Vacation rentals in Derry

5 out of 5 average rating, 42 reviews

A serene coastal view reveals a stone jetty extending into calm waters, dotted with sailboats. Lush greenery frames the foreground, while the distant landscape features a quaint town along the shoreline, under a clear blue sky with scattered clouds.

Home in Rockport

New South End Home Quiet Lane To Old Garden Beach

Newer furnished home, 1/2 mile walk to quaint Bearskin Neck with Rockport shops & galleries. Old Garden Beach 1/4 mile walk down a quiet unpaved lane. 3 BR/3 Bath home available for summer weekly vacations. Family friendly, 3 prkg spaces, 2 decks, new appliances (laundry, microwave & dishwasher), hardwood floors, new rugs & beds, full basement w/ pool table, fenced yard. Several beaches, hiking trails nearby or take a train to Salem, Newburyport, or Boston. Longer term winter rental available

4.96 out of 5 average rating, 302 reviews

The spacious bedroom features two queen beds with light green bedding, positioned beside a large window that allows natural light to fill the room. A modern bathroom is visible in the background, with neutral tones and elegant fixtures. Wooden benches provide additional seating.

Apartment in Winthrop

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

4.84 out of 5 average rating, 111 reviews

An outdoor seating area features bright orange Adirondack chairs arranged around a fire pit, complemented by a shaded area provided by a large umbrella. The cottage is visible in the background, showcasing its coastal charm with fresh landscaping enhancing the inviting space.

Cottage in Newbury

Designer decorated-Sunset Bliss- Beach 3 min walk

Peaceful Plum Island cottage, renovated fall of 2018 and 2023 with New England coastal charm. Open floor plan and water views of the marsh, a short 3 minute walk to the beach. Watch the sun rise over the Atlantic and enjoy the spectacular sunset directly in front of the house for a nightly show. Walk the cottage for ice cream, Rip tide & the Sunset Club for cocktails and dinner. Beach, boating, fishing, wildlife sanctuary, and the historic downtown Newburyport all just 40 miles from Boston!

4.87 out of 5 average rating, 109 reviews

An aerial view captures the scenic coastline and sandy beach lined with boats. A variety of residential buildings dot the landscape, interspersed with greenery. The neighborhood showcases the charm of coastal living, with the sea and a pier visible in the background.

Apartment in Swampscott

Ocean views, Large Deck, Grill, Kid/Dog Friendly

The product of a complete gut renovation in 2020. The unit is 300 yards to Fisherman's Beach at the bottom of the street. The apartment is the 1st floor of a two family home (our family lives upstairs). It consists of 2 bedrooms, 2 full baths, pro kitchen, open living/dining area. The driveway can fit 2 cars (tight). There is additional parking at the bottom of the street. Please see house rules settings for holiday minimum bookings. We are pet friendly, but require case by case approval.

5 out of 5 average rating, 3 reviews

A charming cottage is nestled among vibrant trees, displaying shades of orange and yellow. Outdoor seating is provided by several blue chairs arranged on a manicured lawn, with a pathway leading to a sunroom that features numerous windows allowing natural light to flood the space.

Home in Wells

"In Tempore" Cottage

Relax in this calm, stylish space. New for 2024, "In Tempore Cottage" at Summer Village! Downtime at the right time! Enjoy the many amenities: tennis, pickle ball, putting green, ball fields that provide unobstructed stargazing on clear nights, heated pools, hot tub, indoor gym, playground. Ride the resort trolley in season. Bike, or walk along peaceful forests. New! Discounted rates for fall! **Linens and towels not included. Guests must supply their own or rent from Cottage Linens**

Guest suite in Kittery Point

A round mirror with a wooden frame is positioned in front of a glass-enclosed walk-in shower. The shower features a modern showerhead and a tiled wall, providing a clean and contemporary look.

4.95 out of 5 average rating, 288 reviews

Romantic Spa By The Ocean. Hot Tub. Walk to Dining

Just 10-minutes from charming Portsmouth! Enjoy the crystal-clean hot tub on your private patio. Feet-up pampering and special gifts throughout this adorable Maine coastal getaway. Drive into Portsmouth, or stay-in and pamper yourselves. Walk to the Kittery Point town wharf, historical sites, the Bistro and Wharf Restaurant, and catch views of the lighthouse and spectacular sunsets. 5-minute drive to a beach or world-class restaurants, 10-min to the famous Kittery Outlets.

4.9 out of 5 average rating, 10 reviews

Home in Harrisville

Harrisville Lake House - A Tranquil Get-Away

Welcome to Harrisville Lake House, a tranquil lakeside retreat for family and friends on the shore of Harrisville Pond. Our cherished home is perfect for a week-long escape, where nature’s beauty meets the warmth of a family home. Our home is a treasure trove of antique furniture, worldly keepsakes, and artwork. Fall colors in September and early October are breathtaking! From the haunting call of loons to the majestic flight of bald eagles, nature is a daily delight!

4.96 out of 5 average rating, 78 reviews

A covered porch area is furnished with two white wicker chairs, accompanied by decorative pumpkins and colorful autumn leaves. String lights are draped along the railing, creating a welcoming outdoor space that invites relaxation in a residential setting.

