As a local from the Boston suburbs, I’ve spent years exploring the best vacation rentals Massachusetts has to offer. From charming beach cottages on Cape Cod to serene lake houses in the Berkshires, and even unique treehouses tucked away in the woods, this state is full of cozy escapes.
I’ve personally stayed in countless vacation homes throughout the area, and I’m excited to share my top picks with you. Whether you’re dreaming of a coastal retreat or a peaceful getaway in nature, these 22 Airbnb rentals are perfect for your next Massachusetts adventure.
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The 22 Coolest Airbnb Rentals in Massachusetts
Here are the best Airbnbs in Massachusetts by category, taking into account different amenities, trip types, and budgets. The following sections will cover each listing, and other top vacation rentals, in more detail.
- Top Overall: Modern Vacation Rental in Martha’s Vineyard
- Best Luxury Rental: Classic Wellesley House
- Top Romantic: Secluded A-Frame Airbnb
- Best for Large Groups: Gloucester Condo on the Ocean
- Best Cheap Airbnb: Beachfront Cottage on a Pond
- Coolest Treehouse Airbnb: Enchanted Tiny Tower at Santarella Gardens
- Best Cabin: Traditional Log Cabin on the Cape
- Top with a View: Hilltop Haven in Western MA
- Best Winter Rental: Modern Rental in the Berkshires
- Best Lake House: Lakefront A-Frame Home
- Most Unique: Exotic Spanish Colonial Home
Note: The properties below are featured on Airbnb, VRBO, Booking and Expedia. For each listing, I’ve only included the link to the website with the cheapest rates.
1. The Enchanted Tiny Tower
- 📍 Location: Tyringham
- 💵 Price Per Night: $318/night
- 🛏️ Sleeps: 2 guests
- 🔥 Unique Features: Fairytale architecture, massive mill windows, babbling brook
- 🌟 Perfect For: Romantic getaways 💕, solo retreats 🌲, nature lovers 🍃
Step into the Enchanted Tiny Tower, a storybook hideaway nestled on the historic Santarella Estate in the Berkshires. This whimsical 350 sq. ft. retreat is perfect for couples or solo travelers looking for peace, creativity, and a little bit of magic.
The cozy living area features a dining nook that overlooks a gentle brook, while the kitchenette is equipped with a Ninja Foodi, induction cooktop, and microwave for simple meals.
A spiral staircase leads to the canopied queen bedroom, where massive mill windows bring in the treetop views.
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Outside, wander four acres of gardens, cross stone bridges, or relax by the lily pond. From hiking local trails to catching performances at Tanglewood or Jacob’s Pillow, this charming tower offers a one-of-a-kind Berkshires escape.
- Read more: When is the Best Time to Visit New England
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2. Cozy Chatham Cottage
- 📍 Location: Chatham
- 💵 Price Per Night: $347/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Walk to Hardings Beach, cedar outdoor shower, private back deck
- 🌟 Perfect For: Couples 💑, small families 👨👩👧👦, Cape Cod explorers 🚲
This Cozy Chatham Cottage is a 1950s gem set in a quiet neighborhood just half a mile from Hardings Beach. The home blends vintage charm with modern touches for a laid-back Cape Cod getaway.
Relax in the sunroom, dine at the window-side table for four, or settle into the living room after a day at the beach. The compact kitchen is fully stocked with a gas stove, toaster oven, coffee maker, and filtered water.
French doors open to a private deck with a grill, cedar outdoor shower, and a flower-lined patio complete with a fire pit. Hop on the included bikes to explore Downtown Chatham, grab seafood nearby, or enjoy a sunset ride to the shore.
3. Beautiful Private Beach House
- 📍 Location: Barnstable
- 💵 Price Per Night: $820/night
- 🛏️ Sleeps: 10 guests
- 🔥 Unique Features: Private beach, ocean views, waterfront deck
- 🌟 Perfect For: Families 👨👩👧👦, romantic getaways 💕, beach lovers 🌊
Experience true beachfront living in the heart of Hyannis Port. This spacious 4-bedroom home offers stunning views of the Atlantic and direct access to your own private sandy beach.
