Holiday rentals in Plymouth

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Top-rated holiday rentals in Plymouth

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The entryway features a wooden staircase with white railings leading to the second floor. A cozy seating nook sits beside a window, adorned with decorative pillows. Light-colored walls complement the hardwood flooring, while a console table with a decorative bowl adds a welcoming touch.
Home in Plymouth
5 out of 5 average rating, 153 reviews

Updated Antique in Historic Downtown Plymouth

Updated antique colonial within walking distance to everything historic Downtown Plymouth has to offer- waterfront, boating, shops, restaurants, historic sites, and more. Fenced in backyard with patio overlooking gorgeous, well-maintained garden. Patio has large farm table with umbrella and Weber grill, great for entertaining! This charming in-town location offers you the best of both worlds - walking distance to everything while also being cozy and comfortable to enjoy a day at home to relax.

Top guest favourite
Flat in Plymouth
4.95 out of 5 average rating, 82 reviews

The Blue Door

A 5* Super host rating. Blue Door is right in the heart of Plymouth. It is a lovely apartment that sleeps 4. Everything you want and need for a relaxing stay in Americas home town.All five star reviews. Summer,beach,boating and explore our historic sites., Spring season has much to offer! Festive Christmas, Fall, is of course,a great time., Plymouth hosts the 2nd largest Thanksgiving Day Parade in the country, that marches right in front of our building. The Blue Door in the heart of downtown!

Guest favourite
Home in Plymouth
4.92 out of 5 average rating, 182 reviews

Panoramic ocean views 100 ft above Cape Cod Bay

Our 5-bdrm Nantucket style beach house has a new kitchen & open living space, with a new deck, all overlooking the entire shoreline of Cape Cod Bay from a commanding perch atop a 100-foot bluff. Whales and seals can be seen from your deck. Located in a private community with its own rocky beach access about 5 min walk from the house where you can hunt for shells & observe the ocean wildlife. This beach is ideal for kayaking. Plymouth also boasts 4 of top 10 rated public golf courses in MA.

Top guest favourite
A view of a serene outdoor space featuring a green lawn bordered by a cranberry bog. A fire pit with chairs is situated in the foreground, while a rustic building and tree line create a picturesque backdrop under a cloudy sky.
Guest suite in Duxbury
4.94 out of 5 average rating, 101 reviews

Guest suite on cranberry bog, 1 mile from beach

Why fight the traffic to Cape Cod when you can enjoy New England's beaches, trails and seafood from beautiful Duxbury - just an hour from Boston! Our home is on a gorgeous cranberry bog surrounded by biking and walking trails and just a mile from the beach. Skylights and french doors to a private patio fill the suite with sunlight. Guests enjoy the fire pit, grill and yard in summer or hit the trails on snow shoes and sleds in winter. The bog freezes over too and is great for ice skating!

Top guest favourite
The exterior of the house features a classic design with white wood siding and blue shutters. Flower boxes with blooming plants are placed beneath the windows. A side staircase leads to the entrance, while a well-kept pathway runs alongside the home.
Home in Plymouth
4.93 out of 5 average rating, 159 reviews

Summer dates still available! Book Today!

Summer is a great times to visit Plymouth, from beaches to sunny warm weather, we have it all! Our location is walkable and super safe, and you'll be in the heart of it all. We are less than a block from many beaches, restaurants, nightlife and historical tours. Check out our walk-through video on You Tube. Type WhaleTailInt 2019 in the search for a virtual tour of the entire house. Hop on the "T" and day trip to Boston, or head to Cape Cod for beaches galore and souvenir shopping.

Top guest favourite
An open living area is highlighted by vaulted ceilings and large windows that allow natural light to illuminate the space. A comfortable seating arrangement faces a coffee table, while a dining area with bar stools is situated near the kitchen. A spiral staircase leads to the upper level.
Guest suite in Plymouth
4.95 out of 5 average rating, 115 reviews

Manomet Boathouse Station #31

The Boathouse was a part of the Manomet Coast Guard Station on Manomet Point. When the station was decommissioned and eventually dismantled, the Boathouse was moved and attached to our home as a separate space. Guests will have full and private access to this beautiful and spacious 1,800 square foot home with 11 foot vaulted ceilings and antique southern exposure windows. The open first floor has a living room, kitchen, pool table and bathroom. A spiral staircase leads to the bedroom.

