If you’re looking for a dream couple’s getaway in Massachusetts — this is the only article you need!
My boyfriend and I love the verdant beauty of Massachusetts, especially its historic towns filled with romantic charm, and we’ve spent many vacations here. So, on our last trip, we scoured the state for romantic cabins with unmatched locations, views, and great value for money.
Our search led us to historic Gloucester and Rockport, the Berkshires, Nantucket, and even Orange, which had some incredible rentals.
So after testing each cabin for ourselves and weighing the pros and cons, we narrowed it down to the top four romantic rentals in Massachusetts, ranked on amenities, hosts, privacy, and overall value.
Our goal is to help you save time and money by sharing our personal experiences through this article. So each rental mentioned below is guaranteed to offer an amazing getaway!
Get ready for romance in Massachusetts like never before!
The Romantic Retreat in Gloucester
Source: booking.com Romantic Retreat in Gloucester
My boyfriend and I were looking for a secluded waterfront cabin in Massachusetts and came across this gorgeous little cottage on the sea!
The rental has an ideal location close to great attractions in nearby Gloucester and is only steps away from the beach. We loved our time at this cozy cabin, which has a small living room, a full kitchen on the ground floor, and a lovely upstairs bedroom with large windows letting in ample sunlight.
However, we spent most of our time outdoors in the lovely garden, which had an outdoor dining set and a grill on which my boyfriend made some delicious meals.
In addition, the owners are terrific and have provided everything you need for the stay.
So book this slice of heaven for your next romantic stay in Massachusetts, as it’s one of the best cabin rentals.
Here’s why you’ll agree:
- The facilities: The cabin features a fully-equipped kitchen stocked with all the essentials, a spacious bathroom with towels, comfortable bedding, a flatscreen TV in the living room, a cozy dining area indoors, high-speed Wi-Fi, and private parking.
- The location: The cabin is the perfect place for outdoor lovers, as it’s minutes from beautiful beaches, recreation areas, biking trails, woodlands, and also restaurants and shopping centers in town.
- The hosts: The best part of staying at this property is the hosts, who have included little details; beach chairs and towels to take on the shore, a wagon to make the trip, and stocked the cabin with every amenity you’ll need.
We had an all-around great time here and didn’t encounter any problems. But guests should consider that the parking space is tight for two vehicles, and there’s some ongoing construction nearby.
- The rental is clean, well-stocked, and beautifully furnished,
- There’s a private patio with a grill and an outdoor dining area.
- The rental has a lovely sitting room with comfortable furniture and a TV.
- You’ll enjoy serene water sounds from the beach nearby.
- The location is secluded and offers privacy away from town.
- Hot water was hard to come by in the shower.
- The parking space is small and tight.
Overall, our time at the Romantic Retreat was unmatched, and we highly recommend it to couples as one of the best romantic getaways in Massachusetts!
Romantic Berkshires Cottage
Source: vrbo.com Romantic Berkshires Cottage
If you’re looking for Berkshires cottages for a weekend getaway, book this gorgeous rental secluded on a three-acre lot, that’s one of our favorites for a couple’s trip! The rental offers a fairytale-like setup with — a lush garden outdoors, open spaces indoors, and many cozy nooks to cuddle in.
You’ll especially love the open floor plan, which has one bedroom and one bathroom, a kitchenette, a sitting room, and dining space, all with beautiful views of the property seen from large windows.
Furthermore, we enjoyed taking long walks to the nearby farm, where you can spot sheep grazing, and having nature walks around the property. Our trip was made especially memorable by the host, Frederica, who made sure the rental had everything we needed for a relaxing stay.
So book the romantic Berkshires cottage, which promises an unforgettable getaway in Massachusetts.
Here’s why it’s one of the best:
- The nearby activities: You’re within walking distance from downtown Great Barrington for great shopping, restaurants, and the theater. Plus, the location is an easy drive to the Appalachian Trail hikes and biking trails.
- The amenities: The rental has a well-stocked kitchen, a full bathroom, good Wi-Fi, a flat-screen cable TV with DVD, access to an onsite pool, and spacious indoor and outdoor spaces.
- The attention to detail: The owners have put a lot of details to make the rental feel special, such as a romantic dining space, complimentary champagne, a small workspace, and two kayaks for guest use.
The only thing you need to consider before booking is that the property and pool are shared with another cottage, so you won’t have complete seclusion here.
- The rental is close to Great Barrington, which has historic buildings and fun attractions.
- The hosts are very friendly and accommodating.
- The windows give stunning views of the rolling hills and farmlands.
- The garden has seating areas for watching sunsets and sitting by the pool.
- There’s another cottage nearby, and the pool is shared with other renters.
Basically, if you’re looking to spend quality time with your loved ones — book this rental, as it’s perfect for romantic getaways in Massachusetts!
Dogtown Cabin at Applecart Farms – Pet-Friendly Cabin Rentals in Massachusetts
Source: airbnb.com Dogtown Cabin at Applecart Farms – Pet-Friendly Cabin Rentals in Massachusetts
My boyfriend and I recently rented the Dogtown cabin on a local’s recommendation and had a fantastic time. The pet-friendly cabin was also perfect for our dogs since it’s located on vast farmland with access to beautiful outdoor spaces and is close to downtown Rockport for dining out and exploring.