Inside, you’ll find 2,280 sq. ft. of coastal comfort, with two full bathrooms and two half baths. The fully equipped kitchen is ready for family meals, while the washer/dryer makes beach life easy.
Spend your days building sandcastles, watching the ferries head to Nantucket, or strolling through nearby shops and harborfront restaurants. With plenty of outdoor space and classic Cape Cod style, this is a seaside retreat built for lasting memories.
- Read next: 17 Cool Rentals in Cape Cod
4. Private Lake Cottage
- 📍 Location: Becket
- 💵 Price Per Night: $369/night
- 🛏️ Sleeps: 8 guests
- 🔥 Unique Features: 3-acre wooded setting, 350 sq. ft. deck, walkable lake access
- 🌟 Perfect For: Nature lovers 🌳, families 👨👩👧👦, hikers 🥾, and peaceful getaways 🌌
Tucked away on 3 peaceful acres, this Private Lake Cottage offers a relaxing escape in the Berkshires. The 1911-built home combines vintage charm with modern updates, and the lake is just a short walk from the back door.
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Indoors, cozy up by the wood-burning fireplace or unwind in the bright living room with forest views. The open kitchen and enclosed porch make it easy to cook, dine, and reconnect.
Grill on the oversized deck, gather around the fire pit, or settle in for a game night indoors. Nearby, explore Becket Quarry, hike the Appalachian Trail, or stop by local markets and farm stands.
5. Waterfront Oceanfront Cottage
- 📍 Location: Mashpee
- 💵 Price Per Night: $1,186/night
- 🛏️ Sleeps: 6 guests
- 🔥 Unique Features: Private beach steps away, ocean views from nearly every window
- 🌟 Perfect For: Couples 💕, beach lovers 🌊, small families 👨👩👧
Wake up to the sound of waves in this fully renovated New Seabury cottage overlooking Nantucket Sound. With beach access just steps away, this is classic Cape Cod living with a modern twist.
The 1,300 sq. ft. home features three queen bedrooms, two spa-like bathrooms, and a sunny, open living area. The kitchen is outfitted for meals at home, while the neighborhood invites leisurely walks along shell paths and picket-fenced lanes.
Visit the nearby Popponesset Marketplace for food, shopping, and live music, or spend the day biking, kayaking, or exploring Mashpee Commons. From sunrise coffee by the sea to peaceful evenings by the shore, this is beachfront relaxation at its best.
6. Secluded Berkshires Hideaway
- 📍 Location: Becket
- 💵 Price Per Night: $258/night
- 🛏️ Sleeps: 7 guests
- 🔥 Unique Features: 13 private forested acres, two wildlife ponds, large open lawn
- 🌟 Perfect For: Nature lovers 🌲, families 👨👩👧👦, and peaceful getaways 🌌
Set on 13 acres of private forest, this Berkshires Hideaway offers total seclusion and a chance to truly unplug. No neighbors in sight—just ponds, trees, and quiet.
Step inside, the great room has vaulted ceilings, a brick fireplace, and plush new furnishings. The kitchen features stainless appliances and a breakfast bar that brings everyone together.
Explore community hiking trails in Becket Woods, catch a show at Jacob’s Pillow, or shop in Lee—all just a short drive away. Whether you’re playing lawn games or soaking in the silence, this cabin is your back-to-nature escape.
7. The Chestnut Hill Spanish Colonial
- 📍 Location: Newton
- 💵 Price Per Night: $743/night
- 🛏️ Sleeps: 10 guests
- 🔥 Unique Features: Elegant Spanish Colonial architecture, luxury furnishings, tall ceilings
- 🌟 Perfect For: Family gatherings 👨👩👧👦, college visits 🎓, city explorers
Stay in style at this elegant Spanish Colonial home in Chestnut Hill, directly across from Boston College. With 5 bedrooms and 3.5 bathrooms, there’s room for family get-togethers, group stays, or visiting faculty.