Top guest favourite
The exterior of the home is surrounded by lush greenery and flowering plants, including vibrant roses and colorful azaleas. A spacious screened porch is visible above the flourishing garden. The manicured lawn adds to the inviting setting of this family beach home.
Home in Plymouth
5 out of 5 average rating, 40 reviews

Ocean view home on Cape Cod Bay

Welcome to this family beach home on a 150-foot cliff with breathtaking views over Cape Cod Bay. This is one of the highest oceanfront locations on the entire East Coast. The airy, open living space has an ocean view, including the kitchen. Relax on the spacious screened porch. Take day trips to Plymouth, Boston, Cape Cod, and the islands. Have a picnic in the private cliff garden, and take in the vast, blue expanse below. This is an incredibly peaceful place, with so much to do nearby.

Top guest favourite
Guest house in Plymouth
5 out of 5 average rating, 12 reviews

Stylish Artist Cottage Near Beach &Plimoth Patuxet

Walk to dog-friendly Plymouth Long Beach or Plimoth Patuxet from this renovated 1800s coastal cottage and former artist’s studio that blends New England Charm and modern comfort. Thoughtfully designed with curated antiques, cozy interiors, a private seashell patio, Solo Stove, grill, outdoor shower, and games, The Dory is an intimate retreat for couples, beach weekends, wedding stays, and slow New England getaways just minutes from downtown Plymouth, the harbor, shops, and restaurants.

Guest favourite
Home in Plymouth
4.96 out of 5 average rating, 26 reviews

Amazing Water views! Ocean front, HotTub & More!

Wake up to breathtaking ocean views at this stunning Bay Shore Drive retreat in Plymouth! This coastal home combines modern comfort with seaside charm featuring ensuite baths, a gourmet kitchen, fun indoor entertainment, and oceanfront amenities like a hot tub and fire pit. Just minutes from beaches, dining, and historic attractions, it’s the perfect getaway for families or friends. Long Beach - 5 min Plymouth Rock & Mayflower II-10min. Downtown Plymouth Waterfront-10min.

Guest favourite
A spacious room features a king-sized bed with a neutral quilt and decorative pillows. French doors open to a view of the outdoor area, allowing natural light to illuminate the space. A patterned area rug enhances the room's aesthetic.
Flat in Plymouth
4.91 out of 5 average rating, 175 reviews

Remodeled Studio Apartment in Downtown Plymouth

Come experience the charm and rich history of “America’s Hometown!” Get transported back in time in an 1887 colonial home located in the heart of downtown Plymouth. Enter through the French doors into a recently remodeled studio apartment with a full kitchen, full bath and king-sized bed. All the modern comforts you could ask for in a quaint and cozy rental. Walking distance to restaurants, shopping, Plymouth Rock, the Mayflower and more!

Guest favourite
Home in Plymouth
4.94 out of 5 average rating, 16 reviews

Cozy Family Retreat

Spacious home just 2 miles from the beach, 15 minute ride to downtown Plymouth, and 3 miles from the Sagamore Bridge—perfect for easy Cape Cod access without the traffic. Nestled in the woods with nearby walking trails, ponds, and beaches, it’s the ideal mix of nature and convenience. Close to grocery stores and restaurants, this peaceful retreat is perfect for families or groups looking to explore the coast and unwind.

Top guest favourite
A comfortable living area is presented, featuring a gray sectional sofa with colorful cushions, a wooden coffee table, and decorative flowers. Large windows provide natural light, while a brick column adds character. A dining space is visible in the background, along with a playful wall art piece.
Home in Plymouth
4.97 out of 5 average rating, 91 reviews

Cozy and Comfortable! Walk to Downtown Plymouth

Our well loved home will put you within close proximity of so many activities. Check in and refresh. Make a quick snack/meal from our kitchen stocked with everything needed to prepare a wonderful meal. Plan a day of sightseeing, dining or relaxing in our comfortable living room. WiFi and a smart tv for lazy days.

Popular amenities for Plymouth holiday rentals

When is the best time to visit Plymouth?

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Avg. price$291 SGD$285 SGD$319 SGD$301 SGD$359 SGD$376 SGD$415 SGD$423 SGD$344 SGD$330 SGD$359 SGD$341 SGD
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Frequently Asked Questions

  • What are the best places to stay in Plymouth?

    Visitors frequently stay near the waterfront, close to historic neighborhoods and local dining. The area around downtown has access to cultural sites, family activities, and scenic parks.

  • What are the best things to do in Plymouth with kids?

