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Holiday rentals in Raymond

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Top-rated holiday rentals in Raymond

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

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Guest favourite
The cabin's exterior is captured through a flickering flame, showcasing large glass windows that invite natural light. Surrounded by lush trees, the cozy structure features a modern design, blending seamlessly with the serene outdoors.
Home in Naples
4.99 out of 5 average rating, 167 reviews

LUX Designer Private Waterfront

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Guest favourite
An entryway features a red door, two clocks on the walls, and a small bar table with two stools. A mirror is mounted above the table, and the space is complemented by wood accents and light-colored flooring leading to the kitchenette.
Cottage in Portland
4.9 out of 5 average rating, 602 reviews

Cozy & Quiet Modern Cottage

Modern studio cottage designed and maintained with sustainability and eco-friendliness in mind, located in a quiet and very safe Portland neighborhood only a 7-10 minute drive (and $10-13 Uber/Lyft ride) from downtown Portland, the Old Port, and most local attractions. The cottage is a walkable mile (+/-) from Allagash Brewing (and the 4 other breweries there), and is within walking distance (.5 mi) of the restaurants and bars at Morrill's Corner. This is an LBGTQIA- and BIPOC-friendly space.

Top guest favourite
A charming waterfront cottage is presented with a bright blue door and two red chairs on a stone patio. Lush greenery surrounds the property, enhancing its inviting exterior. The tranquil waters of Pettingill Pond can be seen in the background, reflecting the sky.
Home in Windham
4.95 out of 5 average rating, 179 reviews

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Top guest favourite
The bedroom features a spacious bed dressed in light-colored linens, accompanied by a cozy seating area with a neutral-toned sofa. Two framed artworks are displayed on the wall, and a lamp provides soft illumination, creating a peaceful and restful environment.
Flat in Ferry Village
5 out of 5 average rating, 127 reviews

Cozy SoPo Condo

Welcome to this cozy one-bedroom apartment in Ferry Village, South Portland, Maine. This charming neighborhood is located just across the Casco Bay from Portland, and it's the perfect place to relax and admire the natural beauty of Maine. Enjoy a tour of our gardens and relax on the string light lit patio. The apartment is located on a quiet street, less than a mile walk from Willard Beach. Take a walk on the Greenway to Bug Light park or towards Knightville for some food and drink options.

Top guest favourite
A serene duplex apartment is surrounded by lush greenery, with sunlight filtering through the trees. The exterior features light blue siding, multiple windows, and a neatly maintained lawn. A gravel path leads to a natural area, enhancing the peaceful setting.
Flat in Gray
4.96 out of 5 average rating, 169 reviews

Two bedroom duplex across st from crystal lake

Relax, have fun, spend quality time with friends and family right here at our quiet little place. Two bedrooms, three beds, one pull out couch, we can accommodate up to six guests. We have walking trails, firepit, and a barbecue area. The house sits across the street from crystal lake, with a boat launch 3/4 mile down the road with a parking area. An easy 20-minute drive to Portland. Supermarket, gas station, and restaurant less than five minutes away and ten minutes from Gray exit to 95.

Top guest favourite
A serene lake view is depicted, showcasing calm waters reflecting the sky and surrounding trees. A private dock is visible at the water’s edge, adding to the tranquil atmosphere. The natural landscape features a variety of green hues from the trees lining the shore.
Cottage in Raymond
4.92 out of 5 average rating, 120 reviews

Relax by a Quiet Lake

Charming lakeside cottage only 29' from the waterline, w/65' of private waterfront. The cottage is a 3-season, classic L.C. Andrews, log-sided Maine summer lake home. Cozy atmosphere and a wonderful enclosed porch with amazing waterfront views. Enjoy fishing off the dock, hiking, canoeing, campfire, and exploring surrounding areas. Air conditioning units will ensure your comfort on warm summer nights and high-speed internet will keep your devices connected. Furnishings are family mix.

Guest favourite
A bright living area features a yellow loveseat, a gray circular chair, and a glass coffee table on a woven rug. A vibrant accent wall with colorful patterns adds a lively touch. A potted plant and a lamp complete the cozy ambiance.
Flat in Knightville
4.94 out of 5 average rating, 139 reviews

Sunny Spot with Private Parking

This cozy, 1 bedroom apartment is located in the peaceful neighborhood of Knightville. The Portland Peninsula, which includes the historic Old Port and the downtown arts district, is less than a 10-minute drive across the bridge. The perfect spot for a couple or a fun friend getaway! Several excellent dining spots, coffee shops, and markets are all within walking distance from the house. Bike rentals are 2 blocks away! The local beach is a 5-minute drive /10-minute bike ride.

Top guest favourite
The exterior of a Victorian farmhouse is showcased, featuring classic white siding and multiple large windows. Lush green trees frame the house, while vibrant pink and purple flowers add color to the front yard. A covered porch invites relaxation.
Flat in Lisbon falls
4.94 out of 5 average rating, 510 reviews

Charming Victorian farmhouse 1880's bedrooms-2

Victorian farmhouse 1880's Stay in an "era gone by". Private 2 bedroom. Original hardwood floors. Original pocket doors. Sleeps 6. Has living room, kitchen, dinning area 1 bathroom with tub , study area. Charming town, population 4000+. smoke free house. Private keyless entry. The blue door. Free wifi, cable, roku. Has keurig coffee maker with free coffee, dishes, pots, pans, silverware, nu-wave cooktop, toaster, microwave, fridge, pack n play. Queen beds. W & D private.