Apartment in Northfield

The Lady Grand at Northfield

Comfy, Private, First Floor Appartment. Self Check-In, Parking New England vacation rental within walking distance to our scenic historic main street. Centrally located to bike parks, white water park, numerous skiing and hiking options. In an hour's drive, it is possible to be at the shore, in the mountains or one of our great cities! Our guest suite has a private entrance to a mud room and is fully furnished, full kitchen and bath and can sleep up to 6 people.

4.93 out of 5 average rating, 114 reviews

Cottage in Newburyport

Sunset Waterfront Privacy Beach

Newly renovated waterfront with private beach and panoramic views. Enjoy the private pool (heated June through September). Unmatched privacy and large outdoor living. Front row wildlife views of marsh. Bikes to venture out and discover the island. Evenings by the firepit watching the tides roll in. Amazing sunsets! Private sleeping loft in bedroom 3 perfect for older kids. Modern kitchen with a washer/dryer combo. Wake up to a fresh Tea or Coffee.

4.98 out of 5 average rating, 87 reviews

A spacious lawn is surrounded by trees, providing a serene backdrop for outdoor activities. Comfortable seating is arranged near a firepit, while a rustic barn stands in the distance. A well-maintained walkway leads to the entrance of the charming red house.

Cottage in Hill

The red house

Charming Country Retreat in Hill, NH - Perfect for Families and Groups Welcome to our serene home in the charming town of Hill, New Hampshire! Nestled on 12 scenic acres, this inviting home offers the perfect blend of tranquility and adventure for families and groups looking to escape the hustle and bustle. Feel free to reach out if you have any questions or need additional information. We’re here to help make your stay perfect!

4.81 out of 5 average rating, 186 reviews

An expansive porch features a circular wooden table surrounded by pastel blue chairs. A colorful patterned rug anchors the seating area, with decorative string lights overhead enhancing the space. Lush greenery is visible in a planter, adding a touch of nature.

Home in Hampton Beach

Steps to Beach Fireplace Pat's Porch

Welcome to Pat's Porch, the sister cottage of Lorraine's Landing and a professionally managed beach getaway - Just a 5-minute stroll from the sun-kissed shores and bustling boardwalk of Hampton Beach, this 3-bedroom, 1-bath abode boasts a queen master bedroom and newly updated kitchen. Relax on the expansive porch equipped with a picnic table, lounge chairs, and grill, or unwind indoors with fast wifi and a Samsung Smart TV.

5 out of 5 average rating, 25 reviews

A spacious living area features a comfortable chaise lounge and an open layout connecting to a dining area with modern lighting. A built-in bookshelf filled with colorful books adds a touch of character to the room, while hardwood flooring enhances the overall warmth.

Home in Ogunquit

Hoyts Ahoy

Escape to the coastal beauty of Ogunquit, Maine, where your ideal vacation home awaits. This charming ranch-style 3-bedroom, 1.5-bathroom home has an appealing terrace and yard for gatherings, as well as a side patio with river and ocean views. The comfort and convenience are within steps of downtown Ogunquit, which offers everything from the beach, river, the famed Marginal Way, restaurants, and shops.

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Stay near Derry's top sights

Robert Frost Farm State Historic Site10 locals recommend

603 Brewery & Beer Hall9 locals recommend

La Carreta7 locals recommend

MaryAnn's Restaurant7 locals recommend

The Grind Rail Trail Cafe6 locals recommend

Kelsen Brewing Company5 locals recommend

Other great vacation rentals in Derry

4.81 out of 5 average rating, 108 reviews

A functional kitchen features light gray cabinetry, a white countertop, and essential appliances, including a refrigerator and stove. A window allows natural light to brighten the space. Two stools are positioned at a bar counter, providing additional seating in the open layout.

Apartment in Revere

Home away from home Beach,Logan,Encore, DownTown

4.9 out of 5 average rating, 79 reviews

A serene outdoor area features two dark wooden chairs positioned on a porch, overlooking a vast field of tall grass. The sky is overcast, and a gentle landscape of trees and houses can be seen in the distance.

Home in Hampton

Lux Getaway! Perfect for Groups 8+ppl

5 out of 5 average rating, 38 reviews

A tranquil backyard scene features a spacious pool surrounded by well-maintained paving stones. A cozy pool house is visible in the background, framed by lush trees. A swing set and lounge chairs invite relaxation, while decorative stones and lighting elements enhance the serene setting.

Apartment in Salisbury

North Shore Getaway for Adults

4.96 out of 5 average rating, 251 reviews

Home in Lebanon

Tranquility, Relaxation, Family, Romance

4.94 out of 5 average rating, 16 reviews

A private deck is seen overlooking a calm body of water, featuring a hot tub surrounded by comfortable seating and an umbrella. Autumnal foliage adds color to the landscape, enhancing the tranquil setting by the water's edge.

Home in Sandown

Sunrise Beach Escape

4.84 out of 5 average rating, 31 reviews

Apartment in Brighton

The Curie-Perfect for Monthly Stays

4.96 out of 5 average rating, 145 reviews

Home in Shapleigh

Secluded Lakehouse/2 private docks*Hottub*big yard