    Families often explore Plimoth Patuxet Museums for interactive history, discover local beaches for playing and swimming, and visit Pilgrim Hall Museum for exhibits that introduce Plymouth’s early stories. Parks and nature trails around town make outdoor activities easy to enjoy together.

  • What are some of the best things to do in Plymouth?

    Explore Plymouth Rock, visit the waterfront, and discover living history at Plimoth Patuxet Museums. Stroll historic neighborhoods, walk nature trails, or try guided boat tours for regional views.

  • How is the weather in Plymouth?

    Plymouth has cold winters, with January temperatures near 19–35°F (-7–2°C), and milder summers around 63–82°F (17–28°C) in July. Spring and fall bring moderate temperatures and occasional rain, so layers work well year-round.

  • When is the best time to visit Plymouth?

    Late spring and summer are often recommended for comfortable temperatures and outdoor activities. Fall draws visitors with colorful foliage and local harvest traditions, creating a lively seasonal atmosphere.

  • What are the best places to visit in Plymouth?

    Plymouth Rock and the waterfront are frequently suggested, as well as Plimoth Patuxet Museums for interactive history. The Jenney Interpretive Centre and Brewster Gardens also invite exploration.

  • What are some hiking trails in Plymouth?

    Plymouth has scenic hiking trails in Myles Standish State Forest, as well as paths through Ellisville Harbor State Park and Tidmarsh Wildlife Sanctuary. Trails range from forested loops to coastal walks.

  • What are some family activities we can do in Plymouth?

    Explore hands-on exhibits at museums like Plimoth Patuxet Museums, picnic at waterfront parks, and join local storytelling or seasonal crafts in community centers. The beaches and nearby nature trails are also popular with families.

  • What are some of the best day trip ideas from Plymouth?

    Explore scenic coastal villages, visit Cape Cod for its beaches and art galleries, or experience nature at local parks and state forests around the region. Historical sites and maritime museums nearby add variety to day trips.

  • Are there any pet friendly accommodations available in Plymouth?

    Plymouth has pet friendly stays, especially near waterfront areas and around town. Many hosts welcome pets, making it easy to explore beaches or trails with your companion.

  • What are some local tips for visiting Plymouth?

    Locals recommend layers for changing coastal weather and starting mornings with strolls by the waterfront. Respect historic sites and explore neighborhoods on foot to discover local shops and eateries.

  • What is Plymouth known for?

    Plymouth is known for its historic significance as the site of early Pilgrim settlement and for Plymouth Rock. The town also has vibrant waterfront culture, regional seafood, and interpretive museums.

  • What are the best hidden gems to explore in Plymouth?

    Explore small art galleries, walking paths along lesser-known harbors, and quiet nature preserves tucked around Plymouth. Some historic homes and locally rooted museums share unique stories of the region.

  • What are the best foods to try in Plymouth?

    Regional seafood such as clam chowder, lobster rolls, and scallops are frequently suggested in Plymouth. Local bakeries and cranberry treats also reflect the area’s agricultural traditions.

  • What should I bring for a trip to Plymouth?

    Pack layers for variable coastal weather, sturdy shoes for walking historic sites or trails, and a rain jacket. Sunscreen and reusable water bottles are handy for outdoor activities.

  • What is the nightlife in Plymouth like?

    Plymouth has casual bars, waterfront pubs, and live music venues mainly around the downtown area. Visitors often explore local breweries and relaxed spots offering regional fare alongside evening entertainment.

  • What are the most popular events or festivals in Plymouth?

    Plymouth has holiday parades, annual harvest festivals in autumn, and outdoor concerts during summer. Thanksgiving traditions are often commemorated with historical reenactments and community gatherings.

  • Are there family friendly vacation rentals in Plymouth?

    Many neighborhood stays in Plymouth welcome families, especially near beaches and parks. Listings often have extra bedrooms, outdoor spaces, and proximity to family attractions.

Quick stats about holiday rentals in Plymouth

  • Total holiday rentals

    Explore 510 holiday rentals in Plymouth

  • Nightly prices starting at

    Plymouth holiday rentals start at $64 SGD per night before taxes and fees

  • Verified guest reviews

    Over 24,280 verified reviews to help you choose

  • Family-friendly holiday rentals

    340 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 140 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    240 properties have a dedicated workspace

  • Wifi availability

    500 of Plymouth holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Plymouth rentals

  • 4.9 Average rating

    Plymouth stays are highly rated by guests – averaging 4.9 out of 5!

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