Inside, you’ll find soaring ceilings, designer decor, and a chef’s kitchen. The layout includes two king beds, two queen beds, and two twin beds, plus multiple lounging areas for group relaxation.
Enjoy a stroll to nearby shops and cafes, or take advantage of three off-street parking spots for easy city access. Whether exploring historic Boston or relaxing at home, this stay combines comfort, style, and convenience.
8. Cozy Waterfront Retreat
- 📍 Location: Becket
- 💵 Price Per Night: $418/night
- 🛏️ Sleeps: 6 guests
- 🔥 Unique Features: Private dock, lakeside setting, kayaks included, renovated interior
- 🌟 Perfect For: Families 🏞️, nature lovers 🛶, and peaceful getaways 🌅
Escape to this cozy three-bedroom chalet, set right on the calm shores of Long Bow Lake. With a private dock and provided kayaks, it’s an easy spot to unwind, paddle, and enjoy the simple pleasures of lakefront living.
The warm and inviting interior features an open-concept living space with a wood-burning fireplace, a sunny dining nook, and a fully equipped kitchen—ideal for group meals or morning coffee with a view. Natural light streams in, creating a relaxed, homey feel throughout.
Step outside to fire up the grill on the deck or settle by the water and watch the day fade into a quiet Berkshires evening. Spend afternoons paddling the no-motor lake, lounging in the yard, or stargazing in the stillness.
Nearby, visit Pyramid Lake, catch a performance at Jacob’s Pillow, or browse the shops at Lee Premium Outlets. Whether you’re out exploring or just staying put by the dock, this lakeside escape makes it easy to unplug and recharge.
9. Serene Nature Retreat
- 📍 Location: Becket
- 💵 Price Per Night: $490/night
- 🛏️ Sleeps: 8 guests
- 🔥 Unique Features: Private pond, two fire pits, screened porch, wood-burning fireplace
- 🌟 Perfect For: Families 👨👩👧👦, nature lovers 🌲, peaceful getaways 🏞️
This peaceful three-bedroom, three-bath home sits on 11 private acres in the heart of the Berkshires. With its own pond, forest trails, and two fire pits, it’s designed for quiet reflection or family connection.
Inside, large windows bring the outside in, while a wood-burning fireplace, open living room, and full kitchen create a warm and welcoming atmosphere. The screened porch adds extra space to unwind, dine, or enjoy the breeze bug-free.
Spend your days exploring the wooded grounds, lounging by the pond, or toasting marshmallows by the fire. Whether you’re gathering with family or just craving space to slow down, this retreat invites you to unplug.
Close by, explore Pyramid Lake, Jacob’s Pillow, or the outlets in Lee—each offering its own slice of the Berkshires to round out your stay.
10. Private Lake Retreat
- 📍 Location: Lee
- 💵 Price Per Night: $567/night
- 🛏️ Sleeps: 10 guests
- 🔥 Unique Features: Private spring-fed lake, 36 wooded acres, hot tub on deck
- 🌟 Perfect For: Families 👨👩👧👦, couples 💑, outdoor lovers 🌲, culture seekers 🎭
Tucked into 36 forested acres, this secluded lakefront home offers total privacy and its own spring-fed, 2.5-acre lake. It’s the kind of spot where you can paddle in the morning, hike in the afternoon, and soak in the hot tub under the stars.
The sun-drenched great room features cathedral ceilings, a stone fireplace, and views across the water. A chef’s kitchen and large dining area make it easy to gather, while the home’s layout gives everyone their own space to relax.
Step out onto the deck to grill, unwind by the fire pit, or launch a canoe from your own shoreline. This is outdoor living with modern comfort—ideal in any season.
You’re just minutes from Lenox, Stockbridge, and Tanglewood, putting arts, dining, and culture within easy reach when you’re ready to explore.
11. The 1770 House
- 📍 Location: Colrain
- 💵 Price Per Night: $1112/night
- 🛏️ Sleeps: 14 guests
- 🔥 Unique Features: 130 private acres, pool & spa, indoor cedar hot tub
- 🌟 Perfect For: Family reunions 👨👩👧👦, creative retreats 🎨, holiday gatherings 🦃, outdoor lovers 🌄
Set on 130 private acres with sweeping views of the Green River Valley, the 1770 House is a historic six-bedroom farmhouse reimagined for family gatherings and creative escapes. Original beams and curated art fill the 4,500 sq. ft. space with warmth and character.