Top guest favourite
The exterior of a red barn-style home is surrounded by lush greenery and colorful flower beds. A patio setup includes comfortable seating, a dining table with an umbrella, and a fire pit on a pebbled area, providing an inviting outdoor space.
Home in New Gloucester
4.97 out of 5 average rating, 149 reviews

The Barnhouse with hot tub

Get away with your whole family at this peaceful home in the country. Hear the frogs chirping in the pond, birds tweeting in the treetops and watch chickens roam around. Enjoy the clear, starry nights while relaxing in the hot tub or cozying up by the fire. Centrally located between coast and mountains. Head a hour north to take the family hiking or on the slopes to enjoy the mountains. Head 40 minutes south to take in the coast and see the iconic Maine lighthouse.

Guest favourite
A welcoming living area features warm wood flooring and natural light from multiple windows. Comfortable seating includes a sofa and chairs arranged around a central table. A ceiling fan provides gentle airflow, while double French doors lead to an outdoor space.
Guest suite in Standish
4.92 out of 5 average rating, 116 reviews

Steep Falls Escape, river & falls just steps away

Bright and pleasant 1 bedroom apt with separate entrance, gas fireplace, enclosed porch and large kitchen. Spacious yard to enjoy with pool, fire pit, grill and outdoor seating. Steep Falls is a rural village. Our home is a 5 min walk to the Saco River a favorite destination for canoeing, kayaking or tube floating (after the spring run off!) It is just a 10 min drive to the boat launch for Sebago Lake, one of Maine's largest and most beautiful bodies of water.

Superhost
A spacious living area features wooden accents and a warm-toned ceiling, with a mix of seating options including two black chairs, a tan sofa, and wooden stools. A large wooden coffee table sits atop a light-colored area rug, and a flat-screen TV is mounted on the wall.
Farm stay in Gray
4.84 out of 5 average rating, 338 reviews

The Retreat at Crystal Lake Farm

This getaway features two spacious bedrooms plus an upstairs bedroom loft, sleeping up to 6 with ease. The large bathroom is accessed by both the master bedroom and living room and features on-site laundry. For guests who love to cook the kitchen is fully equipped and the deck is a perfect place to relax in the summer and enjoy the view. In colder seasons guests are encouraged to cozy up by the wood-burning stove or use the outdoor BARREL SAUNA.

Guest favourite
A studio apartment is presented with a queen size bed adorned with a muted blanket. A cozy sitting area includes a light grey sofa, while a small dining table with chairs occupies a portion of the space. A bookshelf is visible, enhancing storage and decor.
Flat in Downtown Portland
4.89 out of 5 average rating, 438 reviews

Central-Local Studio in Vibrant Portland, Maine!

Spacious and private studio apartment, with sitting area, queen size bed, table and chairs for dinning, kitchen and full bathroom. Newly updated appliances in a well maintained building. Wood floors lend charm, while modern decor makes for a contemporary feel. This comfortable space is perfect to come back to after exploring the surrounding neighborhood. The Studio is steps away from Portland's best restaurants, shops, nightlife and more!

Popular amenities for Raymond holiday rentals

When is the best time to visit Raymond?

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Avg. price$364 SGD$347 SGD$315 SGD$315 SGD$353 SGD$378 SGD$440 SGD$427 SGD$357 SGD$315 SGD$377 SGD$322 SGD
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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Raymond?

    Yes! Work meets play with ease at over 120 vacation rentals in Raymond featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Raymond?

    Four-legged friends are welcome in Raymond. Choose from more than 90 vacation rentals for guests traveling with pets.

  • Are there Raymond vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Raymond, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly cabin rentals in Raymond?

    Raymond has more than 20 family-friendly cabin rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do cabin rentals in Raymond have a bbq area?

    Absolutely! We offer over 30 cabin rentals with a bbq area in Raymond. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Raymond have wifi?

    Absolutely! We offer over 30 cabin rentals with wifi in Raymond. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in cabin rentals in Raymond?

    Experience the best of Raymond with our cabin rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Raymond have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Raymond. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Raymond have air conditioning?

    Absolutely! We offer over 30 cottage rentals with air conditioning in Raymond. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Raymond?

    Enhance your stay in our House Rentals with the most popular amenities: over 130 homes with wifi, over 10 homes with a gym, over 100 homes with a bbq area, over 110 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Raymond

  • Total holiday rentals

    Explore 270 holiday rentals in Raymond

  • Nightly prices starting at

    Raymond holiday rentals start at $63 SGD per night before taxes and fees

  • Verified guest reviews

    Over 7,970 verified reviews to help you choose

  • Family-friendly holiday rentals

    220 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 90 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wifi availability

    260 of Raymond holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Raymond rentals

  • 4.9 Average rating

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

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