You can bring up to five guests to this cabin, as it has plenty of space from its master bedroom, sleeping loft, comfy dining room, and a well-equipped kitchen.
Our favorite part was touring the 2500 acres of forested land on Applecart Farms, hiking nearby trails, and playing with the gorgeous farm animals.
Here’s what makes this stunning property one of the most romantic cabins in Massachusetts:
- The comfort and convenience: You can enjoy complete privacy on one of the most secluded properties in Rockport at this farm, which has miles of hiking trails and woodlands surrounding it, access to internet and cell service, and proximity to great attractions in the area.
- The spaces: You can access spacious indoor spaces in this cabin, including a private bedroom and bathroom, a sleeping loft, a dining room and kitchen, a library, and the entire outdoor area.
- The farm animals: There are many horses on the property which you can see from their stables and two golden retrievers that visit guests outside the cabin and are a lot of fun to play with.
The only thing to consider before booking is that the hosts live on the property and are always nearby, so you won’t be completely alone here.
- The cabin is very cozy, well-maintained, and beautifully furnished.
- The indoor spaces are well-insulated and offer complete privacy.
- The cabin is ideal for remote working as there are no distractions and good Wi-Fi.
- Nearby Rockport is a great place to explore in terms of history.
- The hosts offer suggestions for activities nearby and are always around to help.
- The hosts live nearby and often visit during your stay.
Hence, don’t miss a chance to rent the Dogtown cabin, as it’s the best rental for a quiet getaway in Massachusetts.
The Writer’s Retreat – Most Romantic Getaway in Massachusetts
Source: airbnb.com The Writer’s Retreat Cabin – Most Romantic Getaway in Massachusetts
My boyfriend and I found the Writer’s Retreat rental while looking for waterfront cabins and instantly fell in love with it!
You’ll enjoy this cabin’s great location with a deck overlooking Tully Mountain, Tully Pond nearby, closeness to cross-country skiing trails, and nearby lakes for swimming.
We had a relaxing getaway here, especially from the beautiful interiors framed by up-cycled maple floors, custom-built furniture around the place, and breathtaking mountain views from each window. The best parts for us were chilling on the deck facing the pond, having meals on the outdoor dining set, and roasting s’mores on the outdoor fire pit.
Furthermore, the hosts are terrific and ensure guests have a great time with their generous hospitality.
So book the Writer’s Retreat for your next romantic getaway in Massachusetts. Here’s why it’s one of the best:
- The amenities: The rental sleeps two people comfortably from its custom-made queen bed in the master bedroom, plus a writing desk and a flat-screen TV, modern appliances and cooking staples in the kitchen, a custom couch and dining space in the living room, a walk-in shower in the bathroom and a dual washer.
- The location: Guests can enjoy warm nights in Orange from this cabin, which faces Tully Mountain and offers the best views; it is steps away from Tully Nature Pond and nearby Tully Lake for swimming and kayaking.
- The spaces: The cabin is ideal for couples as it has snug spaces, including a comfy living room, a deck with seating, an outdoor fire pit area, and much more for guests to explore on the property.
The only thing guests should consider before booking is that there’s weak cell service in the area — so they need to drive a short distance to make calls.
- The cabin offers stunning mountain views from the indoor and outdoor spaces.
- There is ample firewood provided for the outdoor pit.
- The rental is well-stocked, with all the amenities you’ll need.
- The host, Patti, has kept the cabin in great shape for guest use
- There is spotty cell service in the area, so you need to drive out to get good signals.
All in all, we loved our time at the Writer’s Retreat, and it’s a terrific cabin in Massachusetts for a couples getaway.
What are the most romantic getaways near Cape Cod in Massachusetts?
Some of the best rentals near Cape Cod Bay in Massachusetts include the Antique Cape Cod cabin from the 1960s, the Historic Cape Cod Barn Cottage, and the Windmill Cottage. These rentals are nestled near the shore, offering stunning waterfront views and access to fun activities near Cape Cod.
What are some romantic cabin rentals in Western Massachusetts?
If you’re looking for a getaway in Western Mass, some terrific rentals in the area offer privacy, closeness to nearby attractions, and great views. Some of the best ones include the Round Cottage rental on the Santarella Estate in the Berkshires, the Charming Historic Cottage, and the Romantic Berkshires Cottage, each with modern amenities, well-furnished spaces, and lots of rustic charm.
Is there a romantic cabin near Nantucket Sound in Massachusetts?
The Charming Cabin in South Chatham, the Historic New England Cabin, and the Lighthouse Inn in West Dennis are some of your best bets for romantic rentals close to the water in Nantucket Sound. These rentals offer serene water views, all the essential amenities you’ll need, and the perfect setting for a couple’s getaway.
Winding Up: Romantic Cabin Rentals in Massachusetts
There’s no better way to surprise your significant other than romantic weekend getaways in Massachusetts, and we’ve got the best cabin rentals for just that in this article!
Looking for a waterfront rental in Massachusetts? Book the Writer’s Retreat in Orange.
Need a cabin on lush farmlands? Don’t miss the Dogtown cabin on Applecart Farms.
Want a cozy cabin close to historic towns? Book the Romantic Retreat in Gloucester.
Massachusetts cabins have everything you need for a couple’s escape!
Last Updated on October 27, 2023 by Brian