Holiday houses in Second Cliff

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Top-rated holiday rentals in Second Cliff

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Guest favourite

Guest suite in Winchester

5.0 out of 5 average rating, 104 reviews

Warm and cozy 1st flr sweet guest suite w parking

Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits

23 Feb – 2 Mar

$181 NZD per night

Guest favourite

Loft in Abington

4.99 out of 5 average rating, 119 reviews

Modern, Naturally lit Loft

Enjoy a quiet getaway, with private entrance, in a private loft apartment situated in South Shore, MA. The loft is a large, open floorplan flooded with natural light. Enjoy nature walks at the Abington/Hanover rail trail for a great morning walk or a nice evening on the private balcony. There is a full-size kitchen in the loft at your disposal. We have a parking space in front of the house, fast WIFI, and a designated desk for work if you need it. This loft Is amazingly comfortable and peaceful!

12–19 Sep

$259 NZD per night

Guest favourite

Cabin in Cohasset

4.92 out of 5 average rating, 284 reviews

Lionsgate at Cohasset

Lionsgate is the perfect retreat to refresh the soul. Newly remodeled fully stocked kitchen with comfortable amenities provide a home away from feel. Enjoy a roaring fire in a rustic cabin during the winter or the coolness of a mini split in the summer. Cohasset, jewel of the South Shore is a quintessential New England seaside village located half way between Boston and Cape Cod. The ocean offers abundant recreation opportunities as well as plentiful parks for hiking and biking. A must visit.

21–28 Aug

$319 NZD per night

Guest favourite

Guesthouse in Scituate

4.98 out of 5 average rating, 58 reviews

Serenity House

Take a deep breath while relaxing on this 1+ acre wooded estate surrounded by the Hubbell Woodland Preserve and the Hatherly Golf Course across the street. Walk along seaside estates that greet you on your way to swim at Minot Beach which is a short walk away. Ride your bike to Cohasset Harbor while taking in the view of the fishermen catching lobsters and have dinner at the local restaurants. Listen to the waves and smell the salty ocean air and relax and sleep peacefully at Serenity House!

2–9 Apr

$239 NZD per night

Guest favourite

Apartment in Falmouth

4.98 out of 5 average rating, 117 reviews

Modern Luxury Apt. | 7 min from Commons

This luxury 1Br + 1bth apartment is the perfect getaway. - 650 square feet, newly renovated - 15 Minutes from Old Silver Beach, South Cape Beach, and Falmouth Heights beaches - Steps from 1,700 acres of walking trails (Crane Wildlife) - 7 minutes to Mashpee Commons (shops and restaurants) - 15 minutes to Main Street Falmouth - 13 minutes to Ferry for Marthas Vineyard - 85” smart TV - 5 minutes to Shining Sea Bike Trail - Coffee/Espresso Machine - 2 minutes from Paul Harney Golf Course

25 Oct – 1 Nov

$153 NZD per night

Guest favourite

Guest suite in Peabody

4.98 out of 5 average rating, 177 reviews

Cozy West Peabody Guest Suite

Come enjoy this renovated studio guest suite in the quiet neighborhood of West Peabody! An easy drive to Salem or Boston, close to a woodsy bike trail, and a short drive to local shops and restaurants. Features a fully equipped kitchenette and an outdoor space with a fire pit and charcoal grill. Make use of a Roku TV and fast, reliable WiFi to keep yourself entertained. This is a great space whether you are looking to explore the Boston North Shore or simply embark on a quiet getaway.

9–16 Aug

$233 NZD per night

Guest favourite

Cottage in Bourne

5.0 out of 5 average rating, 143 reviews

140 Steps to Beach with Water Views

This small rustic unique cottage is ready for you to enjoy on Buttermilk Bay. It is located within a sought after cape style cottage community. It offers a pristine private association beach. The cottage has water views from both the living room and deck. Grab the provided beach chairs, cooler and walk a 140 steps from the deck to the beach. You can also Walk, Bike, or Fish on Cape Cod Canal. Close to restaurants, hiking trails and Mass Maritime. Cape Cod Bridge- 5 min.

21–28 Sep

$241 NZD per night

Guest favourite

Guesthouse in Cohasset

4.98 out of 5 average rating, 105 reviews

Lovely 1 Bedroom Guest House. Downtown Cohasset

Lovely guest house. Newly renovated, nicely furnished & clean. Spacious living room/dining room with fully equipped kitchen. Large 1 bedroom & 2 full baths. Convenient location--walk to downtown, harbor, restaurants, churches and the Common. Train to Boston"s South Station 5 min away. Cohasset is the quintessential New England seaside village located on the South Shore of Massachusetts between Boston and Cape Cod. Host lives next door on property.

6–13 May

$407 NZD per night

Guest favourite

Guesthouse in Marshfield

4.98 out of 5 average rating, 51 reviews

Adorable 1 bedroom guest house with ocean view

Take it easy at this unique and tranquil getaway with an amazing ocean view. Enjoy the oversized deck for sunning, and grilling. 1 Queen bedroom and a pull out sleeper sofa in the family room with TV and WiFi. Kitchen includes basic appliances: mini-fridge, microwave, Keurig, toaster, toaster oven, air fryer, and portable cooktop. Amenities include use of sand volleyball court, linens and towels, window A/C, water toys, and 1 parking spot.

28 Dec – 4 Jan

$456 NZD per night

Guest favourite

Guest suite in Scituate

4.91 out of 5 average rating, 174 reviews

Private Scituate Getaway - walk to harbor

Delightful studio apartment with private entrance off historic First Parish Road. Located a mile from Scituate Harbor, beaches, restaurants, golf course, movie theater, shops, and Greenbush train into Boston. Space includes comfortable queen-sized bed, full bathroom, sofa, cable TV and wifi. Additional amenities include ceiling fan, air-conditioning, mini-fridge, Keurig, and microwave.

21–28 Jun

$360 NZD per night

Guest favourite

Guest suite in Scituate

4.97 out of 5 average rating, 119 reviews

Beach Garden Studio

Beautiful studio in Scituate Harbor for one or two. All the conveniences in one small space. Private entrance and bath with views from your private deck and patio. Walk to EVERYTHING. Many great restaurants and shops. Queen size bed. (Some of the older reviews may mention the sleeper, which we replaced with a queen bed.)

26 Oct – 2 Nov

$588 NZD per night

Guest favourite

Guesthouse in Scituate

4.99 out of 5 average rating, 89 reviews

Private Harbor Hideaway -walk Scituate to harbor!

Our Harbor Hideaway is located above the detached garage one block from Scituate's beautiful harbor shops, restaurants, and marina! Come enjoy our many beaches and relax in your private backyard! *Mini splits provide heat and A/C. *Cleanliness is a priority and have it professionally cleaned after each guest.

12–19 Apr

$511 NZD per night