Holiday rentals in Long Pond

4.94 out of 5 average rating, 82 reviews

Cottage in Freetown

Serenity On Long Pond Massachussetts

Come enjoy this beautiful cozy PET FRIENDLY lake front cottage on Long Pond. Direct access to the lake off your own dock and deck (seasonal). Bring your boats and launch from the the town launch less than a mile away. You will have use of 3 kayaks, outside fire pit, and there is nothing better than spending time in the outside screened in porch and deck overlooking the lake. Only 20 minutes to ferry for the Vineyard and Nantucket and within an hour away to Cape Cod, Boston, and Providence.

4.95 out of 5 average rating, 175 reviews

Bungalow in Dartmouth

Updated Vintage Bungalow with Incredible Views

This space has been fully updated in the spring of 2020. Incredible unobstructed panoramic views. It is 400 sq' with an additional 350 sq ' of living space on the deck. The neighborhood is quiet, but you are a stones throw from I-195, making places like Boston, Providence and the Cape and Islands very easy to get to. The décor is bright and funky! Close to UMASS. Extensive custom area and house guide is at the Bungalow with everything you need to know to maximize your experience in the area!

4.77 out of 5 average rating, 109 reviews

Flat in Fairhaven

Main Street on the Park

Welcome to Main Street on the Park! The morning sun will greet you in the bright apartment in our big white house with a yellow front door. Perfect for a romantic getaway or a convenient place to stay if you are in the area for business. A large fenced yard abuts a public park complete with tennis courts, track and walking trail. Explore our small town with a big history, visit its historic buildings, great restaurants and unique shops. The location is convenient to all of the South Coast.

4.98 out of 5 average rating, 305 reviews

Tiny home in Wellfleet

Magical Writers Cabin + hot tub in Wellfleet Woods

Escape to our unique Writer’s Cabin in the peaceful woods of Wellfleet—a magical retreat that feels like you're staying in a treehouse! You'll be surrounded by nature yet just minutes' drive from stunning beaches, crystal-clear ponds, scenic trails, and a short stroll to charming Wellfleet harbor and quaint town center. Relax and unwind at our brand-new Magnolia Spa (opening in June), featuring a hot tub and sauna. On-site massage therapy begins in July—ask us about exclusive guest rates!

4.98 out of 5 average rating, 145 reviews

Home in Scituate

Artist studio in the woods

Take it easy at this unique and tranquil getaway. Be a little bohemian, stay in an artist’s studio for two adults, views of woods and stone walls.walk along a 300 stone wall past a 5000 gallon koi pond, and discover a stone sculpture in the woods. Wall of windows, private deck, queen size bed, kitchenette, full bath, dishwasher, Wi-Fi, cable tv, guest robes, iron and board, kuerig, all necessary utensils. Quite, tranquil, relax. Pool has surcharge $20 if weather is good during your stay.

4.83 out of 5 average rating, 220 reviews

Flat in Bridgewater

Charming New England 2brm Apt. South of Boston

Inviting 2-Bedroom Apartment in Quintessential New England Town Bright & Airy – Skylights fill the cozy living room with natural sunlight. Fully Equipped Kitchen – Compact yet functional with all essentials. Comfortable Bedrooms – 2 well-appointed rooms for restful sleep. Private Driveway & Free Parking Spacious Backyard –Perfect 4 relaxing. Prime Location – 4-minute walk to Bridgewater State U. Ideal 4-Family, travel nurses, healthcare workers, and corporate stays. Book now!

Tiny home in Mattapoisett

4.99 out of 5 average rating, 94 reviews

101 Steps to Beach/Island/Bike Path

Experience the Seaside Town of Mattapoisett. Location! Relax in this cozy cottage that is 101 steps from the front door to the Beach/Island/Bike Path. Enjoy this popular, sought after scenic Path for walking, biking, or a day at the Beach. The path is known for its picturesque coastal views. Walking distance to the Quaint Town, Shipyard Park, and many restaurants. Ned's Point Lighthouse- 5min. Trip to the Vineyard or Nantucket- Ferry 14 min. Quick drive to Cape COD. Sept/Oct-15% OFF!

5 out of 5 average rating, 239 reviews

Guest suite in Uxbridge

Zen Inspired Retreat with Private Forest Trails

Zig-Zag Trails blends modern comfort with the charm of rural living. Set on 65+ acres of private meadows and forests, our master guest suite is the perfect retreat to relax and recharge. Explore scenic zig-zagging trails, perfect for hiking, mountain and E-biking, and unwinding in nature—a haven for outdoor enthusiasts and homebodies alike. 📍 1 hour from Boston 📍 35 minutes from Providence 📍 25 minutes from Worcester Escape to Zig-Zag Trails—where tranquility meets adventure.