The chef’s kitchen includes a Viking range and large island, while multiple cozy lounges, reading nooks, and a dining room make it easy to spread out. Outside, enjoy a seasonal pool, open fields, and walking trails through meadows and woods.
After a day of exploring, relax in the indoor cedar hot tub or gather by the fire pit for stargazing and conversation. Whether you’re celebrating a milestone or simply reconnecting, the home offers both beauty and privacy year-round.
12. White Pond Cottage
- 📍 Location: Dennis
- 💵 Price Per Night: $591/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Private pond beach, canoe, outdoor shower
- 🌟 Perfect For: Couples 🧺, small families 👨👩👧, peaceful nature escapes 🌿
Tucked away on a quiet freshwater pond in Dennis, White Pond Cottage offers simple Cape Cod charm with a private stretch of shoreline just for you.
The cozy 900 sq. ft. layout includes a king bed, queen futon, full kitchen, and both indoor and outdoor showers. A private quarter-mile driveway provides seclusion, while room-darkening shades and plush bedding help ensure a peaceful night.
Spend your days canoeing the pond, dining under the trees, or simply soaking in the stillness. A deck and outdoor dining area provide space to grill and unwind.
When you’re ready to explore, head to the Cape Cod Rail Trail, nearby beaches, or downtown restaurants just a short drive away.
13. Relaxing Lakehouse Getaway
- 📍 Location: Westhampton
- 💵 Price Per Night: $624/night
- 🛏️ Sleeps: 12 guests
- 🔥 Unique Features: Private beach, screened porch, kayaks, canoe, paddleboard
- 🌟 Perfect For: Families 🏕️, nature lovers 🌲, lake adventures 🚣
On the quiet shores of Pine Island Lake, this spacious lakehouse offers easygoing comfort with room for the whole family. A private beach, fire pit, and water gear make it easy to spend your days outside.
Inside, the home features three bedrooms, additional bunks, a fireplace, and a fully stocked kitchen. The screened porch and large living room give everyone space to gather, play games, or enjoy a movie.
Kayak, swim, or fish by day, then settle in around the fire at night. It’s the kind of place where you can unplug without giving up the comforts of home.
Nearby, explore Roberts Meadow Brook, head to Northampton for shopping and dining, or hike Chesterfield Gorge for dramatic views.
14. Cozy Iconic Cabin
- 📍 Location: Sandisfield
- 💵 Price Per Night: $2,010/night
- 🛏️ Sleeps: 12 guests
- 🔥 Unique Features: Indoor endless pool, spa room with yoga space, massive stone fireplace
- 🌟 Perfect For: Large groups 👨👩👧👦, wellness retreats 🧘, all-season getaways ❄️🌲
This iconic 6-bedroom Berkshires cabin is made for memorable group stays. Surrounded by trees, it combines rustic character with luxury features like an indoor endless pool, a spa/yoga room, and dramatic 25-ft ceilings.
Indoors, gather around the massive stone fireplace, cook meals in the full kitchen, or spread out between the cozy common areas and multiple dining spaces. It’s warm, stylish, and spacious throughout.
The location puts you close to Tolland State Forest, Otis Reservoir, and Jacob’s Pillow for outdoor and cultural outings all year long—from winter snowshoeing to summer lake days.
Whether you’re hosting a wellness weekend, celebrating a big occasion, or simply getting away with a group, this cabin delivers space, comfort, and privacy in a setting that feels worlds away.
15. Cozy Tideview Cottage
- 📍 Location: Ipswich
- 💵 Price Per Night: $392/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Direct tidal river access, private deck with sunset views, kayaks
- 🌟 Perfect For: Couples 💑, small families 🐾, nature lovers 🦆
Escape to this charming Ipswich cottage, set along the tidal Eagle Hill River. Designed for couples or small families, this peaceful retreat pairs classic New England charm with waterfront access.
