Vacation rentals in Massachusetts
24 independently run vacation rentals in Massachusetts, run by 2 local hosts. Across Gloucester, Dennis, Beverly Farms, Harwich, Salem and Bellingham. 16 book online on the host's own site and the rest take inquiries, with no guest service fees.
Massachusetts gathers a broad slice of New England in one place: wave-cut headlands and sandy spits, salt marsh and pine wood, mill towns and brick-lined streets. Maritime history runs through many harbors, while inland lakes and low hills invite a quieter rhythm. Spring and fall feel reflective, summer leans coastal, winter rewards fireside time.
Stays span Gloucester, Dennis, Beverly Farms, Harwich, Salem and Bellingham. The mix suits short escapes and longer pauses: 24 places that sleep between 2 and 12 guests, with quiet retreats and homes with a story appearing in equal measure at 4 each. There are 2 condos and 2 cottages, plus 1 set deep in nature, 1 arranged for groups and 1 with a design focus. A few hosts gather more than one place under the same roof, with 2 such sites here.
- Stays
- 24
- Local hosts
- 2
- Sleeps
- 2 to 12
- Pet-friendly
- 2
- Book online
- 16
- Towns
- Gloucester, Dennis, Beverly Farms, Harwich, Salem, Bellingham
Search live availability in Massachusetts
The Dock House
Gloucester, MA
A waterfront home in Gloucester with a private deep-water dock, a seaside hot tub beside an outdoor fire, kayaks, a six-person Lund dinghy and captained charters on our Whaler.
sleeps 8
At a glance: Sleeps 8. Pets welcome (up to 2).
Haven's read: Private and secluded. Immersed in nature. Good for groups. Good for couples. Good for families with children.
Book direct on bookwithhaven.com
Wychmere
Harwich, MA
"Where love meets the sea."
sleeps 8
At a glance: Sleeps 8. Pets welcome.
Book direct on bookwithhaven.com
Sandy Toes & Salty Kisses
Dennis, MA
Cozy beachside cottage with ocean view.
sleeps 6
At a glance: Sleeps 6. No pets.
Book direct on bookwithhaven.com
Dennis Vacation Rental
Dennis, MA
Newly renovated condo by Bass River Marina
sleeps 4
At a glance: Sleeps 4. No pets.
Book direct on bookwithhaven.com
Dennisport Cottage
Dennis, MA
Peaceful backyard oasis in a cozy Dennisport cottage.
sleeps 6
At a glance: Sleeps 6. No pets.
Book direct on bookwithhaven.com
2 Mi to Wychmere, 3 King Beds, Fenced-in, FirePit
Harwich, MA
Charming cottage near beaches and trails.
sleeps 8
At a glance: Sleeps 8. No pets.
Book direct on bookwithhaven.com
Villaggio by the Sea
Beverly, MA
Escape to a Cozy, Scenic Retreat by the Sea.
sleeps 8
At a glance: Sleeps 8. No pets.
Book direct on bookwithhaven.com
Stunning Gloucester (Lanesville) home with beautiful sea views available for one more week in June 2026
Gloucester, MA
Peaceful seaside retreat in modern, tranquil Gloucester home with stunning sea and sunset views
sleeps 6
At a glance: Sleeps 6. No pets.
Book direct on bookwithhaven.com
Cozy West End Cottage w/ Parking 1st & 2nd floors
West End Provincetown, MA
Entire cottage in Provincetown, Massachusetts
sleeps 4
At a glance: Sleeps 4. No pets.
Inquire on bookwithhaven.com
Convenient and spacious 4BR/2.5BA
Randolph, MA
Big home near Boston, Gillette Stadium and More!
sleeps 8
At a glance: Sleeps 8. No pets.
Book direct on bookwithhaven.com
17 Highland St
Gloucester, MA
Charming 3-Bedroom Home in Historic Rocky Neck—Steps from Harbor Views, Art, and Coastal Walks
sleeps 6
At a glance: Sleeps 6. No pets.
Inquire on bookwithhaven.com
Rosea's Home By The Sea - Steps To Front Beach!
Rockport, MA
Steps to the Beach, Luxury at Your Fingertips
sleeps 6
At a glance: Sleeps 6. No pets.
Inquire on bookwithhaven.com
Villaggio by the Sea
Beverly, MA
Escape to a Cozy, Scenic Retreat by the Sea.
sleeps 8
At a glance: Sleeps 8. No pets.
Book direct on bookwithhaven.com
Downtown WaterView Special
Bellingham, MA
A serene escape with water views.
sleeps 2
At a glance: Sleeps 2. No pets.
Book direct on bookwithhaven.com
Nana Bean’s Dream
Dennis, MA
Serene pondside retreat in Dennis.
sleeps 4
At a glance: Sleeps 4. No pets.
Book direct on bookwithhaven.com
Beach Retreat
Gloucester, MA
Experience New England summer at its finest
sleeps 10
At a glance: Sleeps 10. No pets.
Inquire on goldenthreads.ai
Beach Retreat
Gloucester, MA
Experience New England summer at its finest
sleeps 10
At a glance: Sleeps 10. No pets.
Inquire on bookwithhaven.com
The Dock House
gloucester, Massachusetts
A unique and peaceful retreat.
sleeps 8
At a glance: Sleeps 8. No pets.
Inquire on bookwithhaven.com
The Dock House
Gloucester, MA
Unique and Tranquil Getaway
sleeps 8
At a glance: Sleeps 8. No pets.
Book direct on bookwithhaven.com
The Dock House
gloucester, Massachusetts
Unique and Tranquil Getaway
sleeps 8
At a glance: Sleeps 8. No pets.
Inquire on bookwithhaven.com
The Dock House
Gloucester, MA
Unique and Tranquil Getaway
sleeps 8
At a glance: Sleeps 8. No pets.
Inquire on bookwithhaven.com
Historic Brick Mansion
Salem, MA
Federal Period brick mansion on fabled Chestnut Street
sleeps 12
At a glance: Sleeps 12. No pets.
Book direct on bookwithhaven.com
Historic Brick Mansion
Salem, MA
Federal Period brick mansion on fabled Chestnut Street
sleeps 12
At a glance: Sleeps 12. No pets.
Book direct on bookwithhaven.com
South Chatham Cottage
Chatham, MA
sleeps 6
At a glance: Sleeps 6. No pets.
Book direct on bookwithhaven.com
Local hosts
Independent hosts with more than one stay here run their own booking sites. Each links to the host's site, where every home they manage is listed.
- Cape Ann Getaways3 stays here
- Anchor & Isle1 stay here
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Questions about Massachusetts
- How many vacation rentals in Massachusetts are on Haven?
- 24 stays are listed in Massachusetts, run by 2 independent hosts. They are in Gloucester, Dennis, Beverly Farms, Harwich, Salem and Bellingham.
- Do I pay a service fee to book a vacation rental in Massachusetts?
- No. Every stay here is booked or requested on the host’s own website, which charges no guest service fee. You pay the host’s nightly rate, their cleaning fee and the local taxes.
- Are there pet-friendly vacation rentals in Massachusetts?
- Yes. 2 of the 24 stays in Massachusetts list pets as welcome. Each listing names its pet fee and limits.
- Are there vacation rentals in Massachusetts for large groups?
- Yes. The largest stay in Massachusetts sleeps 12. Capacities here run from 2 to 12 guests.
- How do I book direct in Massachusetts?
- Open any stay below. Most pages book online with the full price shown; a stay marked “Inquire” takes your dates and replies from the host directly. Haven adds nothing to the price.
Updated . Listings and counts come from each host's live site.