Spacious Home, 9BR/5BA, Pool, Walk to beach and town.

Manchester-by-the-Sea, Massachusetts
$1659 avg/night
Minimum Stay 6 Nights
Bed 9

Bed

Bath 5

Bath

Home Private Vacation Home

Property Type

Sleep 19

Max Sleeps

Night 6 nights

Min Stay

Enjoy a wonderful vacation in Manchester-by-the-Sea in Cape Ann, the North Shore’s crown jewel (as featured in the prize-winning movie, Manchester-by-the-Sea), combining small town feel and a beach atmosphere. This spacious home is conveniently located on Smiths Point, just steps from famous Singing Beach and a 10-minute walk to downtown Manchester, where you can find parks, restaurants, the town’s grocery store, and Captain Dusty’s ice cream shop!

This home is theperfect spot for vacationing families, large groups, or reunions. The home’s location and amenities provide countless options for guests. The home is also perfect for families attending a wedding in the vicinity. We completed a major cosmetic upgrade in November 2021 with all new wall to wall carpeting, new furniture in the upstairs and downstairs living rooms, all new paint in the sleeping wings and upgraded kitchen appliances. As such, we have slightly increased rates for peak rental season (May - July). Any rentals already booked for 2022 will be granted our original pricing.

This 9 BR/5 BA home sleeps up to 19 people and has 3 master suites in 3 separate wings of the house. It was recently outfitted with large air conditioners in the common areas, and all bedrooms have window units.

Every bathroom has a hair dryer and comes stocked with soap and paper products for your convenience.

The 2 acre plot includes a large private yard with an adjacent pool (open Memorial Day weekend through October 1) and adjoining bowling green enveloped by large pine trees, affording privacy for you and your guests. The bowling green and pool include a croquet set, floats, beach chairs, umbrellas, and countless toys for pool and beach users. (The semi-private pool is shared with two of my cousin's families who only occasionally use the pool). There is a basketball hoop in the driveway.

The driveway and garage accommodates up to 6 cars for parking. (No parking is allowed on any of the streets).

The home offers a gas grill, brand new refrigerator with water dispenser, dishwasher, 2 cooktops (one gas, one electric), 3 sinks, 3 ovens and a microwave. There is both a Keurig coffeemaker and a drip coffeemaker. The large kitchen area is perfect for big groups, with an open dining room that can seat your entire party. There is also a patio on the main level and a deck on the upstairs level, both with outdoor furniture. There is a motorized stairlift for guests who may need it.

Enjoy downtime in a large light-filled living room on the upstairs level with a wood-burning fireplace and magnificent cathedral ceiling with wood beams. There are two TV rooms, one on the upper level and one downstairs. The downstairs TV room has a brand new smart TV where you can access your own streaming platforms. It also has a classic bumper pool table. Next to the downstairs TV room is a large play room equipped with a ping pong table and countless board games and toys for kids (and grownups!) of all ages. Keep the kiddos entertained even in poor weather with legos, building blocks, doll house, games, books, and more. The house is wired for cable and high-speed WiFi.

There is a laundry room with washer and dryer and ample linens and towels available for your use.

For our youngest guests, we offer 2 high chairs, 3 Pack and Plays, a baby bouncy seat, an infant tub, baby gates, and bed rails.

It is an easy 15 minute-walk to the train station, where you can go into Downtown Boston or explore the North Shore. There is also an easy 10-minute walk to the beach, or you can drive to the beach and use the convenient parking lot.

Summer is absolutely perfect, but foliage season, Spring and Winter are also beautiful!

- Bedroom layout -
First floor wing: One Master bedroom with ensuite bathroom, 2 bedrooms with 2 twin beds each, shared hallway bathroom. Sleeps 6.

Second floor wing 1 (closest to kitchen): One Master bedroom, 2 bedrooms - one with 2 twins, and one with 1 twin bed. Shared hallway bath. Sleeps 5.

Second floor wing 2 (closest to living room): One Master bedroom with en suite bathroom, 1 room with 2 twin beds, 1 bedroom with queen bed. One shared hallway bath. Sleeps 6.

