Raymond vacation rentals

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Top-rated vacation rentals in Raymond

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

Guest favorite
Cottage in Pownal
Upscale Timber-Frame Cottage, Shop/Dine/Hike/Bike
Relax and unwind at this cozy post-and-beam cottage in a woodsy setting. Complete with all the modern amenities you will feel at home after exploring all that Maine has to offer. At day’s end ascend to the loft bedroom for a great night's sleep. Please note the current Maine travel restrictions: https://www.maine.gov/covid19 This custom post and beam cottage is brand new. Designed by John Libby, one of the most respected timber frame builders in New England, (www.housesandbarns.com) this space was thoughtfully designed and meticulously built specifically for your enjoyment. This cottage resides on the owner’s property, but is sited on its own two acres nestled among a beautiful stretch of Maine hardwood forest.  Accessible via its own private driveway and surrounded by acres of pristine forest, it is the perfect place to relax among nature. No matter the season the exposed weathered Douglas Fir beams of the building will both welcome you and wrap you in a feeling of comfort and contentment. This complete home has all of the amenities. The kitchen includes natural unpolished granite countertops and brand new appliances including a stainless steel gas oven/range, dishwasher and refrigerator. The whitewashed walls of the hallway and bathroom provide a more modern feel, while showcasing all the wonderful knots of the Maine white pine from which it was milled. An easy-to-access, low/no step corner shower complete with floor to ceiling tile and an oversized vanity make time in the bathroom a pleasure.  The open concept makes for a natural flow through the space and the sitting area comes complete with a queen sofa bed, TV and a gas fired wood-stove. The vaulted ceilings rise 22’ above the floor providing a spacious and beautiful feel. Radiant heat in the finished concrete floors make the space cozy and keep your feet warm. Oversized and lit stairs lead to the loft where you’ll find a king sized bed providing the opportunity for a great night’s sleep.  Large windows make you feel as though your sleeping in the tree tops…come Fall this Oak and Maple forest comes alive with color.  A ceiling fan keeps you cool, in the Summer and moves the heat around come Winter. Enjoy the beautiful outdoors on either the front or back deck, or from your own personal fire pit complete with granite bench. Don’t forget the s’mores! Guests have access to the post and beam cottage as well as the immediate surrounding area. We ask that the property boundaries are respected and that the guests do not go past the rock wall or onto the main house property or neighboring properties/horse farm. The post and beam cottage is on the same property as our primary residence but has it’s own driveway and is situated in a private clearing surrounded by beautiful forest. We will usually be available to welcome you personally and are happy to meet new people and make new friends but we also respect our guests privacy as we expect the same in return. Thank you! This post and beam cottage is in the small town of Pownal, 20 minutes from the wonderful restaurants, sights, and sounds of Portland. It's a 10-minute drive to Freeport and the L.L.Bean flagship store. Bradbury Mountain State Park is two miles away.
Jan 23 – 30
G$50,487 GYD per night
4.99 out of 5 average rating, 320 reviews
Guest favorite
Guest suite in New Gloucester
Peaceful Lakeside Suite w/Firepit and Kayaks
Open the double doors of your suite for direct access to a beautiful Maine lake. With a private entrance, the open concept apartment is in the walk-out basement of our log-cabin style home. Includes a kitchenette, private bathroom, enclosed unheated porch, large flat screen TV with DirecTV, washer & dryer. A patio with firepit is available (except when snow-covered). You may swim and use our kayaks and other boats, in season, at your own risk. Nice views. Quiet and peaceful. Enjoy star-gazing.
May 2 – 9
G$18,872 GYD per night
4.98 out of 5 average rating, 170 reviews
Guest favorite
Guest suite in Raymond, Maine
Rustic knotty pine getaway
lovely completely newly remodeled 2 bedroom 1-1/2 bath completely private upstairs unit with kitchen and private screened in deck. It has a private entrance with plenty of off street parking. located in Maine's lake region area. Walking distance to Raymond beach on Sebago lake. 5 miles to restaurants, shopping and local entertainment. 15 Miles from Portland. 30 to 60 minutes to winter skiing. Kayak, boat, and jet ski rentals nearby. 30 minutes to casino. Electric Vehicle charging on site.
Sep 7 – 14
G$43,467 GYD per night
4.91 out of 5 average rating, 122 reviews

Popular amenities for Raymond vacation rentals

Stay near Raymond's top sights

Seacoast Adventure59 locals recommend
Point Sebago6 locals recommend
Walmart Supercenter14 locals recommend
Bob's Seafood43 locals recommend
Pat's Pizza23 locals recommend
Applebee's Grill + Bar4 locals recommend

