Vacation rentals in Spy Pond

Home in Lakeside Marblehead

The exterior of a historic two-story home is displayed, featuring a muted beige facade with black shutters. Window boxes with colorful flowers add charm, while a small entrance staircase is visible. The surrounding greenery complements the classic architecture.

5 out of 5 average rating, 13 reviews

Charming antique in historic seaside beach town

KaseyRating, 5 stars6 months ago

Sarah was an amazing host. Not only did she let us check in early, she provided welcome snacks and champagne. We truly felt at home in her house and the location was amazing for sight seeing in Marblehead and nearby Salem. Highly recommend for a fall trip!

4.91 out of 5 average rating, 32 reviews

A bright four-season atrium features a large sectional couch, complemented by decorative pillows. Natural light floods the space through the glass ceiling and walls, illuminating the neutral tones of the furniture. A small black coffee table sits in front of the seating area.

Home in Cohasset

Village Colonial with Cohasset Harbor Views

KathrynRating, 5 stars1 month ago

This is a beautiful and spacious home with New England charm and in a great location. The house looks exactly as pictured and was spotless. The rooms were well appointed with lots of space to sit and relax. It’s perfect for visiting this beautiful area of MA. Michael is a responsive and helpful host and very considerate of his guests. We would absolutely stay again and can highly recommend this home for your stay. Five star all the way.

4.87 out of 5 average rating, 109 reviews

A serene morning on the lake is depicted, with two individuals paddling a kayak through mist-covered water. The surrounding landscape features dense trees and gentle hills, while soft light reflects off the calm surface, creating a peaceful atmosphere.

Vacation home in Natick

Private Lakefront with game room/Newly renovated

SamanthaRating, 5 stars4 weeks ago

My family of six was extremely pleased with our stay at Dean’s property. He was incredibly responsive and helpful when I was having trouble making the reservation. The home was exactly as described. Very clean. Plenty of linens and towels. My kids loved the game room. Would definitely stay here again.

4.96 out of 5 average rating, 306 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

CarolineRating, 5 starstoday

We absolutely loved our experience at Frank’s Winthrop basement apartment! Exceptionally good value for the beautiful area, comfy beds & a very easy to use TV for the rainy nights :) The one thing that would have really improved this place for me personally is enhanced privacy. I would have loved to have our basement apartment door lock from the outside. I didn’t feel unsafe by any means because our entrance was locked and had a keypad we shared with the hosts but would have loved to be able to lock the apartment up while we were exploring MA. A separate entrance for guests would have been awesome too but I recognize that is a tough ask renovation wise. My husband was not bothered by it at all but once I mentioned it, he agreed.

4.96 out of 5 average rating, 69 reviews

A child walks along a sandy beach, with waves gently lapping at the shore. The sky above features delicate wispy clouds against a bright blue backdrop. In the distance, beachgoers enjoy the water, and charming coastal houses line the beach.

Apartment in Hull

Anchors Away Inn Cozy Walk to Beach, Courtyard

Alcor DrewRating, 5 stars1 month ago

A nice little apartment close to the beach! I liked the fire pit and the grill especially. The beds were very soft and had a lot of warm blankets. The TV has a lot of wifi capability. The kitchen comes fully stocked with dishes and cookware. The neighborhood is calm and the sea breeze is nice, even if it's chilly out. Fencing around the property gives a lot of privacy in the back yard, and there are chairs out there if the weather permits chilling outside.

4.92 out of 5 average rating, 37 reviews

Cottage in Westford

Beach & pond cottage ! Westford MA and Boston!

MelanieRating, 5 stars6 months ago

We had an absolute blast on our girls getaway weekend!! The cottage and community were amazing, exactly what we were hoping for and Doug couldn't have been nicer or more helpful. He was always available by text or phone. The cottage was clean, nicely equipped, and a great location!! We will definitely be renting this cottage again on our next trip!!! Thanks for having us... we loved every minute!! 🧙🧙🧙

Condo in Lakeside Marblehead

An expansive view of the harbor is captured, showcasing numerous sailboats anchored in the water. Lush green grass and wooden benches frame the scene, with a flagpole standing nearby. A large tree casts shade on the area, contributing to a peaceful atmosphere.

