours south of the White Mountains. We are 1.9 miles from 93N/S ramp. Free Private, onsite parking & Private entrance. We look forward to hosting you in beautiful NH!

Apr 5 – 12

G$22,780 GYD per night

Guest favorite

Home in Greenfield

4.93 out of 5 average rating, 119 reviews

Charming House on 7 Acres in Rural New Hampshire

This magical place has been our home away from home for twenty years and we are excited to share it with you. We hope you'll experience the same time-out-of-time feeling we get when sitting out on the deck in the early morning or looking up on a moonless night as the Milky Way snakes its way across the dark sky. The house sits on seven mostly wooded acres that abut a scenic beaver pond. The property is located on a quiet unpaved road in rural New Hampshire.

Dec 7 – 14

G$36,657 GYD per night

Guest favorite

Guest suite in Peterborough

4.99 out of 5 average rating, 120 reviews

Meadow View

Explore our sunlit sanctuary in a 275-year-old farmhouse. Our 'in-law' suite is a cozy retreat. Adjacent to Casalis State Park, enjoy scenic trails for biking, hiking at all seasons. Immerse in Peterborough's charm yoga studios, coffee shops and restaurants. Meadow View offers a 750 sq ft private suite with a king-size bed, clawfoot bathtub, and a mini kitchen. Your comfort is our priority. Experience the perfect blend of historic charm and comfort.

Sep 8 – 15

G$23,623 GYD per night