Warm wood accents and exposed beams create a relaxed coastal vibe, while a fully equipped kitchen and cozy living room offer space to unwind. The private deck overlooks the marsh, perfect for morning coffee or sunset cocktails.
Launch a kayak from the dock, paddle through quiet waters, or stroll to Clark Beach for a swim. Explore the trails at Crane Estate, then head to Downtown Ipswich for fresh seafood and boutique shopping.
Spend your days paddling at high tide, spotting wildlife from the deck, or simply soaking in the stillness—this cottage is the perfect coastal hideaway.
16. Mermaid Cottage
- 📍 Location: Dennis
- 💵 Price Per Night: $258/night
- 🛏️ Sleeps: 8 guests
- 🔥 Unique Features: Post & beam design, jetted tub, fire pit, baby gear
- 🌟 Perfect For: Families 👨👩👧👦, beach lovers 🏖️, Cape Cod explorers 🚲
Mermaid Cottage is a bright and welcoming Cape Cod getaway in Dennis, just minutes from the shore. This 3-bedroom, 2-bath post-and-beam home combines rustic details with family-friendly convenience.
Gather in the open living and dining area, cook together in the well-stocked kitchen, or relax with a book in the sunlit sitting room. Beach gear, baby items, and linens are included for a hassle-free stay.
After a day at Mayflower Beach or Corporation Beach, return to the private backyard for s’mores around the fire pit. Unwind in the jetted tub or sip wine under the stars on the deck. You’re also close to Cape Playhouse, charming shops, and local dining spots—perfect for a classic Cape Cod retreat.
17. Direct Waterfront Lake House
- 📍 Location: Sturbridge
- 💵 Price Per Night: $582/night
- 🛏️ Sleeps: 8 guests
- 🔥 Unique Features: Private peninsula, lakefront views, heated 4-season sunroom
- 🌟 Perfect For: Families 👨👩👧👦, lake lovers 🌊, fishing fanatics 🎣, sunset seekers 🌅
This Sturbridge lake house sits on its own private peninsula, offering panoramic water views from nearly every angle. With space for up to 8 guests, it’s a quiet escape that’s still close to local attractions.
A cozy living room opens onto a heated 4-season sunroom, perfect for sipping coffee while watching the water. The galley kitchen is ready for home-cooked meals, and the first-floor bedroom features a queen bed plus twin bunk beds.
Spend your days on the private beach, paddling the lake with the canoe or kayaks, or fishing from the dock. Nearby, explore Old Sturbridge Village, grab a craft brew at Tree House Brewery, or hike in Wells State Park. For antique lovers, the Brimfield Antique Show is just a short drive away.
18. The Sand Hills Seaside Inn
- 📍 Location: Scituate
- 💵 Price Per Night: $1,233/night
- 🛏️ Sleeps: 15 guests
- 🔥 Unique Features: Oceanfront balconies, private beach access, 6 bathrooms, chef’s kitchen
- 🌟 Perfect For: Large family gatherings 👨👩👧👦, wedding parties 💍, seaside retreats 🌊
Once a beloved bed and breakfast, The Sand Hills Seaside Inn is now a private oceanfront rental in Scituate. With space for 15 guests, this 5-bedroom home is perfect for reunions, weddings, or coastal getaways.
Enjoy the chef’s kitchen, spacious open living areas, and 3 full floors of relaxing space. Oceanfront decks invite you to unwind with a sea breeze, while the private beach is just steps away.
Wander to Scituate Lighthouse, explore the shops and restaurants in Scituate Harbor, or gather around the stone fire pit after a day by the waves. This classic New England inn offers room for everyone with views that stretch to the horizon.
19. Eliza Cottage
- 📍 Location: Nantucket
- 💵 Price Per Night: $608/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Harbor views, luxury finishes, heated marble floors
- 🌟 Perfect For: Couples 💑, small families 👨👩👧, Nantucket romantics 🐚
Eliza Cottage is an elegant Nantucket retreat with views of the harbor and Children’s Beach. Perfect for couples or small families, this polished getaway pairs modern luxury with coastal charm.