4.99 out of 5 average rating, 175 reviews

Harbor Hideaway

Kenneth Rating, 5 stars3 weeks ago

Our stay was very comfortable in this warmth, clean, beautiful home with a comfy bed with all the amenities given. Kristen’s hospitality is amazing from her gestures and extra special touches of food, drinks and yummy snacks. Inviting home away from home with a raining season we enjoy staying in too. Thank You. Kenneth & April Phillips Ranch , California

4.98 out of 5 average rating, 379 reviews

A multi-story coastal home is seen from a rocky shoreline, surrounded by lush greenery. Several white Adirondack chairs are positioned on the patio, enhancing outdoor relaxation. The gray exterior of the house features a large balcony with white railings, blending harmoniously with the natural landscape.

Apartment in Salem

Winter Island Retreat

ShaniRating, 5 stars1 week ago

AMAZING only starts to describe this place. We stayed for 5 night and really didn't want to leave. The large windows off the bedroom open up to the ocean and the sunrise. The kitchen is a full kitchen and well stocked with all the things you need to make meals. The feel of the place is cozy, open and clean. David came down to meet us and share some local spots when we 1st got there. He was quick to reply when I did message him a could of questions. Great host, Amazing place.... 100% hope I get to stay here again!

5 out of 5 average rating, 34 reviews

A private balcony features two dark wood chairs positioned for optimal views of the surrounding landscape. The scene captures the expanse of water in the distance, framed by a cloudy sky. An urban setting is visible below, highlighting the coastal charm.

Apartment in Beverly

#1 Top Flr Waterview|Lux Design|Pvt Balcony

JonathanRating, 5 stars1 week ago

This was my third time at Darryl’s‘s place and I will be back again. For the simple fact that if you need to be in the Beverly and Salem area this is a perfect location to post up and walk to everything you need. Or, drive if you must. There’s a train to Boston a couple blocks away.Darryl‘s place itself has everything you need to feel and operate like you’re at home. See you again soon, Darryl.

Apartment in Lakeside Marblehead

A modern kitchen space features sleek cabinetry and a marble countertop with bar seating for two. Natural light filters through a nearby window, illuminating an artistic water-themed wall piece. A pendant light hangs above the bar, enhancing the clean design.

5 out of 5 average rating, 3 reviews

Captains Qs 2 bed, downtown MHD sleeps 4, parking

MelanieRating, 5 stars6 months ago

Great weekend in Marblehead! Locals are super friendly and make you feel welcome and almost at home :) The location is more than perfect! Beds and sofa are very comfy and kitchen has everything you need. The fireplace and second tv in one of the bedroom were a plus. Hosts were very helpful and go the extra mile to make sure everything is ok. Due to our busy schedule we didn’t get the chance to meet with them but we will definitely be back!! Thank you !! Mel, Blake, Dave and Keven.

4.95 out of 5 average rating, 21 reviews

A bright bedroom features a spacious bed dressed in crisp white linens. Three windows offer panoramic views of the water, allowing natural light to fill the space. A white shelving unit stands to the side, enhancing the room's functionality.

Home in Hull

Every room a water view updated kitchen & bath

JohnRating, 5 stars4 months ago

Excellent experience. Easy check in and the place was perfect, she even had some snacks waiting for us upon arrival. Easy walk to the ferry into Boston, and easy parking. It was winter, but there were plenty of outdoor activities so we'd love to come back during the summer. Older house but so charming and great location. Overall great communication before, during, and after; she even offered to ship a shoe my niece left behind to us. Would love to come back and would absolutely recommend to anyone looking for a great place in Hull.

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Other great vacation rentals in Spy Pond

5 out of 5 average rating, 22 reviews

A large window offers a panoramic view of a serene coastline, highlighting gentle waves and a bluish sky. Here, natural light brightens the interior space, while framed grasses and nearby houses add context to the landscape.

Home in Ipswich

Capeview Cottage

GillianRating, 5 stars6 months ago

This place had the most amazing view.

4.86 out of 5 average rating, 178 reviews

The entrance to the bungalow features a welcoming wooden door with a decorative glass panel. Soft lighting illuminates the path and entryway, surrounded by well-maintained plants. Stone steps lead up to the door, creating a charming approach to the home.

Home in Beverly

Beverly Beach House- Upper Deck

RachelRating, 5 stars5 months ago

We stayed here for a week, and fell in love with it! The house has so much charm and character. We thoroughly enjoyed our stay, and want to stay there again. It was within walking distance to many places, including a beach. A definite charm in Beverly! The host was amazing! She was very responsive to our questions, and checked in a few times to see if we needed anything, which I appreciated. You are missing out if you don’t stay here!

