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

Guest suite in Bridgton

4.98 out of 5 average rating, 157 reviews

Barn on Pleasant-walk to town

Welcome to our charming loft in a peaceful neighborhood, ideal for comfort and convenience. This well maintained property provides a cozy living space. The loft features a kitchenette, a beautiful stone fireplace and a big, comfy reclining couch. Visit Bridgton this spring and summer, walking distance to Highland Lake, shops, and restaurants. Just minutes from Pleasant Mountain for hiking, 30 minutes from North Conway, and an hour from Portland a perfect central location to relax after exploring

May 16 – 23

G$28,725 GYD per night
Guest favorite

Guest suite in New Gloucester

4.98 out of 5 average rating, 170 reviews

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.

Jun 11 – 18

G$24,739 GYD per night
Guest favorite

Home in Naples

4.98 out of 5 average rating, 133 reviews

Kayak to the Causeway-50s cottage with modern vibe

Find out why the Maine life is the best life at Moonstone Cottage. Play on the shores of Long Lake, stroll the Naples Causeway, eat your way around Portland, and hike the mountains of western Maine before coming home to relax around the fire pit, lounge on the deck, and get a feel for the way life should be. Kayaks are waiting for you on the private association beach, or rent a boat from the marina to explore 40 miles of open water. Restaurants, live music, and the market are a short walk away.

Apr 4 – 11

G$30,546 GYD per night

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

Guesthouse in New Gloucester

4.89 out of 5 average rating, 106 reviews

On the water Boathouse!

Dec 5 – 12

G$49,616 GYD per night
Guest favorite

Guest suite in Freeport

4.96 out of 5 average rating, 193 reviews

Weather's Edge, Freeport

May 18 – 25

G$14,582 GYD per night
Guest favorite

Cabin in Lovell

4.98 out of 5 average rating, 246 reviews

Secluded, cozy cabin nestled in the Maine woods

Sep 14 – 21

G$23,804 GYD per night
Guest favorite

Apartment in Gorham

4.96 out of 5 average rating, 194 reviews

Cozy Private 1 Bedroom Apartment - Gorham Village

Apr 17 – 24

G$23,825 GYD per night
Guest favorite

Cottage in Raymond

4.95 out of 5 average rating, 22 reviews

Relaxing New England Lakeside Getaway

May 2 – 9

G$37,874 GYD per night
Guest favorite

Home in Windham

4.95 out of 5 average rating, 60 reviews

Waterfront Gem walkable to Restaurants!

Nov 16 – 23

G$33,151 GYD per night
Guest favorite

Apartment in Casco

4.9 out of 5 average rating, 29 reviews

Country Village Getaway

Sep 6 – 13

G$23,895 GYD per night
Guest favorite

Home in Raymond

4.82 out of 5 average rating, 17 reviews

The Raymond Cottage

Sep 25 – Oct 2

G$40,899 GYD per night
Guest favorite

Cottage in Raymond

4.9 out of 5 average rating, 90 reviews

Relax by a Quiet Lake

Oct 10 – 17

G$36,001 GYD per night
Guest favorite

Home in Raymond

5.0 out of 5 average rating, 12 reviews

37(B)Shore Road Raymond Maine - Dragonfly Landing

May 31 – Jun 7

G$126,503 GYD per night
Guest favorite

Tiny home in Naples

5.0 out of 5 average rating, 37 reviews

LUX Designer Private Waterfront

Dec 7 – 14

G$121,741 GYD per night
Guest favorite

Cottage in Raymond

4.93 out of 5 average rating, 30 reviews

Sensational House on Sebago Lake

Nov 3 – 10

G$106,224 GYD per night

Other great vacation rentals in Raymond

Guest favorite

Cabin in Naples

4.89 out of 5 average rating, 84 reviews

Songo Lock Cabins #2

Jan 27 – Feb 3

G$28,799 GYD per night
Guest favorite

Cabin in Bridgton

4.89 out of 5 average rating, 38 reviews

Rustic Elegance: a glamping getaway

Jan 12 – 19

G$24,202 GYD per night
Guest favorite

Home in Gray

4.95 out of 5 average rating, 43 reviews

cozy 3 bedroom ranch with deck and screen porch

Feb 11 – 18

G$50,546 GYD per night
Guest favorite

Vacation home in Raymond

5.0 out of 5 average rating, 13 reviews

Paradise Point on Panther Pond

Feb 24 – Mar 3

G$159,638 GYD per night
Guest favorite

Guest suite in Raymond

4.96 out of 5 average rating, 73 reviews

Sebago Lake Waterfront Studio

Feb 28 – Mar 7

G$43,112 GYD per night
Guest favorite

Cottage in Windham

4.92 out of 5 average rating, 73 reviews

Tranquil waterfront cottage

Sep 9 – 16

G$82,778 GYD per night
Guest favorite

Cottage in Windham

5.0 out of 5 average rating, 65 reviews

Romantic waterfront cottage for two in Maine

Aug 20 – 27

G$64,942 GYD per night
Guest favorite

Home in Gray

5.0 out of 5 average rating, 18 reviews

Little Sebago Lakefront Getaway

Nov 5 – 12

G$43,855 GYD per night
Guest favorite

Home in Raymond

5.0 out of 5 average rating, 29 reviews

Cheerful 3 Bedroom Home for your Maine Getaway

Jun 2 – 9

G$47,312 GYD per night
Superhost

Cottage in Windham

4.9 out of 5 average rating, 10 reviews

Relaxing 2 bed cottage on Little Sebago Lake

May 18 – 25

G$60,981 GYD per night
Guest favorite

Cabin in Oxford

4.93 out of 5 average rating, 94 reviews

Thompson Lake, Oxford, Maine. Pine Cottage

Jan 24 – 31

G$28,843 GYD per night
Guest favorite

Home in Casco

4.96 out of 5 average rating, 28 reviews

Charming Lakefront Getaway

Jan 15 – 22

G$92,559 GYD per night

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$12,563 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 cottage rentals in Raymond?

    Raymond has more than 70 family-friendly cottage 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 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 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 Cottage Rentals in Raymond?

    Enhance your stay in our Cottage Rentals with the most popular amenities: over 50 homes with a bbq area, over 40 homes with air conditioning, over 70 homes with wifi, 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