One brand new queen sized pullout sofa available for your use. Sleeps 2.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    9 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 7500 Sq Ft (697 Sq M)
  • KITCHEN

    Coffee/tea Maker Dishwasher Kitchen Island Microwave Oven Refrigerator Stovetop Toaster Water Dispenser
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Not Required Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi, With Speed Of 250+ Mbps (good For 3–5 People Or Up To 10 Devices)
  • OUTDOORS

    Balcony Garden Gas Grill Outdoor Furniture
  • POOL/SPA

    Fence Around The Pool Heated Pool Private Pool
  • BATHROOMS

    5 Bathrooms Bathtub Or Shower Hair Dryer Soap Toilet Paper Towels Provided
  • THINGS TO DO

    Birdwatching Nearby Cycling Nearby Fishing Nearby Fitness Facilities Nearby Golf Nearby Hiking/biking Trails Nearby Power Boating Nearby Scuba Diving Nearby Water Park Nearby Windsurfing Nearby
  • ENTERTAINMENT

    Arcade/game Room Books DVD Player Games Pool Or Billiards Table Table Tennis TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Fireplace
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Baby Monitor Children's Books Children's Dinnerware Children's Toys Highchair Playground Pool Toys Travel Crib
  • LOCATION HIGHLIGHTS

    In A Village In The City Center In The Mountains Near A Health Or Beauty Spa Near A Hospital Near A Zoo Near The Ocean Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 19

Map Map

School District Availability

Review Review

  • Stephen M.

    Submitted Jun 16, 2026

    Stayed Jun 12, 2026

    Owner and caretaker were fabulous. The property had every amenity and plenty of space. Second time we stayed there. I highly recommend 20 Proctor Street for a stay.

  • John S.

    Submitted Aug 3, 2025

    Stayed Jul 13, 2025

    Large home with great grounds and pool. Everything was clean and organized for our family reunion at Good Harbor beach. Great location to Singing beach and other amenities.

  • Kirsten D.

    Submitted Aug 2, 2025

    Stayed Jul 26, 2025

    Communication with the owner and manager was excellent from start to finish. The location is amazing, with short walk to downtown one way (shops, restaurants, etc) and Singing Beach the other. The home is older so don’t expect brand new everything, but we knew that and it was still very clean and nice. Multiple gathering areas, both inside and outside, made everything very enjoyable and easy!!!

  • Sheila M.

    Submitted Jul 7, 2025

    Stayed Jun 28, 2025

    The house had everything we needed. One of our guests had surgery in the last months and there was a stair climber. Perfect for our guest. There was a room of toys, games and puzzles and books. Our children never wanted to leave. The pool was great and private. Wonderful walks to town and the beach. Thanks for the memories.

  • Betty D.

    Submitted Jun 30, 2025

    Stayed Jun 18, 2025

    Second year staying at this comfy house which is a short walk to Singing Beach as well as to town center and has a pool. Had almost all our meals at the house which has an extremely well equipped kitchen. Lots of room to spread out as a large group. Had children 3-9 years old and adults including me and hubby in our 70s. House remains comfortable and a relaxing place to be.

  • Donna E.

    Submitted Jun 17, 2025

    Stayed Jun 8, 2025

    We were a reunion of 4 family groups so the fact that this home has wings gave everyone the privacy they needed to refresh before the next exciting family activity. The property manager kept in close contact and provided assistance & advice as needed. We would definitely recommend!!

  • Roy G.

    Submitted Oct 20, 2024

    Stayed Oct 11, 2024

    Walks to Singing beach and downtown. Train to Salem for Haunted Happenings. Short drive to Gloucester for lobster and a schooner ride. Big meals made in the big well equipped kitchen. Great week.

  • Pamela T.

    Submitted Sep 15, 2024

    Stayed Sep 3, 2024

    We had a large group of friends here for a wedding weekend and the spacious house and grounds were perfect for us. There is a wonderful walled game garden and pool area and the house is a mid century modern dream. Lots of.privacy but close.to beach and town

  • Julie L.

    Submitted Jul 28, 2024

    Stayed Jul 20, 2024

    After agonizing over the choice of properties for a family reunion with a group of adults from 20-something to 80-something, I chose Maggie's place. It was a huge hit! Our group has stayed in a number of VRBOs over the years, less and more expensive than this, but this one turned out to be the very best! The interior photos (especially the kitchen) don't convey the spaciousness. I was a little hesitant that the pool might be shared: would we feel awkward, or intrusive? No! We had it to ourselves and it was spectacular. We felt like honored, appreciated guests and had more than enough privacy. The grounds are idyllic and the whole place has a wonderful vibe.

  • Paul M.

    Submitted Jul 24, 2024

    Stayed Jul 14, 2024

    The house and property were well suited for our two families traveling together. The play room was great for the kids and even better for the adults keeping an eye on them! The large property with the pool area worked out perfect for all outdoor activities and the newer deck on the second floor was a great spot for a cup of coffee in the morning! Wouldn’t change a thing!

Your dates are Available!

Total

Includes taxes and fees
$1,659+
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