Other great vacation rentals in Raymond

Guest favorite
Cottage in Raymond
Relax by a Quiet Lake
May 6 – 13
G$28,288 GYD per night
4.9 out of 5 average rating, 90 reviews
Guest favorite
Cottage in Raymond
Relaxing New England Lakeside Getaway
Jul 3 – 10
G$61,946 GYD per night
4.95 out of 5 average rating, 22 reviews
Guest favorite
Home in Raymond
The Raymond Cottage
Sep 7 – 14
G$35,645 GYD per night
4.82 out of 5 average rating, 17 reviews
Guest favorite
Home in Windham
Waterfront Gem walkable to Restaurants!
Feb 4 – 11
G$28,128 GYD per night
4.95 out of 5 average rating, 58 reviews
Guest favorite
Home in Raymond
37(B)Shore Road Raymond Maine - Dragonfly Landing
Jun 28 – Jul 5
G$110,243 GYD per night
5.0 out of 5 average rating, 12 reviews
Guest favorite
Cottage in Raymond
Sensational House on Sebago Lake
Nov 16 – 23
G$91,494 GYD per night
4.93 out of 5 average rating, 29 reviews
Guest favorite
Tiny home in Naples
LUX Designer Private Waterfront
Oct 11 – 18
G$127,648 GYD per night
5.0 out of 5 average rating, 34 reviews
Guest favorite
Vacation home in Raymond
Cedar Lane Lodge - Luxury Lake House
Feb 10 – 17
G$208,936 GYD per night
5.0 out of 5 average rating, 16 reviews
Guest favorite
Vacation home in Raymond
Paradise Point on Panther Pond
Jun 6 – 13
G$108,293 GYD per night
5.0 out of 5 average rating, 13 reviews
Guest favorite
Home in Raymond
Lakehouse Retreat on Jordan Bay, Sebago Lake
May 6 – 13
G$53,683 GYD per night
4.94 out of 5 average rating, 49 reviews
Superhost
Home in Casco
Fully Updated Lake View Home on Thomas Pond
Nov 12 – 19
G$45,426 GYD per night
4.82 out of 5 average rating, 44 reviews
Guest favorite
Cabin in Poland
Cozy cabin on the lake with the loons
Feb 14 – 21
G$22,847 GYD per night
4.91 out of 5 average rating, 22 reviews

Other great vacation rentals in Raymond

Guest favorite
Guest suite in Raymond
Sebago Lake Waterfront Studio
Jan 18 – 25
G$37,609 GYD per night
4.96 out of 5 average rating, 73 reviews
Guest favorite
Apartment in Casco
Country Village Getaway
Nov 24 – Dec 1
G$20,999 GYD per night
4.9 out of 5 average rating, 29 reviews
Guest favorite
Cottage in Windham
Romantic waterfront cottage for two in Maine
Aug 20 – 27
G$56,885 GYD per night
5.0 out of 5 average rating, 65 reviews
Guest favorite
Home in Casco
Cozy Lakefront Getaway
Jan 15 – 22
G$80,320 GYD per night
4.96 out of 5 average rating, 28 reviews
Guest favorite
Cottage in Windham
Tranquil waterfront cottage
Sep 9 – 16
G$72,655 GYD per night
4.92 out of 5 average rating, 73 reviews
Guest favorite
Cottage in Windham
The Purple House by Pettingill Pond
Dec 8 – 15
G$46,197 GYD per night
4.84 out of 5 average rating, 45 reviews
Guest favorite
Cottage in Sebago
Recently renovated waterfront! Cedar Side Cottage
Sep 16 – 23
G$77,620 GYD per night
5.0 out of 5 average rating, 67 reviews
Superhost
Cottage in Windham
Relaxing 2 bed cottage on Little Sebago Lake
Aug 17 – 24
G$54,617 GYD per night
4.9 out of 5 average rating, 10 reviews
Guest favorite
Home in Raymond
Cheerful 3 Bedroom Home for your Maine Getaway
May 31 – Jun 7
G$41,577 GYD per night
5.0 out of 5 average rating, 29 reviews
Guest favorite
Cabin in Naples
Crooked River Private Paradise
Nov 27 – Dec 4
G$68,246 GYD per night
5.0 out of 5 average rating, 12 reviews
Superhost
Home in Sebago
Pine&Eagle LakeViews Family&DogFriendly LakeAccess
Oct 19 – 26
G$54,875 GYD per night
4.86 out of 5 average rating, 22 reviews
Guest favorite
Home in Raymond
Cozy Cottage in Raymond
Jun 25 – Jul 2
G$36,178 GYD per night
5.0 out of 5 average rating, 7 reviews

Quick stats about vacation rentals in Raymond

Total rentals

290 properties

Rentals with dedicated workspaces

140 properties have a dedicated workspace

Pet-friendly rentals

90 properties allow pets

Family-friendly rentals

230 properties are a good fit for families

Total number of reviews

6K reviews

Nightly prices starting at

G$12,599 GYD before taxes and fees

Frequently Asked Questions

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

    Yes! Work meets play with ease at over 140 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 family-friendly house rentals in Raymond?

    Raymond has more than 100 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do cottage rentals in Raymond have a bbq area?

    Absolutely! We offer over 50 cottage rentals with a bbq area in Raymond. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Raymond have wifi?

    Absolutely! We offer over 70 cottage rentals with wifi in Raymond. Enjoy a tailored experience with all the comforts you desire.

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

    Experience the best of Raymond with our apartment rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do cabin rentals in Raymond have air conditioning?

    Absolutely! We offer over 30 cabin 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 80 homes with air conditioning, over 110 homes with wifi, over 130 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Raymond