4.92 out of 5 average rating, 13 reviews

Home in Wakefield

60 Jordan-New Construction Townhome

Tara JeanRating, 5 stars1 week ago

We stayed at this beautiful home in our hometown while dealing with an insurance claim at our own house, and it truly felt like a home away from home. The space was incredibly comfortable, clean, and welcoming. Our hosts were so kind and accommodating, making a stressful time so much easier. We’re so grateful for their hospitality and would absolutely recommend this place to anyone looking for a homey and happy stay.

4.88 out of 5 average rating, 102 reviews

Home in Ipswich

Hillside Ocean View 2BR with Private Beach Access

PatriciaRating, 5 stars3 weeks ago

Mark’s place was retro and quaint. It brought back special childhood memories of the house I was raised in back East. We loved our time here. This home is cozy and welcoming and has everything you could need to enjoy your stay. Mark provided homemade banana bread and coffee. That was very much appreciated since we didn’t arrive until 11 pm and there were no stores open. The views were very cool and a great place for birdwatching. It’s a short walk to two different beaches and a friendly neighborhood to walk through. Ipswich is a wonderful town with lots of things to see and do. We would definitely like to book this place again. Thanks Mark.

4.96 out of 5 average rating, 27 reviews

The open living space features a large kitchen island with seating and a spacious dining area overlooking the living room. Natural light floods the space through large windows, highlighting the modern decor and elegant light fixtures. Stairs lead to the upper level, inviting exploration.

Home in Swampscott

Master Suite with magnificent views of the ocean

JaimeRating, 5 stars3 months ago

We had a lovely long weekend at Natasha's gorgeous home. Spotlessly clean, with modern upgrades and appliances. The layout is a bit unusual as the house has been renovated and split into at least 2 units. Located on main road into Swampscott, with a view of the ocean (across the road) out the front windows--very beautiful even in the middle of winter! We had snow 2 out of 3 nights, and on the first of these there was a gentleman outside shoveling the driveway and back steps around noon. But by our check out time (noon) on Monday, nobody had cleared the snow. Got our car out ok, and we cleared off the back steps so we could bring our luggage out. There was conflicting info between the listing and what we were told by the owner re check-in and check out times--we messaged owner (twice) to clarify check out time and never heard back from her, so called her on check out morning--she apologized and honored the original listing. Info in owner's instruction booklet at house needs updating.

4.98 out of 5 average rating, 195 reviews

A fire pit is surrounded by colorful adirondack chairs in a grassy area, with bright yellow flowers adding a pop of color. The view in the background includes a landscape of greenery leading to the water, suggesting a peaceful outdoor space for gatherings.

Home in Ipswich

Stagehill Beach House

EmilyRating, 5 stars1 day ago

We stayed at Katie’s home over a weekend to celebrate my sisters upcoming marriage. Ever person spent the weekend gushing about how adorable this place was. It was full of charm and we LOVED it. We had a bonfire, walked to the beach, and loved having an outdoor space to hang out. Katie was wonderful and responsive! She was so kind and flexible. This was truly one of the best Airbnb experiences I’ve ever had.

4.99 out of 5 average rating, 81 reviews

The kitchen features modern white cabinetry and a marble countertop. A stainless steel gas range and exhaust hood are prominently displayed. Natural light from a window illuminates a nearby sink, which is accompanied by a potted orchid and overlooks a serene view of the meadow.

Apartment in Boston

New 3 bedroom, 2 bath unit, meadow view!

CiaraRating, 5 stars1 week ago

Simon elevates hosting to a whole new level and provides a tough act to follow. He pays attention to detail and has carefully considered and included all the things that will make you feel both welcomed and comfortable. The home is spotless, very modern and tastefully decorated. The linens are of a great quality and the beds are super comfortable. The master shower is wonderful, and Simon has so thoughtfully provided amenities in the bathrooms and the kitchen. The location of the home is great in a quiet neighborhood with parking spaces provided. The home has lovely natural light and even great views out of the windows. Both Simon and his home is a standout and so far, my best experience with Airbnb to date. Simon goes above and beyond to make your stay a luxurious one and by that, he makes it hard to leave but easy to want to return to.