Rest easy in the king bedroom with premium linens, and make use of the gourmet kitchen with Viking and Sub-Zero appliances. The living area features a custom pull-out sofa and Sonos sound system for cozy nights in.
Step out to the private patio with teak furniture and a gas grill, then head to Main Street for boutique shopping or stroll along Nantucket Harbor. This home offers effortless island living with thoughtful details throughout.
20. The Scarab
- 📍 Location: Wellesley
- 💵 Price Per Night: $1,355/night
- 🛏️ Sleeps: 8 guests
- 🔥 Unique Features: Third-floor “sky tower” loft, walk-to-town location, fire pit, modern kitchen
- 🌟 Perfect For: Families 👨👩👧👦, reunions 🎉, retreats ✨, college visits 🎓
Built in 1907 by Katharine Lee Bates, The Scarab is a historic Wellesley estate where classic design meets modern updates. With 5 bedrooms and flexible gathering spaces, it’s ideal for family get-togethers or college visits.
Gather on the open-plan first floor, complete with a chef’s kitchen and multiple living areas. Upstairs, unwind in the spacious main suite with its en suite bath and sleeping porch. The third-floor “sky tower” loft is perfect for reading or daydreaming.
Step outside to relax by the fire pit or walk just half a mile to Wellesley’s Town Center for cafes, boutiques, and the train to Boston. Whether you’re celebrating or simply relaxing, this home offers a warm welcome.
21. Modern Treehouse
- 📍 Location: Truro
- 💵 Price Per Night: $380/night
- 🛏️ Sleeps: 8 guests
- 🔥 Unique Features: Multi-level deck with views, outdoor shower, air conditioning
- 🌟 Perfect For: Families 🏖️, nature lovers 🌲, beach explorers 🌊
Perched among the trees in Truro, this modern treehouse offers a peaceful Cape Cod escape with beach access nearby. The 3-bedroom, 3-bath design features soaring ceilings, wood accents, and plenty of windows to frame the view.
A full kitchen and spacious living areas make group meals easy, while multiple decks invite you to grill, dine outdoors, or lounge in the breeze. There’s even an outdoor shower for rinsing off after a day at the beach.
Explore Corn Hill Beach, hike in the Cape Cod National Seashore, or head into Provincetown for dining and art galleries. From sunbathing and hiking to quiet afternoons with a book, this retreat offers the best of the Outer Cape.
22. The Writer’s Retreat
- 📍 Location: Orange
- 💵 Price Per Night: $192/night
- 🛏️ Sleeps: 2 guests
- 🔥 Unique Features: Private lakefront, fire pit, canoe & kayak, rustic tiny home
- 🌟 Perfect For: Writers ✍️, couples 💑, nature lovers 🌲, unplugging 📵
Set on the quiet shores of Tully Pond, The Writer’s Retreat is a tiny home built for reflection. This 325-square-foot escape offers lake views from nearly every angle and a peaceful setting for couples or solo guests.
Reclaimed barn wood, built-in furniture, and a gas wood stove create a warm, rustic feel. A queen bed and full bathroom add comfort, while the main living space faces the water for uninterrupted views of Tully Mountain.
Step outdoors to your private shoreline, where a canoe and kayak await. Explore Tully Trail’s waterfalls, hike Tully Mountain, or simply relax by the fire pit and let ideas flow. This is an unplugged stay designed for quiet minds and big ideas.
The Best Airbnb Rentals in Massachusetts in 2025
Have you ever stayed in a unique Airbnb vacation rental in Massachusetts? Let me know in the comments or on Insta, as I’m always looking to add to this round-up of the best Airbnbs in Massachusetts!
Looking for more cool places to visit in New England? Check out these destinations:
– Coolest Airbnb Rentals in the White Mountains
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– Best Time of Year to Visit Massachusetts
– Coolest Airbnbs in New York State
– Most Beautiful Airbnbs in the Berkshires
– Best Places to Stay in Vermont
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