5 out of 5 average rating, 4 reviews

Guest house in Westport

The Swift's Nest

Visiting the Farm Coast? Why not stay on a Farm! The Swift's Nest is a guest house located on our working farm and garden. The studio apartment is private and accessed by a farm lane that will take you past our apiary, orchard and wildflower gardens. Located above our honey room, this generous studio enjoys exceptional views. Distant winter views of the Westport River are replaced by a bright pastoral of wildflowers, hayfields, and forests in the summer. Come enjoy and relax.

4.97 out of 5 average rating, 119 reviews

Flat in Taunton

*Warm and Inviting*Rustic design Airbnb*Taunton*

This warm and inviting, rustic style apartment is located in the Historical district of Taunton, prime location for all the “Hotspots” of Mass. Minutes to routes 24, 44, 495, and route 138. Perfect for long term stays/Short term or traveling nurses! Your home-away-from-home awaits you! We provide Free: ✔Coffee, also decaf/Tea ✔WIFI ✔Netflix/ cable/Disney+ ✔Snacks ✔Basic cable ✔Quality toiletries and soaps ✔Iron/Ironing board ✔Board games ✔Level 1-2 EV charging port

4.89 out of 5 average rating, 136 reviews

Guest house in Dartmouth

Lovely Lakeside Cottage

Keep it simple at this peaceful and centrally-located cottage. Lovely lakeside cottage with open floor plan. Centrally located in southeastern Massachusetts with short drives to Boston, Providence, Newport, and Cape Cod. Several beaches within 20 minutes. Washer/ Dryer on site and California King Size bed. A simple five (5) minute ride to UMass Dartmouth. Cottage has a living room, full kitchen, bedroom, full bath, and small dining area.

4.94 out of 5 average rating, 271 reviews

Flat in Westport

15 Acres of Open Fields & 15 Minutes to the Beach

This is a ground level apartment. It sits in the walkout basement of the main residence. It has 7 east facing windows. Tons of light and faces the 15 acres of field. It was a dairy farm previously so the house is a converted cow barn. It is quiet and serine, far off the road. Enjoy walks in the fields or sit on the swing in the gardens.

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Other great holiday rentals in Long Pond

4.95 out of 5 average rating, 20 reviews

Home in Wareham

The Perfect Restful Retreat

SarahRating, 5 starstoday

Kristen was great! Very responsive and catered to our needs! House was great and looked just like the pictures! Can’t wait to visit again!

Private room in Fairhaven

4.88 out of 5 average rating, 543 reviews

Peaceful Suite with a Harbor View

Us AndRating, 5 stars3 days ago

Unbeatable location and view, with so many thoughtful little touches. Hosts could not have been nicer.

4.99 out of 5 average rating, 167 reviews

Cottage in Marion

Little Boho Retreat by the Beach

RobertRating, 5 stars3 weeks ago

Felicia and Little Boho Retreat by the Beach deserve all the raving reviews. In all honesty I wish I could give more than five stars. The cottage is cozy, well-stocked, and every attention to detail is notable. Felicia thought of everything. The cottage is a destination in and of itself, to say nothing of the wonderful places we visited on The Cape, as well as Plymouth, Wareham, and Marion. I feel like there is so much more to do and experience on Dexter Beach and in this area. We definitely would like to return to this spot.

4.96 out of 5 average rating, 199 reviews

Treehouse in Wareham

Mink Cove Treehouse

LydiaRating, 5 stars6 days ago

My fiance and I had such a wonderful stay! The view was so stunning and there was so much to do. I’ve honestly never slept better in my life— the rain pitter-pattered against the open windows at night and it was so peaceful. Susan is so kind and answered any question I had. I hope to visit again some time soon!!

5 out of 5 average rating, 7 reviews

Home in Kingston

Cozy Modern 2BR near Grays Beach

JulieRating, 5 stars1 day ago

Totally as advertised. Very clean and homey with helpful instructions to make our stay easy. David was responsive and very helpful.

Private room in Fairhaven

4.96 out of 5 average rating, 185 reviews

The Captain James Henry Swift House Circa 1844

RobertRating, 5 stars1 week ago

We had a very comfortable 3 days in a lovely space. We were "wowed" by the quality of the restorations. The furnishings, the window treatments and the floors, all stunningly beautiful. The bathroom has a terrific shower. The television was very easy to use. At one point we noticed that the water from the faucet had gone brown. Within 10 minutes of our noticing, Lisa had messaged us and explained that the town was flushing the fire hydrants and asked that we contact her if we were inconvenienced. We especially appreciated her proactive attention. Lisa and Tony were very respectful of our privacy. The space is quiet and peaceful. We'd love to return here when we come back to Fairhaven.

4.96 out of 5 average rating, 162 reviews

Private room in Dighton

Clean & Serene $60 private bedrm &bath kitchen use

CindyRating, 5 stars3 days ago

We loved staying at Michael's place. Nice cozy home and beautiful yard. He was the prefect host. The only issue we found was when the bedroom window was opened the traffic outside of house is frequent and loud but earplugs take care of that if you are noise sensitive. He definitely deserves a 5 star rating !!!!